Courtesy: Portside Real Estate Group
207-747-4236
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.
Courtesy: Keller Williams Realty
207-879-9800
Whether you are just starting out or downsizing, 136 Dawson St will meet your needs. This freshly painted three-bedroom, one-bath home features hardwood floors, a comfortable layout, and lots of natural light. The generously sized backyard includes a deck and is fenced on three sides, creating an inviting space for outdoor enjoyment. A rear shed provides convenient storage for tools and seasonal items. In the basement, a partially finished room offers a head start on additional living space—ideal for a home office, den, or hobby area. Ideally located on a dead end street you are just steps from the bus route and 2 minutes to a K-8 public school, a branch of the SoPo library and the municipal golf course. You are close to the ME Mall and major highways and this home's location allows easy access to Willard Beach, excellent restaurants, two theaters, bowling, and head across the Casco Bay Bridge or onto I-295 for a quick trip to Portland's Old Port.
Courtesy: Cates Real Estate
207-701-5600
Wilkenson Farm - Established 1920 - Charming and efficient 3-bedroom Cape/Farmhouse, proudly situated on a hill in the sought-after Sunset Park neighborhood in South Portland. Key Features You'll Love: Classic Charm: Step inside to find timeless details like classic wood trim and built-ins, offering the warmth and character of a mature home. Flexible Living: Enjoy two main living spaces that can adapt to your needs—whether you envision a dedicated dining room space, a home office nook or workout area, or an expanded living room. Energy Efficient Updates: Cozy up by the wood fireplace for ambiance, and take comfort in recent energy-saving upgrades, including efficient heat pumps and a brand-new heating system. The basement has also been sealed and additional blown-in insulation has been installed for maximum energy efficiency. First-Floor Convenience: The home boasts a highly desirable first-floor bedroom and first-floor laundry located in a custom dining nook off of the kitchen. Oversized, Ready-to-Use Lot: Enjoy a large oversized lot including a fenced-in backyard that is a gardener's dream, featuring custom cedar raised beds. Surrounding the house a French perimeter drain has been installed to prevent any water intrusion into the home. Fabulous Location: Enjoy a quick, convenient drive to the stunning beaches of Scarborough, the vibrant downtown of Portland, or the South Portland shopping district. Easy access to I-95 and I-295 makes your commute a breeze. This home is move-in ready with fantastic bones, offering the perfect opportunity to personalize and truly make it your own!
Courtesy: RE/MAX By The Bay
207-773-2345
Perched like the prow of a ship with panoramic waterfront vistas, 2 Drew Road presents incomparable seaside living. This unique home is sited on a promontory along the coast with premier views over Maine's iconic lighthouses, Fort Gorges, and the bustling shipping channel. A natural wooded buffer ensures an uncommon level of privacy, allowing the beauty of the ocean to take center stage. Multiple outdoor living spaces, including a stone patio and rooftop deck, invite you to host, relax in the sun, or simply watch the boats sail by. The original 1920's cottage has been updated and expanded for modern living. The open layout centers on a chef's kitchen and large dining area, while the sunroom sparkles with a wall of windows and outdoor access. Gather with family and friends in the sunken living room with a gas fireplace and stunning views. A calming retreat, the primary bedroom on the first floor overlooks easterly sunrises and the gardens, with year round comfort from a heat pump. A second bedroom on the main level is ideal for guests, near the contemporary full bathroom with curbless shower. Upstairs, a spacious third bedroom lives like a suite, with room for an office, its own private deck, and a second full bath. Enjoy the convenience of an attached two car garage, with mudroom, pantry, and laundry room. Beyond the property itself, Danforth Cove residents enjoy access to a private neighborhood beach and tennis courts. It's a coastal lifestyle of rare privilege just minutes from the shopping and dining in South Portland, and the vibrant sites of downtown Portland.
Courtesy: Cottage & Co Real Estate
207-653-1188
This sun-drenched, end unit townhouse condo offers privacy and comfort in a pretty, wooded setting. The first floor features an eat-in kitchen and living room with a nice deck overlooking the woods, a fantastic place to unwind and enjoy the outdoors. The second floor offers two bedrooms and a full bath. The full, unfinished basement provides plenty of storage space with the potential for a bonus room, home gym, or office. The low condo fees make this property affordable for first-time buyers, part-timers or investors. Located in a desirable residential area with easy access to local amenities, Wainwright athletic fields, shopping, RTs 95 and 295, and it's a 15-minute drive to downtown Portland with its many cultural and dining options. Two parking spaces per unit. Pets are welcome as per condo rules. Conifer Woods is a professionally managed condominium association.
Courtesy: Keller Williams Realty
207-775-2121
Tastefully remodeled first floor unit with a unique professionally landscaped patio (see photos) with direct access to walking trail. The open concept living space offers custom kitchen with stainless appliances, quartz countertops. Breakwater has much to offer, close to Bug Light Park, Green Belt walking/biking trail. There is 24/7 security, community garden, bicycle storage and more.
Courtesy: Signature Homes Real Estate Group, LLC
207-885-0500
Set on a quiet residential street in South Portland, this single-family home offers space, flexibility, and an opportunity to make it your own. The main level features an open living and kitchen area with pitched ceilings and a wall of windows that brings in natural light and creates an airy feel. One bedroom and a full bath with laundry on this level allow for easy single-floor living, while still offering room to grow. The lower level provides additional finished space with multiple rooms and a second full bath. This separation allows for a variety of uses such as additional living space, work-from-home options, guest accommodations, or hobby areas, depending on your needs. This home is a great opportunity for buyers who value space, layout flexibility, and location and who are looking for a home to personalize and make their own.
Courtesy: Regency Realty Group
207-253-1500
This one-bedroom/one-bath condo is filled with natural light and offers endless possibilities. Bring your imagination! The unit, located on the 6th floor, has a beautiful city view of Portland and has elevator access. Located next to the Greenbelt, Breakwater is close to shopping, dining, transit, and parks. Everything you need right at your doorstep. Breakwater is a well-managed condo association. There is an on-site laundry, elevators, a garden club, 24-hour security, an on-site building manager, and bicycle storage. Whether you're looking for a weekend getaway or purchasing your first home, this is an opportunity you do not want to miss. Schedule your private showing today.
Courtesy: F.O. Bailey Real Estate
207-781-1111
Just Reduced! They say the perfect property doesn't exist, but 17 Spring Street comes impressively close. This beautifully updated two-bedroom, one-bath home offers effortless single-level living, wrapped in the kind of neighborhood charm people dream about when they imagine life in Maine. Inside, fresh paint, hardwood floors, and thoughtful updates throughout make this home truly move-in ready. Step outside to a private deck with hot tub, a brand-new patio, and a fully fenced yard, creating your own peaceful retreat for morning coffee, summer evenings, or quiet nights under the stars. The backyard features new raised garden beds, perfect for growing vegetables, herbs, or flowers. The front yard is framed by a stunning wall of hydrangeas that bloom all summer long. The lifestyle is what sets this home apart. Start your mornings with a stroll to Willard Beach, indulge in pastries from Scratch Baking, pizza from DiPietro's, Thai food at Pom's, brunch at Bistro Leluco, martinis at David's, or ice cream at Willard Scoops. As the sun sets, wander down to Bug Light and take in sweeping views of Portland Harbor and the city skyline. Just minutes from downtown Portland's theaters, restaurants, and cultural offerings, yet nestled in one of South Portland's most beloved neighborhoods, this home strikes the perfect balance between small town and city living. Easy. Charming. Quintessential Maine. Your next chapter begins at 17 Spring Street.
Courtesy: Keller Williams Realty
207-553-2605
Spacious South Portland home on a rare double corner lot and offering a bright, open floor plan designed for comfortable living and future potential. The main level features a first-floor bedroom and full bath, a stainless-steel-appliance kitchen, large living room with dining area, and efficient natural gas heat complemented by mini-split heating and cooling. Enjoy mornings on the finished front porch, then retreat upstairs to multiple bedrooms, an additional living area/entertainment space and versatile seating or office area. A full, partially finished basement provides endless possibilities for storage or expansion, while the oversized lot opens the door to future expansion opportunities.
Courtesy: Rockstar Real Estate
207-317-1338
Welcome to 30 Sokokis Street, an ideally located 3-bedroom, 2-full-bath home set on a corner lot in an established residential street in the heart of South Portland. This inviting property offers a flexible layout designed to adapt to a variety of living needs. The main living areas are filled with natural light and flow comfortably for everyday living and entertaining. The back deck offers a welcome extension of the dining space seasonally. The finished basement features a large bonus room, and a full bathroom, making it perfect for a family room, home office, gym, or guest space, adding valuable versatility to the home. Conveniently located just minutes from schools, shopping, dining, local beaches, and downtown Portland, this home combines neighborhood charm with practical convenience. Whether you're seeking a primary residence or an investment opportunity, 30 Sokokis Street offers space, flexibility, and location in one of Southern Maine's most desirable communities. OPEN HOUSE SUNDAY JAN. 4TH 11:00AM-2:00PM
Courtesy: Keller Williams Realty
207-775-2121
Location, location, location! Spring Point is a sought-after waterfront community just minutes from Portland, with easy access to shopping, services, beaches, restaurants, Spring Point Marina, and more. This nicely updated condominium features an updated kitchen, a spacious living and dining area, a generous bedroom with ample closet space, and one full bath. Step out from the living room onto your private balcony—perfect for enjoying summer outdoor living. Additional highlights include reserved parking, ample guest parking, and carefree living within a well-established association offering 24-hour security.
Courtesy: Portside Real Estate Group
207-536-4222
Offering just over 1,400 square feet of finished living space, this ideally designed 3 bedroom 2.5 bath home includes a two-car garage and is centrally located with convenient access to I-95, the Maine Mall, local eateries and the Portland International Jetport. Scheduled for completion mid March, this property delivers quality craftsmanship and finishes throughout. Additional expansion potential is available in the unfinished daylight basement should you require more space. We are pleased to invite you to experience 447 Main Street, South Portland; a home that will not disappoint. Come make this house your home!
Courtesy: RE/MAX Shoreline
207-553-7500
Perhaps the Best Buy in the City! This freshly painted newly carpeted, Bright Sunny unit featuring an updated bath and new Stainless appliances awaits your finishing touches. With Fore River and City of Portland Skyline views this 8th floor Penthouse unit would make a perfect pied-a-terre or ideal for student or faculty member of nearby colleges. Located within walking distance to Willard Beach, Bug Light Park and the City of South Portland Green Beltway. Stroll, walk, jog, bike ride and coastal living do not pass up this opportunity.
Courtesy: Signature Homes Real Estate Group, LLC
207-885-0500
Discover the charm of this lovingly maintained, one-owner, single-level home tucked away on a quiet cul-de-sac in a highly sought-after neighborhood. Featuring an open-concept layout, this home offers effortless flow for everyday living and entertaining. The beautifully finished lower level includes a spacious family room and bathroom—perfect for guests, hobbies, or additional living space. Outside, enjoy a gorgeous, landscaped yard with full irrigation, ideal for relaxing or play. Complete with a 2-car attached garage, this home blends comfort, convenience, and pride of ownership in every detail.
Courtesy: Regency Realty Group
207-253-1500
Modern Condo Living at Its Best Welcome to your new home. This beautifully designed condo, located on South Portland's waterfront, offers the perfect blend of comfort, style, and convenience. Featuring an open-concept layout and abundant natural light, this residence is ideal for both relaxing and entertaining. Enjoy a modern kitchen with sleek finishes and access to building amenities including elevators. Located in a desirable neighborhood close to shopping, dining, transit, and parks, this condo puts everything you need right at your doorstep. Whether this is your first home, you're downsizing, or investing, this is an opportunity you do not want to miss. Schedule your private showing today.
Courtesy: EXP Realty
888-439-8743
DON'T MISS OUT on this incredible opportunity! Priced to sell as-is with expansion potential in one of South Portland's most desirable locations. This iconic 4-unit property delivers versatility for investors, multi-generational living, or anyone seeking a flexible home-based business setup. Originally built in 1900, this late-19th-century New Englander blends Colonial Revival character with timeless craftsmanship and period details throughout. Rich woodwork, hardwood floors, stained-glass accents, built-ins, and high ceilings create an atmosphere filled with warmth and charm. The property features four distinct spaces, including three spacious residential units — a first-floor 3 BR, two upper-level 2 BR units — and a dedicated home-occupancy suite once used as a pet-grooming business, perfect for a salon, studio, or office. A handsome fireplace, wrap-around enclosed porch, and large sun-filled rooms add to its appeal. An attached barn with loft and one-car garage offers incredible versatility, ideal for storage, a workshop, or potential in-law/ADU conversion. Set on a beautifully landscaped .84-acre corner lot with mature trees, gardens, and a tranquil stream, there may also be potential for a buildable lot (buyer to verify). Located minutes from Downtown Portland, Willard Beach, Bug Light Park, Spring Point Lighthouse, and Southern Maine Community College, with easy access to Portland International Jetport, Casco Bay Ferry Lines, and top-rated South Portland schools, this is coastal Maine living at its best. Bring your vision and unlock the potential of this one-of-a-kind property in the heart of South Portland. So much opportunity to live, work, and invest all in one prime location!
Courtesy: Pine Tree Realty of Maine
207-893-8006
Charming Cape Near Willard Beach!! Discover this inviting 3-bedroom, 1-bath Cape nestled on a quiet dead-end street just a short walk from beautiful Willard Beach. This home offers classic charm and comfortable living in one of South Portland's most desirable neighborhoods. Enjoy a spacious, beautifully landscaped yard—perfect for gardening, entertaining, or simply relaxing outdoors. A bright three-season sunroom provides the ideal spot to enjoy morning coffee or unwind at the end of the day. Additional features include a one-car garage, a well-maintained exterior, and a location close to local shops, restaurants, and scenic coastal trails.
Courtesy: RE/MAX By The Bay
207-773-2345
Unparalleled grandeur and pristine craftsmanship define this waterfront estate in South Portland's coveted Loveitts Field neighborhood, magnificently positioned along the ship channel entrance to Portland Harbor. A soaring entryway reveals 10 foot ceilings and bold marble pillars that set the stage for elegant living. The bespoke kitchen showcases two islands, granite countertops, and professional grade appliances, perfectly designed for both everyday living and grand entertaining. Formal dining and living rooms open to a terrace with sweeping ocean and Ram Island views. An elevator services all three levels, ensuring comfort and convenience throughout the home. The primary suite is a sanctuary with a fireplace, balcony, walk-in closet, and a marble bath featuring a soaking tub overlooking Portland Head Light. The lower level exudes old world charm with a stone detailed kitchen, marble fireplace, and private theater. Outdoor living is resort like with a heated pool, terraces, and 100 feet of waterfront showcasing your private front row seat to the boats of Casco Bay and Portland Harbor. An elegant coastal beauty unlike anything else on the market.
Courtesy: Cottage & Co Real Estate
207-653-1188
Looking for a private oasis in the heart of South Portland? Then welcome to 1 Karynel Drive, an end unit townhouse in sought after Dows Woods Association. With no two units being the same in the entire association, this two bedroom, two and half bath almost 1600 square foot unit boasts owner maintained mature landscaping, galley style kitchen with plenty of storage and private den/office area overlooking the living room. The downstairs has a large living room perfect for entertaining or quiet nights at home, a dining room suitable for multiple guests or dinner for two. Upstairs it has two nice sized bedrooms, laundry room and loft area that can be used as an office or guest room. A rare bonus area, for Dows Woods, is a full dry basement that is great for storage or future finishing. Enjoy morning coffee while observing local wildlife or nighttime star gazing with minimal ambient light infractions, all while being minutes to downtown and beaches.
Courtesy: F.O. Bailey Real Estate
207-781-1111
Still time to pick your finishes in this new colonial in Thornton Heights. This established residential neighborhood is close to the airport, Maine Mall, interstates 295 and 95. A new home that borders a park. Features include 3 bedrooms 2.5 baths. First floor open floor plan with, living room, diningroom, kitchen, hall with 1/2 bath, back deck and front composite porch. Second floor has 3 bedrooms, primary with ensuite, as well as a second full bath. Daylight basement with future finish ability. Easy to show.
Courtesy: EXP Realty
888-439-8743
Reintroduced and priced with its newly defined .35± acre lot, this South Portland home offers comfort, space, and room to grow. The large, level yard provides plenty of space for outdoor living, gardening, or play, while the unfinished area above the two-car garage offers great potential for future expansion — think office, studio, or bonus room. Inside, you'll find a bright and practical layout with updated flooring, newer windows, and recent system improvements for peace of mind. The kitchen features granite countertops and stainless appliances, opening to the dining and living areas for easy flow. With five bedrooms and two full baths, there's flexibility for guests or a home workspace. Conveniently located near Willard Beach, the Greenbelt Trail, and downtown Portland, this home combines space, value, and location in one inviting package.
Courtesy: F.O. Bailey Real Estate
207-781-1111
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.
Courtesy: F.O. Bailey Real Estate
207-781-1111
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.
Courtesy: F.O. Bailey Real Estate
207-781-1111
An exceptional and increasingly rare offering in South Portland's coveted Willard Beach neighborhood — now presenting potential for a 12+-unit condominium development (subject to approvals), or an extraordinary multi-generational family compound directly on the beach. Set on a premier waterfront site with sweeping views of Spring Point Ledge Lighthouse, Casco Bay, and the islands, this unique property includes two residences positioned to capture the beauty and energy of Maine's coastline from multiple perspectives. The larger home, recently remodeled, offers four to five bedrooms and expansive living spaces designed to maximize ocean views and natural light. Wake to sunrises over Casco Bay, watch working boats pass through the harbor, and experience true waterfront living from nearly every vantage point. The second residence enjoys its own distinct outlook across the ocean, creating flexibility for guest accommodations, rental income, or extended family living. If utilized as a private compound, there is also potential for an additional buildable lot located in front of the smaller residence, creating the rare opportunity for three separate living spaces — the primary home, guest residence, and an additional homesite (subject to approvals). Broker Owned
South Portland is located in Maine. South Portland, Maine has a population of 26,428. South Portland is less family-centric than the surrounding county with 26.04% of the households containing married families with children. The county average for households married with children is 30.7%.
The median household income in South Portland, Maine is $73,899. The median household income for the surrounding county is $80,679 compared to the national median of $69,021. The median age of people living in South Portland is 43.2 years.
The average high temperature in July is 78.4 degrees, with an average low temperature in January of 11 degrees. The average rainfall is approximately 49 inches per year, with 55.8 inches of snow per year.
