958 houses for sale in Winthrop Beach

Well located on High Street, this rarely available, solid, three-family building is just a few blocks from Monument Square and close to town center shops, restaurants and transportation. Investors, developers: this 3-unit dwelling is a prime investment or condo-conversion opportunity. Unit 1: this special 2BR/1BA unit features a private entrance, and spans 1000sf with a sun-drenched living/dining room. Units 2 and 3 each offer 1050sf, 3BR/1BA floor plates of bright living space with great entertaining flow. An unfinished basement with 1189sf offers potential for future development and features direct street access and five large windows. A large common roof deck with panoramic skyline/city views completes the building. All three units currently leased with a 5% cap rate at the current rent roll. Significant NOI upside, projected to exceed a 6.25% cap rate, through market-rate lease renewals. Two leases coming up

A rare South Boston offering, this brick row single-family stands apart with a design more reminiscent of the South End. Across from a lush park, the home is thoughtfully curated with a focus on scale, light, and architectural detail, creating a refined, timeless feel. Spanning three levels, it features an open-concept main floor with 12-foot ceilings and new windows that flood the space with natural light. The kitchen, dining, and living areas flow seamlessly, extending to a private patio. The layout offers two true primary suites, two guest bedrooms, and a flexible office or gym. Updated systems include three-zone heating and two-zone AC (2021). A private roof deck with Brazilian Ipe wood, built-in grill, and outdoor amenities creates an ideal entertaining space. Two side-by-side garage spots complete this rare and elevated offering. For buyers seeking something beyond the typical South Boston product, this home delivers a distinctive blend of character, scale, and thoughtful design

Everett GEM! Excellent investment opportunity in featuring a well-maintained 4-unit building, including one commercial, Offering strong income potential and upside. Located in a desirable Everett neighborhood with convenient access to major employers, transit, shopping, and amenities, this property benefits from strong rental demand and steady cash flow potential. Ideal for investors seeking a stabilized asset with additional units and recent capital improvements already in place

Prime South Boston Opportunity: Character, Scale, and Unmatched PotentialWelcome to 408 West 2nd Street, a classic South Boston multi-family property that perfectly balances historic character with incredible modern potential. Situated in one of Boston's most dynamic and sought-after neighborhoods, this turn-of-the-century two-family home is a rare find for savvy investors, developers, or owner-occupants looking to establish their roots and generate rental income simultaneously.Spanning three floors at 1,570 square feet, this structurally sound 1910 build offers a versatile layout currently configured with 4 bedrooms and 2 bathrooms.The Potential: Whether you are looking to execute a high-end luxury renovation, add building height and massing, maintain it as a high-yield income generator, or craft a stunning bi-level owner's unit while renting the other unit-Opportunities abound!

Located on a gas-lit street near Monument Square, this rarely available, 4BR/3.5BA, two-family home offers 3,593+sf and an extraordinary opportunity for an owner occupant, investor/developer, or buyer looking to convert into a spectacular single family home. The grand entrance is defined by soaring ceilings, period moldings, and a sweeping staircase that leads to an impressive formal living room. An elegant dining room flows into a chef's kitchen with luxury finishes and top-tier appliances. A charming family room w/wet bar and gas FP provides an inviting hub for daily living. A spacious primary suite w/FP has ample closet space and marble spa bath. An addt'l bedroom and full bath complete this level. The separate entrance, 1BR rental unit in the rear of the first floor is well maintained. The crown jewel is an expansive 480sf private roof deck w/head house, wet bar, and panoramic views of the harbor, Monument, and Boston skyline. A lush garden patio completes this special offering

Located on a gas-lit street near Monument Square, this rarely available, 4BR/3.5BA, two-family home offers 3,593+sf and an extraordinary opportunity for an owner occupant, investor/developer, or buyer looking to convert into a spectacular single family home. The grand entrance is defined by soaring ceilings, period moldings, and a sweeping staircase that leads to an impressive formal living room. An elegant dining room flows into a chef's kitchen with luxury finishes and top-tier appliances. A charming family room w/wet bar and gas FP provides an inviting hub for daily living. A spacious primary suite w/FP has ample closet space and marble spa bath. An addt'l bedroom and full bath complete this level. The separate entrance, 1BR rental unit in the rear of the first floor is well maintained. The crown jewel is an expansive 480sf private roof deck w/head house, wet bar, and panoramic views of the harbor, Monument, and Boston skyline. A lush garden patio completes this special offering

Modern Sophistication in Malden! Built in 2019, this stunning 4-bedroom, 3.5-bathroom Colonial offers over 3,000 sq. ft. of meticulously designed living space. The first floor features a bright, open-concept layout w/ gleaming hardwoods, a cozy fireplace, and chef-inspired kitchen equipped w/ stainless steel appliances and gas range while your dining area looks out over your spacious deck. A sun-drenched flex room serves as the ultimate home office or a gracious first-floor bedroom. Upstairs, the primary suite serves as a true retreat w/ a private ensuite bath and 2 closets. 2 add. spacious bedrooms and dedicated laundry complete the second level. The massive, fully finished basement includes a full bath and laundry hook up, w/ private ext. access perfect for a home gym, media room, guest suite or possible ADU. Enjoy summer evenings on the rear deck overlooking a quaint backyard. 2-car det. garage, owned solar, central air, and tankless hot water. Minutes to local shopping, parks and h

Welcome to 29 Oakland Ave! Come check out this solid longtime family-owned three-family home, just steps from Broadway and the bus line! This very desirable property features a great layout with three spacious units, each offering 2 bedrooms, 1 bathroom, and a comfortable living room. The property includes a large driveway with parking for up to five vehicles, a oversized rear yard, separate electrical services, and nicely sized rooms throughout. Whether you're an owner-occupant or investor, this is a fantastic opportunity to own a solid multi-family property in a convenient location. Ready for its next owner and will be delivered vacant!

Located on a gas-lit street near Monument Square, this rarely available, 4BR/3.5BA, two-family home offers 3,593+sf and an extraordinary opportunity for an owner occupant, investor/developer, or buyer looking to convert into a spectacular single family home. The grand entrance is defined by soaring ceilings, period moldings, and a sweeping staircase that leads to an impressive formal living room. An elegant dining room flows into a chef's kitchen with luxury finishes and top-tier appliances. A charming family room w/wet bar and gas FP provides an inviting hub for daily living. A spacious primary suite w/FP has ample closet space and marble spa bath. An addt'l bedroom and full bath complete this level. The separate entrance, 1BR rental unit in the rear of the first floor is well maintained. The crown jewel is an expansive 480sf private roof deck w/head house, wet bar, and panoramic views of the harbor, Monument, and Boston skyline. A lush garden patio completes this special offering

Welcome to 582 E 7th St-a single-family home in the heart of South Boston. This home offers a blend of modern amenities and classic charm. With 4 bed and 2.5 baths, there is plenty of space to accommodate your lifestyle. As you enter, you'll be greeted by gorgeous hardwood floors that flow throughout the home. The kitchen is a chef's dream, featuring an island, stainless-steel appliances, and ample counter and storage space. The home also boasts fantastic private outdoor spaces to enjoy year-round. Relax or entertain guests on the private roof deck with gorgeous city and water views, or host gatherings in the private backyard. Modern comforts abound with central AC and gas heat ensuring your year-round comfort. Washer/dryer hook ups in the basement and on the 3rd floor. Additional storage and finishing potential await in the basement. An incredible opportunity to own in one of Boston's most beloved neighborhoods. Close to the beach, L Street bathhouse and many shops and restaurants!

MOTIVATED SELLERS* Welcome to this one of a kind, gorgeous Victorian home offering stunning charm and over 4,300 SqFt of living space! From the moment you enter, you're greeted by soaring ceilings, rich original woodwork, and beautifully preserved details that add warmth and character throughout. The expansive layout features 5 spacious bedrooms and 3.5 baths, including a private primary suite with a sitting area or home office and a walk-in closet. Enjoy multiple living with two separate staircases and entertaining areas, a large updated kitchen with stainless steel appliances, and a bright four-season sunroom that opens to a deck overlooking the backyard. The finished third-floor suite complete with its own kitchen, living area, bedroom, and full bath, offers incredible flexibility for extended family or guests. Updates include a two-story rear addition, kitchen, bathrooms, mini splits, roof, solars (purchased), and many more! Beautiful backyard, detached garage, and ample parking

Coming Soon! Rare opportunity in a coveted Charlestown location. This multifamily offers two side-by-side units, each w/ private entrance. Unit 1, with central air, features a charming 1BD layout w/ kitchen, full bath, in-unit laundry, and direct access to an oversized fenced yard. Unit 2 is a sun-drenched 2+ BD duplex spanning two levels, w/ 3 full baths and a private deck-ideal for relaxing or entertaining. The main level includes kitchen w/ gas cooking, separate dining/living areas, and full bath; upper level offers two well-proportioned bedrooms w/ ensuite baths plus bonus office/den. Shared yard + includes two lots. Upper unit leased through 8/31/26; lower unit occupied w/out formal lease. Mitsubishi slim units in #2. Convenient to public transportation, Whole Foods, and downtown Boston. 2 LOTS 1058SF and 1548SF

Welcome to this beautiful single-family home located on a quiet street in Malden. Offering an incredible blend of modern living, flexible space, and future potential, this home features 3 spacious bedrooms, 3.5 bathrooms, and an impressive layout designed for today's lifestyle. The property includes two bonus rooms perfect for a home office, guest rooms, or playroom, plus an extra loft space that adds even more versatility. The finished lower level presents outstanding ADU potential with its own wet bar and additional dining or entertaining area, making it ideal for extended family, guests, or future rental possibilities.Enjoy the convenience of off-street parking and a prime commuter-friendly location just minutes from Route 1, I-93, and the Fellsway, providing quick access to Boston and surrounding areas. Close proximity to shopping, parks, schools, public transportation, and Malden Center makes this home an exceptional opportunity for both homeowners and investors

Offered for the first time in over a century, 419 E. 3rd St presents a rare opportunity to own a meticulously maintained 3-family in the heart of South Boston. Held within the same family since 1913, this legacy property blends pride of ownership with thoughtful modernization, making it equally compelling for investors and end-users alike. Ideally situated in a prime, central location, residents enjoy effortless access to neighborhood favorites, shops, restaurants, public transportation, and the Seaport. Extensively updated over the past 15+ years, each unit has been fully renovated since 2008, resulting in a truly turnkey investment with strong rental appeal. All three units feature spacious, well-designed layouts, central A/C, in-unit laundry, and abundant storage throughout. A true generational asset in one of Boston's most sought-after neighborhoods, 419 E. 3rd St is a rare offering that combines history, condition, and location in one exceptional package

8 Lawrence Street offers the rare opportunity to enjoy the space and lifestyle of a suburban home right in the heart of Charlestown. With over 4,000 sq. ft. of custom-designed living space, this newly constructed home redefines luxury city living. Enter directly from the attached garage into an expansive open-concept main floor, where a sun-filled living room is framed by detailed crown molding and millwork. The gourmet chef's kitchen flows seamlessly into a dedicated dining room that opens to a private patio and backyard, a true rarity in the city. The 2nd floor is home to a luxurious primary suite with 2 spacious walk-in closets and a spa-like en-suite bathroom, plus a secondary bedroom with its own en-suite and a laundry room. On the 3rd floor, you'll find 2 additional bedrooms with en-suite baths, along with a home office overlooking the surrounding greenery. A full roof deck offers sweeping views of Charlestown and the city skyline

MOTIVATED SELLER: Classic semi-attached two-unit building in the heart of one of the most desirable South Boston locations. The first floor is in need of a complete renovation (Note: potential for combining the first floor and basement to form a lower duplex). It includes two bedrooms and one bathroom. There is a good-sized side and rear yard area with lots of potential. The windows are newer. Upstairs features a nicely renovated duplex unit. The main level includes a large living area that opens into a large formal dining room. The generous eat-in kitchen has beautiful cabinetry, stainless steel appliances, and granite counters. A large, fully renovated bath and laundry room with access to a rear deck completes this level. Upstairs, you enter the large primary bedroom, with a walk-in closet, and access to a half bath. There is an additional guest bedroom on this level, which can also be accessed by the rear staircase. Building sold in as-is condition

The Property consists of a three-story building containing twelve (12) units comprised of eight (8), 2-Bedroom/1-Bathroom units and four (4) 1-Bedroom/1-Bathroom units with 11,070 square feet of living area in 14,760 gross square feet on a 0.149-acre parcel. The building has separate utilities and the tenants are responsible for their own electricity, electric heat and hot water. The building features a coin operated laundry facility in the basement, individual tenant storage spaces in the basementand eight (8) off street parking spaces. Several of the units have been renovated, featuring hardwood floors, cherry colored wood cabinets, granite countertops and stainless-steel appliances

81 Chelsea Street presents a compelling investment opportunity in the rapidly growing Everett market. This well-maintained 8-unit multifamily property consists entirely of spacious 1-bedroom, 1-bathroom units, offering a highly desirable and easy-to-manage unit mix. The building underwent a full renovation just a few years ago, featuring updated interiors, modern finishes, and improved systems that minimize near-term capital expenditures. Each unit is designed to attract and retain quality tenants, supporting strong and consistent rental income. Ideally located with convenient access to major routes, public transportation, and the ongoing development transforming Everett, this property is perfectly positioned for long-term appreciation. Whether you're expanding your portfolio or seeking a turnkey asset in a high-demand rental market, 81 Chelsea Street delivers stability, growth potential, and solid returns. Can be sold as a package with 91 Chelsea St right next door - MLS #73535690

Don't miss this adorable attached single-family home in the heart of South Boston's coveted West Side neighborhood. Blending charm and modern updates, this inviting residence features an updated kitchen with refinished butcher-block countertops, stainless steel appliances, vaulted ceilings, and a stunning skylight that fills the space with natural light. The first floor offers an open-concept kitchen and dining area, a cozy living room, and a bedroom. Upstairs you'll find the spacious primary bedroom complete with a skylight and walk-in closet, along with an adjacent full bathroom featuring a tub/shower combination. The finished lower level provides additional space for a home office, gym, or media room and a second full bathroom. Enjoy the private rear deck ideal for relaxing or entertaining. Recent upgrades include newer mini-splits for heatingandcooling and a newer water heater. Conveniently located minutes from W Broadway and numerous trendy restaurants including Lincoln, Loco, Cap

Single family (attached) home in the heart of South Boston for under $1M- 463 E 6th Street is an exceptional opportunity for development, expansion, or an end user seeking renovation potential, situated three blocks from Carson Beach and the Harborwalk. Lovingly maintained by the same family for over 65 years, this home offers a spacious, sun-filled, eat-in kitchen which opens to a generously sized deck-perfect for relaxing outdoors. Currently 3 bedrooms and 1 full bath, with a bonus water closet on the upper level, a walkout basement with laundry, ample storage, and direct exterior access - ideal for future expansion, a home office or gym. A unique value-add opportunity in a prime South Boston location. Come see!

OPEN HOUSE 5/9 12PM TO 1:30PM AND 5/10 1PM TO 3PM. In the vibrant setting of Everett, MA, this single family residence awaits. This property, originally constructed in 1933, presents a unique opportunity for a new family to embrace a home with a storied past, ready to inspire a contemporary lifestyle. the generous living are provides an abundance of room for diverse activities and personal pursuits. Plenty of rooms offer individual havens for quiet contemplation and restorative rest, including a master bedroom with a full bathroom. With four full bathrooms ensures remarkable convenience and comfort, streamlining daily routines with effortless ease. This single family residence offers a substantial foundation for creating a life filled with comfort, convenience, and individual expression. Include a private bedroom in the lower lever with private living space. come take a look at the open house

258-270 K street is an exceptionally rare corner lot development opportunity with multiple curb cuts in the heart of South Boston. 258-266 K street is formally the site of the beloved Joseph's Bakery and consists of 3700 usable sf + basement on a 5368 sf lot. 268-270 K street, the adjacent building is a 3228 sf well maintained 2-family on a 6603 sf lot. Additionally, this parcel has 10 gated parking spaces, an extreme rarity in Southie! The of the 2 parcels would give the buyer a combined 11,971 sf lot. Located in the South Boston Neighborhood MFR zoning district, there is a wide array of allowed and conditional uses for redevelopment. With approval, highest and best use is expected to be a fully residential conversion or a mixed use retail/residential conversion. The multifamily residential subdistrict dimensional regulations including FAR, frontage, building height, etc. can be found in article 68 table D on the Boston planning and development agency website

Spacious 3-Family Home in Everett - Exceptional Lot and Upgrades! This large 3-family home sits on one of the largest lots in Everett, approximately 9,963 sq. ft offering ample parking for 8+ cars, a large garage, and a shed for extra storage. All units have been remodeled within the last 12 years, featuring modern gourmet kitchens with plenty of cabinet space, stainless steel appliances, double-door refrigerators, dishwashers, deep sinks, microwaves, granite countertops, and recessed lighting. Each unit includes a modern tile bathroom. While each unit reflects its own unique style, they are all similar in design and quality, ensuring consistency throughout the property. This property combines modern updates with spacious living and an unbeatable location, making it ideal for investors or owner-occupants seeking rental income

Exceptional value in South Boston! West facing 2 unit/condo building located on a quiet side street in Southie. Bright and sunny with three floors of updated living located two blocks from all popular bars, restaurants, shopping, and public transportation on E Broadway. Ideal for owner occupant with rental income, Airbnb, extended family, Au pair suite, use as an expansive single family home, or keep as an investment property. Unit 1, a bright and open studio with a full sized kitchen, sitting area, alcove for a queen sized bed, large closet, WFH station, and full bath with tub. Unit 2 boasts an open floor plan perfect for entertaining in your open kitchen and living room complimented by a half bath. The third floor is comprised of 2 large bedrooms, ample closet space, and an updated full bath with tub and tile surround. Direct access from both units to the common yard and garden fenced in for privacy and outdoor entertaining. Common laundry and ample storage in the basement

Well located on High Street, this rarely available, solid, three-family building is just a few blocks from Monument Square and close to town center shops, restaurants and transportation. Investors, developers: this 3-unit dwelling is a prime investment or condo-conversion opportunity. Unit 1: this special 2BR/1BA unit features a private entrance, and spans 1000sf with a sun-drenched living/dining room. Units 2 and 3 each offer 1050sf, 3BR/1BA floor plates of bright living space with great entertaining flow. An unfinished basement with 1189sf offers potential for future development and features direct street access and five large windows. A large common roof deck with panoramic skyline/city views completes the building. All three units currently leased with a 5% cap rate at the current rent roll. Significant NOI upside, projected to exceed a 6.25% cap rate, through market-rate lease renewals. Two leases coming up