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One of a kind! Queen Anne Victorian. Two blocks from Cottage Park Yacht Club. Over 4,400 square feet of living space with 6 bedrooms, 3.5 fully renovated baths, 2nd floor laundry room and 2 finished basement rooms. Stunning details include high ceilings, hand carved newel posts and mantels, 3 Chelsea tile fireplaces, oak flooring and woodworking, wainscoted staircases, window seat, pocket doors, and butlers pantry. Oversized windows provide an abundance of natural light. Bright kitchen featuring custom cherry cabinetry, Vermont soapstone countertops, and SS appliances, including a Sub-Zero refrigerator and a 6 burner Viking gas range. The almost 15,000 square foot lot has a 2 car garage with ample additional parking, a shed, and large private gazebo area. A beautiful copper finial topping the peak of the turret, clapboards, scalloped shingles, 2 wraparound porches, and perennial gardens add to this gem’s curb appeal. Availalbe for the first time in 30 years.

6 Beds ⋅ 4 Baths ⋅ 73424484 MLS

One of a kind! Queen Anne Victorian. Two blocks from Cottage Park Yacht Club. Over 4,400 square feet of living space with 6 bedrooms, 3.5 fully renovated baths, 2nd floor laundry room and 2 finished basement rooms. Stunning details include high ceilings, hand carved newel posts and mantels, 3 Chelsea tile fireplaces, oak flooring and woodworking, wainscoted staircases, window seat, pocket doors, and butlers pantry. Oversized windows provide an abundance of natural light. Bright kitchen featuring custom cherry cabinetry, Vermont soapstone countertops, and SS appliances, including a Sub-Zero refrigerator and a 6 burner Viking gas range. The almost 15,000 square foot lot has a 2 car garage with ample additional parking, a shed, and large private gazebo area. A beautiful copper finial topping the peak of the turret, clapboards, scalloped shingles, 2 wraparound porches, and perennial gardens add to this gem’s curb appeal. Availalbe for the first time in 30 years.

191 Cottage Park Road, Winthrop

Listing courtesy of Listing Agent: Anthony Giacalone Jr. from Listing Office: Tony's Realty.

$1,650,000

Deal fell through due to buyer's financing. Rare opportunity to own a spacious waterfront duplex offering versatility, income potential, and breathtaking coastal living just minutes from Boston and Logan Airport. This well-designed property features 4+ bedrooms with finished lower levels on each side, each offering three additional rooms--ideal for extended family, home offices, or flexible living space. With potential for an additional unit ADU(Accessory Dwelling Unit), this property presents an outstanding opportunity for multi-generational living or added rental income(buyer to perform due diligence). Two separate newer boilers , the convenience of a 2 car garage and ample storage, all while taking in serene water views and direct access to the shoreline lifestyle Winthrop is known for. Perfectly located near beaches, marinas, restaurants, and public transportation, this gem combines suburban coastal charm with unbeatable proximity to the city. Floor plans attached.

8 Beds ⋅ 7 Baths ⋅ 73465296 MLS

Deal fell through due to buyer's financing. Rare opportunity to own a spacious waterfront duplex offering versatility, income potential, and breathtaking coastal living just minutes from Boston and Logan Airport. This well-designed property features 4+ bedrooms with finished lower levels on each side, each offering three additional rooms--ideal for extended family, home offices, or flexible living space. With potential for an additional unit ADU(Accessory Dwelling Unit), this property presents an outstanding opportunity for multi-generational living or added rental income(buyer to perform due diligence). Two separate newer boilers , the convenience of a 2 car garage and ample storage, all while taking in serene water views and direct access to the shoreline lifestyle Winthrop is known for. Perfectly located near beaches, marinas, restaurants, and public transportation, this gem combines suburban coastal charm with unbeatable proximity to the city. Floor plans attached.

201-203 Cliff Avenue, Winthrop

Listing courtesy of Listing Agent: Constance Doto from Listing Office: Connie Doto Realty Group.

$1,600,000

Welcome to the Highlands, Winthrop’s most coveted neighborhood- where modern design meets sweeping Boston views. This newly renovated two-family sits high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main unit offers an open layout with living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area opening to a skyline deck. A first-floor bedroom, full bath, and mudroom add versatility. Upstairs features three bedrooms, including a luxe primary suite with Juliet balcony, walk-in closet, and spa bath with steam shower, soaking tub, heated floors, and double vanity.The lower-level one-bedroom unit includes its own kitchen, laundry, French doors to the yard, and private entrance—perfect for multi-generational living, au pair, or income. With a tiered backyard, three-car parking, and one of Winthrop’s premier addresses, this home blends sophistication, flexibility, and unmatched city views.

5 Beds ⋅ 4 Baths ⋅ 73458947 MLS

Welcome to the Highlands, Winthrop’s most coveted neighborhood- where modern design meets sweeping Boston views. This newly renovated two-family sits high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main unit offers an open layout with living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area opening to a skyline deck. A first-floor bedroom, full bath, and mudroom add versatility. Upstairs features three bedrooms, including a luxe primary suite with Juliet balcony, walk-in closet, and spa bath with steam shower, soaking tub, heated floors, and double vanity.The lower-level one-bedroom unit includes its own kitchen, laundry, French doors to the yard, and private entrance—perfect for multi-generational living, au pair, or income. With a tiered backyard, three-car parking, and one of Winthrop’s premier addresses, this home blends sophistication, flexibility, and unmatched city views.

144 Quincy Ave, Winthrop

Listing courtesy of Listing Agent: Leighann Eruzione from Listing Office: Lantern Residential.

$1,550,000

Stunning 6-bedroom, 3 full bath single-family home with a private in-law suite offering its own separate entrance and laundry ideal for extended family or additional income potential. Set on a corner lot, this home includes an additional parcel at 16 Elmwood Ave (separate address), adding exceptional value and opportunity. Enjoy beautiful water views from the charming front porch and the primary bedroom. Three finished levels provide flexible living space to fit a variety of needs. The beautifully renovated chef’s kitchen is the centerpiece, showcasing a massive island with seating, coffee bar, and a customized pantry. Opening to a dining area and a warm, inviting living room with fireplace. A fenced backyard and abundant parking complete this rare coastal offering combining seaside serenity with effortless access to Boston.

6 Beds ⋅ 3 Baths ⋅ 73479928 MLS

Stunning 6-bedroom, 3 full bath single-family home with a private in-law suite offering its own separate entrance and laundry ideal for extended family or additional income potential. Set on a corner lot, this home includes an additional parcel at 16 Elmwood Ave (separate address), adding exceptional value and opportunity. Enjoy beautiful water views from the charming front porch and the primary bedroom. Three finished levels provide flexible living space to fit a variety of needs. The beautifully renovated chef’s kitchen is the centerpiece, showcasing a massive island with seating, coffee bar, and a customized pantry. Opening to a dining area and a warm, inviting living room with fireplace. A fenced backyard and abundant parking complete this rare coastal offering combining seaside serenity with effortless access to Boston.

142 Washington Ave, Winthrop

Listing courtesy of Listing Agent: Fritha Burns from Listing Office: Charlesgate Realty Group, llc.

$1,475,000

Custom built in 2021, 38 Nahant Avenue was put together with real attention to detail and the finishes back it up. This home runs on Savant for full smart home control, plus Ring cameras for security. The kitchen is built around a full Thermador appliance package, including three Thermador columns: a full fridge, a full freezer, and a wine fridge. The exterior is Hardie plank with a 7 inch exposure, oversized black Pella windows, a paver driveway and a rear covered deck for year round use. Inside you get 9 foot ceilings on the main level and 10 foot ceilings on the second floor, with 17 in ceiling speakers wired throughout the first floor alone. The primary suite has its own bath with a walk in shower, freestanding tub, and dual vanity. A first floor master suite and an upstairs office with ocean views wrap the the floor plan on the main living levels. Downstairs there is a fully framed out and roughed basement ready for your finishing touches.

4 Beds ⋅ 3 Baths ⋅ 73549582 MLS

Custom built in 2021, 38 Nahant Avenue was put together with real attention to detail and the finishes back it up. This home runs on Savant for full smart home control, plus Ring cameras for security. The kitchen is built around a full Thermador appliance package, including three Thermador columns: a full fridge, a full freezer, and a wine fridge. The exterior is Hardie plank with a 7 inch exposure, oversized black Pella windows, a paver driveway and a rear covered deck for year round use. Inside you get 9 foot ceilings on the main level and 10 foot ceilings on the second floor, with 17 in ceiling speakers wired throughout the first floor alone. The primary suite has its own bath with a walk in shower, freestanding tub, and dual vanity. A first floor master suite and an upstairs office with ocean views wrap the the floor plan on the main living levels. Downstairs there is a fully framed out and roughed basement ready for your finishing touches.

38 Nahant Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

$1,475,000

Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. The units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture.Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

5 Beds ⋅ 3 Baths ⋅ 73541145 MLS

Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. The units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture.Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

516 Pleasant St, Winthrop

Listing courtesy of Listing Agent: Amanda George from Listing Office: Lamacchia Realty, Inc..

$1,331,000

Prime coastal investment opportunity in highly sought-after Winthrop! This 4-family property is directly across from the ocean with beach access and sits on a rare double lot, offering additional outdoor living, or expansion potential. Ideal for investors, owner-occupants, or multi-generational living. Unit 1 features 2 bedrooms. Unit 2 offers 2-3 bedrooms plus a home office w in-unit laundry hookups (could be used as a 3rd bdrm). Unit 3 consists of 3 bedrooms w a 3 seasons porch that views Boston skyline. Unit 4 is a 1-bedroom unit with the best views in the house. The property benefits from its prime coastal location with easy access to the beach, public transportation, restaurants and local amenities. Whether you’re looking to expand your investment portfolio or live by the water while generating income, this property delivers unmatched versatility and location.

8 Beds ⋅ 4 Baths ⋅ 73502452 MLS

Prime coastal investment opportunity in highly sought-after Winthrop! This 4-family property is directly across from the ocean with beach access and sits on a rare double lot, offering additional outdoor living, or expansion potential. Ideal for investors, owner-occupants, or multi-generational living. Unit 1 features 2 bedrooms. Unit 2 offers 2-3 bedrooms plus a home office w in-unit laundry hookups (could be used as a 3rd bdrm). Unit 3 consists of 3 bedrooms w a 3 seasons porch that views Boston skyline. Unit 4 is a 1-bedroom unit with the best views in the house. The property benefits from its prime coastal location with easy access to the beach, public transportation, restaurants and local amenities. Whether you’re looking to expand your investment portfolio or live by the water while generating income, this property delivers unmatched versatility and location.

419 Revere St, Winthrop

Listing courtesy of Listing Agent: Regina McKennon from Listing Office: 117 Realty.

$1,325,000

Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive improvements throughout. The open-concept layout is filled with natural light and showcases a beautifully appointed kitchen with custom cabinetry, quartz countertops, stainless steel appliances, a beverage refrigerator, and a large center island. Occupying the entire third level, the private primary suite offers breathtaking water views, a private balcony, a walk-in closet, and a spa-inspired bath. A rare opportunity to own a thoughtfully reimagined coastal home where panoramic water views, abundant natural light, and extensive recent reconstruction come together in one exceptional setting.

4 Beds ⋅ 3 Baths ⋅ 73534719 MLS

Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive improvements throughout. The open-concept layout is filled with natural light and showcases a beautifully appointed kitchen with custom cabinetry, quartz countertops, stainless steel appliances, a beverage refrigerator, and a large center island. Occupying the entire third level, the private primary suite offers breathtaking water views, a private balcony, a walk-in closet, and a spa-inspired bath. A rare opportunity to own a thoughtfully reimagined coastal home where panoramic water views, abundant natural light, and extensive recent reconstruction come together in one exceptional setting.

89R Upland, Winthrop

Listing courtesy of Listing Agent: David Cody from Listing Office: Orchard Park Realty.

$1,317,500

Located in one of the most desirable neighborhoods in town, this grand home has been the home to 4 generations of the same family since it was built. It has been cherished by the same family for over 100 years. Rich original woodwork and timeless character can be found throughout. Step into the sun-filled enclosed front porch before entering the impressive foyer featuring a stunning quarter-sawn oak staircase. The spacious kitchen offers endless potential for renovation and customization. The second floor features a generous landing, 5 large bedrooms, and a three-quarter bath. The third floor offers three additional spacious rooms plus a bonus area leading to a loft space, providing flexibility for extended living, office, or creative use. Situated on a corner lot with ample backyard space, this property is a rare opportunity to restore and personalize a truly special home.

5 Beds ⋅ 2 Baths ⋅ 73514990 MLS

Located in one of the most desirable neighborhoods in town, this grand home has been the home to 4 generations of the same family since it was built. It has been cherished by the same family for over 100 years. Rich original woodwork and timeless character can be found throughout. Step into the sun-filled enclosed front porch before entering the impressive foyer featuring a stunning quarter-sawn oak staircase. The spacious kitchen offers endless potential for renovation and customization. The second floor features a generous landing, 5 large bedrooms, and a three-quarter bath. The third floor offers three additional spacious rooms plus a bonus area leading to a loft space, providing flexibility for extended living, office, or creative use. Situated on a corner lot with ample backyard space, this property is a rare opportunity to restore and personalize a truly special home.

264 Court Rd, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.

$1,300,000

BACK ON MARKET - buyer's financing fell through! Investors/Savvy buyers looking to build equity…RARE opportunity to purchase a FOUR UNIT property just steps to the ocean in the coastal Town of Winthrop! Each unit offers two bedrooms plus an office/study. Utilities are separate, there is basement storage, a backyard and off street parking for two cars. Conveniently located close to shopping, a variety of fun eateries, bus to the Blue Line, and downtown Boston - this is an excellent opportunity for investors or owner-occupants seeking versatility and long-term value.

8 Beds ⋅ 4 Baths ⋅ 73473238 MLS

BACK ON MARKET - buyer's financing fell through! Investors/Savvy buyers looking to build equity…RARE opportunity to purchase a FOUR UNIT property just steps to the ocean in the coastal Town of Winthrop! Each unit offers two bedrooms plus an office/study. Utilities are separate, there is basement storage, a backyard and off street parking for two cars. Conveniently located close to shopping, a variety of fun eateries, bus to the Blue Line, and downtown Boston - this is an excellent opportunity for investors or owner-occupants seeking versatility and long-term value.

43-45 Ocean Avenue, Winthrop

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.

$1,280,000

HIGHLY DESIREABLE TRIPLE DECKER!! 3 Family INCOME PROPERTY Within Walking Distance to The Beach. Each Unit Boasts 3+ Bedrooms, Large Eat-In Modern Kitchens W/ Plenty of Counter & Cabinet Space, Ceramic Tile Floors in 1st & 3rd Units. 1st Floor Unit Renovated 3 Years Ago Has a Modern Kitchen, Granite Counters, Bathroom w/ Ceramic Tile, Quartz Vanity Top, Full Tub Surround, New Paint, Hardwood & Ceramic Tile Floors. The 3rd Floor Was Renovated Several Years Ago w/ Ceramic Tile Floor in Kitchen & Bathroom, as Well as Full Ceramic in The Bathroom and Full Tub Surround. 2nd Needs Cosmetics. Each unit has a Private Rear Deck & Plenty of Off-Street Parking w/ TWO SEPARATE DRIVEWAYS. Conveniently Located On Bus Line and Minutes From the Blue Line Train Make This EZ Access to BOSTON for Tenants Working Both In Boston & at Logan Airport Who Don't Want to Pay Boston Rents, But Still Want to Be Close to Work, Social Life, Arts etc. RENTS ARE BELOW MARKET FOR FAMILY. MARKET RENTS ARE 3200 PER UNIT

9 Beds ⋅ 3 Baths ⋅ 73531573 MLS

HIGHLY DESIREABLE TRIPLE DECKER!! 3 Family INCOME PROPERTY Within Walking Distance to The Beach. Each Unit Boasts 3+ Bedrooms, Large Eat-In Modern Kitchens W/ Plenty of Counter & Cabinet Space, Ceramic Tile Floors in 1st & 3rd Units. 1st Floor Unit Renovated 3 Years Ago Has a Modern Kitchen, Granite Counters, Bathroom w/ Ceramic Tile, Quartz Vanity Top, Full Tub Surround, New Paint, Hardwood & Ceramic Tile Floors. The 3rd Floor Was Renovated Several Years Ago w/ Ceramic Tile Floor in Kitchen & Bathroom, as Well as Full Ceramic in The Bathroom and Full Tub Surround. 2nd Needs Cosmetics. Each unit has a Private Rear Deck & Plenty of Off-Street Parking w/ TWO SEPARATE DRIVEWAYS. Conveniently Located On Bus Line and Minutes From the Blue Line Train Make This EZ Access to BOSTON for Tenants Working Both In Boston & at Logan Airport Who Don't Want to Pay Boston Rents, But Still Want to Be Close to Work, Social Life, Arts etc. RENTS ARE BELOW MARKET FOR FAMILY. MARKET RENTS ARE 3200 PER UNIT

117 Revere St, Winthrop

Listing courtesy of Listing Agent: Peter Marino from Listing Office: Peter A. Marino Realty.

$1,260,000

Winthrop -Hard to Find 3 Family Home - Ocean views from this 3 -Family Home located on quiet one-way street with short walk to the ocean in Winthrop. The first floor unit has kitchen, living room, 2 bedrooms & 1 bath. The second floor unit has kitchen, living room, 3 Bedrooms, 1 bath, washer & dryer in unit. The third floor unit has kitchen, living room, 2 bedrooms, office or den, 1 bath, washer & dryer in unit. All three units have modern kitchens, hardwood floors, porches, plenty of parking for 6+ cars off street, plus new asphalt roof. Just minutes to seaside walking and bike baths on Winthrop Beach.

8 Beds ⋅ 3 Baths ⋅ 73457896 MLS

Winthrop -Hard to Find 3 Family Home - Ocean views from this 3 -Family Home located on quiet one-way street with short walk to the ocean in Winthrop. The first floor unit has kitchen, living room, 2 bedrooms & 1 bath. The second floor unit has kitchen, living room, 3 Bedrooms, 1 bath, washer & dryer in unit. The third floor unit has kitchen, living room, 2 bedrooms, office or den, 1 bath, washer & dryer in unit. All three units have modern kitchens, hardwood floors, porches, plenty of parking for 6+ cars off street, plus new asphalt roof. Just minutes to seaside walking and bike baths on Winthrop Beach.

37 Trident Ave, Winthrop

Listing courtesy of Listing Agent: David Parish from Listing Office: Connor Real Estate.

$1,250,000

Stunning turn of the century three family home in a prime commuter location! Unit 1 &3 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.

7 Beds ⋅ 3 Baths ⋅ 73510154 MLS

Stunning turn of the century three family home in a prime commuter location! Unit 1 &3 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.

22 Adams St, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.

$1,240,000

Well-located 4-family investment property in the heart of Winthrop’s Cottage Hill neighborhood. 10–12 Charles Street offers four separately metered units totaling 3,688 square feet on a 6,127 sq ft lot, with strong in-place income and upside. The unit mix consists of two larger units and two one-bedroom units, appealing to both long-term renters and owner-occupants seeking supplemental income. Current rents total approximately $8,550 per month, with additional room for optimization over time. The property features off-street parking for six vehicles, a major value driver in this coastal submarket, along with a full unfinished basement ideal for storage and future improvements. Several units have been refreshed, providing a solid balance of immediate cash flow and long-term capital improvement potential. Located just blocks from the ocean, public transportation, schools, and Winthrop Center amenities, this asset benefits from strong rental demand driven by proximity to Boston & Logan.

7 Beds ⋅ 4 Baths ⋅ 73475129 MLS

Well-located 4-family investment property in the heart of Winthrop’s Cottage Hill neighborhood. 10–12 Charles Street offers four separately metered units totaling 3,688 square feet on a 6,127 sq ft lot, with strong in-place income and upside. The unit mix consists of two larger units and two one-bedroom units, appealing to both long-term renters and owner-occupants seeking supplemental income. Current rents total approximately $8,550 per month, with additional room for optimization over time. The property features off-street parking for six vehicles, a major value driver in this coastal submarket, along with a full unfinished basement ideal for storage and future improvements. Several units have been refreshed, providing a solid balance of immediate cash flow and long-term capital improvement potential. Located just blocks from the ocean, public transportation, schools, and Winthrop Center amenities, this asset benefits from strong rental demand driven by proximity to Boston & Logan.

10-12 Charles St, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

$1,180,000

Panoramic breathtaking views offered with this oceanfront Contemporary home via wall of windows & 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 & is open to the kitchen designed for both functionality & 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 & 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 & is plumbed for a bath. Paved drive for off street parking, access to beach from lower level. Enjoy the seasons from your ocean front home!

3 Beds ⋅ 2 Baths ⋅ 73529299 MLS

Panoramic breathtaking views offered with this oceanfront Contemporary home via wall of windows & 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 & is open to the kitchen designed for both functionality & 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 & 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 & is plumbed for a bath. Paved drive for off street parking, access to beach from lower level. Enjoy the seasons from your ocean front home!

32 Faun Bar Avenue, Winthrop

Listing courtesy of Listing Agent: Evelyn Rockas from Listing Office: Coldwell Banker Realty - Lynnfield.

$1,175,000

In the sought after Winthrop HIGHLANDS you'll find this quality built THREE FAMILY home. This is your opportunity to become an owner occupied investor! Each unit features a comfortable layout with a generous amount of natural light and functional living spaces. The first floor has three bedrooms, second floor one and the third unit is on two levels with two bedrooms. The property has been well maintained and offers separate utilities, one off street parking space, and a nicely landscaped backyard. You'll enjoy beautiful ocean views and it's just steps to Halford Beach. Pride of ownership is evident throughout. Winthrop by the Sea is just six miles to Boston, has a variety of wonderful restaurants, walk/jog trails, access to the Blue Line and close to Logan Airport - 22 Upland Road is an outstanding opportunity to own a home and collect rental income in one smart investment,

6 Beds ⋅ 4 Baths ⋅ 73473241 MLS

In the sought after Winthrop HIGHLANDS you'll find this quality built THREE FAMILY home. This is your opportunity to become an owner occupied investor! Each unit features a comfortable layout with a generous amount of natural light and functional living spaces. The first floor has three bedrooms, second floor one and the third unit is on two levels with two bedrooms. The property has been well maintained and offers separate utilities, one off street parking space, and a nicely landscaped backyard. You'll enjoy beautiful ocean views and it's just steps to Halford Beach. Pride of ownership is evident throughout. Winthrop by the Sea is just six miles to Boston, has a variety of wonderful restaurants, walk/jog trails, access to the Blue Line and close to Logan Airport - 22 Upland Road is an outstanding opportunity to own a home and collect rental income in one smart investment,

22 Upland Road, Winthrop

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.

$1,150,000

One of a kind. 10+ rooms of meticulousness combining warmth and character. Built 1925 in the New England coastal Maze area, nearby Cottage Park Yacht Club. 3 solid wood entry doors lead to amazing flow on main level with sunny exposures thru oversized windows. Designed by MIT architect John Whitmore. Flood insurance is NOT required in this sought after location. Gas fireplace in living room adds to ambience. Talented master woodworker CUSTOM designed the perfect kitchen with stainless steel, abundant cabinets for storage +butlers pantry. Kitchen Opens to Fantastic ADDITION featuring wooden beams, exposed brick fireplace wall, built ins, skylights and picture window overlooking exquisite tree species. Bonus 1/2 bath on main level. 6 spacious bedrooms (home offices/gym) plus 2 full bathrooms. UPDATED electric and plumbing. 3 heating zones and cooling. 3 car parking in driveway. A seaside paradise ideal for dog walks,beaching, boating. Short distance to vibrant town center + Boston.

6 Beds ⋅ 3 Baths ⋅ 73427022 MLS

One of a kind. 10+ rooms of meticulousness combining warmth and character. Built 1925 in the New England coastal Maze area, nearby Cottage Park Yacht Club. 3 solid wood entry doors lead to amazing flow on main level with sunny exposures thru oversized windows. Designed by MIT architect John Whitmore. Flood insurance is NOT required in this sought after location. Gas fireplace in living room adds to ambience. Talented master woodworker CUSTOM designed the perfect kitchen with stainless steel, abundant cabinets for storage +butlers pantry. Kitchen Opens to Fantastic ADDITION featuring wooden beams, exposed brick fireplace wall, built ins, skylights and picture window overlooking exquisite tree species. Bonus 1/2 bath on main level. 6 spacious bedrooms (home offices/gym) plus 2 full bathrooms. UPDATED electric and plumbing. 3 heating zones and cooling. 3 car parking in driveway. A seaside paradise ideal for dog walks,beaching, boating. Short distance to vibrant town center + Boston.

66 Lowell Road, Winthrop

Listing courtesy of Listing Agent: Stacey Steck from Listing Office: Gibson Sotheby's International Realty.

$1,141,500

Located just steps from the Atlantic, 24 Trident Ave delivers the rare combination of ocean lifestyle and investment fundamentals that rarely surfaces at this price point just minutes from Boston. This property delivers immediate income and serious long-term upside. Two leased (TAW) units generate $4,300/mo with the first-floor updated unit delivered vacant — perfect for an owner-occupant who wants tenants covering the mortgage from day one. This well-maintained 3-family sits less than a tenth of a mile to the beach, with ocean views from the upper floors. Each unit is laid out across a single floor with 3 bedrooms, a full bath, and 7 rooms — the kind of space that keeps good tenants in place. Three off-street parking spaces come with the property, and a full unfinished basement adds storage that owners and tenants will both put to use. Downtown Boston, Logan Airport, Route 1A, and public transportation are all minutes away, making this a prime opportunity that won't last.

10 Beds ⋅ 3 Baths ⋅ 73510613 MLS

Located just steps from the Atlantic, 24 Trident Ave delivers the rare combination of ocean lifestyle and investment fundamentals that rarely surfaces at this price point just minutes from Boston. This property delivers immediate income and serious long-term upside. Two leased (TAW) units generate $4,300/mo with the first-floor updated unit delivered vacant — perfect for an owner-occupant who wants tenants covering the mortgage from day one. This well-maintained 3-family sits less than a tenth of a mile to the beach, with ocean views from the upper floors. Each unit is laid out across a single floor with 3 bedrooms, a full bath, and 7 rooms — the kind of space that keeps good tenants in place. Three off-street parking spaces come with the property, and a full unfinished basement adds storage that owners and tenants will both put to use. Downtown Boston, Logan Airport, Route 1A, and public transportation are all minutes away, making this a prime opportunity that won't last.

24 Trident Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

$1,140,000

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!!

6 Beds ⋅ 4 Baths ⋅ 73460507 MLS

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!!

47 Bellevue Ave, Winthrop

Listing courtesy of Listing Agent: Jessica Pumphret from Listing Office: Blue Sky Realty.

$1,107,000

Winthrop is one of the last undervalued waterfront towns in Greater Boston, and opportunities like this don't sit long. 11 Pearl Ave is a vacant 3-family just a block from the ocean, generating $10,500/month at market rents with zero displacement headaches. Three floors, 11 bedrooms total, 4,032 sq ft of income-producing space on a town where the average days on market keeps shrinking. 3 separate heat systems, and 200-amp electric. Flood insurance runs about $2,600/year. Live in one, rent two, or hold all three. Priced at $1,050,000 with a cap rate that pencils with room for improvement and valuate add. Don't sleep on Winthrop.

11 Beds ⋅ 3 Baths ⋅ 73491764 MLS

Winthrop is one of the last undervalued waterfront towns in Greater Boston, and opportunities like this don't sit long. 11 Pearl Ave is a vacant 3-family just a block from the ocean, generating $10,500/month at market rents with zero displacement headaches. Three floors, 11 bedrooms total, 4,032 sq ft of income-producing space on a town where the average days on market keeps shrinking. 3 separate heat systems, and 200-amp electric. Flood insurance runs about $2,600/year. Live in one, rent two, or hold all three. Priced at $1,050,000 with a cap rate that pencils with room for improvement and valuate add. Don't sleep on Winthrop.

11 Pearl Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

$1,100,000

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.

3 Beds ⋅ 2 Baths ⋅ 73510262 MLS

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.

21 Sewall Ave, Winthrop

Listing courtesy of Listing Agent: Jodi Dilorenzo from Listing Office: Century 21 North East.

$1,065,000

The street name; 'Harbor View Ave" says it all! Sweeping unobstructed views of the open ocean, Boston Harbor, & city skyline! Nestled atop one of Winthrop’s highest elevations, delivering a rare combination of breathtaking coastal scenery & beach access. This sun-drenched 3 unit home offers 4 bedrooms, 3 full baths, garage parking, making it ideal for homeowners, developers, or investors. From every room, take in panoramic ocean views, watch the sunrise over the Atlantic, ships in the harbor, and the Boston skyline glittering at night. Just feet away, public stairs directly to Yirrell Beach. At the end of the street, Winthrop Yacht Club offers even more coastal lifestyle perks. Whether you choose to expand, develop, or convert to condos (buyer to perform their own due diligence), this property offers unmatched value and vision. Elevated above flood zone, you'll enjoy peace of mind with views that rival any along the New England coast—all just minutes from Boston!

4 Beds ⋅ 3 Baths ⋅ 73443354 MLS

The street name; 'Harbor View Ave" says it all! Sweeping unobstructed views of the open ocean, Boston Harbor, & city skyline! Nestled atop one of Winthrop’s highest elevations, delivering a rare combination of breathtaking coastal scenery & beach access. This sun-drenched 3 unit home offers 4 bedrooms, 3 full baths, garage parking, making it ideal for homeowners, developers, or investors. From every room, take in panoramic ocean views, watch the sunrise over the Atlantic, ships in the harbor, and the Boston skyline glittering at night. Just feet away, public stairs directly to Yirrell Beach. At the end of the street, Winthrop Yacht Club offers even more coastal lifestyle perks. Whether you choose to expand, develop, or convert to condos (buyer to perform their own due diligence), this property offers unmatched value and vision. Elevated above flood zone, you'll enjoy peace of mind with views that rival any along the New England coast—all just minutes from Boston!

41 Harbor View Ave, Winthrop

Listing courtesy of Listing Agent: Brian Perrin from Listing Office: Brian J. Perrin Real Estate.

$1,050,000

Don’t miss this luxury oceanfront penthouse style condo with unbeatable views in one of Winthrop’s most sought after neighborhoods. Enjoy sunset views from BOTH your ocean private decks, perfect for relaxing or entertaining overlooking the Atlantic. Gutted & converted in 2022 from top to bottom, 191 Court has modern smart-home features including smart thermostats, WiFi-connected blinds, and Ring security system for comfort & energy efficiency. Take in the expansive floor plan beaming with sunlight & original restored hardwood floors throughout. The kitchen features top of the line smart appliances, a wine fridge & oversized island opening to the living room. Custom shutters & blinds hang on every window. Each bedroom features custom California closets, stunning on suites, and the main living space has a view of the ocean, no matter what window you look out. The current sellers have enjoyed living here for years, and you will too. Do not miss 191 Court Road!

4 Beds ⋅ 4 Baths ⋅ 73454724 MLS

Don’t miss this luxury oceanfront penthouse style condo with unbeatable views in one of Winthrop’s most sought after neighborhoods. Enjoy sunset views from BOTH your ocean private decks, perfect for relaxing or entertaining overlooking the Atlantic. Gutted & converted in 2022 from top to bottom, 191 Court has modern smart-home features including smart thermostats, WiFi-connected blinds, and Ring security system for comfort & energy efficiency. Take in the expansive floor plan beaming with sunlight & original restored hardwood floors throughout. The kitchen features top of the line smart appliances, a wine fridge & oversized island opening to the living room. Custom shutters & blinds hang on every window. Each bedroom features custom California closets, stunning on suites, and the main living space has a view of the ocean, no matter what window you look out. The current sellers have enjoyed living here for years, and you will too. Do not miss 191 Court Road!

191 Court Rd Unit 3, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

$999,900

This spacious multi-family offers 7 bedrooms and 3 full baths across 3,628 sq ft, with high ceilings on a 6,429 sq ft lot. Rarely available in Winthrop, it delivers exceptional size, flexibility, and strong rental potential. A cabin-style garage plus a driveway for 4 cars adds convenience, while the lot provides inviting outdoor space. Interiors are well maintained and move-in ready.The first-floor unit features 6 rooms and a full bath. The second unit spans two levels, offering 8 rooms and 2 full baths: the second floor includes the main living space, while the third floor adds additional rooms, a full bath, skylights, and wood floors, ideal for extended family or a private guest suite.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking strong income potential.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking income potential.

7 Beds ⋅ 3 Baths ⋅ 73508785 MLS

This spacious multi-family offers 7 bedrooms and 3 full baths across 3,628 sq ft, with high ceilings on a 6,429 sq ft lot. Rarely available in Winthrop, it delivers exceptional size, flexibility, and strong rental potential. A cabin-style garage plus a driveway for 4 cars adds convenience, while the lot provides inviting outdoor space. Interiors are well maintained and move-in ready.The first-floor unit features 6 rooms and a full bath. The second unit spans two levels, offering 8 rooms and 2 full baths: the second floor includes the main living space, while the third floor adds additional rooms, a full bath, skylights, and wood floors, ideal for extended family or a private guest suite.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking strong income potential.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking income potential.

308 Bowdoin, Winthrop

Listing courtesy of Listing Agent: The Liriano Team from Listing Office: Liriano Realty.

$995,000

AMAZING 2 family home that just was updated inside and out! THE LOCATION IS PERFECT side street loca in Winthrop Center & just 1/2 mile to the beach. It will be delivered vacant & ready to MOVE RIGHT INTO. The larger unit (2nd & 3rd Flr) has 4 bedrooms and it's own private rear deck & enclosed front porch. The 1st floor unit is 3 bedrooms & has it's own deck. All decks are maintenance-free composite decks, yard is fenced in, shed for storage, Beautiful lot with a new block wall, & more. Roof is newer, and all utilities are SEPERATE! One of the heating systems is a wall-mount gas Navien system! Washer & dryer hookups in each unit. All appliances are BRAND NEW - never been used. Although it is an older home with "older stuff" - you can move right in without even picking up a paint brush. Located within walking distance to coffee shops, restaurants, schools and parks offering both convenience and town center charm. SELLER PAYING FOR 1 YR HOME WARRANTY!

7 Beds ⋅ 2 Baths ⋅ 73470613 MLS

AMAZING 2 family home that just was updated inside and out! THE LOCATION IS PERFECT side street loca in Winthrop Center & just 1/2 mile to the beach. It will be delivered vacant & ready to MOVE RIGHT INTO. The larger unit (2nd & 3rd Flr) has 4 bedrooms and it's own private rear deck & enclosed front porch. The 1st floor unit is 3 bedrooms & has it's own deck. All decks are maintenance-free composite decks, yard is fenced in, shed for storage, Beautiful lot with a new block wall, & more. Roof is newer, and all utilities are SEPERATE! One of the heating systems is a wall-mount gas Navien system! Washer & dryer hookups in each unit. All appliances are BRAND NEW - never been used. Although it is an older home with "older stuff" - you can move right in without even picking up a paint brush. Located within walking distance to coffee shops, restaurants, schools and parks offering both convenience and town center charm. SELLER PAYING FOR 1 YR HOME WARRANTY!

72 Fremont St, Winthrop

Listing courtesy of Listing Agent: from Listing Office: Proactive Realty.

$994,000

Experience coastal living at its finest at 156 Locust Street. Just steps from the beach, this beautifully renovated 5-bedroom, 3-bathroom home offers over 2,500 square feet of stylish living space with ocean views and exceptional indoor-outdoor living. Renovated in 2022, the home blends modern luxury with timeless coastal charm. The stunning primary suite provides a private retreat, while a versatile first-floor fifth bedroom offers flexibility as a home office, bonus room, guest space, or playroom. Enjoy central air, sun-filled living spaces, and seamless access to the private fenced backyard and expansive deck, perfect for entertaining or relaxing after a day at the beach. Recent updates include heating systems (2024 & 2025), a hot water heater (2025), and upgraded 200-amp electrical service. Wake up to ocean views from the front balcony and enjoy a turnkey coastal lifestyle in one of Winthrop's most desirable seaside locations.

5 Beds ⋅ 3 Baths ⋅ 73541368 MLS

Experience coastal living at its finest at 156 Locust Street. Just steps from the beach, this beautifully renovated 5-bedroom, 3-bathroom home offers over 2,500 square feet of stylish living space with ocean views and exceptional indoor-outdoor living. Renovated in 2022, the home blends modern luxury with timeless coastal charm. The stunning primary suite provides a private retreat, while a versatile first-floor fifth bedroom offers flexibility as a home office, bonus room, guest space, or playroom. Enjoy central air, sun-filled living spaces, and seamless access to the private fenced backyard and expansive deck, perfect for entertaining or relaxing after a day at the beach. Recent updates include heating systems (2024 & 2025), a hot water heater (2025), and upgraded 200-amp electrical service. Wake up to ocean views from the front balcony and enjoy a turnkey coastal lifestyle in one of Winthrop's most desirable seaside locations.

156 Locust St, Winthrop

Listing courtesy of Listing Agent: The Jenkins Group from Listing Office: Keller Williams Realty.

$990,000

Outstanding Winthrop investment opportunity offering strong income potential in a highly desirable coastal community. This newly renovated two-family property features two spacious units (2BR and 4BR), ideal for owner-occupants seeking rental income or investors looking to expand their portfolio. Both units provide modern living with off-street parking for four vehicles total. Conveniently located just minutes from major highways, public transportation, shopping, beaches, and local schools, this property combines location, flexibility, and long-term upside in one exceptional offering.1st Open House Sat FEB 28TH (12-2 PM)

6 Beds ⋅ 2 Baths ⋅ 73480670 MLS

Outstanding Winthrop investment opportunity offering strong income potential in a highly desirable coastal community. This newly renovated two-family property features two spacious units (2BR and 4BR), ideal for owner-occupants seeking rental income or investors looking to expand their portfolio. Both units provide modern living with off-street parking for four vehicles total. Conveniently located just minutes from major highways, public transportation, shopping, beaches, and local schools, this property combines location, flexibility, and long-term upside in one exceptional offering.1st Open House Sat FEB 28TH (12-2 PM)

50-52 Wilshire St, Winthrop

Listing courtesy of Listing Agent: Lou Markakis from Listing Office: Lynnway Associates.

$975,000

Welcome to 5 Quincy Avenue, an architecturally stunning Bungalow located in Winthrop's highly sought-after Highlands neighborhood . This sun-filled 3-bedroom, 2-bath Craftsman home has an open-concept living and dining area featuring original rich oak woodwork, built-in cabinets, hardwood floors, decorative molding, wainscoting, fireplace and a New Furnace! The renovated eat-in kitchen, equipped with stainless steel appliances and marble countertops, overlooks a private backyard with an inground heated swimming pool, ideal for summer entertaining. The home's classic details are beautifully complemented by contemporary elements. Both renovated baths feature marble and subway tile. Ample storage is available throughout the property. The home also features a large front porch with partial ocean views, an attached one-car garage, and a two-car driveway. Easy access to Boston only six miles away. Experience the feeling of living like you are on vacation in this sea side community.

3 Beds ⋅ 2 Baths ⋅ 73447236 MLS

Welcome to 5 Quincy Avenue, an architecturally stunning Bungalow located in Winthrop's highly sought-after Highlands neighborhood . This sun-filled 3-bedroom, 2-bath Craftsman home has an open-concept living and dining area featuring original rich oak woodwork, built-in cabinets, hardwood floors, decorative molding, wainscoting, fireplace and a New Furnace! The renovated eat-in kitchen, equipped with stainless steel appliances and marble countertops, overlooks a private backyard with an inground heated swimming pool, ideal for summer entertaining. The home's classic details are beautifully complemented by contemporary elements. Both renovated baths feature marble and subway tile. Ample storage is available throughout the property. The home also features a large front porch with partial ocean views, an attached one-car garage, and a two-car driveway. Easy access to Boston only six miles away. Experience the feeling of living like you are on vacation in this sea side community.

5 Quincy Avenue, Winthrop

Listing courtesy of Listing Agent: William R. Raye from Listing Office: William Raveis R.E. & Home Services.

$965,000

OPEN HOUSE CANCELED! Welcome to the Highlands, where coastal living meets modern comfort. This beautifully maintained single-family offers water views, thoughtfully updated living spaces, and the flexibility today's buyers desire. The sun-filled main level features gleaming hardwood floors throughout, an upgraded kitchen, and an open layout that flows seamlessly to the spacious rear deck overlooking the fenced backyard with a private hot tub—perfect for entertaining or relaxing. Upstairs, the spacious primary suite offers a generous walk-in closet, while two additional bedrooms provide comfortable accommodations. The finished lower level provides versatile bonus living space ideal for a family room, home office, gym, or guest suite. Enjoy the best of indoor-outdoor living with inviting spaces designed for both everyday comfort and effortless entertaining. Just moments from the beach, this move-in-ready home combines modern updates, flexible living space, and an exceptional location.

3 Beds ⋅ 3 Baths ⋅ 73550478 MLS

OPEN HOUSE CANCELED! Welcome to the Highlands, where coastal living meets modern comfort. This beautifully maintained single-family offers water views, thoughtfully updated living spaces, and the flexibility today's buyers desire. The sun-filled main level features gleaming hardwood floors throughout, an upgraded kitchen, and an open layout that flows seamlessly to the spacious rear deck overlooking the fenced backyard with a private hot tub—perfect for entertaining or relaxing. Upstairs, the spacious primary suite offers a generous walk-in closet, while two additional bedrooms provide comfortable accommodations. The finished lower level provides versatile bonus living space ideal for a family room, home office, gym, or guest suite. Enjoy the best of indoor-outdoor living with inviting spaces designed for both everyday comfort and effortless entertaining. Just moments from the beach, this move-in-ready home combines modern updates, flexible living space, and an exceptional location.

50 Floyd St, Winthrop

Listing courtesy of Listing Agent: Leighann Eruzione from Listing Office: Bowdoin Real Estate Partners.

$960,000

A forever home that doubles as your summer escape. Located in one of Winthrop's most desirable neighborhoods, this beautifully renovated single-family home offers three levels of coastal living. Step through the foyer and you’re greeted by soaring ceilings, a statement fireplace, and a dining space designed for memorable family dinners and entertaining alike. The chef’s kitchen steals the show with quartzite countertops, custom cabinetry, a professional grade Thermador gas range and water views. Completing the main level is a cozy den and heated sunroom. Upstairs offers four spacious bedrooms and a beautifully renovated full bath, while the entire third floor functions as a private guest suite complete with full bathroom and flex space ideal for a home officet, gym, or Peloton setup. Enjoy close proximity to Yirrell Beach, Ingleside Park, Belle Isle Seafood, The Half Cookie, Orient Heights Station, and and countless local cafés and restaurants - all just 6 miles from Boston

5 Beds ⋅ 2 Baths ⋅ 73518328 MLS

A forever home that doubles as your summer escape. Located in one of Winthrop's most desirable neighborhoods, this beautifully renovated single-family home offers three levels of coastal living. Step through the foyer and you’re greeted by soaring ceilings, a statement fireplace, and a dining space designed for memorable family dinners and entertaining alike. The chef’s kitchen steals the show with quartzite countertops, custom cabinetry, a professional grade Thermador gas range and water views. Completing the main level is a cozy den and heated sunroom. Upstairs offers four spacious bedrooms and a beautifully renovated full bath, while the entire third floor functions as a private guest suite complete with full bathroom and flex space ideal for a home officet, gym, or Peloton setup. Enjoy close proximity to Yirrell Beach, Ingleside Park, Belle Isle Seafood, The Half Cookie, Orient Heights Station, and and countless local cafés and restaurants - all just 6 miles from Boston

57 Loring Rd, Winthrop

Listing courtesy of Listing Agent: Dmitriy Khesin from Listing Office: Rise Signature Homes.

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