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Perched above the rocky shoreline of Casco Bay, 1 Bay Road offers an extraordinary blend of refined coastal living and classic Maine beauty. Designed in 1951 by John Howard Stevens and completely reimagined with a full renovation, this 3,720-square-foot waterfront residence captures sweeping, unobstructed ocean views from nearly every room, creating a rare sanctuary just minutes from Portland's vibrant downtown. Step inside to sun-filled living spaces where walls of windows frame sailboats drifting across the bay and the ever-changing colors of the Atlantic. The home features 3 bedrooms and 6 baths, including beautifully updated suites designed for comfort and privacy. Elegant living and dining areas flow effortlessly toward the water, making the property ideal for both quiet relaxation and gracious entertaining. A modern, well-appointed kitchen anchors the main level, while thoughtfully designed gathering spaces, a walk-out lower level, and ocean-facing terrace invites connection to the outdoors. The property's generous waterfront lot offers privacy, fresh salt air, and panoramic shoreline vistas that define Maine's coastal lifestyle. Whether serving as a year-round residence or a cherished retreat, 1 Bay Road delivers the rare opportunity to own a premier piece of South Portland's coastline—where luxury, tranquility, and natural beauty meet.

3 Beds ⋅ 6 Baths

Perched above the rocky shoreline of Casco Bay, 1 Bay Road offers an extraordinary blend of refined coastal living and classic Maine beauty. Designed in 1951 by John Howard Stevens and completely reimagined with a full renovation, this 3,720-square-foot waterfront residence captures sweeping, unobstructed ocean views from nearly every room, creating a rare sanctuary just minutes from Portland's vibrant downtown. Step inside to sun-filled living spaces where walls of windows frame sailboats drifting across the bay and the ever-changing colors of the Atlantic. The home features 3 bedrooms and 6 baths, including beautifully updated suites designed for comfort and privacy. Elegant living and dining areas flow effortlessly toward the water, making the property ideal for both quiet relaxation and gracious entertaining. A modern, well-appointed kitchen anchors the main level, while thoughtfully designed gathering spaces, a walk-out lower level, and ocean-facing terrace invites connection to the outdoors. The property's generous waterfront lot offers privacy, fresh salt air, and panoramic shoreline vistas that define Maine's coastal lifestyle. Whether serving as a year-round residence or a cherished retreat, 1 Bay Road delivers the rare opportunity to own a premier piece of South Portland's coastline—where luxury, tranquility, and natural beauty meet.

1 Bay Rd, South Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

Selling Office: Cottage & Co Real Estate.

$2,525,000

Presenting a rare chance to acquire a landmark site at one of South Portland's most iconic, high-traffic intersections. Located at 279 Main Street, this property boasts combined traffic counts exceeding 25,000 VPD and offers immediate access to I-295 and high-density residential neighborhoods. The site currently features a 10,578 SF freestanding building with a drive-thru, providing a strong foundation for redevelopment or an owner-user transition. With additional excess land included, the highest and best use lies in a full-scale redevelopment project, supported by available site plan proposals. Secure a strategic foothold in a premier location with short-term holding income potential while you finalize your vision for this transformative site.

279 Main St, South Portland

Listing courtesy of Keller Williams Realty.

Selling Office: Non MREIS Agency.

$2,150,000

Step into this custom-built contemporary Cape Cod-style home, set in the desirable seaside neighborhood of Loveitt's Field. Take in the ever-changing waterscape as ships, ferries, and sailboats make their way through the Ship Channel and Casco Bay toward Cushing Island. The living space is anchored by a generous wall of windows showcasing ocean views, while soaring ceilings create a spacious, airy feel. The open-concept design makes entertaining a breeze, and allows the living area to flow with ease into the sizable kitchen and dining area. As you round the corner, you'll find the first of two primary suites. Tucked down a separate wing from the main living space, this suite is a peaceful retreat for guests or for those who prefer the ease of single-floor living. With laundry also located on the main level, you truly have everything you need. Head up the custom staircase to the second level, where you'll find a well-appointed guest room, currently being used as an office. With minimal effort, this flexible space could easily transition back to a guest bedroom, with its own full bath conveniently located just across the hall. Continue down the hall to the home's second primary suite, complete with two walk-in closets and a private balcony boasting the kind of ocean sunrises you dream about. The en-suite leaves nothing to be desired, with a generous soaking tub, tiled walk-in shower, and dual sinks. Rounding out the second floor is a charming reading nook at the top of the stairs, complete with custom built-in shelving, perfect for your favorite books and treasured collections. Outside, extensive custom hardscaping and beautiful gardens create the perfect setting to entertain friends and family or simply sit back and relax with your favorite beverage at the end of the day. If a dip in the ocean is more appealing, take a quick walk to Willard Beach along the neighborhood sidewalk and enjoy the salt air and breeze of the ocean.

3 Beds ⋅ 4 Baths

Step into this custom-built contemporary Cape Cod-style home, set in the desirable seaside neighborhood of Loveitt's Field. Take in the ever-changing waterscape as ships, ferries, and sailboats make their way through the Ship Channel and Casco Bay toward Cushing Island. The living space is anchored by a generous wall of windows showcasing ocean views, while soaring ceilings create a spacious, airy feel. The open-concept design makes entertaining a breeze, and allows the living area to flow with ease into the sizable kitchen and dining area. As you round the corner, you'll find the first of two primary suites. Tucked down a separate wing from the main living space, this suite is a peaceful retreat for guests or for those who prefer the ease of single-floor living. With laundry also located on the main level, you truly have everything you need. Head up the custom staircase to the second level, where you'll find a well-appointed guest room, currently being used as an office. With minimal effort, this flexible space could easily transition back to a guest bedroom, with its own full bath conveniently located just across the hall. Continue down the hall to the home's second primary suite, complete with two walk-in closets and a private balcony boasting the kind of ocean sunrises you dream about. The en-suite leaves nothing to be desired, with a generous soaking tub, tiled walk-in shower, and dual sinks. Rounding out the second floor is a charming reading nook at the top of the stairs, complete with custom built-in shelving, perfect for your favorite books and treasured collections. Outside, extensive custom hardscaping and beautiful gardens create the perfect setting to entertain friends and family or simply sit back and relax with your favorite beverage at the end of the day. If a dip in the ocean is more appealing, take a quick walk to Willard Beach along the neighborhood sidewalk and enjoy the salt air and breeze of the ocean.

9 Loveitts Field Rd, South Portland

Listing courtesy of Portside Real Estate Group.

Selling Office: Keller Williams Realty.

$1,975,000

Set along one of the Willard neighborhood's most desirable quiet streets, with beach access at the end of the road and just moments from Willard Square, this exceptional coastal residence offers sweeping views of Casco Bay and a rare opportunity to own a beautifully reimagined home. Thoughtfully renovated and impeccably maintained, the 3,784± sqft property blends classic New England character with elevated modern living. A gracious wraparound porch welcomes you into sun-filled interiors featuring rich hardwood floors, refined finishes, an elegant wet bar, and a seamless floor plan designed for both everyday living and entertaining. The expansive eat-in kitchen flows effortlessly into the formal dining room and inviting living room with a gas fireplace, while oversized windows frame water views and fill the home with natural light. Step onto the rear deck to enjoy morning coffee or evening gatherings while watching cruise ships and boats pass by. The second level offers a tranquil primary suite with a private upper deck, along with four additional bedrooms - three (in addition to the primary) have water views - plus a laundry area and a dedicated office space. Flexible by design, the layout easily accommodates five bedrooms or four bedrooms with two private offices. Outside, the beautifully landscaped yard creates a private garden retreat with stonework, curated plantings, and multiple outdoor living areas. Enjoy the stone patio with outdoor kitchen, garden swing, outdoor shower, and two elevated decks positioned to capture sea breezes and panoramic views. The finished lower level adds exceptional versatility with a spacious family room and game room, while a custom mudroom provides built-in storage and access to the detached two-car garage. Just moments from Willard Beach, Scratch Baking Co., and Willard Scoops, with an easy commute to Portland, this is coastal Maine living at its finest - where location, comfort, and luxury come together in one remarkable offering

5 Beds ⋅ 3 Baths

Set along one of the Willard neighborhood's most desirable quiet streets, with beach access at the end of the road and just moments from Willard Square, this exceptional coastal residence offers sweeping views of Casco Bay and a rare opportunity to own a beautifully reimagined home. Thoughtfully renovated and impeccably maintained, the 3,784± sqft property blends classic New England character with elevated modern living. A gracious wraparound porch welcomes you into sun-filled interiors featuring rich hardwood floors, refined finishes, an elegant wet bar, and a seamless floor plan designed for both everyday living and entertaining. The expansive eat-in kitchen flows effortlessly into the formal dining room and inviting living room with a gas fireplace, while oversized windows frame water views and fill the home with natural light. Step onto the rear deck to enjoy morning coffee or evening gatherings while watching cruise ships and boats pass by. The second level offers a tranquil primary suite with a private upper deck, along with four additional bedrooms - three (in addition to the primary) have water views - plus a laundry area and a dedicated office space. Flexible by design, the layout easily accommodates five bedrooms or four bedrooms with two private offices. Outside, the beautifully landscaped yard creates a private garden retreat with stonework, curated plantings, and multiple outdoor living areas. Enjoy the stone patio with outdoor kitchen, garden swing, outdoor shower, and two elevated decks positioned to capture sea breezes and panoramic views. The finished lower level adds exceptional versatility with a spacious family room and game room, while a custom mudroom provides built-in storage and access to the detached two-car garage. Just moments from Willard Beach, Scratch Baking Co., and Willard Scoops, with an easy commute to Portland, this is coastal Maine living at its finest - where location, comfort, and luxury come together in one remarkable offering

71 Myrtle Ave, South Portland

Listing courtesy of Keller Williams Realty. 207-553-2400

Selling Office: Portside Real Estate Group.

$1,641,900

Remarkable shingle-style home rebuilt and reimagined from a former life as a well-loved 1920's cottage. In 2025, this 3 bedroom, 2.5 bath home was constructed with custom, handcrafted finishes and a gracious, open floor plan with plenty of natural light. Designer kitchen features Carrera marble surfaces, a coffee/wet bar station and walk-in pantry. The kitchen opens to a den with gas fireplace leading to half bath and laundry. The expansive living/dining room with french doors opens to an amazing veranda overlooking the landscaped yard with granite steps and walkways. Sunny primary suite plus 2 additional bedrooms complete the second level. Located in the seaside neighborhood of Loveitts Field, this property is in close proximity to beaches, shopping and all the trendy restaurants of Greater Portland. Excellent opportunity!

3 Beds ⋅ 3 Baths

Remarkable shingle-style home rebuilt and reimagined from a former life as a well-loved 1920's cottage. In 2025, this 3 bedroom, 2.5 bath home was constructed with custom, handcrafted finishes and a gracious, open floor plan with plenty of natural light. Designer kitchen features Carrera marble surfaces, a coffee/wet bar station and walk-in pantry. The kitchen opens to a den with gas fireplace leading to half bath and laundry. The expansive living/dining room with french doors opens to an amazing veranda overlooking the landscaped yard with granite steps and walkways. Sunny primary suite plus 2 additional bedrooms complete the second level. Located in the seaside neighborhood of Loveitts Field, this property is in close proximity to beaches, shopping and all the trendy restaurants of Greater Portland. Excellent opportunity!

63 Cloyster Rd, South Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

Selling Office: Town & Shore Real Estate.

$1,625,000

Set on nearly an acre in South Portland's Hawthorne Woods, this thoughtfully designed 3,200± SF home pairs clean lines with high-performance construction and effortless everyday living. The sun-filled interior features wide white oak floors, Scandinavian-inspired cabinetry, custom tile, and a well-appointed kitchen with premium appliances. All supported by triple-pane windows, heat pumps, and a full heat recovery ventilation system. Outside, a stone patio with an electronically controlled pergola and gas fire pit creates a seamless extension of the living space. This is a home where the quality and setting are best understood in person, offering a level of design, efficiency, and privacy that sets it apart. Perfectly tucked in a private neighborhood just minutes to South Portland's downtown and the Old Port, with easy access to some of Maine's most beautiful beaches.

4 Beds ⋅ 3 Baths

Set on nearly an acre in South Portland's Hawthorne Woods, this thoughtfully designed 3,200± SF home pairs clean lines with high-performance construction and effortless everyday living. The sun-filled interior features wide white oak floors, Scandinavian-inspired cabinetry, custom tile, and a well-appointed kitchen with premium appliances. All supported by triple-pane windows, heat pumps, and a full heat recovery ventilation system. Outside, a stone patio with an electronically controlled pergola and gas fire pit creates a seamless extension of the living space. This is a home where the quality and setting are best understood in person, offering a level of design, efficiency, and privacy that sets it apart. Perfectly tucked in a private neighborhood just minutes to South Portland's downtown and the Old Port, with easy access to some of Maine's most beautiful beaches.

55 Hawthorne Ln, South Portland

Listing courtesy of Portside Real Estate Group.

Selling Office: Marsden Real Estate.

$1,475,000

This rare year-round beachfront offering features breathtaking 180-degree ocean views, a generous open lot, situated on highly desirable Willard Beach. Cherished by the same family for over 50 years, the classic 4-bedroom, 2-bath Cape-style home is filled with timeless coastal charm and captures stunning water views from nearly every room, including the expansive deck, sunroom, dining room, and both first- and second-floor bedrooms. Bay windows in the living room invite in refreshing sea breezes and frame the ever-changing seascape. Enjoy panoramic vistas of the Portland Ship Channel, historic Fort Gorges, and Casco Bay from this exceptional waterfront setting. Ideally located on a quiet dead-end street near Willard Square, you're moments with downtown Portland just minutes away. Whether you choose to enhance the existing home or build your custom oceanfront retreat, this is a rare opportunity to secure a premier location and embrace the very best of Maine coastal living.

4 Beds ⋅ 2 Baths

This rare year-round beachfront offering features breathtaking 180-degree ocean views, a generous open lot, situated on highly desirable Willard Beach. Cherished by the same family for over 50 years, the classic 4-bedroom, 2-bath Cape-style home is filled with timeless coastal charm and captures stunning water views from nearly every room, including the expansive deck, sunroom, dining room, and both first- and second-floor bedrooms. Bay windows in the living room invite in refreshing sea breezes and frame the ever-changing seascape. Enjoy panoramic vistas of the Portland Ship Channel, historic Fort Gorges, and Casco Bay from this exceptional waterfront setting. Ideally located on a quiet dead-end street near Willard Square, you're moments with downtown Portland just minutes away. Whether you choose to enhance the existing home or build your custom oceanfront retreat, this is a rare opportunity to secure a premier location and embrace the very best of Maine coastal living.

15 Myrtle Ave, South Portland

Listing courtesy of Town & Shore Real Estate.

Selling Office: Keller Williams Realty.

$1,300,000

Welcome to your dream home, completely renovated in 2024! This stunning property in the highly sought-after Willard Square combines modern amenities with convenient living. Perfectly positioned within walking distance to delightful restaurants and the serene Willard Beach, this home is a true gem. **Key Features:** - **Main House:** The main residence boasts three spacious bedrooms and three luxurious baths, including an ensuite bedroom featuring a massive closet, laundry facilities, and a luxurious soaking tub and shower. Each room is designed for comfort with abundant natural light. - **In-Law Apartment:** The first-floor apartment offers a private haven with its own direct entry garage and private entrance. - **Outdoor Oasis:** Enjoy beautifully landscaped grounds and a sparkling pool--perfect for summer gatherings or tranquil evenings under the stars. - **Cozy Living Spaces:** Gather around any of the three fireplaces that add warmth and charm throughout the home, creating cozy nooks for relaxation. - **Modern Conveniences:** The home is equipped with efficient heat pumps for year-round comfort and a direct entry garage for both units, ensuring easy access. - **Gourmet Kitchen:** Experience culinary bliss in the well-appointed kitchen featuring a large island and a gas stove--ideal for entertaining or whipping up family meals. - **Functional Office Nook:** Need a workspace? The first-floor office nook offers a private area to focus on work or study.

4 Beds ⋅ 4 Baths

Welcome to your dream home, completely renovated in 2024! This stunning property in the highly sought-after Willard Square combines modern amenities with convenient living. Perfectly positioned within walking distance to delightful restaurants and the serene Willard Beach, this home is a true gem. **Key Features:** - **Main House:** The main residence boasts three spacious bedrooms and three luxurious baths, including an ensuite bedroom featuring a massive closet, laundry facilities, and a luxurious soaking tub and shower. Each room is designed for comfort with abundant natural light. - **In-Law Apartment:** The first-floor apartment offers a private haven with its own direct entry garage and private entrance. - **Outdoor Oasis:** Enjoy beautifully landscaped grounds and a sparkling pool--perfect for summer gatherings or tranquil evenings under the stars. - **Cozy Living Spaces:** Gather around any of the three fireplaces that add warmth and charm throughout the home, creating cozy nooks for relaxation. - **Modern Conveniences:** The home is equipped with efficient heat pumps for year-round comfort and a direct entry garage for both units, ensuring easy access. - **Gourmet Kitchen:** Experience culinary bliss in the well-appointed kitchen featuring a large island and a gas stove--ideal for entertaining or whipping up family meals. - **Functional Office Nook:** Need a workspace? The first-floor office nook offers a private area to focus on work or study.

49 Smith St, South Portland

Listing courtesy of Landing Real Estate.

Selling Office: Landing Real Estate.

$1,300,000

Located just steps away from Willard Beach, this 3-bedroom, 2.5-bath home with an attached 1-bedroom, 1-bath Accessory Dwelling Unit (ADU) has tons to offer. This light-filled home was remodeled from top to bottom. Stairs were relocated, new windows and doors installed and a whole new 3rd level added. The updated kitchen, with stainless steel appliances, custom wood cabinets, quartz countertops, and island is now open to the dining room, living room and exterior deck and patio allowing an integrative flow between indoor and outdoor living. A combined Powder room/laundry room and separate mudroom finish off the first floor living space. The second level consists of 2-bedrooms, a shared bath (with 2 separate vanities) and an additional room that can function as an office or nursery. Like the main level, wide-plank white oak engineered hardwood floors flow throughout this and the third level of the house. The third level of the home is where you will find the ultimate primary suite with a large walk-in closet, primary bath with large soaking tub and shower, and access to a 7 1/2' x 13' ft. covered deck with year round views of peaks island and the bay. And finally, there is the attached ADU. With its own separate entrance, this light filled space offers cathedral ceilings, a full kitchen, bath, bedroom and small patio. Great for an in-law suite, guest space or rental. Located within walking distance to Willard Beach, Willard Scoops, Scratch Bakery and other equally desirable local shops and restaurants make this a real gem - don't miss it! Realtor owned. FIRST OPEN - SUNDAY MARCH 29TH 10 AM - NOON

4 Beds ⋅ 3 Baths

Located just steps away from Willard Beach, this 3-bedroom, 2.5-bath home with an attached 1-bedroom, 1-bath Accessory Dwelling Unit (ADU) has tons to offer. This light-filled home was remodeled from top to bottom. Stairs were relocated, new windows and doors installed and a whole new 3rd level added. The updated kitchen, with stainless steel appliances, custom wood cabinets, quartz countertops, and island is now open to the dining room, living room and exterior deck and patio allowing an integrative flow between indoor and outdoor living. A combined Powder room/laundry room and separate mudroom finish off the first floor living space. The second level consists of 2-bedrooms, a shared bath (with 2 separate vanities) and an additional room that can function as an office or nursery. Like the main level, wide-plank white oak engineered hardwood floors flow throughout this and the third level of the house. The third level of the home is where you will find the ultimate primary suite with a large walk-in closet, primary bath with large soaking tub and shower, and access to a 7 1/2' x 13' ft. covered deck with year round views of peaks island and the bay. And finally, there is the attached ADU. With its own separate entrance, this light filled space offers cathedral ceilings, a full kitchen, bath, bedroom and small patio. Great for an in-law suite, guest space or rental. Located within walking distance to Willard Beach, Willard Scoops, Scratch Bakery and other equally desirable local shops and restaurants make this a real gem - don't miss it! Realtor owned. FIRST OPEN - SUNDAY MARCH 29TH 10 AM - NOON

464 Preble St, South Portland

Listing courtesy of Angle Associates.

Selling Office: Cottage & Co Real Estate.

$1,250,000

A timeless Cape Cod in an exceptional coastal Maine neighborhood. Set in the desirable seaside community of Loveitts Field, this light-filled home blends classic New England charm with everyday livability. Thoughtfully maintained and recently updated, this home offers a flexible floor plan with three bedrooms, one and a half baths, two sunrooms, a freshly painted interior, and a brand-new natural gas-fired boiler with on-demand hot water and seven heating zones. Beautiful red oak hardwood flooring and a wood-burning fireplace add warmth and character. Outside, enjoy a freshly painted exterior, expansive deck, brand-new lawn, professional landscaping with lighting and irrigation, new front and side walkways, and a newly paved driveway leading to the two-car garage. Additional storage can be found in the shed. Located in a quiet residential setting with a private yard and ocean views, just minutes from Willard Beach, SMCC, waterfront parks, and Portland's vibrant dining scene.

3 Beds ⋅ 2 Baths

A timeless Cape Cod in an exceptional coastal Maine neighborhood. Set in the desirable seaside community of Loveitts Field, this light-filled home blends classic New England charm with everyday livability. Thoughtfully maintained and recently updated, this home offers a flexible floor plan with three bedrooms, one and a half baths, two sunrooms, a freshly painted interior, and a brand-new natural gas-fired boiler with on-demand hot water and seven heating zones. Beautiful red oak hardwood flooring and a wood-burning fireplace add warmth and character. Outside, enjoy a freshly painted exterior, expansive deck, brand-new lawn, professional landscaping with lighting and irrigation, new front and side walkways, and a newly paved driveway leading to the two-car garage. Additional storage can be found in the shed. Located in a quiet residential setting with a private yard and ocean views, just minutes from Willard Beach, SMCC, waterfront parks, and Portland's vibrant dining scene.

83 Loveitts Field Rd, South Portland

Listing courtesy of JM Real Estate.

Selling Office: Town & Shore Real Estate.

$1,140,000

Located in the highly desirable Willard Beach neighborhood of South Portland, 238 Preble Street presents a rare opportunity to own a well-maintained 4-unit investment property just moments from the beach and vibrant Willard Square. Each spacious unit offers 2 bedrooms and 1 bathroom, providing strong rental appeal in one of Southern Maine's most sought-after coastal communities. Three of the four units have been fully renovated, featuring updated kitchens, baths, flooring, and modern finishes while maintaining the property's classic New England charm. Tenants enjoy easy access to Willard Beach, local restaurants, coffee shops, markets, and downtown Portland just minutes away. Whether you're looking to expand your portfolio or owner-occupy with additional rental income, this property combines location, lifestyle, and investment potential in an exceptional package.

4 Baths

Located in the highly desirable Willard Beach neighborhood of South Portland, 238 Preble Street presents a rare opportunity to own a well-maintained 4-unit investment property just moments from the beach and vibrant Willard Square. Each spacious unit offers 2 bedrooms and 1 bathroom, providing strong rental appeal in one of Southern Maine's most sought-after coastal communities. Three of the four units have been fully renovated, featuring updated kitchens, baths, flooring, and modern finishes while maintaining the property's classic New England charm. Tenants enjoy easy access to Willard Beach, local restaurants, coffee shops, markets, and downtown Portland just minutes away. Whether you're looking to expand your portfolio or owner-occupy with additional rental income, this property combines location, lifestyle, and investment potential in an exceptional package.

238 Preble St, South Portland

Listing courtesy of Cottage & Co Real Estate.

Selling Office: Portside Real Estate Group.

$1,060,000

2 Beds ⋅ 3 Baths

3 Puffin Way Unit 12, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Coldwell Banker Realty.

$1,030,000

Rare opportunity to acquire an exceptional five-unit multifamily property in one of South Portland's most desirable neighborhoods. Set on approximately 0.60 acres, this offering combines strong current income, value-add potential, and an attractive owner-occupied opportunity. The property has been meticulously maintained with extensive capital improvements, including roofing, a rebuilt front fire escape and deck system, electrical upgrades, an efficient natural gas heating system, exterior improvements, and a beautiful brick patio. This is a true turnkey asset with a level of care rarely found in today's multifamily market. The owner's residence features a townhouse-style layout with expansive living areas, flexible bonus space, a barn, and a stunning great room above. Enjoy views toward the Portland skyline and Casco Bay from the private deck, while large windows provide abundant natural light. The grounds include a circular driveway, mature gardens, green space, and a detached one-car garage. The generous lot offers a setting rarely found this close to Portland and South Portland amenities, with potential future expansion or redevelopment opportunities. The property consists of three one-bedroom apartments, one studio apartment, and a spacious two-bedroom owner's unit. Current rents are below market, providing immediate upside potential. Tenants pay their own electricity, while the owner provides heat and hot water through an efficient natural gas boiler. With approximately $88,000 in net operating income and a 6.4% cap rate, this property offers stable cash flow, strong tenant profiles, and long-term upside. Whether seeking a quality investment, owner-occupied multifamily, or future development opportunity, 32 Clemons Street is one of Greater Portland most compelling offerings.

6 Baths

Rare opportunity to acquire an exceptional five-unit multifamily property in one of South Portland's most desirable neighborhoods. Set on approximately 0.60 acres, this offering combines strong current income, value-add potential, and an attractive owner-occupied opportunity. The property has been meticulously maintained with extensive capital improvements, including roofing, a rebuilt front fire escape and deck system, electrical upgrades, an efficient natural gas heating system, exterior improvements, and a beautiful brick patio. This is a true turnkey asset with a level of care rarely found in today's multifamily market. The owner's residence features a townhouse-style layout with expansive living areas, flexible bonus space, a barn, and a stunning great room above. Enjoy views toward the Portland skyline and Casco Bay from the private deck, while large windows provide abundant natural light. The grounds include a circular driveway, mature gardens, green space, and a detached one-car garage. The generous lot offers a setting rarely found this close to Portland and South Portland amenities, with potential future expansion or redevelopment opportunities. The property consists of three one-bedroom apartments, one studio apartment, and a spacious two-bedroom owner's unit. Current rents are below market, providing immediate upside potential. Tenants pay their own electricity, while the owner provides heat and hot water through an efficient natural gas boiler. With approximately $88,000 in net operating income and a 6.4% cap rate, this property offers stable cash flow, strong tenant profiles, and long-term upside. Whether seeking a quality investment, owner-occupied multifamily, or future development opportunity, 32 Clemons Street is one of Greater Portland most compelling offerings.

32 Clemons St, South Portland

Listing courtesy of Benchmark Real Estate.

Selling Office: Gardner Real Estate Group.

$975,000

Historic character, exceptional craftsmanship, and modern energy efficiency come together in this beautifully restored Second Empire home in South Portland's desirable Meetinghouse Hill neighborhood. Thoughtfully renovated by SoPo Cottage in 2024-25, this amazing residence offers over 2,327 square feet of elegant, comfortable living space where every detail has been carefully considered. Inside, period charm blends seamlessly with modern living. The sun-filled interior features a stunning custom kitchen, beautifully renovated bathrooms, a welcoming living room with a gas fireplace and custom built-ins throughout. Flexible living spaces include a sunroom, home office, and finished lower level - providing room to work, relax and entertain. Beyond its beauty, the home has been transformed with a focus on performance and sustainability. Extensive insulation and air sealing improvements, energy-efficient windows, and high-efficiency heat pumps create year-round comfort while helping to reduce energy bills. The renovation included all new electrical and plumbing for peace of mind and true turnkey living. The outdoor spaces are equally impressive. Professionally designed landscaping creates a private backyard oasis complete with a spacious patio and custom fire pit - perfect for gathering with friends, enjoying summer evenings, or relaxing under the stars. The generous yard offers room for gardening, recreation and entertaining. A highly walkable community, it's close to local restaurants, ice cream, the library, beaches and Mill Creek park. The nearby Greenbelt Walkway has 16 miles of trails, starting at Bug Light Park. 9 Haven Road offers the rare opportunity to own a thoughtfully restored historic home that combines timeless architecture, modern efficiency, and exceptional outdoor living in one of South Portland's most sought-after neighborhoods.

3 Beds ⋅ 3 Baths

Historic character, exceptional craftsmanship, and modern energy efficiency come together in this beautifully restored Second Empire home in South Portland's desirable Meetinghouse Hill neighborhood. Thoughtfully renovated by SoPo Cottage in 2024-25, this amazing residence offers over 2,327 square feet of elegant, comfortable living space where every detail has been carefully considered. Inside, period charm blends seamlessly with modern living. The sun-filled interior features a stunning custom kitchen, beautifully renovated bathrooms, a welcoming living room with a gas fireplace and custom built-ins throughout. Flexible living spaces include a sunroom, home office, and finished lower level - providing room to work, relax and entertain. Beyond its beauty, the home has been transformed with a focus on performance and sustainability. Extensive insulation and air sealing improvements, energy-efficient windows, and high-efficiency heat pumps create year-round comfort while helping to reduce energy bills. The renovation included all new electrical and plumbing for peace of mind and true turnkey living. The outdoor spaces are equally impressive. Professionally designed landscaping creates a private backyard oasis complete with a spacious patio and custom fire pit - perfect for gathering with friends, enjoying summer evenings, or relaxing under the stars. The generous yard offers room for gardening, recreation and entertaining. A highly walkable community, it's close to local restaurants, ice cream, the library, beaches and Mill Creek park. The nearby Greenbelt Walkway has 16 miles of trails, starting at Bug Light Park. 9 Haven Road offers the rare opportunity to own a thoughtfully restored historic home that combines timeless architecture, modern efficiency, and exceptional outdoor living in one of South Portland's most sought-after neighborhoods.

9 Haven Rd, South Portland

Listing courtesy of Cottage & Co Real Estate.

Selling Office: Legacy Properties Sotheby's International Realty.

8 Sand Pebble Way Unit 8, South Portland

$975,000

Live the coastal lifestyle just moments from Willard Beach, local restaurants, bakeries, and the waterfront in this beautifully maintained free-standing condo that lives like a single-family home -- without the hassle of landscaping, lawn care and snow plowing, allowing you to fully enjoy this highly sought-after beachside location. Meticulously cared for and filled with natural light, this home offers a flexible floor plan with first-floor bedroom potential, featuring two bedrooms and a full bath with custom tile shower on the main level. Upstairs offers two additional bedrooms, a full bath with Jacuzzi tub and skylight, and exceptional closet space throughout. The inviting living room showcases hardwood floors, elegant custom built-ins, and a gas fireplace with granite surround, creating a warm and sophisticated focal point. The dining area flows seamlessly into the kitchen and out to a private brick patio surrounded by mature landscaping, including a beautiful Japanese maple, hydrangea, and perennial gardens -- the perfect setting for relaxing or entertaining. The kitchen features Corian countertops, a stylish red center island, fresh paint, and convenient access to the mudroom, garage entry, and half bath. An oversized two-car garage with rear storage space and walkout access to the backyard adds both functionality and convenience. A rare opportunity to enjoy spacious, low-maintenance living in one of South Portland's most desirable coastal neighborhoods.

4 Beds ⋅ 3 Baths

Live the coastal lifestyle just moments from Willard Beach, local restaurants, bakeries, and the waterfront in this beautifully maintained free-standing condo that lives like a single-family home -- without the hassle of landscaping, lawn care and snow plowing, allowing you to fully enjoy this highly sought-after beachside location. Meticulously cared for and filled with natural light, this home offers a flexible floor plan with first-floor bedroom potential, featuring two bedrooms and a full bath with custom tile shower on the main level. Upstairs offers two additional bedrooms, a full bath with Jacuzzi tub and skylight, and exceptional closet space throughout. The inviting living room showcases hardwood floors, elegant custom built-ins, and a gas fireplace with granite surround, creating a warm and sophisticated focal point. The dining area flows seamlessly into the kitchen and out to a private brick patio surrounded by mature landscaping, including a beautiful Japanese maple, hydrangea, and perennial gardens -- the perfect setting for relaxing or entertaining. The kitchen features Corian countertops, a stylish red center island, fresh paint, and convenient access to the mudroom, garage entry, and half bath. An oversized two-car garage with rear storage space and walkout access to the backyard adds both functionality and convenience. A rare opportunity to enjoy spacious, low-maintenance living in one of South Portland's most desirable coastal neighborhoods.

8 Sand Pebble Way Unit 8, South Portland

Listing courtesy of Peninsula Real Estate LLC.

Selling Office: Portside Real Estate Group.

$973,952

Phase III Open - Only 4 single level & 6 2-storny w/primary on 1st floor available. New Construction! This 55plus community are craftsman-designed homes sited on 18+ designed landscaped acres. This community has17 twin villas consisting of 34 homes offering unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a zero clearance tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), & pre-wiring for EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are our upgraded Model Home. GPS. 761 Main Street South Portland ME behind King Wood Condominiums.

2 Beds ⋅ 3 Baths

Phase III Open - Only 4 single level & 6 2-storny w/primary on 1st floor available. New Construction! This 55plus community are craftsman-designed homes sited on 18+ designed landscaped acres. This community has17 twin villas consisting of 34 homes offering unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a zero clearance tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), & pre-wiring for EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are our upgraded Model Home. GPS. 761 Main Street South Portland ME behind King Wood Condominiums.

6 Plover Way Unit 19, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Coldwell Banker Realty.

$949,700

Rare Willard Beach opportunity! Just steps from the sand and an easy stroll to neighborhood favorites including Scratch Baking Co., local restaurants, and ice cream shops, this beautifully renovated coastal home offers the very best of seaside living. Thoughtfully updated throughout, the home features a stunning new kitchen, beautifully renovated bathrooms, and sun-filled living spaces that create a bright, welcoming atmosphere. Situated on a sunny corner lot with partial water views and refreshing ocean breezes, the home blends timeless charm with modern comfort. The flexible floor plan offers comfortable living today, while the walk-up attic presents exciting potential for future expansion and the opportunity to capture even more expansive views of Casco Bay. Outside, a private patio and manageable yard provide the perfect setting for relaxing or entertaining after a day at the beach, and a storage shed offers convenient space for bikes, paddleboards, and beach gear. Whether you're seeking a year-round residence, a seasonal getaway, or simply a chance to live in one of Southern Maine's most beloved coastal neighborhoods, this turnkey home delivers an exceptional lifestyle just moments from the shoreline.

4 Beds ⋅ 2 Baths

Rare Willard Beach opportunity! Just steps from the sand and an easy stroll to neighborhood favorites including Scratch Baking Co., local restaurants, and ice cream shops, this beautifully renovated coastal home offers the very best of seaside living. Thoughtfully updated throughout, the home features a stunning new kitchen, beautifully renovated bathrooms, and sun-filled living spaces that create a bright, welcoming atmosphere. Situated on a sunny corner lot with partial water views and refreshing ocean breezes, the home blends timeless charm with modern comfort. The flexible floor plan offers comfortable living today, while the walk-up attic presents exciting potential for future expansion and the opportunity to capture even more expansive views of Casco Bay. Outside, a private patio and manageable yard provide the perfect setting for relaxing or entertaining after a day at the beach, and a storage shed offers convenient space for bikes, paddleboards, and beach gear. Whether you're seeking a year-round residence, a seasonal getaway, or simply a chance to live in one of Southern Maine's most beloved coastal neighborhoods, this turnkey home delivers an exceptional lifestyle just moments from the shoreline.

44 Myrtle Ave, South Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

Selling Office: Keller Williams Realty.

$947,935

Phase II now open for reservations for a 2025 Occupancy. New Construction! Take it all in from a stunning vantage point within The Enclave at South Portland. These exclusive 55+ craftsman-designed homes are sited on 18+ wonderfully designed landscaped acres. This community of just 17 twin villas consisting of 34 homes offers 2 incredible floor plans. Unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The Coolidge, single-level living, and the Essex, two-level living, both with the primary ensuite bedroom on the 1st floor. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a huge tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), solar ready & pre-wiring for two EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model in October; We can't wait to show it off to you! Photos shown are a facsimile of a prior community in MA.

2 Beds ⋅ 3 Baths

Phase II now open for reservations for a 2025 Occupancy. New Construction! Take it all in from a stunning vantage point within The Enclave at South Portland. These exclusive 55+ craftsman-designed homes are sited on 18+ wonderfully designed landscaped acres. This community of just 17 twin villas consisting of 34 homes offers 2 incredible floor plans. Unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The Coolidge, single-level living, and the Essex, two-level living, both with the primary ensuite bedroom on the 1st floor. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a huge tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), solar ready & pre-wiring for two EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model in October; We can't wait to show it off to you! Photos shown are a facsimile of a prior community in MA.

4 Puffin Ln Unit 13, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Coldwell Banker Realty.

$945,211

Beautiful 55 Plus Community. Fully Furnished model available to be seen

2 Beds ⋅ 3 Baths

Beautiful 55 Plus Community. Fully Furnished model available to be seen

2 Puffin Way Unit 14, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Portside Real Estate Group.

$937,026

Phase III Open - Only 4 single level & 6 2-storny w/primary on 1st floor available. New Construction! This 55plus community are craftsman-designed homes sited on 18+ designed landscaped acres. This community has17 twin villas consisting of 34 homes offering unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a zero clearance tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), & pre-wiring for EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are our upgraded Model Home. GPS. 761 Main Street South Portland ME behind King Wood Condominiums.

2 Beds ⋅ 3 Baths

Phase III Open - Only 4 single level & 6 2-storny w/primary on 1st floor available. New Construction! This 55plus community are craftsman-designed homes sited on 18+ designed landscaped acres. This community has17 twin villas consisting of 34 homes offering unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a zero clearance tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), & pre-wiring for EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are our upgraded Model Home. GPS. 761 Main Street South Portland ME behind King Wood Condominiums.

24 Plover Way Unit 34, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Coldwell Banker Realty.

$935,000

Privacy, character and convenience are the touchstones of this custom built 4 BR/2.5 bath home on 1.1 acres less than 10 minutes to the Old Port. Situated on a quiet cul-de-sac in one of South Portland's premier neighborhoods. Spacious light filled living areas greet you and the well-designed circular floor plan offer flexibility and living at its upmost comfort. Come see the large eat-in kitchen with a new butcher block topped island. The antique restored wood beams offer a special grandness while the newly installed pellet stove instantly warms the kitchen during those chilly Maine evenings. Check out the amazing great room with its soaring ceilings and oversized windows. Again the antique wood beams make their stately appearance! This room is centered with a magnificent double sided fieldstone fireplace. The family room boasts gleaming hardwood floors, the second side of the double sided fireplace, beautiful built-ins and a slider which you can exit to the expansive cedar deck overlooking the lush yard and bubbling brook. The formal dining room is perfect for family holiday meals. An updated 1/2 bath and beautiful laundry room round out the first floor of this home. Upstairs the discerning buyer will find 4 large sized bedrooms. The primary suite features a cork floor, with a walk-in closet. Enjoy the spa-like primary bath featuring two sinks, a separate shower, soaking tub and abundant natural light. Downstairs, the finished walk out basement features a home office/gym/workout space, in addition to a workshop area. This property is close to the back entrance of Hinckley Park and the new Petrlik Conservation Area. This one-of-a-kind property boasts an extra large yard, mature perennials, Level 2 EV charger and a freshly painted interior and exterior. Open Houses Saturday 9/19 1-3pm and Sunday 9/20 1-3pm.

4 Beds ⋅ 3 Baths

Privacy, character and convenience are the touchstones of this custom built 4 BR/2.5 bath home on 1.1 acres less than 10 minutes to the Old Port. Situated on a quiet cul-de-sac in one of South Portland's premier neighborhoods. Spacious light filled living areas greet you and the well-designed circular floor plan offer flexibility and living at its upmost comfort. Come see the large eat-in kitchen with a new butcher block topped island. The antique restored wood beams offer a special grandness while the newly installed pellet stove instantly warms the kitchen during those chilly Maine evenings. Check out the amazing great room with its soaring ceilings and oversized windows. Again the antique wood beams make their stately appearance! This room is centered with a magnificent double sided fieldstone fireplace. The family room boasts gleaming hardwood floors, the second side of the double sided fireplace, beautiful built-ins and a slider which you can exit to the expansive cedar deck overlooking the lush yard and bubbling brook. The formal dining room is perfect for family holiday meals. An updated 1/2 bath and beautiful laundry room round out the first floor of this home. Upstairs the discerning buyer will find 4 large sized bedrooms. The primary suite features a cork floor, with a walk-in closet. Enjoy the spa-like primary bath featuring two sinks, a separate shower, soaking tub and abundant natural light. Downstairs, the finished walk out basement features a home office/gym/workout space, in addition to a workshop area. This property is close to the back entrance of Hinckley Park and the new Petrlik Conservation Area. This one-of-a-kind property boasts an extra large yard, mature perennials, Level 2 EV charger and a freshly painted interior and exterior. Open Houses Saturday 9/19 1-3pm and Sunday 9/20 1-3pm.

55 Higgins Ln, South Portland

Listing courtesy of RE/MAX Shoreline.

Selling Office: Signature Homes Real Estate Group, LLC.

$934,032

2 Beds ⋅ 3 Baths

22 Plover Way Unit 33, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Coldwell Banker Realty.

$925,000

There are houses with plenty of square footage, and then there are homes that truly give everyone room to live. Welcome to 13 Crestview Drive. Set on over half an acre in a lovely neighborhood, this beautifully maintained and beautifully updated Colonial offers the kind of space that's difficult to find. Multiple living areas create room to gather when you want to be together and space to spread out when you don't. Whether it's holiday dinners, movie nights, homework around the kitchen table, hosting overnight guests, working from home, or finally having that dedicated playroom, home gym, or hobby space you've always wanted, the flexible layout adapts effortlessly to the rhythms of everyday life. Thoughtful updates, pride of ownership, and timeless design make this a home you can simply move into and enjoy from day one. A third-floor bonus room adds even more versatility, while the walkout basement presents opportunities to expand, entertain, or create additional living space as your needs evolve. Outside, the generous yard offers plenty of room to relax, garden, play, or entertain, all surrounded by a neighborhood where evening walks, bike rides, and kind waves from neighbors feel like part of the daily routine. The location is equally compelling. In the sought-after Grandview neighborhood, you're just minutes from schools, parks, the South Portland Community Center, shopping, restaurants, beaches, and the vibrant waterfronts of both South Portland and downtown Portland. It is a setting that strikes a rare balance between peaceful residential living and exceptional convenience. Some homes simply check the boxes. Others become the backdrop for life's biggest moments. 13 Crestview Drive offers the space, flexibility, and location to be exactly that.

4 Beds ⋅ 3 Baths

There are houses with plenty of square footage, and then there are homes that truly give everyone room to live. Welcome to 13 Crestview Drive. Set on over half an acre in a lovely neighborhood, this beautifully maintained and beautifully updated Colonial offers the kind of space that's difficult to find. Multiple living areas create room to gather when you want to be together and space to spread out when you don't. Whether it's holiday dinners, movie nights, homework around the kitchen table, hosting overnight guests, working from home, or finally having that dedicated playroom, home gym, or hobby space you've always wanted, the flexible layout adapts effortlessly to the rhythms of everyday life. Thoughtful updates, pride of ownership, and timeless design make this a home you can simply move into and enjoy from day one. A third-floor bonus room adds even more versatility, while the walkout basement presents opportunities to expand, entertain, or create additional living space as your needs evolve. Outside, the generous yard offers plenty of room to relax, garden, play, or entertain, all surrounded by a neighborhood where evening walks, bike rides, and kind waves from neighbors feel like part of the daily routine. The location is equally compelling. In the sought-after Grandview neighborhood, you're just minutes from schools, parks, the South Portland Community Center, shopping, restaurants, beaches, and the vibrant waterfronts of both South Portland and downtown Portland. It is a setting that strikes a rare balance between peaceful residential living and exceptional convenience. Some homes simply check the boxes. Others become the backdrop for life's biggest moments. 13 Crestview Drive offers the space, flexibility, and location to be exactly that.

13 Crestview Dr, South Portland

Listing courtesy of Waypoint Brokers Collective.

Selling Office: Landing Real Estate.

$910,000

Set on .85 acres in one of South Portland's few elevated neighborhoods, this spacious Colonial offers a surprising amount of room to live, work, and gather. The main floor welcomes you with an easy, open layout featuring wood floors, a bright living area, and a refreshed kitchen with new appliances. A first-floor half bath and dedicated laundry room add everyday convenience. Upstairs, you'll find five bedrooms and three full baths, including two well-separated primary suites. One suite features a spiral staircase to a loft--perfect for reading, working, or relaxing. The oversized bedroom above the garage sits on the third floor, offering privacy and versatility. Custom built-ins, abundant natural light, and thoughtful room separation add character and practicality throughout. The full basement includes a finished full bath, while a 12-zone irrigation system keeps the grounds beautifully maintained. Ideally located near the Wainwright Field Complex and the Greenbelt, this home combines generous square footage, an adaptable layout, and prime access to recreation--making it a rare opportunity in South Portland. Open House Saturday 12/13 & Sunday 12/14 11am-1pm

5 Beds ⋅ 5 Baths

Set on .85 acres in one of South Portland's few elevated neighborhoods, this spacious Colonial offers a surprising amount of room to live, work, and gather. The main floor welcomes you with an easy, open layout featuring wood floors, a bright living area, and a refreshed kitchen with new appliances. A first-floor half bath and dedicated laundry room add everyday convenience. Upstairs, you'll find five bedrooms and three full baths, including two well-separated primary suites. One suite features a spiral staircase to a loft--perfect for reading, working, or relaxing. The oversized bedroom above the garage sits on the third floor, offering privacy and versatility. Custom built-ins, abundant natural light, and thoughtful room separation add character and practicality throughout. The full basement includes a finished full bath, while a 12-zone irrigation system keeps the grounds beautifully maintained. Ideally located near the Wainwright Field Complex and the Greenbelt, this home combines generous square footage, an adaptable layout, and prime access to recreation--making it a rare opportunity in South Portland. Open House Saturday 12/13 & Sunday 12/14 11am-1pm

96 Crestview Dr, South Portland

Listing courtesy of Duston Leddy Real Estate.

Selling Office: Duston Leddy Real Estate.

$905,000

Built in 2021 and thoughtfully designed for modern living, this beautifully appointed three-bedroom, two-and-a-half-bath home offers the ease and privacy of a single-family home just moments from Willard Beach. The light-filled, open-concept main level features hardwood floors and a stylish kitchen with quartz countertops, stainless steel appliances, gas range, two-tone cabinetry and generous storage. A gas fireplace with tiled surround anchors the living room, while sliding glass doors open to a spacious deck and fenced backyard - ideal for entertaining and summer evenings. A first-floor bedroom provides added flexibility. Upstairs, the primary suite features a beautifully tiled walk-in shower and double vanity, while an additional bedroom enjoys its own bath. Convenient second-floor laundry completes the upper level. The recently finished lower level adds valuable living space with a second fireplace, perfect for a family room, home office or fitness area. Less than half a mile from Willard Beach, this stand-alone condominium has no association fee and offers an exceptional combination of newer construction, low-maintenance living and one of South Portland's most desirable coastal locations.

3 Beds ⋅ 3 Baths

Built in 2021 and thoughtfully designed for modern living, this beautifully appointed three-bedroom, two-and-a-half-bath home offers the ease and privacy of a single-family home just moments from Willard Beach. The light-filled, open-concept main level features hardwood floors and a stylish kitchen with quartz countertops, stainless steel appliances, gas range, two-tone cabinetry and generous storage. A gas fireplace with tiled surround anchors the living room, while sliding glass doors open to a spacious deck and fenced backyard - ideal for entertaining and summer evenings. A first-floor bedroom provides added flexibility. Upstairs, the primary suite features a beautifully tiled walk-in shower and double vanity, while an additional bedroom enjoys its own bath. Convenient second-floor laundry completes the upper level. The recently finished lower level adds valuable living space with a second fireplace, perfect for a family room, home office or fitness area. Less than half a mile from Willard Beach, this stand-alone condominium has no association fee and offers an exceptional combination of newer construction, low-maintenance living and one of South Portland's most desirable coastal locations.

43 Smith St, South Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

Selling Office: King + Miller Real Estate.

$902,000

Open House Sunday, July 26th, from 12-2. Come home to your beautifully customized 4 bedroom, 2 bath Colonial situated in the heart of vibrant South Portland. Enjoy the warmth and comfort of radiant heat and a cozy gas fireplace. The kitchen features granite counters, quality custom cabinetry, a large walk in pantry, and tile flooring. The first floor bedroom is presently utilized as a convenient office space, and sits adjacent to a full bath with laundry. The living room is lifted with a beautiful cathedral ceiling, abundant natural light, and a door leading to a spacious, newly re-built deck overlooking the backyard. The second floor includes a generous bedroom over the garage, with a private deck offering lovely views of the Portland skyline. The space presents excellent potential for a future ensuite. Two additional bedrooms and a second full bath complete the spacious upper level. A newly finished basement room adds valuable living space with durable vinyl plank flooring, ideal for play, hobbies, or a home theater. An additional basement area offers even more flexibility with plenty of room for a workshop or extra storage. The expansive backyard includes an oversized shed, and the home is further complemented by an attached heated two car garage. Located minutes from Mill Creek, multiple beaches, parks, restaurants, and downtown Portland, this spacious home offers exceptional convenience and charm. Take that next step to come home and schedule a tour of this must-see property today.

4 Beds ⋅ 2 Baths

Open House Sunday, July 26th, from 12-2. Come home to your beautifully customized 4 bedroom, 2 bath Colonial situated in the heart of vibrant South Portland. Enjoy the warmth and comfort of radiant heat and a cozy gas fireplace. The kitchen features granite counters, quality custom cabinetry, a large walk in pantry, and tile flooring. The first floor bedroom is presently utilized as a convenient office space, and sits adjacent to a full bath with laundry. The living room is lifted with a beautiful cathedral ceiling, abundant natural light, and a door leading to a spacious, newly re-built deck overlooking the backyard. The second floor includes a generous bedroom over the garage, with a private deck offering lovely views of the Portland skyline. The space presents excellent potential for a future ensuite. Two additional bedrooms and a second full bath complete the spacious upper level. A newly finished basement room adds valuable living space with durable vinyl plank flooring, ideal for play, hobbies, or a home theater. An additional basement area offers even more flexibility with plenty of room for a workshop or extra storage. The expansive backyard includes an oversized shed, and the home is further complemented by an attached heated two car garage. Located minutes from Mill Creek, multiple beaches, parks, restaurants, and downtown Portland, this spacious home offers exceptional convenience and charm. Take that next step to come home and schedule a tour of this must-see property today.

101 Parrott St, South Portland

Listing courtesy of EXP Realty.

Selling Office: Cates Real Estate.

$895,000

Set in an established neighborhood on nearly half an acre, 167 Pilgrim Road offers space and flexibility for easy, everyday living. Inside, a functional layout welcomes you with a generous mudroom and first-floor laundry to keep life organized—perfect after beach days or time outdoors. The kitchen opens to a living room anchored by a fireplace and built-ins, creating a warm central gathering space. A formal dining room is ready for holidays and hosting, while a flexible den works beautifully as a home office, playroom, or quiet retreat. A three-season room wrapped in windows overlooks the backyard and seamlessly connects indoor and outdoor living. In warmer months, step out to the spacious patio, greenhouse, and established gardens—thoughtfully designed for growing, gathering, and enjoying the seasons. Upstairs, the primary suite enjoys backyard views, ample closet space, and a full bath. Three additional bedrooms, another full bath, and convenient storage complete the second level. A full basement offers even more room to expand. A standout feature is the 4+ car garage with an unfinished second floor—a rare opportunity for hobbyists, outdoor enthusiasts, or anyone seeking exceptional storage and creative space. At 167 Pilgrim Road, you'll find room to breathe while remaining close to the coast, local markets, beaches, and all that makes South Portland such a treasured Maine community.

4 Beds ⋅ 3 Baths

Set in an established neighborhood on nearly half an acre, 167 Pilgrim Road offers space and flexibility for easy, everyday living. Inside, a functional layout welcomes you with a generous mudroom and first-floor laundry to keep life organized—perfect after beach days or time outdoors. The kitchen opens to a living room anchored by a fireplace and built-ins, creating a warm central gathering space. A formal dining room is ready for holidays and hosting, while a flexible den works beautifully as a home office, playroom, or quiet retreat. A three-season room wrapped in windows overlooks the backyard and seamlessly connects indoor and outdoor living. In warmer months, step out to the spacious patio, greenhouse, and established gardens—thoughtfully designed for growing, gathering, and enjoying the seasons. Upstairs, the primary suite enjoys backyard views, ample closet space, and a full bath. Three additional bedrooms, another full bath, and convenient storage complete the second level. A full basement offers even more room to expand. A standout feature is the 4+ car garage with an unfinished second floor—a rare opportunity for hobbyists, outdoor enthusiasts, or anyone seeking exceptional storage and creative space. At 167 Pilgrim Road, you'll find room to breathe while remaining close to the coast, local markets, beaches, and all that makes South Portland such a treasured Maine community.

167 Pilgrim Rd, South Portland

Listing courtesy of Portside Real Estate Group.

Selling Office: Blue Lobster Real Estate.

$891,429

New 55 Plus Community! New Construction! Take it all in from a stunning vantage point within The Enclave at South Portland. These exclusive 55+ craftsman-designed homes are sited on 18+ wonderfully designed landscaped acres. This community of just 17 twin villas consisting of 34 homes offers 2 incredible floor plans. Unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The Coolidge, single-level living, and the Essex, two-level living, both with the primary ensuite bedroom on the 1st floor. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a huge tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), solar ready & pre-wiring for two EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are a facsimile. GPS. 757 Main Street South Portland ME behind King Wood Condominiums.

2 Beds ⋅ 3 Baths

New 55 Plus Community! New Construction! Take it all in from a stunning vantage point within The Enclave at South Portland. These exclusive 55+ craftsman-designed homes are sited on 18+ wonderfully designed landscaped acres. This community of just 17 twin villas consisting of 34 homes offers 2 incredible floor plans. Unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The Coolidge, single-level living, and the Essex, two-level living, both with the primary ensuite bedroom on the 1st floor. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a huge tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), solar ready & pre-wiring for two EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are a facsimile. GPS. 757 Main Street South Portland ME behind King Wood Condominiums.

17 Plover Way Unit 27, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Keller Williams Realty.

$880,000

Welcome to this newly built residence in the coveted Meeting House Hill neighborhood, just a short walk to Willard Beach and a quick drive to area favorites including Two Lights, Robinson Woods, Kettle Cove, and Higgins Beach. Here, timeless craftsmanship, high-performance design, & coastal living come together w/ ease. Set on a corner lot, this sun-filled home offers thoughtful design and strong energy performance, with solar panels, triple-pane windows, advanced insulation, and a three-zone heat pump for year-round comfort. Built by a team with more than 25 years of experience in high-efficiency and Net Zero homes, it is designed to produce more energy than it uses--helping lower electricity costs year-round. Inside, nine-foot ceilings and an open-concept layout create an airy, light-filled setting suited to daily living and entertaining. The kitchen features custom soft-close cabinetry, a generous pantry, granite countertops, tile backsplash, farmhouse sink, and stainless-steel appliances--including a bottom-freezer refrigerator, gas range with ventilation hood, dishwasher, and microwave--centered around an oversized island. The primary suite includes a custom-tiled glass shower, double vanity with granite countertops, and walk-in closet. Two additional bedrooms with ceiling fans, a full bath, and a conveniently located second-floor laundry room complete the upper level. The finished lower level adds flexible living space, with an expansive tiled room, a Hearthstone soapstone wood stove, and a full bath--well suited for guests, recreation, or a home office. Outdoors, a private mahogany deck offers a welcoming setting for quiet mornings or easy entertaining. Additional highlights include a spacious single-car garage equipped with a built-in Level 2 EV charger. Back on the market due to a change in personal circumstances, the seller is prepared to move forward, creating a meaningful opportunity for the next buyer.

3 Beds ⋅ 4 Baths

Welcome to this newly built residence in the coveted Meeting House Hill neighborhood, just a short walk to Willard Beach and a quick drive to area favorites including Two Lights, Robinson Woods, Kettle Cove, and Higgins Beach. Here, timeless craftsmanship, high-performance design, & coastal living come together w/ ease. Set on a corner lot, this sun-filled home offers thoughtful design and strong energy performance, with solar panels, triple-pane windows, advanced insulation, and a three-zone heat pump for year-round comfort. Built by a team with more than 25 years of experience in high-efficiency and Net Zero homes, it is designed to produce more energy than it uses--helping lower electricity costs year-round. Inside, nine-foot ceilings and an open-concept layout create an airy, light-filled setting suited to daily living and entertaining. The kitchen features custom soft-close cabinetry, a generous pantry, granite countertops, tile backsplash, farmhouse sink, and stainless-steel appliances--including a bottom-freezer refrigerator, gas range with ventilation hood, dishwasher, and microwave--centered around an oversized island. The primary suite includes a custom-tiled glass shower, double vanity with granite countertops, and walk-in closet. Two additional bedrooms with ceiling fans, a full bath, and a conveniently located second-floor laundry room complete the upper level. The finished lower level adds flexible living space, with an expansive tiled room, a Hearthstone soapstone wood stove, and a full bath--well suited for guests, recreation, or a home office. Outdoors, a private mahogany deck offers a welcoming setting for quiet mornings or easy entertaining. Additional highlights include a spacious single-car garage equipped with a built-in Level 2 EV charger. Back on the market due to a change in personal circumstances, the seller is prepared to move forward, creating a meaningful opportunity for the next buyer.

77 Oneil St, South Portland

Listing courtesy of Cottage & Co Real Estate.

Selling Office: Portside Real Estate Group.

$878,487

New 55 Plus Community! New Construction! Take it all in from a stunning vantage point within The Enclave at South Portland. These exclusive 55+ craftsman-designed homes are sited on 18+ wonderfully designed landscaped acres. This community of just 17 twin villas consisting of 34 homes offers 2 incredible floor plans. Unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The Coolidge, single-level living, and the Essex, two-level living, both with the primary ensuite bedroom on the 1st floor. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a huge tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), solar ready & pre-wiring for two EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are a facsimile. GPS. 757 Main Street South Portland ME behind King Wood Condominiums.

2 Beds ⋅ 3 Baths

New 55 Plus Community! New Construction! Take it all in from a stunning vantage point within The Enclave at South Portland. These exclusive 55+ craftsman-designed homes are sited on 18+ wonderfully designed landscaped acres. This community of just 17 twin villas consisting of 34 homes offers 2 incredible floor plans. Unmatched quality details & craftsmanship with exceptional HERS & Energy Star features. The Coolidge, single-level living, and the Essex, two-level living, both with the primary ensuite bedroom on the 1st floor. The showstopper - Primary Ensuite will make you feel like your home is truly a staycation suite featuring an ensuite bathroom with a huge tiled shower and an immense walk-in closet. The home is filled with abundant light, 10' ceilings with large transom windows, hardwood flooring, and the highest quality woodwork. The driveway surfaces are stone pavers that show quality before entering the home. Allow your gatherings to overflow onto your well-landscaped patio area, connecting to nature & outdoor entertaining. Allowances for appliances and lighting are available. Energy Recovery Ventilation (ERV), solar ready & pre-wiring for two EV cars are just some of the energy efficiencies built into these homes. With the unique opportunity to select from various options and customization, you can create a new home that perfectly reflects your taste and style in this sought-after location close to shopping and dining and an overabundance of world-class recreation. Right here in the area you love. The community has a public gardening feature exclusively for homeowners. Furnished model to come soon; we can't wait to show it off to you! Photos shown are a facsimile. GPS. 757 Main Street South Portland ME behind King Wood Condominiums.

21 Plover Way Unit 34, South Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Keller Williams Realty.

How much is your home worth?

How much is your home worth?