958 houses for sale in Winthrop Beach

Come discover Winthrop, a charming coastal community just minutes from Boston that feels a world away. This timeless Victorian is filled with natural light, character, and historic charm. Situated on a corner lot just a few homes from the water, you'll enjoy ocean breezes and stunning sunsets from the inviting front porch. Offering generous living space and endless potential, this home is ready for your vision and personal touches. Multiple porches provide opportunities to take in ocean views, while the spacious second floor features generously sized bedrooms. The third floor offers bonus living space and access to a private deck. Located in one of Winthrop's most desirable neighborhoods, this is a rare opportunity to restore a grand Victorian to its former glory. Renovated homes of this size and location have commanded prices exceeding $1.2M. Note some images are AI generated to show homes potential

Beautifully maintained 3-bedroom single-family ranch in desirable Winthrop offering comfortable one-level living plus the bonus of a spacious finished lower level, providing versatile additional rooms for a variety of needs. The main floor features a welcoming living room with fireplace, updated eat-in kitchen, recessed lighting, modern full bath with tile flooring, and three bedrooms with hardwood floors and ceiling fans. The finished basement includes two bonus rooms, a full bath, laundry room, and separate storage area. Abundant closet space provides excellent storage throughout. Enjoy the large backyard and deck, perfect for entertaining, relaxing, or outdoor dining. Potential future ADU possibilities may exist, subject to local zoning and approvals. Conveniently located near beaches, waterfront dining, parks, a local fitness center, and just minutes from Boston, this home offers the best of beach-town living

Want to live in Winthrop's Highlands area' This beautifully renovated 3-BR, 2-Bath home offers the perfect blend of coastal charm and modern upgrades, featuring 2 car parking, water views, hardwood and porcelain tile floors. NO flood insurance required. A recent front room addition with sunset deck enhances both living space and the home's connection to its surroundings. Chef's kitchen featuring a Wolf 6-burner stove, built-in microwave, Sub-Zero refrigerator, beverage center, custom cabinetry. A large center island with abundant cabinet space makes this a true focal point of the home. Enjoy ocean views and a short walk to the beach. The outdoor space has been thoughtfully landscaped featuring flower beds in the front and side, vegetable beds, and a beautifully finished backyard with raised beds, perennials, fire pit, water fountain and an all-stone design creating a peaceful, Zen-like setting. Additional generous storage in the basement with potential for future extra living space

Stunning 2022 rebuild-taken down to the original foundation and rebuilt with a fresh, nearly-new feel throughout! This townhome-style condo feels like a single-family, nearly 2,000 sq ft, featuring 3 beds, 3 full baths, private outdoor space, and 2-car parking. NO monthly condo or HOA fees; annual master insurance just $1,670. A standout alternative to East/South Boston with quick Downtown Boston access via MBTA and highways. Sun-filled main floor with open living/dining, stylish kitchen boasting high-end appliances, two-tone cabinetry, large island, plus deck access. Upstairs includes two bedrooms with a primary suite showcasing dramatic cathedral ceilings. Finished lower level ideal for media room, gym, or guest space. Near marinas, waterfront parks, transit, and dog-friendly Belle Isle Marsh. Special financing from SIRVA Mortgage

Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms and 2 bed.Kitchen has Induction Stove Top Granite Island and Counter Tops.Stainless Steel Induction Wall Microwave and Wall Oven.Top of the line Stainless Steel Refrigerator and Dishwasher.Granite tile floor. Plenty of Cabinet Space. Beautiful Tiger Hardwood Floors and Natural Woodwork Throughout. Crown Moldings and Chair Rails.Wood Fireplace in Living Room. There's a closet from the kitchen that was used as a staircase to the Basement that's finished with a huge full bath washer and dryer, Family Room and bedroom. That can be added in on the room count to 7 rooms 3 beds 2 full baths. 2nd floor 4 Large Rooms and 2 Bed.Plenty of Cabinet Space.Beautifull Hardwood Floors and All Natural Woodwork Throughout. Huge Living room. Dining Room has a spot for wall A/C. 4 Car Parking, Nice Huge Fenced in Yard with a Large Patio and Shed. Plenty of Parking Around The House Because of the corner Lot.5

Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you'll find newer flooring, fresh interior paint, updated lighting, and a beautifully remodeled kitchen complete with stainless steel appliances. The home also features an updated bathroom, newer windows, and exterior doors throughout. The first floor boasts an open and versatile layout with a modern kitchen, spacious living and dining areas, and a bedroom currently being used a home office-all enhanced by water views. Upstairs, you'll find two well-appointed bedrooms and a full bathroom. Conveniently located near public transportation, including bus routes with direct access to the MBTA

Presenting 275 Webster Street - a rare, fully leased four-family asset situated in the heart of Jeffries Point, East Boston's most coveted and rapidly evolving neighborhood. Just steps from Piers Park, the Harborwalk, and Maverick MBTA Station, this turn-key building has been meticulously rebuilt from the studs with extensive capital improvements including 4 new HVAC systems, full insulation, all-new windows, doors, and sliders, upgraded 200AMP electrical, a full sprinkler system, Hardie Plank siding, new hardwood floors, a rear granite patio, and reconstructed front steps. Each spacious unit showcases contemporary finishes, in-unit laundry, and strong tenant appeal. An exceptional opportunity for investors seeking a low-maintenance, high-performing property in one of Boston's most competitive submarkets. A perfect fit for 1031 exchange buyers looking for stabilized income and long-term upside in a supply-constrained rental market

Nestled on a peaceful street between the shoreline of Donovan's Beach and the green space of Ingleside Park, this beautifully renovated single-family home offers exceptional flexibility and comfort across multiple levels. Thoughtfully updated from the rooftop to the lower level, the home is truly move-in ready with modern finishes and inviting spaces throughout. Sun-filled interiors create the perfect balance of open gathering areas and quiet workspaces, while large windows bring in abundant natural light. Designed for both everyday living and entertaining, the layout provides versatility for a variety of lifestyles. Step outside to an incredible outdoor setting ideal for relaxing, dining, and enjoying every season. With coastal charm, nearby recreation, and turnkey convenience, this home presents a rare opportunity to enjoy the very best of Winthrop living

Introducing coastal living in this luxurious two-family home set on one of Winthrop's most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat. Enjoy updated electric, beautiful updated countertops, top-of-the-line appliances, new plumbing fixtures, sun-filled rooms, wood restored fireplaces, front/back porches, fenced in yard and flexible layouts designed for comfort and value. Coastal breezes, nearby beaches, marinas, and shoreline paths capture Winthrop's coveted seacoast charm. A private 3-4 car driveway completes this versatile property-ideal as a luxury residence, premier investment, or both. Don't miss this smart investment opportunity. More pictures coming soon!

Panoramic breathtaking views offered with this oceanfront Contemporary home via wall of windows and sliders across the front! From the foyer, step down to the living room with fireplace, cathedral ceiling, sliders to deck overlooking the ocean! The dining room also offers large ocean views with slider to deck and is open to the kitchen designed for both functionality and gathering with a convenient peninsula. The main level full bath is spacious with sauna, whirlpool tub, laundry. The 2nd floor main bedroom has walk-in closet, sink and stunning views plus access to loft area on the third level with storage, unfinished room. Two additional bedrooms, full bath and loft area perfect for home office complete the 2nd floor. Beyond the interior, a large deck extends across the front of the home. Unfinished basement with potential for expansion with bonus room and is plumbed for a bath. Paved drive for off street parking, access to beach from lower level. Enjoy the seasons from your ocean fro

Come discover Winthrop, a charming coastal community just minutes from Boston that feels a world away. This timeless Victorian is filled with natural light, character, and historic charm. Situated on a corner lot just a few homes from the water, you'll enjoy ocean breezes and stunning sunsets from the inviting front porch. Offering generous living space and endless potential, this home is ready for your vision and personal touches. Multiple porches provide opportunities to take in ocean views, while the spacious second floor features generously sized bedrooms. The third floor offers bonus living space and access to a private deck. Located in one of Winthrop's most desirable neighborhoods, this is a rare opportunity to restore a grand Victorian to its former glory. Renovated homes of this size and location have commanded prices exceeding $1.2M. Note some images are AI generated to show homes potential

Well maintained 2 Family in Orient Heights! Immediate potential for rental income as well as strong development upside. Two 2 Beds, bonus Office and Private Decks in excellent condition. 2024 New Roof and brand new boiler. Extremely tall basement ceiling height, approx 12 feet. Located on a desirable street ideal for condo conversion or high end rentals. Enjoy direct views from the back deck overlooking Suffolk Downs, which is being transformed into a large scale mixed use community with expansive open space, destination retail, dining, and transit oriented infrastructure. Exceptional investment opportunity with strong demand. Buyer to do due diligence, sold as is

Stunning 2022 rebuild-taken down to the original foundation and rebuilt with a fresh, nearly-new feel throughout! This townhome-style condo feels like a single-family, nearly 2,000 sq ft, featuring 3 beds, 3 full baths, private outdoor space, and 2-car parking. NO monthly condo or HOA fees; annual master insurance just $1,670. A standout alternative to East/South Boston with quick Downtown Boston access via MBTA and highways. Sun-filled main floor with open living/dining, stylish kitchen boasting high-end appliances, two-tone cabinetry, large island, plus deck access. Upstairs includes two bedrooms with a primary suite showcasing dramatic cathedral ceilings. Finished lower level ideal for media room, gym, or guest space. Near marinas, waterfront parks, transit, and dog-friendly Belle Isle Marsh. Special financing from SIRVA Mortgage

Stunning turn of the century three family home in a prime commuter location! Unit 1 and3 offers a spacious layout with large living room, formal dining room, kitchen, 2 bedrooms. Unit 2 offers smilar layout with 3 bedrooms and private deck. Tucked away on a quiet side street just above the town center, yet only a half-block to the bus line, restaurants, and everyday amenities. Enjoy easy access to Deer Island, beaches, and scenic bike trails. Ample on street parking with nearby public lots. Strong rental potential with 2-bedroom units commanding $2,500+. Perfect for investors or owner-occupants seeking location, space, and income opportunity

Steps from the shore, this corner lot offers coastal living w a wide, expansive front porch perfect for catching the harbor breeze or entertaining. This move-in ready home features 2,700 sq.ft. of spacious living and an unbeatable beachside location. The interior boasts hardwood floors throughout most of the home, featuring four bedrooms and 2.5 bathrooms. Additionally, a finished third floor offers a versatile space for a home office or yoga studio, while the finished lower level is perfect for a home gym. The airy first floor features 8' ceilings and a seamless flow between the fireplaced living and dining rooms. The kitchen comes fully equipped with granite countertops, and the upper levels offer bedrooms with select water views. The property includes a driveway and a one-car garage. It is ideally situated just steps from the beach, parks, dining, and the MBTA water shuttle, providing easy access to Boston's Waterfront, the Seaport, and Logan Airport. Minutes into Boston

Stunning turn of the century three family home in a prime commuter location! Unit 1 and3 offers a spacious layout with large living room, formal dining room, kitchen, 2 bedrooms. Unit 2 offers smilar layout with 3 bedrooms and private deck. Tucked away on a quiet side street just above the town center, yet only a half-block to the bus line, restaurants, and everyday amenities. Enjoy easy access to Deer Island, beaches, and scenic bike trails. Ample on street parking with nearby public lots. Strong rental potential with 2-bedroom units commanding $2,500+. Perfect for investors or owner-occupants seeking location, space, and income opportunity

Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you'll find newer flooring, fresh interior paint, updated lighting, and a beautifully remodeled kitchen complete with stainless steel appliances. The home also features an updated bathroom, newer windows, and exterior doors throughout. The first floor boasts an open and versatile layout with a modern kitchen, spacious living and dining areas, and a bedroom currently being used a home office-all enhanced by water views. Upstairs, you'll find two well-appointed bedrooms and a full bathroom. Conveniently located near public transportation, including bus routes with direct access to the MBTA

Introducing coastal living in this luxurious two-family home set on one of Winthrop's most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat. Enjoy updated electric, beautiful updated countertops, top-of-the-line appliances, new plumbing fixtures, sun-filled rooms, wood restored fireplaces, front/back porches, fenced in yard and flexible layouts designed for comfort and value. Coastal breezes, nearby beaches, marinas, and shoreline paths capture Winthrop's coveted seacoast charm. A private 3-4 car driveway completes this versatile property-ideal as a luxury residence, premier investment, or both. Don't miss this smart investment opportunity. More pictures coming soon!

Character, space, updates, and strong rental history - this well maintained two family checks all the boxes! Tucked away on a charming tree lined street, the home blends timeless detail with thoughtful improvements across three finished levels. Original hardwood floors, detailed moldings, classic wainscoting, and french doors bring warmth and charm throughout, while recent updates to the kitchens, bathrooms, lighting, paint, flooring, plumbing, and electrical add a more turn key feel. Unit 1 offers 2 bedrooms, an eat in kitchen, formal living and dining rooms, and 1 bath. Unit 2 spans two levels with an updated kitchen, living and dining rooms, two bedrooms, office, full bath, plus additional finished third-floor living space with another bedroom, full bath, and sitting area. Generating $7,350/month in rental income. Complete with a private backyard, driveway, garage, laundry in the basement and convenient access to Orient Heights station and Constitution Beach!

Character, space, updates, and strong rental history - this well maintained two family checks all the boxes! Tucked away on a charming tree lined street, the home blends timeless detail with thoughtful improvements across three finished levels. Original hardwood floors, detailed moldings, classic wainscoting, and french doors bring warmth and charm throughout, while recent updates to the kitchens, bathrooms, lighting, paint, flooring, plumbing, and electrical add a more turn key feel. Unit 1 offers 2 bedrooms, an eat in kitchen, formal living and dining rooms, and 1 bath. Unit 2 spans two levels with an updated kitchen, living and dining rooms, two bedrooms, office, full bath, plus additional finished third-floor living space with another bedroom, full bath, and sitting area. Generating $7,350/month in rental income. Complete with a private backyard, driveway, garage, laundry in the basement and convenient access to Orient Heights station and Constitution Beach!

~~PRICE IMPROVEMENT~~ Introducing 24 FAIRVIEW STREET - a charming 4-bedroom, 1.5 bath Victorian in a prime, central location offering inside and outside enjoyment. This beautiful home has been enjoyed and maintained by the same family for many years and offers timeless appeal throughout. First floor has a family room, living room w/ a fireplace, modern kitchen w/ s/s appliances, separate dining area and a butler's pantry leading to a formal dining room. There are two separate staircases leading to the second floor. The sun filled landing has four bedrooms off of it including a spacious main bedroom w/ two closets, a full tiled bathroom and a conveniently located laundry room w/ storage. The third floor offers a full unfinished attic. Utilities are updated. Summer vacation/family fun starts in the fenced in yard which includes an in ground pool, patio, and a garden area. Close to schools, shopping, public transportation and just 6 miles to Boston

Beautifully maintained 3-bedroom single-family ranch in desirable Winthrop offering comfortable one-level living plus the bonus of a spacious finished lower level, providing versatile additional rooms for a variety of needs. The main floor features a welcoming living room with fireplace, updated eat-in kitchen, recessed lighting, modern full bath with tile flooring, and three bedrooms with hardwood floors and ceiling fans. The finished basement includes two bonus rooms, a full bath, laundry room, and separate storage area. Abundant closet space provides excellent storage throughout. Enjoy the large backyard and deck, perfect for entertaining, relaxing, or outdoor dining. Potential future ADU possibilities may exist, subject to local zoning and approvals. Conveniently located near beaches, waterfront dining, parks, a local fitness center, and just minutes from Boston, this home offers the best of beach-town living

~~PRICE IMPROVEMENT~~ Introducing 24 FAIRVIEW STREET - a charming 4-bedroom, 1.5 bath Victorian in a prime, central location offering inside and outside enjoyment. This beautiful home has been enjoyed and maintained by the same family for many years and offers timeless appeal throughout. First floor has a family room, living room w/ a fireplace, modern kitchen w/ s/s appliances, separate dining area and a butler's pantry leading to a formal dining room. There are two separate staircases leading to the second floor. The sun filled landing has four bedrooms off of it including a spacious main bedroom w/ two closets, a full tiled bathroom and a conveniently located laundry room w/ storage. The third floor offers a full unfinished attic. Utilities are updated. Summer vacation/family fun starts in the fenced in yard which includes an in ground pool, patio, and a garden area. Close to schools, shopping, public transportation and just 6 miles to Boston

Spacious 4-bed, 2.5-bath single-family home in Winthrop-where coastal living meets effortless access to Boston. Set near Belle Isle Marsh, enjoy kayaking in calm waters, nearby ocean beaches, yacht clubs, and a scenic seaside golf course-all part of Winthrop's rare small-town feel. Easy access to the major route in town means smoother, lower-traffic commutes in and out of the city. Inside, sun-filled living areas, a bright kitchen, a separate bonus family room, and a finished lower level with bar and fireplace offer flexible space for entertaining and everyday living. A large fenced yard adds privacy and room to relax, while owned solar panels provide energy efficiency and long-term savings. A standout opportunity combining lifestyle, convenience, and value

Spacious 4-bed, 2.5-bath single-family home in Winthrop-where coastal living meets effortless access to Boston. Set near Belle Isle Marsh, enjoy kayaking in calm waters, nearby ocean beaches, yacht clubs, and a scenic seaside golf course-all part of Winthrop's rare small-town feel. Easy access to the major route in town means smoother, lower-traffic commutes in and out of the city. Inside, sun-filled living areas, a bright kitchen, a separate bonus family room, and a finished lower level with bar and fireplace offer flexible space for entertaining and everyday living. A large fenced yard adds privacy and room to relax, while owned solar panels provide energy efficiency and long-term savings. A standout opportunity combining lifestyle, convenience, and value