South Portland Homes with Trees/Woods View

Welcome to South Portland, Maine—a charming coastal city nestled in Cumberland County, where the beauty of nature meets vibrant urban living. Just across the harbor from Portland, South Portland boasts stunning waterfront views, lush parks, and a friendly community atmosphere that makes it a perfect place to call home.

One of the most enchanting features of South Portland is its homes that offer breathtaking views of trees and wooded landscapes. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These homes provide a serene escape from the hustle and bustle of city life, allowing residents to enjoy the tranquility of their surroundings while still being conveniently located near urban amenities.

South Portland is renowned for its commitment to preserving green spaces, with numerous parks and trails that encourage outdoor activities and exploration. The nearby Greenbelt Walkway offers miles of scenic paths perfect for walking, jogging, or biking, making it easy to immerse yourself in the natural beauty that surrounds you. Whether you’re sipping coffee on your deck while watching the sunrise over the trees or taking a leisurely stroll through one of the many local parks, the connection to nature is an integral part of life in South Portland.

With its blend of vibrant community life, stunning natural beauty, and homes that provide the perfect view of trees and woods, South Portland is truly a gem of Maine. Come and discover the charm of this delightful city, where every day feels like a retreat into nature!

Newest South Portland Homes with Trees/Woods View

$410,000

3 Beds ⋅ 1 Baths

A rare opportunity to own an affordable Colonial offering solid structure and endless potential in one of South Portland's most convenient locations! Maintained by one owner for 39 years, this well-loved home features classic hardwood floors, a bright living room, a formal dining room, and fresh paint throughout. The generous kitchen offers tile flooring, an abundance of cabinetry, and a desk nook. All 3 bedrooms and the full bath are located upstairs.. Outside, enjoy a large, fully fenced backyard with a back deck and mature trees. Sold as-is with no further seller updates, this home provides a solid foundation ready for the next owner to bring their own ideas, make modern improvements, and build instant equity. Minutes to highways, shopping, and dining. Open House Sunday 09-13-2026 from 11am - 12:30pm.

12 Ridgeland Ave, South Portland

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. (207)749-4699

$579,000

3 Beds ⋅ 1 Baths

Tucked into a peaceful South Portland neighborhood just minutes from Knightville, beaches, and downtown Portland, 122 Boothby offers that rare combination of convenience and comfort. Inside, natural light fills the home, where thoughtful updates have created spaces that feel fresh, warm, and easy to live in. The bright and spacious kitchen features under-cabinet lighting, an oversized island, and a functional layout, equally suited to quiet weeknight dinners and evenings gathered with friends. Three bedrooms, custom built-ins, hardwood floors, and a beautifully renovated bathroom are complemented by practical improvements including updated lighting, cordless blinds, an insulated foundation, and an energy-efficient heat pump water heater. Out back, the yard feels like a private retreat, with plenty of space for al fresco dinners, morning coffee, gardening, or just a shady afternoon beneath the trees. Trout Brook trail is just steps away, while South Portland's everyday conveniences are a short drive down the road. Walk, run, or bike through the surrounding neighborhoods, spend the afternoon at the beach, grab dinner or ice cream in South Portland, or cross the bridge into Portland for a night out. Light-filled, thoughtfully updated, and incredibly well situated, 122 Boothby is a home that makes it easy to settle in, and difficult to leave.

122 Boothby Ave, South Portland

Listing courtesy of Locations Real Estate Group LLC.

$495,000

3 Beds ⋅ 3 Baths

Set within a quiet and convenient South Portland neighborhood, this thoughtfully designed condominium offers almost 2,000 square feet of finished living space across four levels. A direct connection to the Greenbelt places miles of trails at your doorstep, while Willard Beach, local shops, restaurants, and the energy of Portland are all within easy reach by bike--including a scenic ride across the bridge to the Old Port. The main level is designed for effortless everyday living and entertaining, with an open arrangement connecting the kitchen, dining, and living spaces. An updated gas fireplace provides a natural focal point, while a sunny deck extends the living space outdoors. A powder room is discreetly positioned near the stairway to the lower level. Two bedrooms, a full bath, and a conveniently located laundry area occupy the second floor. The private primary suite encompasses the entire third level, creating a generous retreat with ample room for a sitting area or exercise space. A well-appointed bath and two oversized walk-in closets complete the suite, offering a comfortable and restorative beginning and end to the day. The finished lower level adds another versatile dimension to the home, equally suited to a media room, home office, playroom, or fitness space. With its flexible floor plan, thoughtful updates, and exceptional access to South Portland's trails, beaches, and Portland amenities, this residence offers a distinctly connected and easygoing coastal lifestyle.

60 Gary L Maietta Pkwy Unit 18, South Portland

Listing courtesy of Keller Williams Realty. 207-650-6176

$635,000

4 Beds ⋅ 2 Baths

Location, Location, Location!!!! Welcome home to this 4 Bedroom/1.5 Bathroom nestled in a peaceful neighborhood with an ideal location. At the heart of the home is a thoughtfully designed kitchen that flows seamlessly into open dining area and cozy sitting space - perfect for everyday living and entertaining. The 1st floor also features a spacious family room with cathedral ceiling and a wood stove creating a warm and welcoming gathering. A convenient half bath and laundry room complete the main level. Upstairs you'll find four bedrooms and full bathroom, offering plenty of space for family, guests, or a home office. The home also offers an exciting opportunity to finish a primary suite with its own bathroom. The plumbing is already in place and ready for your finishing touches. Heat pumps on both 1st and 2nd floor provide efficient heating and cooling. It helps to keep you comfortable year-round while potentially reducing energy costs during the colder months. Built in 1929, this charming home has been thoughtfully updated and improved to meet today's standards. Numerous upgrades include: added insulation, removal of the original asbestos siding, beautiful wood floors throughout, an updated kitchen, new windows and a durable interlock metal roof. Two new bedrooms were added over the garage, along with new driveway and many other improvements. Step outside onto the beautiful deck and enjoy the peaceful backyard, surrounded by nature. The location is hard to beat with easy access to beaches, shopping, Mill Creek Park, Eastern Trails, local restaurants and a short drive to Portland's Old Port. With generous living space, future potential and a location close to so much of what the area has to offer, this home is ready to welcome its next owner.

66 Fessenden Ave, South Portland

Listing courtesy of Keller Williams Realty.

$429,000

2 Beds ⋅ 2 Baths

REMARKABLE VALUE. EXCEPTIONAL LOCATION. WORRY-FREE LIVING. Welcome to 22 Bayberry Way, offering one of the best locations within one of South Portland's most desirable condominium communities. Quiet, private, and surrounded by nature, this spacious 2-bedroom, huge bonus room over garage, 1.5-bath, 1-car garage home offers over 1,300 SF, an attached garage, and a private brick patio abutting the woods. It lives far more like a home than a typical condo, at a fraction of what comparable space, privacy, and amenities would cost just minutes away in Portland. UPDATED AND UPGRADED. The owner has done a host of updates and upgrades, including fresh paint, new flooring, updated bath and kitchen finishes, and higher-end appliances. Outside, enjoy a low/no maintenance exterior where the owners have just updated siding, windows, doors, skylights, and more. The result is exactly what condominium living should be: low-maintenance, stress-free, and truly lock-and-leave, ideal for a full-time residence, second home, or snowbird lifestyle. The first floor features an open kitchen and dining area, separate living room with wood-burning fireplace, half bath, and direct garage access. Step outside to the private brick patio and peaceful wooded setting. Upstairs are 3 generous bedrooms, a full bath with laundry, and excellent storage. LOCATION. T-Ledge is a professionally managed, pet-welcoming community with a remarkably reasonable condo fee. Just off Highland Avenue, you're minutes from Hinckley Park, South Portland Community Center, nature trails, Fort Williams, beaches, shopping, downtown Portland and major commuter routes. Space. Privacy. Garage. Outdoor living. Extensive improvements. Exceptional management. 22 Bayberry Way is an extraordinary Greater Portland value.

22 Bayberry Way Unit 22, South Portland

Listing courtesy of Benchmark Real Estate.

$689,000

3 Beds ⋅ 2 Baths

Walk to Willard Beach. Watch the sunset at Bug Light. Grab coffee at Scratch Baking Co. Stroll the Greenbelt. Welcome to 204 Preble Street. Nestled in one of South Portland's most beloved coastal neighborhoods, this charming 2-3 bedroom, 2-bath home is full of character and modern updates, offering the opportunity to enjoy a lifestyle that few locations can match. From your front door, you're just a short walk to Willard Beach, Bug Light Park, the Greenbelt Walkway, Southern Maine Community College, Spring Point Ledge Light, and the vibrant restaurants, cafés, and shops of Knightville and Mill Creek. Downtown Portland is just minutes away, making commuting, dining, and entertainment effortlessly accessible. Inside, you'll find a warm and inviting floor plan featuring hardwood floors, a sun-filled living room, and an updated eat-in kitchen designed for both everyday living and entertaining. The flexible layout provides options for additional bedrooms, guests, a home office, or creative space, while the private primary suite offers a comfortable retreat with generous storage. Seasonal views of Casco Bay add another reminder that the Maine coast is woven into everyday life here. Outside, enjoy a yard with space to garden, relax, or gather with family and friends. Whether you're looking for a year-round home or a place to embrace the best of coastal Maine, 204 Preble Street offers an exceptional combination of location, lifestyle, and opportunity. More than a home, it's a way of life in one of South Portland's most treasured neighborhoods.

204 Preble St, South Portland

Listing courtesy of Keller Williams Realty.

$515,000

3 Beds ⋅ 2 Baths

Welcome to eco-friendly, low-cost living in one of Southern Maine's most desirable locations! This beautiful 3-bedroom ranch at 8 Kenneth Road in South Portland offers over 1,400 square feet of well-designed space, highlighted by an open-concept kitchen and a completely modernized full bathroom on the main floor. The expanded footprint includes a finished basement with a half bath, providing the perfect setup for a family room, home office, or guest space. What truly sets this South Portland home apart are the owned solar panels on the roof, drastically reducing utility bills and providing long-term affordability in today's competitive market. Situated in an incredible neighborhood just minutes from local beaches, parks, shopping, and downtown Portland, this property perfectly blends modern upgrades with unbeatable cost savings.

8 Kenneth Rd, South Portland

Listing courtesy of RE/MAX Oceanside.

$395,900

2 Beds ⋅ 2 Baths

Tucked away in the peaceful, impeccably maintained Heron Cove Association, this private 2-bedroom, 2-bath condo offers the ease of true one-story living. Surrounded by beautifully landscaped grounds and overlooking the Long Creek River, this home borders the scenic Long Creek Trails, creating a serene, nature-filled setting while remaining just minutes from shopping, dining, transportation, and everyday conveniences. A detached one-car garage and ample guest parking provide added convenience for both homeowners and visitors. Inside, the bright, open living and dining area features a cozy natural gas fireplace and expansive windows that frame the tranquil, sanctuary-like surroundings. Enjoy the comfort and efficiency of natural gas heat with a new natural gas boiler installed in 2023, along with additional updated appliances, making this home truly move-in ready. Both spacious bedrooms feature full en-suite bathrooms, offering exceptional comfort, privacy, and flexibility for guests or shared living. Whether you're looking to downsize without compromise, enjoy low-maintenance living, or simply relax in one of the area's most desirable and quiet communities, this home is an outstanding opportunity. Offering exceptional value in the neighborhood, this is a rare chance to own a beautifully maintained, private retreat with the perfect blend of privacy, convenience, and easy living--don't miss it before it's gone!

26 Cormorant Pl Unit 26, South Portland

Listing courtesy of Locations Real Estate Group LLC.

$899,900

3 Beds ⋅ 4 Baths

Introducing a thoughtfully designed 20-unit luxury condominium community nestled in the sought-after Willard Beach area of South Portland. Each residence offers approximately 2,350 square feet of refined living space across three levels. This unit does not have an elevator. The second floor features an elegant open-concept layout that includes the living room, kitchen, dining area, a separate office, a stylish half bath and a porch off of the Livingroom--perfect for modern living and entertaining. On the ground floor, a versatile efficiency suite with a full bath, kitchenette, and private patio offers an ideal space for a caregiver, in-law, or guest. The top floor is home to a spacious primary bedroom with an ensuite bath featuring a tiled shower and a private porch overlooking the treed ridge behind the property. A guest bedroom, additional full bath, and laundry room complete the upper level. Hardwood floors run throughout, and each unit is equipped with two efficient heat sources and cooling for year-round comfort. Set in a quiet neighborhood, the development abuts 4+- acres of protected city-owned land, providing privacy and a natural buffer. Residents will enjoy walking distance to Willard Beach, SMCC, marinas, restaurants, and local shops. Each home also includes a one-car garage, making this an exceptional blend of luxury, location, and lifestyle.

119 Summit Ter Unit 6, South Portland

Listing courtesy of F.O. Bailey Real Estate.

$917,400

2 Beds ⋅ 3 Baths

Coolidge-Single Level Layout - Having 2220 +/- sf. with a beautiful sunroom. This 55 plus 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. Visit our furnished model. Photos shown are of our upgraded Model Home. GPS. 761 Main Street South Portland ME behind King Wood Condominiums. New furnished model located at 3 Puffin

2 Plover Way Unit 17, South Portland

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

$947,872

3 Beds ⋅ 4 Baths

Introducing a thoughtfully designed 20-unit luxury condominium community nestled in the sought-after Willard Beach area of South Portland. Each residence offers approximately 2,350 square feet of refined living space across three levels, with a private elevator for enhanced convenience. The second floor features an elegant open-concept layout that includes the living room, kitchen, dining area, a separate office, a stylish half bath and a porch off of the Livingroom—perfect for modern living and entertaining. On the ground floor, a versatile efficiency suite with a full bath, kitchenette, and private patio offers an ideal space for a caregiver, in-law, or guest. The top floor is home to a spacious primary bedroom with an ensuite bath featuring a tiled shower and a private porch overlooking the treed ridge behind the property. A guest bedroom, additional full bath, and laundry room complete the upper level. Hardwood floors run throughout, and each unit is equipped with two efficient heat sources and cooling for year-round comfort. Set in a quiet neighborhood, the development abuts 4+- acres of protected city-owned land, providing privacy and a natural buffer. Residents will enjoy walking distance to Willard Beach, SMCC, marinas, restaurants, and local shops. Each home also includes a one-car garage, making this an exceptional blend of luxury, location, and lifestyle.

119 Summit Ter Unit 5, South Portland

Listing courtesy of F.O. Bailey Real Estate.

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