South Portland Real Estate

Welcome to South Portland, Maine – a vibrant coastal city that perfectly blends small-town charm with urban amenities. Nestled in Cumberland County, South Portland is just a short drive from the bustling city of Portland, making it an ideal location for those seeking a peaceful yet connected lifestyle.

One of South Portland's standout features is its stunning waterfront along the shores of Casco Bay. Residents and visitors alike can enjoy picturesque views, sandy beaches, and a plethora of recreational activities. The city's parks, such as Willard Beach and Bug Light Park, offer perfect spots for picnics, outdoor sports, and leisurely strolls while taking in the breathtaking scenery.

South Portland is also known for its rich history and tight-knit community. The city boasts a variety of local shops, restaurants, and cafes, where you can savor delicious cuisine and support local businesses. The vibrant arts scene, highlighted by galleries and cultural events, adds to the city’s unique character.

Families will appreciate the excellent schools and safe neighborhoods, making South Portland a great place to raise children. With a commitment to sustainability, the city is actively working towards green initiatives, ensuring a healthy environment for future generations.

Whether you're drawn to the beautiful coastline, the welcoming community, or the convenient access to urban life, South Portland offers a little something for everyone. Discover the charm of this Maine gem and find your perfect home in a city that truly embraces the best of coastal living.

Newest Listings in South Portland

$525,000

3 Beds ⋅ 2 Baths

Enjoy privacy, convenience, and easy condominium living in this inviting end unit! Set against a wooded backdrop, this home offers a spacious front-to-back living room with fireplace, a separate dining room, an attached garage, and the convenience of first-floor laundry. Upstairs are two bedrooms and a generously sized office or study featuring extensive built-in shelving, ideal for working from home, reading, or hobbies. A full basement provides excellent additional storage and workspace. Recent exterior improvements include a new roof, replacement windows throughout, rebuilt front wall, and new vinyl siding providing modern updates that are built to last. With lawn care and snow removal handled by the association, you can spend more time enjoying your home and South Portland's convenient location near shopping, recreation, and commuter routes. A wonderful opportunity to make this well-located home your own!

14 Wisteria Way Unit 4, South Portland

Listing courtesy of Demetria Real Estate.

$575,000

3 Beds ⋅ 2 Baths

Welcome to 91 Scott Road in South Portland, Maine! This 3-bedroom, 1.5-bathroom home has been lovingly maintained by the same owners since it was built in 1999. Located at the end of a dead-end road, it offers a surprising amount of privacy for a South Portland address, with a wooded backyard that creates your own little oasis. The open-concept layout was ahead of its time, with the kitchen, casual dining area, and living room flowing seamlessly into one another on the first floor. A half bathroom with first-floor laundry and an additional room that could serve as a formal dining room, playroom, or home office round out the main level. Upstairs, you'll find three bedrooms and a full bathroom, along with a versatile space above the 2-car garage currently being used as a rec room. Whether you envision a game room, hobby space, additional living area, or potentially an ADU (subject to city approvals and requirements), this space offers plenty of possibilities. Just off the rec room, a large deck overlooks the wooded backyard, a great spot for morning coffee, summer gatherings, or simply enjoying the outdoors. The unfinished basement provides even more potential for additional living space, a home gym, or storage. Recent updates include a new roof in 2024 and a new shed in 2022 for additional storage. Just 10 minutes from Downtown Portland and the Portland Jetport, 15 minutes from several Southern Maine beaches, 30 minutes from the lakes, and less than 1 hour and 45 minutes from Boston, 91 Scott Road offers a unique combination of privacy, flexibility, accessibility, and opportunity. The property abuts the South Portland trail system, with trails leading toward local schools and the outdoors right from home. With convenient access to South Portland schools, shopping, dining, and the amenities of Greater Portland, this home offers plenty of room to make the most of Maine living. Come check it out today. Welcome home!

91 Scott Rd, South Portland

Listing courtesy of Keller Williams Realty.

$975,000

2 Beds ⋅ 3 Baths

EXCEPTIONAL WATERFRONT LIVING WITH PANORAMIC CASCO BAY AND PORTLAND SKYLINE VIEWS. Experience waterfront living at its finest from this exceptionally renovated 2 BR, 2.5 BA condominium overlooking Casco Bay. Encompassing 1,300 square feet across the top two floors of an intimate 15-residence building, this beautifully appointed home offers sweeping views of Portland's iconic skyline, the working harbor, and the picturesque mooring field of the Centerboard Yacht Club. With its coveted western exposure, spectacular sunsets over the water provide a breathtaking backdrop to everyday living. Thoughtfully designed for both comfortable living and effortless entertaining, the open-concept main level features a beautifully equipped kitchen with new premium Wolf conduction stove, an expansive Quartzite breakfast bar, and seamless flow into the dining and living areas. A gas fireplace adds warmth and ambiance, while a private balcony invites you to relax and take in the ever-changing waterfront scenery. Upstairs, the primary suite offers a spacious walk-in closet and private bath, while a second bedroom and full bath provide comfortable accommodations for guests or a dedicated home office. Convenient second-floor laundry and an additional private balcony complete the upper level. Beyond the residence, enjoy access to beautifully landscaped waterfront gardens, inviting outdoor dining areas, and a beach available for association use. Two tandem reserved parking spaces in the secure underground garage, elevator access, central air conditioning, and dedicated storage add an exceptional level of convenience. Offered with the option to purchase substantially furnished, this remarkable residence presents an opportunity for effortless coastal living. Whether enjoyed as a year-round home or a seasonal retreat, its combination of sophisticated comfort, captivating views, and proximity to Portland's acclaimed restaurants, shops, and cultural attractions.

215 High St Unit 307, South Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$579,900

3 Beds ⋅ 2 Baths

Classic Colonial character meets thoughtfully updated comfort in this three-bedroom, two-bathroom South Portland home, positioned on a corner lot in a wonderfully convenient neighborhood. Across 1,306 square feet and two floors, the layout offers inviting everyday spaces plus flexible areas ready to evolve with your needs. Recent improvements add meaningful peace of mind. New Marvin windows welcome natural light, while a new asphalt roof and updated heating system support comfort through Maine's changing seasons. Both bathrooms have been refreshed, bringing a more current feel to the home's practical floor plan. Extra space sets this property apart. A nearly finished room in the basement could serve as a recreation area, office, fitness space, or hobby room. Above the garage, a bonus room creates another valuable option and could become a fourth bedroom, guest retreat, or dedicated workspace. The location makes daily life and leisure easy to balance. Hinckley Park is about 0.7 miles away, putting outdoor recreation and green space close at hand. South Portland High School is about 1.3 miles from home, and the surrounding city places shopping, dining, services, and greater Portland destinations within convenient reach. With its corner-lot setting, updated essentials, and flexible bonus rooms, this new listing presents an appealing opportunity to settle into one of southern Maine's most connected communities. See how comfortably this South Portland Colonial can fit your next chapter—book your private showing today.

39 Walker St, South Portland

Listing courtesy of Real Estate 2000 ME/NH.

$1,556,000

4 Beds ⋅ 6 Baths

Welcome to an unparalleled contemporary estate offering ultimate luxury, privacy, and resort-style living on 1.76 private, landscaped acres in South Portland. Boasting over 6,100 square feet of expansive living space, this architectural masterpiece perfectly pairs grand entertaining areas with cozy everyday comfort. The heart of the home features a massive chef's kitchen and an elegant family room anchored by a stately fireplace. Ascend effortlessly via the internal passenger elevator to discover four spacious bedrooms, including a spectacular primary suite. The amenity package is truly second to none: host unforgettable movie nights in your own private theater/media room, maintain your health routines in the dedicated workout gym, or unwind year-round in the spectacular indoor in-ground pool room. Outside, iconic stone walls frame a sprawling yard complete with an incredible 7-bay garage, providing unmatched vehicle and recreational storage. Centrally located just minutes from Cape Elizabeth's sandy beaches, local parks, Mill Creek shopping, and the vibrant culture of downtown Portland. Experience Maine living at its absolute finest.

1050 Highland Ave, South Portland

Listing courtesy of Waypoint Brokers Collective.

$585,000

3 Beds ⋅ 2 Baths

Excellent opportunity to live on a wonderful street in close proximity to the Willard Beach area and all of the Cottage Road shops and restaurants. This 3-4 bedroom home has been in the same family for over 50 years and features beautiful wood floors throughout, large eat-in kitchen and sunny exposures in most rooms. A 1982 addition added a sizeable bedroom and/or family room and a spacious 3 season room overlooking the backyard which offers garden beds and rocky features.. Updated furnace and hot water heater plus a detached 1 car garage make this a very desirable home within minutes to downtown Portland and many outdoor activities.

23 Victory Ave, South Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$600,000

2 Beds ⋅ 3 Baths

Nestled in the heart of Dows Woods is 3 Karynel, one of the premiere units in the association. This 2 bedroom 2.5 bath home has been totally redone and ready for you to move in. The first floor boasts hardwood floors throughout. A gourmet kitchen with high end stainless steel appliances, perfect for elegant dinner parties or family taco night. The formal dining area flows freely into the livingroom which boasts a cozy gas fireplace and reading nook. The 3 season room adds to your living space for 9 months of the year and opens up to the new deck, which is great for grilling. When you arrive on the 2nd floor you are greeted with a full tiled bath dedicated to the second bedroom or guests and tiled laundry room. The true gem upstairs is the primary bedroom with a large tiled bathroom and huge walk in closet. Both the first and second floors are accented by gorgeous crown molding and extra wide baseboards. A rare bonus in Dows Woods is a unit that has a two car garage and finished basement, which this townhouse has, along with plenty of storage. All this can be enjoyed along with incredible sunsets and abundant wildlife right outside your front door on the large corner lot.

3 Karynel Dr Unit 3, South Portland

Listing courtesy of Cottage & Co Real Estate.

$543,500

3 Beds ⋅ 3 Baths

Tucked away at the end of a quiet dead end road, this 3 bedroom South Portland condo offers privacy, space, and an unbeatable connection to the outdoors. Built in 2008, the home features a bright, open main level where sunlight pours through the windows. The kitchen is finished with stainless appliances, granite countertops, and a handy pantry, and flows easily into the dining area. Step out to the large deck for morning coffee or summer dinners. Upstairs, the primary suite includes a full bath and two walk-in closets, while two additional bedrooms share a second full bath. The finished basement adds flexible living space for a family room, office, or guest area, with storage still to spare. An attached one car garage keeps you out of the weather and has room for bikes, kayaks, and all your outdoor gear. And then there's the backyard bonus: a wooded path leads directly to Wainwright athletic fields and the Greenbelt Walkway, so you can walk or bike all the way to Bug Light and the waterfront without ever getting in the car. All this in a central location close to shopping, dining, and everything South Portland has to offer, with Portland's waterfront and the Old Port just a short ride across the Casco Bay Bridge.

17 Old Bog Road Unit 17, South Portland

Listing courtesy of Sebago to the Sea Realty LLC.

$549,900

3 Beds ⋅ 1 Baths

*** RATE BUY DOWN AVAILABLE *** Enjoy easy living in this 3 bedroom, 1 bath home in a convenient South Portland location. An updated kitchen, wood floors, and charming period details add character, while the deck and 2 car garage offer added appeal. The finished loft above the garage offers expansion possibilities. Close to the golf course, with easy access to the highway, downtown Portland, the Maine Mall, and Mill Creek.

59 Hall St, South Portland

Listing courtesy of Duston Leddy Real Estate.

$649,000

2 Baths

Some neighborhoods just have it, and South Portland's Meetinghouse Hill is one of them. Set in one of the city's most beloved pockets, 80 Jordan Avenue offers a compelling opportunity to own a two-unit property that combines neighborhood charm, everyday convenience, and some seriously appealing outdoor space. Tree-lined streets, neighborhood cafés, local restaurants, parks, and easy access to the beaches and Portland waterfront give Meetinghouse Hill a personality all its own. It's the kind of place where you can leave the car behind, wander out for coffee, grab dinner close to home, or simply enjoy being part of a neighborhood that feels like a neighborhood. Inside, the property offers two distinct units, each with two bedrooms and one bathroom. Hardwood floors, original character, and comfortable, functional layouts provide a solid foundation, while opportunities for cosmetic improvements offer a clear path to adding value over time. Individually metered utilities add another layer of practicality for investors and owner-occupants alike. Outside is where the property really stretches its legs. A generous, fenced backyard with mature landscaping, a patio, and room to gather, garden, or simply unwind offers an outdoor experience that's not always easy to find with a two-unit property. An elevated deck provides another inviting place to enjoy the setting, while off-street parking adds everyday convenience. Whether you're looking to expand your investment portfolio or put down roots with rental income helping to carry the load, 80 Jordan Avenue offers a compelling combination of flexibility, neighborhood appeal, and outdoor livability in one of South Portland's most desirable locations.

80 Jordan Ave, South Portland

Listing courtesy of Waypoint Brokers Collective. jeremy@waypointbrokers.com

$595,000

3 Beds ⋅ 2 Baths

802 Highland Ave, South Portland

Listing courtesy of F.O. Bailey Real Estate.

$710,000

4 Beds ⋅ 3 Baths

*** OPEN HOUSE Saturday 10/24 from 11:00am - 1:00pm *** Welcome to 30 Tamarack Drive! This well-maintained Colonial offers the perfect blend of space, comfort, and convenience. Featuring 4 bedrooms, 2.5 bathrooms, hardwood floors, and a cozy wood-burning fireplace, there's plenty of room to spread out and feel at home. The half - finished basement provides additional flexible living space while still maintaining ample storage. The attached two-car garage also offers additional storage above. Step outside onto the brand new deck and patio, perfect for relaxing, entertaining, and enjoying the warmer months. The well landscaped lot and mature gardens make outdoor upkeep a breeze. Location is everything, and this home delivers! With the Wainwright Sports Complex just across Highland Avenue, you'll have easy access to playgrounds, sports fields, walking and cross-country ski trails. Only 4.5 miles to downtown Portland, and under 5 miles to local beaches including Fort Williams and Bug Light Park.

30 Tamarack Dr, South Portland

Listing courtesy of Down To Earth Real Estate.

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South Portland Real Estate

Newest Listings in South Portland

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