Winthrop, MA Homes

/11
Est $337,049 Not Listed For Sale
- 2 Beds
- 1 Bath
- 714 Sq Ft
300 Governors Dr Unit 4, Winthrop, MA 02152

300 Governors Dr Unit 4, Winthrop, MA 02152

/42
$639,000 Pending
- 4 Beds
- 2 Baths
- 1,483 Sq Ft
54 Townsend St, Winthrop, MA 02152

Welcome to this delightful charming home located in the highly sought-after Point Shirley section of Winthrop.With 7+ rooms, 3+ bdrms, and 13⁄4 baths, this lovingly maintained home offers timeless character and stunning views. Begin your day on the charming front porch perfect for morning coffee, a good book, or an evening beverage while soaking in the coastal scenery. Inside, the living room

Cathie Curran Charlesgate Realty Group, llc

54 Townsend St, Winthrop, MA 02152
/32
$850,000 Sold Jul 17, 2025
- 1,998 Sq Ft
- $425/SF
- 12 Days On Market
- 3 Beds
- 2 Baths
- Built 1900
81 Lowell Rd, Winthrop, MA 02152

Charming seaside living awaits at 81 Lowell Road in Winthrop- this neighborhood is a hidden gem! This beautifully maintained 3-bedroom, 2-bath home blends classic character with modern updates like 2024 central HVAC. Enjoy a sun-filled living and dining room, updated kitchen with stainless steel appliances, gas range, and hardwood floors throughout. Upstairs, the bright bedrooms have spacious

Randall Horn Entourage Realty LLC

81 Lowell Rd, Winthrop, MA 02152

/12
Est $335,280 Not Listed For Sale
- 2 Beds
- 1 Bath
- 772 Sq Ft
200 Governors Dr Unit 6, Winthrop, MA 02152

200 Governors Dr Unit 6, Winthrop, MA 02152

/29
$635,000 Pending
- 3 Beds
- 1 Bath
- 1,614 Sq Ft
55 Johnson Ave Unit 1, Winthrop, MA 02152

Welcome to 55 Johnson Ave, a beautifully renovated condo offering a clean, modern aesthetic in one of Winthrop’s most sought-after seaside neighborhoods. Just blocks from the beach, this thoughtfully updated home blends comfort, functionality, and coastal charm in a vibrant community setting. Step inside to discover a bright and inviting living space featuring refinished hardwood floors, a

Nick Murphy Compass

55 Johnson Ave Unit 1, Winthrop, MA 02152
/36
$691,000 Sold Jul 15, 2025
- 1,986 Sq Ft
- $348/SF
- 62 Days On Market
- 4 Beds
- 2 Baths
- Built 1910
226 Court Rd Unit 226, Winthrop, MA 02152

Rare find in the desirable Maze Area! Renovated in 2020 this 2nd-floor condo with private entrance offers 2 levels, garage, and a move-in ready layout to enjoy the summer breezes. Updates include a newer furnace, roof, and plumbing. The spacious front deck features ocean views. The main level offers a living room with fireplace, and wall scones, dining room with built-in, mini-split A/C and a

Elizabeth Ferrara Cottage Hill Real Estate

226 Court Rd Unit 226, Winthrop, MA 02152

/19
Est $369,943 Not Listed For Sale
- 2 Beds
- 1 Bath
- 780 Sq Ft
100 Governors Dr Unit 16, Winthrop, MA 02152

100 Governors Dr Unit 16, Winthrop, MA 02152

/35
$850,000 Pending
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
89-91 Sagamore Ave, Winthrop, MA 02152

Welcome to this well-maintained 2-family property located in the desirable Lower Highlands neighborhood of Winthrop by the Sea. This home is just a short stroll to the beach, shops and local dining! Perfect for homeowners seeking rental income or investors alike! The main unit features 3 bedrooms, 1 bathroom, and a bright, open, inviting living area. A finished family room and half bath on the

Christine D'Ambrosio Lantern Residential

89-91 Sagamore Ave, Winthrop, MA 02152
/27
$800,000 Sold Jul 14, 2025
- 1,769 Sq Ft
- $452/SF
- 41 Days On Market
- 4 Beds
- 2 Baths
- Built 1912
77 Otis St, Winthrop, MA 02152

Welcome to coastal living on Point Shirley. This beautifully renovated 4BD, 2BA home invites you to slow down and enjoy life by the beach. Start your day watching the sun rise from your yoga/sunroom, or with a cup of coffee on your front porch. With tall ceilings and an open-concept layout you'll have sight lines from the living room to the dining room to the modern kitchen with quartz counters,

Molly Walker Coldwell Banker Realty - Scituate

77 Otis St, Winthrop, MA 02152

/24
Est $351,645 Not Listed For Sale
- 2 Beds
- 1 Bath
- 780 Sq Ft
100 Governors Dr Unit 15, Winthrop, MA 02152

100 Governors Dr Unit 15, Winthrop, MA 02152

/40
$559,900 Pending
- 3 Beds
- 2 Baths
- 1,724 Sq Ft
41 Sargent St, Winthrop, MA 02152

Welcome home to 41 Sargent Street. Set on one of Winthrop’s most desirable picturesque tree-lined streets and just a short walk to the ocean, this 3 Bed, 2 Bath lovely Colonial is just waiting to be lovingly restored for it's next chapter. Offering convenience and charm and a thoughtful flow throughout. With a large sun-filled kitchen, 1st floor laundry & full bath, and a vast & versatile living

Erin Dinsmoor Keller Williams Realty Metropolitan

41 Sargent St, Winthrop, MA 02152
/28
$678,000 Sold Jul 14, 2025
- 1,372 Sq Ft
- $494/SF
- 12 Days On Market
- 3 Beds
- 2 Baths
- Built 1949
183 Pauline St, Winthrop, MA 02152

Welcome to 183 Pauline St. in the desirable town of Winthrop. Owned by the same family for generations, this 3 bed, 2 bath cape cod style home is in need of some updating but has much to offer. Mostly hardwood flooring throughout with picture windows in living/dining room, kitchen that leads to the deck overlooking level backyard, primary bedroom & full bath complete the first level. Second level

Jared Freni RE/MAX Andrew Realty Services

183 Pauline St, Winthrop, MA 02152

/19
Est $349,493 Not Listed For Sale
- 2 Beds
- 1 Bath
- 782 Sq Ft
1100 Governors Dr Unit 19, Winthrop, MA 02152

1100 Governors Dr Unit 19, Winthrop, MA 02152

/32
$594,900 Pending
- 2 Beds
- 2 Baths
- 985 Sq Ft
10 Somerset Ave Unit 206, Winthrop, MA 02152

Welcome to The Somerset—Winthrop’s newest boutique condo development, where coastal charm meets modern luxury. This spacious 2-bedroom, 2-bath home is designed for effortless living, featuring a sun-drenched open layout, private balcony, and oversized walk-in wardrobes in both bedrooms. Enjoy a sleek kitchen with stainless steel appliances, quartz countertops, and soft-close cabinetry, flowing

Charlesgate New Development Team Charlesgate Realty Group, llc

10 Somerset Ave Unit 206, Winthrop, MA 02152
/28
$520,000 Sold Jul 11, 2025
- 1,219 Sq Ft
- $427/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 1880
30 Crystal Cove Ave Unit 2, Winthrop, MA 02152

Nestled in Winthrop’s sought-after Crystal Cove neighborhood, this beautifully maintained two-level condo perfectly combines timeless character with stylish comfort. A grand staircase serves as the home’s architectural showpiece, adding elegance and a sense of grandeur. The sun-filled unit features an updated kitchen, two bedrooms and renovated bathrooms offering modern finishes and

Erica Gore Century 21 Seaport

30 Crystal Cove Ave Unit 2, Winthrop, MA 02152

/20
Est $320,878 Not Listed For Sale
- 2 Beds
- 1 Bath
- 772 Sq Ft
1100 Governors Dr Unit 1, Winthrop, MA 02152

1100 Governors Dr Unit 1, Winthrop, MA 02152

/20
$383,000 Pending
- 1 Bed
- 1 Bath
- 475 Sq Ft
10 Somerset Ave Unit 403, Winthrop, MA 02152

The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage

Charlesgate New Development Team Charlesgate Realty Group, llc

10 Somerset Ave Unit 403, Winthrop, MA 02152
/40
$935,000 Sold Jul 10, 2025
- 2,124 Sq Ft
- $440/SF
- 4 Days On Market
- 4 Beds
- 2 Baths
- Built 1920
96-98 Woodside Ave, Winthrop, MA 02152

Excellent investment or owner-occupant opportunity in the heart of Winthrop! This two-family home features over 2,100 sq. ft. of living space, including a first-floor unit with 6 rooms, 2 bedrooms, and 1 bath, and a second-floor unit with 7 rooms, 2 bedrooms, and 1 bath—providing a total of 13 rooms across both units. The 3rd floor, unfinished walk-up attic is already plumbed and ready for future

John Young Ledge & Young Real Estate

96-98 Woodside Ave, Winthrop, MA 02152

/4
Est $343,304 Not Listed For Sale
- 2 Beds
- 1 Bath
- 811 Sq Ft
1000 Governors Dr Unit 17, Winthrop, MA 02152

1000 Governors Dr Unit 17, Winthrop, MA 02152

/7
$500,000 Pending
- 1 Bed
- 1 Bath
- 633 Sq Ft
10 Somerset Ave Unit 211, Winthrop, MA 02152

Welcome to The Somerset—Winthrop’s newest boutique condo development! This collection of 29 thoughtfully designed homes offers studios, 1-bed, 1+ bed, and 2-bedroom layouts with quality finishes and a coastal vibe. Enjoy open-concept living, stainless steel appliances, quartz countertops, central A/C, and stylish modern touches. Most units include garage parking, and select homes feature private

Charlesgate New Development Team Charlesgate Realty Group, llc

10 Somerset Ave Unit 211, Winthrop, MA 02152
/39
$1,195,000 Sold Jul 07, 2025
- 3,100 Sq Ft
- $385/SF
- 46 Days On Market
- 5 Beds
- 4 Baths
- Built 1915
121 Circuit Rd, Winthrop, MA 02152

Experience elevated coastal living in this exquisitely renovated 5-bed, 2 full-bath, 2 half-bath home in Winthrop. Fully transformed in 2021, it blends timeless charm with modern sophistication across four finished levels. Enjoy the beautiful refinished hardwood floors, in home office space, designer kitchen with quartz countertops, premium finishes, and a pot filler — perfect for cooking and

Joe Quigley Compass

121 Circuit Rd, Winthrop, MA 02152

/33
Est $356,796 Not Listed For Sale
- 2 Beds
- 1 Bath
- 909 Sq Ft
1000 Governors Dr Unit 7, Winthrop, MA 02152

1000 Governors Dr Unit 7, Winthrop, MA 02152

/14
$399,999 Pending
- 2 Beds
- 1 Bath
- 664 Sq Ft
53 Trident Ave Unit 303, Winthrop, MA 02152

Experience coastal living in this updated 2-bedroom, 1-bath condo located just steps from beautiful Winthrop Beach. Situated on the third floor of a well-maintained building, this unit features an eat-in kitchen equipped with stainless steel appliances, an in-unit washer and dryer, and freshly painted interiors. Enjoy the convenience of hardwood floors throughout, beautiful bay windows, and a

Sara Vienneau Rappoli Century 21 North East

53 Trident Ave Unit 303, Winthrop, MA 02152
/34
$575,000 Sold Jul 01, 2025
- 896 Sq Ft
- $642/SF
- 6 Days On Market
- 2 Beds
- 2 Baths
- Built 1925
12 Sewall Ave Unit 1, Winthrop, MA 02152

Exceptional Opportunity in Winthrop's Premier Location!This is your chance to own a beautiful condo in one of Winthrop's most sought-after areas!We are thrilled to present this stunning, totally renovated 2-bedroom, 2-bathroom condominium, boasting some water views. This beautiful condo has been meticulously transformed to offer the ultimate in modern living, featuring: A brand new kitchen with

Jorge Betancur Century 21 Mario Real Estate

12 Sewall Ave Unit 1, Winthrop, MA 02152

/36
Est $645,971 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,365 Sq Ft
20 Taylor St, Winthrop, MA 02152

20 Taylor St, Winthrop, MA 02152

/31
$749,900 Pending
- 5 Beds
- 2.5 Baths
- 2,394 Sq Ft
426 Winthrop St, Winthrop, MA 02152

Welcome home to this open concept colonial home in sought after Winthrop! The home offers gleaming hardwood floors with a sunken living room equipped with a surround sound system throughout. The personally crafted kitchen/dining area has beautiful maple cabinets & granite countertops. Entertain family and friends through elegant French doors leading to a to a large patio and with fenced yard

Jim Fitzgerald RE/MAX Realty Plus

426 Winthrop St, Winthrop, MA 02152
/26
$480,000 Sold Jun 30, 2025
- 694 Sq Ft
- $692/SF
- 23 Days On Market
- 2 Beds
- 1 Bath
- Built 1900
24 Elliot St, Winthrop, MA 02152

This sun-filled bungalow offers the perfect blend of city access and coastal charm. Located minutes from Boston & steps from the Beach! This home features a private driveway, backyard, spacious deck & garden area—ideal for relaxing or entertaining. The front sunroom is perfect for morning coffee or a quiet reading nook. Enjoy quick access to local restaurants, shops, beaches, and the scenic

Jonathan Mathews Legacy Realty Advisors LLC

24 Elliot St, Winthrop, MA 02152

/34
Est $758,317 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,786 Sq Ft
255 Main St, Winthrop, MA 02152

255 Main St, Winthrop, MA 02152

/29
$989,000 Pending
- 7 Beds
- 4 Baths
- 3,800 Sq Ft
170 Cottage Park Rd, Winthrop, MA 02152

A rare opportunity with a 2 family home on one of the best streets in Winthrop! One block to the ocean. Several locale yacht clubs. A few blocks to the town center with many shops, a few great cafes, several excellent restaurants, Great sized yard with a basketball court. One car garage and 4 car off street tandem parking. Refinished hardwoods throughout the entire home. Tiled bathrooms,

Aaron Daigneault Blue Sky Realty

170 Cottage Park Rd, Winthrop, MA 02152
/33
$1,120,000 Sold Jun 27, 2025
- 5,178 Sq Ft
- $216/SF
- 5 Days On Market
- 9 Beds
- 3 Baths
- Built 1890
36 Forrest St, Winthrop, MA 02152

Offers due Mon 5/19@6pm- this wonderful beachside beauty w/ over 5000sf has been cherished & occupied by the same family for over 60 years. This property provides many options to the owner occupant, investor, or developer alike. All three units offer 3 beds, in unit laundry, formal dining rooms, eat-in kitchens, gorgeous original hardwoods, stunning waterviews from front porches and rear porches

Susan Collins Coldwell Banker Realty - Boston

36 Forrest St, Winthrop, MA 02152

/34
Est $872,979 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,250 Sq Ft
38 Banks St, Winthrop, MA 02152

38 Banks St, Winthrop, MA 02152

/10
$340,000
- 1 Bath
- 338 Sq Ft
600 Shirley St Unit 15, Winthrop, MA 02152

Patrick Casey East Key Realty

600 Shirley St Unit 15, Winthrop, MA 02152
/12
$290,000 Sold Jun 27, 2025
- 610 Sq Ft
- $475/SF
- 45 Days On Market
- 2 Beds
- 1 Bath
- Built 1900
267 Washington Ave Unit 5, Winthrop, MA 02152

GREAT INVESTMENT OPPORTUNITY OR OWNER OCCUPY......Why rent when this 2 bedroom updated unit can give you a start in homeownership? Conveniently located on the Bus Line to the Blue Line and looking out to the harbor and Lewis Lake with just steps to the ocean! Yes, the beach is at the top of the street. This top floor unit has hardwood floors throughout, pretty set of windows in the living

Sharon Tallent Compass

267 Washington Ave Unit 5, Winthrop, MA 02152

/5
Est $1,175,941 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 4,494 Sq Ft
200 Main St, Winthrop, MA 02152

200 Main St, Winthrop, MA 02152

/39
$885,000 Sold Jun 26, 2025
- 2,454 Sq Ft
- $361/SF
- 5 Days On Market
- 6 Beds
- 2 Baths
- Built 1910
437 Winthrop St, Winthrop, MA 02152

Detached Two Family that is conveniently located right next to Winthrop Center. This two-family Has a ton of updates that includes, Newer Roof, Newer windows, Newer electric service, wiring and electric panels, forced air by gas(can easily add Central A/C) Newer kitchen upstairs and more. There is a level fenced-in yard with two large balconies, There are two separate storage rooms in the

Jeffrey Bowen eRealty Advisors, Inc.

437 Winthrop St, Winthrop, MA 02152

/29
Est $950,419 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,988 Sq Ft
144 Main St, Winthrop, MA 02152

144 Main St, Winthrop, MA 02152

/33
$850,000 Sold Jun 26, 2025
- 2,468 Sq Ft
- $344/SF
- 47 Days On Market
- 4 Beds
- 3 Baths
- Built 1900
42 Triton Ave, Winthrop, MA 02152

Proudly maintained in Winthrop by the Sea! Every detail is designed for comfort & convenience. Featuring 4 bedrooms & 3 full bathrooms. The primary suite is a true retreat, spacious walk-in closet & a stunning spa-like bathroom. Additional space in the lower level provides endless possibilities for a home office, gym, or entertainment area along w/ a 3/4 bathroom. You'll enjoy cooking w/the 5

Mary Ann Cash Charlesgate Realty Group, llc

42 Triton Ave, Winthrop, MA 02152

/39
Est $822,142 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,500 Sq Ft
80 Read St, Winthrop, MA 02152

80 Read St, Winthrop, MA 02152

/42
$1,300,000 Sold Jun 26, 2025
- 4,102 Sq Ft
- $317/SF
- 45 Days On Market
- 6 Beds
- 3 Baths
- Built 1906
158 Highland Ave, Winthrop, MA 02152

BOM due to buyer financing!! Last price drop! Don't miss it!! A Rare opportunity! Well maintained oversized 3-family, in Winthrop's most desirable area "The Highland's." Just steps from the beach, close to schools, shops, and restaurants. Convenient access to bus/train lines. Solid investment! Tons of updates inside & out. Nice corner lot. Each unit features many updates including kitchens &

Anthony Tammaro United Brokers

158 Highland Ave, Winthrop, MA 02152

/33
Est $994,317 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
79 Read St, Winthrop, MA 02152

79 Read St, Winthrop, MA 02152

Showing Results 281 - 320, Page 8 of 18

Massachusetts Suffolk County Winthrop

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage