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$485,000
2 Beds ⋅ 1 Baths
Sun-filled and picture-perfect, welcome to 164 Pearl Street! This second-floor condo in the heart of Portland oozes charm at every turn. Just steps from the Old Port, East Bayside and city hotspots, this thoughtfully updated unit boasts a Walk Score of 99 and features a nearly-new bathroom with radiant floor heating, modernized systems, in-unit laundry and dedicated storage. Enjoy summer dinners on your private balcony and cozy winter evenings by the gas fireplace. The building has been extensively renovated in recent years. With so much out your front door you may never need a car, though a leased parking space around the corner is available to the new owner if desired.

164 Pearl St Unit B, Portland

Listing courtesy of Portside Real Estate Group.

$2,100,000
2 Beds ⋅ 1 Baths
A truly rare offering on Great Diamond Island, 218 West Shore Drive is a year-round waterfront property where Maine island living, extraordinary history, and unforgettable sunset views converge. Part of historic Fort McKinley, a coastal defense installation constructed between 1890 and 1910 to protect Portland Harbor, the property occupies a commanding waterfront position with sweeping views toward the Portland skyline. Set on almost 3 acres with 266 feet of water frontage, it offers a meaningful connection to both the island's storied past and the surrounding seascape. The charming cottage is attached to an original mining casemate and features an inviting living area opening to a waterside patio, two bedrooms, and one bath, with the primary bedroom located within the original casemate. Additional historic structures include a renovated second bunker, currently used as a den/office and a workshop with potential for a third bedroom, as well as a rangefinder station and gun battery. Tucked along a private cove with beautiful westerly sunset views, this one-of-a-kind property offers privacy, character, and a remarkable connection to the sea. As part of the Diamond Cove Association, residents enjoy amenities including a pool, tennis and pickleball courts, a bowling alley, and a basketball court. Accessible by ferry or private boat, Great Diamond Island also offers a marina, an inn, and restaurants, creating an exceptional opportunity for year-round island living just minutes from Portland.

218 W Shore Dr, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$1,190,000
2 Beds ⋅ 3 Baths
Experience one of Portland's most coveted waterfront settings at Chandler's Wharf, where the energy of the Old Port meets the beauty of Casco Bay. Meticulously renovated throughout, this exceptional townhouse offers 2 bedrooms, 2 full bathrooms, and a half bath. The custom kitchen features Calacatta marble countertops, bespoke oak cabinetry and paneling, and a curated collection of premium appliances including a Wolf gas range, Sub-Zero refrigerator, and Miele dishwasher. The living room, centered around an Ortal gas fireplace, opens to a private deck overlooking the harbor, where boats and Portland's iconic working waterfront create an ever-changing view. Upstairs, the primary suite offers a beautifully appointed bath with heated floors, including a heated shower floor. A versatile loft provides space for a home office, media room, fitness area, or guest accommodations. Exceptional custom millwork and thoughtful craftsmanship are evident throughout, while two covered garage parking spaces provide a level of convenience rarely found in the Old Port. Opportunities to enjoy true waterfront living just steps from Portland's acclaimed restaurants, boutiques, galleries, and marinas are exceptionally rare.

512 Chandlers Wharf, Unit 512, Portland

Listing courtesy of RE/MAX By The Bay.

$959,000
3 Beds ⋅ 3 Baths
Nestled in one of Portland's most sought-after neighborhoods, this beautifully maintained home offers the perfect balance of privacy, convenience, and access to the outdoors. Ideally located just one mile from the Northeastern University Roux Institute and minutes from downtown Portland and Falmouth, the neighborhood features more than 10 acres of HOA common land with scenic walking trails connecting directly to Quarry Run Dog Park. Offering 2,765± square feet of finished living space, the home's gently sloping lot fills the finished lower level with abundant natural light, creating bright, welcoming spaces that feel connected to the outdoors. Radiant heated floors throughout the home--including the lower level and garage--provide exceptional comfort in every season. Inside, wood floors extend throughout the home, while the spacious primary suite features a walk-in closet and a beautifully renovated en-suite bath (2023). Lovingly maintained by only its second owner, the home reflects years of meticulous care. A newer roof, installed in 2021, adds lasting value and peace of mind. The private backyard is a true sanctuary, featuring mature perennial gardens, raised vegetable beds, an irrigation system, and an invisible fence for dogs. Whether you're gardening, entertaining, or simply unwinding, the peaceful setting offers exceptional privacy. *Some listing photos have been virtually enhanced to illustrate the home's potential. Enhancements include digital furniture removal and virtual furnishings.

132 Pheasant Hill Dr, Portland

Listing courtesy of Portside Real Estate Group.

$789,500
3 Beds ⋅ 2 Baths
Location, location, location! This Deering Center home preserves its classic charm with original mouldings and wood flooring throughout. Upon entry, you are greeted by a center hall featuring a grand staircase. The first floor includes two living rooms, a formal dining room, an updated kitchen, a sunporch, and a full bath. The rear living room opens onto a private garden with a spacious patio, and the home includes both front and rear staircases. The second floor provides three generous bedrooms and a large bathroom, while the third-floor bonus room offers an ideal, quiet space for an office. Perfectly situated, this property is just minutes from shopping, downtown Portland, the Portland International Jetport, and local neighborhood restaurants and boutiques. There is a full basement and 1 car garage.

74 Lawn Ave, Portland

Listing courtesy of Keller Williams Realty.

$610,000
2 Beds ⋅ 2 Baths
Exceptional value on Munjoy Hill with this bright, well maintained two bedroom, two bath condo offering sweeping views of Casco Bay and effortless Portland living. Conveniently located on the first floor offering an open floor plan with hardwood and tile flooring, generous in unit storage, and a private primary suite. Located in the secure, elevator and ramp accessible Portland House, residents benefit from heated garage parking, concierge services, onsite gym, community room with lending library, and a beautifully kept outdoor patio with seating overlooking the bay. Most utilities included in HOA fee, including heat, hot water, water/sewer, cable and internet, making ownership simple and predictable. Just steps from the Eastern Promenade, you'll have immediate access to over 70 acres of green space, the Eastern Prom Trail, Fort Allen Park, tennis and pickleball courts, East End Beach, food trucks, and Portland's iconic waterfront. The building's lobby and community spaces have been recently renovated creating a welcoming feel. Residents also enjoy access to the rooftop 'Red Carpet' area for spectacular views of fireworks, cruise ships, and the harbor. A rare opportunity to enjoy convenience, amenities, and one of Portland's most coveted locations.

45 Eastern Promenade Unit 1C, Portland

Listing courtesy of Portside Real Estate Group.

$899,000
3 Beds ⋅ 2 Baths
Some homes provide a place to stay. Others become the place everyone wants to gather. Perched on the cherished north end of Peaks Island, just moments from the shoreline of Casco Bay, 45 Centennial Street is one of those rare places where the pace slows, memories are made and every season brings something worth looking forward to. Mornings begin with coffee on the second-floor balcony as the sun rises over the bay. Days are spent exploring the water or wandering quiet island roads. Evenings end beneath brilliant stars, the harbor replacing the noise of everyday life. Originally built in 1900 and thoughtfully updated, this year-round New Englander blends historic charm with contemporary comfort. Rich wood floors, a granite kitchen, open living and dining spaces, inviting bedrooms including a classic bunkroom, an updated bath and efficient heat pumps create a home that is as comfortable in January as it is during the height of summer. Outside, a workshop shed opens up possibilities for artists, makers, remote work, storage or weekend projects. Mooring opportunities are available by application through the Portland Harbormaster, while nearby kayaking, boating and fishing make the water an extension of your backyard. Minutes bring you to the ferry, local cafés, lobster rolls, tennis courts, live music and the welcoming village that has made Peaks Island one of Maine's most treasured communities. Offered fully furnished, 45 Centennial Street isn't simply move-in ready, it's ready to be lived in from the moment you arrive. Whether you're searching for a year-round home, a seasonal retreat or a gathering place for the people who matter most, see what island living feels like from the inside.

45 Centennial St, Portland

Listing courtesy of Portside Real Estate Group.

$525,000
2 Beds ⋅ 2 Baths
Welcome home to this inviting two-bedroom, 1.5-bath condo that perfectly blends character, convenience, and city living. Nestled in an intimate three-unit association, this condo combines the warmth and charm of a classic Portland property while placing you just a short walk from the award-winning restaurants, breweries, boutiques, and waterfront that make downtown Portland one of New England's most sought-after destinations. Sunlight fills the spacious interior, highlighting beautiful hardwood floors, oversized windows, and versatile living spaces that can accommodate everything from a home office to a fitness area or creative studio. The generously sized kitchen features abundant cabinetry, a large pantry, and plenty of room to prepare meals and gather with family and friends. A dedicated parking space eliminates the hassle of city parking, while the secure basement storage provides the perfect place for bicycles, seasonal items, and outdoor gear. Whether you're searching for your first home, a low-maintenance city residence, or an investment in one of Maine's most desirable locations, this condo combines location, lifestyle, and value in one exceptional package. Walking distance to downtown Portland, USM, Back Cove, Sea Dogs Stadium and Portland Expo.

11 William St Unit 1, Portland

Listing courtesy of Keller Williams Realty.

$525,000
2 Beds ⋅ 2 Baths
Welcome to the iconic Portland House Condominiums. Sitting prominently atop of Munjoy Hill it serves as a landmark to Portland's famous Eastern Promenade. From the private balcony, this spacious 2 bedroom, 4th floor unit offers views of Back Cove and Casco Bay in the distance and a close up view of the vibrant activity in one of Portland's most desirable neighborhoods, loved by locals and visitors alike. This unit offers a spacious living/dining area, a primary bedroom with private bath, plus a second bedroom and full guest bath. The efficient galley kitchen works well as is or could be reconfigured to your personal taste. You will also enjoy a staffed front entry desk and added amenities such as heat, hot water, cable, internet, a common outdoor patio with grilling area, a common, beautifully furnished community room and a workout room, all bundled into the monthly HOA fee. Parking is a breeze with garage parking and direct elevator access to the building. Just outside is Eastern Prom Park offering walking trails, a public beach, a playground, tennis courts, food trucks and much more! Here, local residents and visitors assemble for picnics, sports and enjoying the spectacular views and ocean breezes. The very same view you will cherish day in and day out from your own balcony! Nearby restaurants invite you to experience the cuisine of some of North America's best award winning chefs and bakers just minutes from your front door. Don't miss this opportunity to live at one of Portlands most desirable locations!

45 Eastern Promenade Unit 4J, Portland

Listing courtesy of RE/MAX Shoreline.

$699,000
2 Beds ⋅ 2 Baths
If you've been searching for a condo in Portland, you already know opportunities like this are rare. Intentionally priced to generate immediate interest, this represents one of Portland's strongest values. Perfectly positioned at the gateway to the Old Port and the Arts District, 25 High Street boasts an exceptional Walk Score of 94, placing nationally recognized restaurants, cafés, galleries, the working waterfront, shopping, recreation and everyday conveniences just steps from your front door. Perched on the waterside upper level, Unit 410 is filled with natural light and enjoys glimpses of Inner Casco Bay and Portland's iconic working waterfront. Nearly 1,200± SF offers an open-concept design where the beautifully appointed kitchen flows seamlessly into spacious living and dining areas. Two generous bedrooms, two full baths, in-unit laundry and quality finishes throughout deliver the comfort, style and functionality discerning buyers expect. The professionally managed, pet-friendly association welcomes both dogs and cats with no size or breed restrictions and features a fitness center, elevator, secure entry and on-site storage. Even more impressive, the remarkably affordable $395/month condominium fee is roughly half that of many competing Portland condominium communities. Whether you're looking for a full-time residence, a sophisticated in-town retreat or a true lock-and-leave lifestyle, this move-in-ready home delivers exceptional quality, outstanding value and one of Portland's most desirable urban locations. Upper-floor, waterside residences with this combination of location, light, amenities, affordability and value simply don't come along often.

25 High St Unit 410, Portland

Listing courtesy of Benchmark Real Estate.

$595,000
1 Beds ⋅ 1 Baths
If you choose to live in Portland, the Eastern Promenade is the place to be! Here is your chance to gaze out of your big bank of windows and see all of the harbor traffic that you can take in. Step into this top floor condominium unit and feel energized by the vaulted ceilings and tons of natural light all day long. This open concept offers an open floor plan perfect for you to set up just exactly how you want to live. The kitchen allows you to eat in and converse with guests while preparing your next meal. Just off the kitchen is your own large private deck with ocean views, perfect for entertaining. The bedroom is extra-large with sky lights, and the beautiful full bath includes a smartly tiled shower. There is in unit laundry as well as one dedicated parking space that comes with this unit along with basement storage. Just across the street, enjoy 66 acres of gentle sloping grass to enjoy the panoramic Casco Bay Views. The East End Beach is nearby and so is Portland's Old Port where you can experience the best cuisine, coffee shops, galleries and so much more!

38 Eastern Promenade Unit C, Portland

Listing courtesy of Gardner Real Estate Group.

$1,990,000
4 Beds ⋅ 4 Baths
Architecturally striking and newly custom-built, this extraordinary West End residence exemplifies contemporary luxury living on Portland's Peninsula. Designed to maximize sustainability, natural light and year-round comfort, the home features Therma-Steel insulated panels, Marvin windows, Boral cementitious and wood siding, Azek trim, soaring ceilings, translucent polycarbonate elements and a dramatic two-story light shaft that fills the home with natural light. At the heart of the home is a spectacular custom kitchen completed in 2026. Rift-cut oak cabinetry, integrated storage, a statement island, a paneled refrigerator, black granite countertops and backsplash, and premium Thermador appliances- including a newly added natural gas range- create a space that is as functional as it is stunning. Additional enhancements include an appliance garage and dedicated coffee station, a custom floating dining credenza, motorized blinds, and a newly installed washer and dryer. Spanning three thoughtfully designed levels, the residence offers three bedrooms, two and a half baths, and exceptional flexibility. Crowning the home is a sun-drenched winter garden- a top-floor retreat beneath skylights and a translucent roof system capturing natural light and glimpses of Casco Bay. Additionally, the ground level features a studio apartment with custom kitchen, laundry, full bath, private entrance and outdoor space- ideal for rental income, guests, or a home office/creative studio. Rare outdoor living spaces extend the interiors, offering six covered porches and an enclosed backyard. A climate-controlled garage is a rare Peninsula amenity. Perched in Portland's coveted West End, within walking distance of restaurants, the Old Port and the waterfront, this one-of-a-kind residence offers an extraordinary opportunity to own a modern architectural masterpiece in one of Maine's most desirable locations.

5 Salem St, Portland

Listing courtesy of Peninsula Real Estate LLC.

$419,000
1 Beds ⋅ 1 Baths
Portland's West End on a quiet, tree-lined street, this beautifully renovated one-bedroom condo blends historic charm with modern updates. The condo showcases elegant turn-of-the-century architectural details that highlight its timeless character, while thoughtful updates provide comfortable contemporary living. The condo fee covers heat and hot water, supporting low-maintenance, predictable ownership. Deeded 1- off-street parking space, a highly desirable feature in the West End. . Additional conveniences include on-site laundry and a pet-friendly association. Ideal as a first home, investment property, or stylish pied-à-terre, this residence offers exceptional walkability to Portland's acclaimed restaurants, boutique shopping, and waterfront attractions, placing you at the center of peninsula living. Call for viewing today!

138 Pine St Unit 2, Portland

Listing courtesy of Marsden Real Estate.

$645,000
1 Beds ⋅ 2 Baths
Portland, Maine living in the heart of the Old Port, Portland's historic waterfront neighborhood is luxury living at it's best! Portland will keep you active with popular restaurants, boutiques, stores, parks, museums, and everyday amenities just a stones throw away. This super clean and modern single level residence at Hobson's Landing showcases luxury customization and finishes throughout. The open-concept living space features a large living room with a gas fireplace and adjoining private deck. Spend time at the welcoming kitchen with top notch finishes and purposeful design. The bright and cozy 1 bedroom, 1.5 bath condominium includes an ensuite primary bedroom with a walk-in closet and bath with double vanities and radiant heated floors. The Laundry closet, connects the walk in wardrobe closet and the primary bedroom perfectly. deeded garage parking. Added amenities include multiple large outdoor courtyards, a club room with a full kitchen, concierge service, fitness center, dog wash facility and media room!

383 Commercial St Unit 413, Portland

Listing courtesy of Elevate Maine Realty.

$949,900
2 Beds ⋅ 2 Baths
Between Portland's vibrant Old Port and the open waters of the Atlantic lies one of Maine's most beloved island communities. Nestled into the west-facing landscape of Peaks Island, this charming year-round home captures sweeping views of Diamond Passage and Casco Bay, offering a front-row seat to unforgettable sunsets and the rhythms of island life. Filled with natural light, the home's inviting interior features warm wood floors, fresh finishes, and abundant windows framing coastal vistas throughout. The open-concept main level seamlessly connects the spacious kitchen with breakfast bar, dining area, and beam-accented living room, creating an ideal setting for both everyday living and entertaining. Sliding doors open to a generously sized Ipe wood deck, where optional canopy coverage provides comfort for outdoor dining, morning coffee, or evening gatherings overlooking the water. A full bath, coat closet, and welcoming covered front porch complete the first floor. Upstairs, a sun-drenched loft offers exceptional flexibility as a home office, artist's studio, reading nook, guest space, or play area. The primary bedroom occupies the home's distinctive turret, blending unique architectural character with captivating water views. A second bedroom, full bath with skylight and walk-in shower, and convenient laundry area complete the upper level. Outside, the .12-acre lot invites gardening, outdoor entertaining, fireside evenings, and peaceful relaxation. Whether hosting friends, tending flowers, or simply enjoying the sea air, the property offers a wonderful extension of the home's easygoing coastal lifestyle. Just moments from beaches, village shops, quiet island lanes, and the ferry landing, 30 Pleasant Avenue offers the rare opportunity to enjoy year-round island living with comfort, character, and Casco Bay views.

30 Pleasant Ave, Portland

Listing courtesy of Portside Real Estate Group.

$1,395,000
3 Baths
Enjoy seasonal views of Back Cove and the Portland skyline from this rare three-unit property in one of the city's most desirable locations. Step out your door to the Back Cove Trail for morning walks, or enjoy coffee on your deck while taking in the water views. With strong rental income potential, this property offers the ideal opportunity to offset your mortgage while living in a premier setting. The owner-occupant third floor unit is filled with natural light and features 1 bedroom and 1 bathroom with an open kitchen, dining, and living area. Two private decks extend the living space outdoors, including one with views overlooking Back Cove. The second floor spans the entire level and offers exceptional light throughout. It includes a spacious living room, a separate dining room with original built-ins, a large kitchen, two well-sized bedrooms, and an updated bathroom. A private deck completes this inviting unit. The first floor also occupies the full level and features a sun-filled layout with a spacious living room and gas fireplace, a dining room with built-ins, and an updated kitchen with granite countertops and new cabinetry. This unit also enjoys a private deck for outdoor living. The basement provides dedicated storage for each unit along with coin-operated laundry. Additional amenities include parking for up to four vehicles and a rare two-car garage. Numerous updates have been completed in recent years, making this a well-maintained and versatile investment opportunity. A truly special offering on Back Cove that combines location, views, and income potential.

31 Bates St, Portland

Listing courtesy of Vitalius Real Estate Group, LLC.

$775,000
1 Beds ⋅ 2 Baths
Located in Portland's historic Old Port, this sun-filled corner unit at Chandler's Wharf offers sweeping harbor and city views with eastern, southern, and western exposures. The one-bedroom, 1.5-bath residence has been thoughtfully updated with a remodeled kitchen and baths, new windows, a heating and cooling mini-split system, and new appliances. Enjoy the private deck overlooking the waterfront - an ideal spot to relax and take in the scenery. Property includes garage parking for owner and guest, and is located in a gated community. Experience a walkable urban lifestyle in the heart of Portland, just steps from the city's vibrant restaurants, shops, and waterfront attractions.

715 Chandlers Wharf, Unit 715, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$822,589
2 Beds ⋅ 2 Baths
Life Re-Imagined! Building 3, Stevens Square at Baxter Woods! This growing new neighborhood is on its way to be one of the most exciting places to live in Portland Maine! Stevens Square represents Portland's first 55+ condominium community adjacent to hundreds of acres of woods and walking trails. Complete with convenient dog washes, crackling fire pits, and available community center with saltwater pool and gym, this 2nd floor south facing unit has it all. Nicely balanced living spaces focused with designer chosen appointments, including ensuite bedrooms, private deck and lots of wonderful light. This unit faces the beautiful and protected Baxter Woods. Enjoy the large gathering room and sky deck at your fingertips. Covered parking and storage also included. A well-rounded life begins at the Square!

75 Mcauley Way Unit 205, Portland

Listing courtesy of Gardner Real Estate Group.

$675,000
3 Beds ⋅ 2 Baths
Welcome to 13 Atlantic Street, Unit 1--with water views and walkable convenience in Portland's vibrant East End. Enjoy breathtaking vistas of Casco Bay from this charming 3 bedroom residence with recent renovations in 2019. It is ideally situated just moments from downtown. Nestled in one of the city's most beloved neighborhoods, this home offers easy access to local cafés, boutiques, the Eastern Promenade, and the waterfront. Whether you're starting your day with sunrise over the bay or strolling to dinner in the Old Port, this location is quintessential Portland living.

13 Atlantic St Unit 1, Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$1,350,000
2 Beds ⋅ 2 Baths
Fabulous lifestyle in the heart of Portland's historic waterfront neighborhood, where residents enjoy a truly walkable lifestyle with acclaimed restaurants, boutiques, museums, and everyday conveniences just steps from home. This stunning sun-drenched corner residence at Hobson's Landing showcases exceptional customization throughout. The open-concept floor plan features a spacious living room with a gas fireplace and adjoining private deck and a beautifully appointed kitchen with premium finishes and thoughtful design. The pristine two-bedroom, two-bath condominium includes an ensuite primary bedroom with a walk-in closet and bath with double vanities and radiant heated floors. Additional highlights include a gracious entry hall, laundry closet, deeded garage parking, and a separate storage space. Residents enjoy an impressive collection of amenities, including expansive outdoor terraces and a club room with a full kitchen, fireplace and deck, as well as a lobby with concierge service, a fitness center, dog wash station, reservable guest suite, work/study space, and access to shared bicycles and a Tesla.

383 Commercial St Unit 300, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$925,000
2 Baths
Deering Highlands Two-Unit: Set on a beautifully landscaped quarter-acre corner lot in Portland's highly desirable Highlands neighborhood, this charming two-unit home offers gorgeous outdoor space, flexible layouts and comes fully vacant for the next owner's personalized use. The first-floor unit offers 2 bedrooms, while the second-floor unit features 3 bedrooms. In addition to large living rooms, both units enjoy their own sun porch, creating bright and inviting spaces to unwind throughout the seasons. The expansive yard features mature landscaping, raised garden beds, and a private patio. The first floor has been recently refreshed; the second floor invites upgrades to suit the buyer's use and aesthetic. A detached two-car garage provides valuable parking and storage, while the unfinished attic presents an exciting opportunity for expansion. Just minutes from local parks, trails, restaurants, and downtown Portland, this is a unique opportunity to own a classic Deering Highlands property.

169 Longfellow St, Portland

Listing courtesy of Vitalius Real Estate Group, LLC.

$769,000
1 Beds ⋅ 1 Baths
Experience waterfront living at its finest in Hobson's Landing, Portland's premier luxury condominium community. This beautifully appointed one-bedroom residence offers sophisticated design, high-end finishes, and effortless single-level living in the heart of the city's vibrant waterfront district. The thoughtfully designed floor plan features an open-concept living space filled with natural light, a chef-inspired kitchen with premium appliances, custom cabinetry, and quartz countertops, and a spacious primary suite with ample storage and a spa-like bath. Floor-to-ceiling windows showcase captivating city and waterfront views while creating a seamless connection between indoor comfort and the beauty of Portland Harbor. Residents of Hobson's Landing enjoy an unparalleled amenity package, including concierge service, fitness center, club room, reservable guest suite, dog wash station, and beautifully landscaped outdoor spaces. Just outside your door, explore Portland's award-winning restaurants, boutiques, marinas, and scenic waterfront trails. Whether you're seeking a year-round residence, a convenient in-town retreat, or a low-maintenance lifestyle, this exceptional home offers luxury, convenience, and the very best of Portland living.

387 Commercial St Unit 432, Portland

Listing courtesy of Waypoint Brokers Collective. ali@waypointbrokers.com
$257,000
Set on an island just three miles off of Portland Maine sits an amazing development and community named Diamond Cove. Dating back to the Spanish American War originally constructed as an army fort, Diamond Cove was reimagined in the 1990's: The barracks, officers' quarters and support staff buildings have been transformed into luxury properties. This resort type community also features a marina, pool, gym, tennis courts an Inn and two restaurants, plus a game room and antique bowling alley and more. There are also 5 different beaches that are for the exclusive use of the residents. The original developer also carved out waterfront and water view private home lots. Lot 7 is the last available lot on Diamond Cove. This water view lot has an impressive western exposure featuring amazing sunsets overlooking Casco Bay looking across to the Foreside and Portland. With a nice open and level building window, this a great opportunity to build your summer or year-round dream home. Diamond Cove is incredibly private and only allows golf carts (no cars or trucks allowed for owners/guests) which makes for a safe and peaceful haven for children and adults alike. A quick 20-minute water taxi or slightly longer ferry ride will you bring to the vibrant dining and shopping hub of Portland's Old Port.

119 W Shore Dr, Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$1,995,000
6 Baths
Perched atop Munjoy Hill, 5 Merrill Street sets the standard for luxury living. Built in 2019, this exceptional two-unit residence offers two townhouse-style, condo-quality homes with contemporary design and designer finishes throughout - a rare find in Portland. Each unit features 1,725 square feet of thoughtfully elevated living space, with 3 bedrooms and 2.5 bathrooms. The designer kitchens are appointed with custom cabinetry, white quartz countertops, Miele appliances, and abundant storage. Throughout both residences, you'll find gorgeous walnut flooring, stunning tile selections, 10-foot ceilings, and distinctive craftsman details. Water views can be enjoyed from two levels, but the true showstopper is the third-floor primary suite, where panoramic views over Casco Bay create an unforgettable retreat, whether enjoyed from inside or from the private rooftop deck. Each unit also includes covered parking and a private patio/yard area, ideal for summer grilling and outdoor entertaining. All this, just moments from Portland's Eastern Promenade, with easy access to acclaimed restaurants, coffee shops, and the very best of Portland.

5 Merrill St, Portland

Listing courtesy of Portside Real Estate Group.

$1,700,000
4 Beds ⋅ 3 Baths
Combining exceptional amenities, an unbeatable location, sophisticated style, and generous living space, 135 Sheridan Street #404 represents a rare offering in Portland's condominium market--a one-of-a-kind residence in the heart of the coveted East End. Created through the seamless combination of two units, this penthouse corner unit offers over 2,300 square feet of thoughtfully designed single-level living. The home features four bedrooms, two full baths, and one half bath, with an open layout that lives even larger thanks to soaring ceilings and sweeping views of the city skyline and Back Cove. South-facing windows flood the interior with natural light year-round, while two private decks extend the living space outdoors, creating a bright, airy atmosphere perfect for everyday living and entertaining. Situated on a quiet residential street, the building is steps from everything that makes Portland's East End one of Maine's most desirable neighborhoods. Acclaimed restaurants, bars, coffee shops, bakeries, breweries, distilleries, music and theater venues, parks, the Eastern Prom, Portland Trails, and the waterfront are all within easy walking distance. Professionally managed and meticulously maintained, the building offers true low-maintenance living. The property includes an unheard-of three deeded parking spaces--two in the attached heated garage and one surface space directly adjacent to the building. Additional features include efficient natural gas heat, central air conditioning, and a gas fireplace. Recent improvements include a renovated primary bathroom with heated tile floors and a curbless walk-in shower and custom built-ins throughout for your library, art, and collectibles. Also includes two large secure storage units to keep your living area clutter free. Offering an extraordinary combination of size, location, views, parking, and amenities, 135 Sheridan Street #404 is a unicorn in Portland's premier East End neighborhood.

135 Sheridan St Unit 404, Portland

Listing courtesy of Real Broker.

$1,400,000
3 Beds ⋅ 2 Baths
Located on a corner lot on coveted Munjoy Hill, 42 Montreal Street is an impeccably renovated, single family house with three bedrooms and two bathrooms. This high quality renovation features copper flashing and downspouts, cedar clapboard siding, a red cedar shingle roof, and a meticulously rebuilt historic cupola. Water views and sweeping vistas of Casco Bay create a stunning backdrop, while the cupola provides a perfect perch for watching summer fireworks over the harbor. Inside, hardwood floors and thoughtfully preserved architectural details blend timeless character with everyday comfort. Outside, a glorious private garden filled with roses and perennial plantings offers exceptional privacy and beauty, creating an extraordinary urban oasis. Multiple outdoor living areas invite entertaining, relaxing, and enjoying Maine's seasons. This absolutely charming mansard-roof cottage enjoys a quiet, private pocket of Portland's East End, just steps from parks, trails, restaurants, shops, and the waterfront. Walk to tennis courts, a boat launch, and a sandy beach, embracing the very best of the East End lifestyle. Beautifully cared for inside and out, this special property offers a rare opportunity to enjoy Portland's vibrant coastal lifestyle from one of Munjoy Hill's most desirable locations.

42 Montreal St, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$735,000
2 Beds ⋅ 1 Baths
Enjoy easy, low maintenance living in Portland's highly desirable Mason Block community. This thoughtfully designed condo offers an efficient and versatile floor plan with an open concept living area with gas fireplace, kitchen with center island, spacious primary bedroom with a customized walk in closet, and a flexible second bedroom that works equally well as a guest room, home office, or den. The private deck extends your living space outdoors, while heat pumps provide efficient heating and air conditioning year round. Building amenities and features include elevator access, covered garage parking, private storage unit, and a beautifully landscaped shared terrace for residents to enjoy. Ideally located in Portland's East End, you'll be just blocks from the waterfront, marinas, restaurants, coffee shops, galleries, museums, and everything downtown Portland has to offer.

62 India St Unit 308, Portland

Listing courtesy of Waypoint Brokers Collective.

$525,000
2 Beds ⋅ 2 Baths
In Portland's coveted East End, this corner unit residence is an invitation to experience a lifestyle shaped by harbor light, historic character, and the energy of one of the city's most cherished neighborhoods. Framed by sweeping views of Casco Bay from nearly every room, this home is filled with an ever-changing coastal backdrop. Just steps from the Eastern Promenade, neighborhood cafes, and nationally recognized restaurants, the location offers a rare blend of waterfront tranquility, exceptional walkability and vibrant city living. Equally suited to a lock-and-leave retreat or full-time residence, this is where the very best of East End living comes together in perfect balance.

45 Eastern Promenade Unit BG, Portland

Listing courtesy of Keller Williams Realty. 207-576-8771
$799,000
2 Beds ⋅ 2 Baths
Welcome to Chandlers Wharf building 7. A stand alone brick building sited on a private pier in the heart of Portlands Old Port. A premiere waterfront lifestyle awaits you with unobstructed views of lobster boats, yachts and harbor tours. Start your day on your covered balcony watching the sunrise with your morning coffee listening to the cry of the ospreys. The residence is a light filled end unit with expansive windows offering illumination throughout the day. This rare first floor one level condominium also has its own private entrance. An open concept kitchen,dining and living area has been updated recently. The kitchen would delight most chefs with high end appliances and a good amount of counter space. It's an easy walk to a few excellent fish markets. The kitchen is open to the dining and living room area And with over 1000 square feet the space feels spacious and functional. Highlights are a master bedroom suite that really feels private. Plenty of storage with deep closets. The guest bedroom has a bathroom from the hall adjacent to the room. Both bathrooms have been renovated with tile and shiplap. Other amenities include laundry in the unit and an ample entry area with an additional pantry closet. The charm of a working waterfront combined with world class restaurants and boutiques, a vibrant art and music scene make this spot very special whether it is your main residence or pied-a-terre

703 Chandlers Wharf, Unit 703, Portland

Listing courtesy of RE/MAX Shoreline.

$1,495,000
3 Beds ⋅ 2 Baths
Buffered by natural beauty and protected land, this remarkable seaside property delights the senses at every turn. The sparkle of the tide, rustle of foliage, salty sea breezes, birdsong, and spectacular sunrises & sunsets create an atmosphere of uncommon tranquility. Set on a generous, sun-drenched lawn just steps from the shore, this 3 BR, 2 BA home blends coastal elegance with timeless cottage architecture. Meticulously maintained, the year-round residence reflects pride of ownership. Water views and natural light grace nearly every room, while quality craftsmanship and tasteful design create spaces that are both beautiful and functional. At the heart of the home, the bright and inviting kitchen encourages effortless gathering. Open to the living and dining areas, it features custom-crafted pantry and buffet cabinetry beneath a vaulted ceiling. A woodstove adds warmth and ambiance on cooler days, while oversized glass sliders frame the picturesque landscape and seamlessly connect the interior to the outdoors. Designed for entertaining and everyday enjoyment alike, the expansive, partially covered deck overlooks the water and extends the living space. Stone patios create inviting destinations for outdoor dining and evening fires by the sea. Whether hosting family & friends or enjoying a quiet moment alone, the setting is simply unforgettable. The primary BR offers a walk-in closet and private balcony w/ outdoor shower overlooking the shoreline. Additional amenities include a 1st flr BR with nearby full BA, a cozy study/artist's nook, 2nd-flr laundry, mud rm. The exterior features high-quality, low-maintenance materials, delightful landscaping, raised garden beds, a charming children's play area complete with sandpit & secret path, and a newly constructed deluxe shed. Enhanced by countless details that elevate it from ordinary to exceptional, this private coastal retreat offers the best of island living. Enjoy easy access to village shops and ferry landing.

17 3rd St, Portland

Listing courtesy of Portside Real Estate Group.

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