Luxury homes for sale & real estate in Winthrop, MA

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NEW 20 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
Welcome to 94 Winthrop Shore Drive, a truly unique home directly across from Winthrop Shore Beach, offering beautiful water views and an incredible coastal setting. The home is highlighted by a dramatic, light-filled main living area with soaring ceilings, expansive windows overlooking the water, hardwood floors, and distinctive architectural details. Generous living and dining spaces provide plenty of room for entertaining, while the flexible floor plan offers multiple possibilities for everyday living, extended family, guests, or a private retreat. Kitchen areas on both the upper and lower levels add convenience and flexibility to the home’s versatile layout. The basement provides v

$1,095,000

2 beds3 baths2,649 sq ft

Water views • Coastal setting • Main living area

94 Winthrop Shore Dr, Winthrop, MA 02151

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ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
All offers due by Tuesday 9/15 at noon. Situated on one of Winthrops most desirable tree-lined streets in the most sought after neighborhood- the Maze, this charming four-bedroom home blends original character with thoughtful updates and inviting spaces for everyday living. The welcoming living room features a built-in window seat and wood-burning fireplace. An updated kitchen with butler’s pantry opens to the formal dining room with built-in china cabinet. A first-floor bedroom or den, new three-season sunroom, and oversized full bath with laundry add convenience and flexibility to your first floor plan. Upstairs are three spacious bedrooms, including an expansive primary bedroom spa

$979,000

4 beds2 baths2,126 sq ft

Butler's pantry • Oversized full bath • Built-in window seat

41 Emerson Rd, Winthrop, MA 02152

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
Welcome to coastal living at its best — where ocean views meet sweeping golf course views, and the beach is just a five-minute walk from your front door. Fully rebuilt in 2025, this exceptional 3-bedroom, 3-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless. Step inside to gleaming hardwood floors and beautiful natural light flowing through the open living space. At the heart of the home is a chef’s kitchen with a large center island, quality finishes, and plenty of room to gather, cook, entertain,

$850,000

3 beds3 baths1,780 sq ft

Spa-like bathrooms • Tankless hot water • Ocean views

194 Washington Ave #3, Winthrop, MA 02152

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
Welcome to 190 Pleasant Street, a spacious two-family home offering approximately 4,251 square feet of living space across three levels. Featuring 13 total rooms, seven bedrooms, two full bathrooms and two half bathrooms, this property presents an excellent opportunity for an owner-occupant, investor or multigenerational household. Each unit offers generous living space, while the home’s flexible layout provides plenty of potential to customize and add value. Conveniently located near Winthrop’s beaches, local shops, restaurants, public transportation and Boston. Bring your vision and discover everything this well-located two-family property has to offer!

$949,000

7 beds3 baths4,251 sq ft

Flexible layout • Two family home • Local shops

190 Pleasant St, Winthrop, MA 02152

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
A fantastic value for this home. It’s an opportunity to make it your own, and enjoy the quaint town of Winthrop by the sea. Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces giving warmth & charm to the living spaces. Extensive updates include all new mechanical systems including elec. wiring, FWA furnace, cent A/C, on-demand HW, mini-split heat pump/AC units, plumbing lighting, all providing peace of mind for years to come. Generous space, new paint &

$979,900

6 beds2.5 baths3,263 sq ft

Fwa furnace • 2 fireplaces • Cent a/c

217 Pleasant St, Winthrop, MA 02152

Property at 25 Locust St #2, Winthrop, MA 02152, 3 beds, 2 baths

$875,000

3 beds2 baths1,770 sq ft

25 Locust St #2, Winthrop, MA 02152

Property at 1001 Shirley St #2, Winthrop, MA 02152, 2 beds, 2.5 baths

$865,000

2 beds2.5 baths1,806 sq ft

1001 Shirley St #2, Winthrop, MA 02152

Property at 200 Main St #1, Winthrop, MA 02152, 3 beds, 2.5 baths

$975,000

3 beds2.5 baths2,100 sq ft

200 Main St #1, Winthrop, MA 02152

Property at 174 Bartlett Rd, Winthrop, MA 02152, 5 beds, 5.5 baths

$2,100,000

5 beds5.5 baths6,224 sq ft

174 Bartlett Rd, Winthrop, MA 02152

Property at 70 Edgehill Rd, Winthrop, MA 02152, 4 beds, 3.5 baths

$1,199,999

4 beds3.5 baths1,904 sq ft

70 Edgehill Rd, Winthrop, MA 02152

Property at 3 Seal Harbor Rd Ph 33, Winthrop, MA 02152, 3 beds, 3 baths

$1,230,000

3 beds3 baths1,913 sq ft

3 Seal Harbor Rd Ph 33, Winthrop, MA 02152

Property at 32 Irwin St, Winthrop, MA 02152, 6 beds, 4 baths

$1,100,000

6 beds4 baths2,949 sq ft

32 Irwin St, Winthrop, MA 02152

Property at 3 Seal Hbr #336, Winthrop, MA 02152, 2 beds, 1.5 baths

$859,900

2 beds1.5 baths1,674 sq ft

3 Seal Hbr #336, Winthrop, MA 02152

Property at 43 Loring Rd, Winthrop, MA 02152, 3 beds, 1.5 baths

$939,900

3 beds1.5 baths2,371 sq ft

43 Loring Rd, Winthrop, MA 02152

Property at 66 Sunnyside Ave, Winthrop, MA 02152, 5 beds, 2 baths

$999,888

5 beds2 baths2,635 sq ft

66 Sunnyside Ave, Winthrop, MA 02152

Property at 100 Sargent St, Winthrop, MA 02152, 6 beds, 5.5 baths

$1,450,000

6 beds5.5 baths5,278 sq ft

100 Sargent St, Winthrop, MA 02152

Property at 63-69 Putnam St, Winthrop, MA 02152, 16 beds, 14 baths

$2,250,000

16 beds14 baths10,000 sq ft

63-69 Putnam St, Winthrop, MA 02152

Property at Undisclosed address, Winthrop, MA 02152, 6 beds, 5 baths

$1,400,000

6 beds5 baths— sq ft

Undisclosed address, Winthrop, MA 02152

Property at 93 1/2 Winthrop Shore Dr, Winthrop, MA 02152

$900,000

Land0.32 acre (lot)

93 1/2 Winthrop Shore Dr, Winthrop, MA 02152

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FLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
A meticulously renovated four-bedroom single-family raised Cape at 9 Crestway Rd, East Boston. This 2,619-square-foot home features new exterior vinyl siding, windows, and roof. The interior has been updated with new plumbing, electrical, bathrooms, and appliances, offering a harmonious blend of classic charm and modern living. The heart of the home is the kitchen, featuring a practical peninsula that creates an inviting space for culinary exploration and casual gatherings. The living room provides a comfortable retreat, enhanced by the warmth and character of a fireplace. This spacious Cape Cod-style home sits on a 4,310-square-foot lot with a private yard for outdoor enjoyment. Practical

$1,199,000

4 beds4 baths2,619 sq ft

Private yard • Covered patio • Exclusive kitchen

9 Crestway Rd, East Boston, MA 02128

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
Incredible opportunity to own a fully renovated, turnkey multi-family home in an ultra desirable, uber-convenient East Boston location. Currently located in an EBR-4 zoning district, this three family home has been meticulously maintained and updated over the years. The property comes fully tenanted at market rate rents - with room to increase in the future. Updated kitchens, hardwood floors, new HVAC systems, in-building coin-op laundry and separate systems round out some of the features. This home offers a walk-up roof deck with panoramic views - great outdoor space with back patio and yard. Amazing location along MBTA bus route - walking distance to both Orient Heights and Wood Island MB

$1,375,000

6 beds3 baths3,284 sq ft

Fully renovated • New hvac systems • Updated kitchens

651 Bennington St, East Boston, MA 02128

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
Developer Opportunity in Prime East Boston – Rare ½-acre parcel with 200’ of frontage and 100’ depth, zoned EBR-3, allowing up to six units per 55’ of frontage. Perfect for investment, new construction, or a custom project in one of Boston’s most desirable neighborhoods. Conveniently located just moments from the East Boston Yacht Club, Constitution Beach, Porrazzo Skating Rink, and Wood Island Bay Edge Park, this oversized lot blends coastal living with urban convenience. Residents can enjoy nearby tennis courts, a playground, scenic waterfront access, and beautiful harbor views, ideal for an active, outdoor lifestyle. Situated in a rapidly growing area

$3,695,000

3 beds2 baths2,752 sq ft

Rare parcel • Zoned ebr-3 • Oversized lot

176 Coleridge St, East Boston, MA 02128

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
LOCATION, LOCATION, LOCATION! Here’s your opportunity to own a well-maintained, spacious two-family townhouse-style home in a fantastic commuter-friendly location!Perfectly situated just minutes from Beachmont Blue Line Station, Revere Beach, shopping, restaurants, Suffolk Downs, and more, this property offers easy access to Boston and surrounding communities while putting everyday conveniences right at your fingertips. The larger unit offers a spacious and versatile layout with a kitchen, dining room, living room, den, full bathroom, and laundry on the first floor. Upstairs, you’ll find three bedrooms and a second full bathroom, providing plenty of room for family and guests. T

$949,900

4 beds3 baths2,614 sq ft

Two family layout • 5,074 sq ft lot • 4 parking spots

130 Washburn Ave, Revere, MA 02151

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
BRAND NEW CONSTRUCTION THREE FAMILY Condos are selling from $600 a foot to $800 a foot, especially with parking. Comes with 3 Parking! 95% Completed. Condo Quality. Located in Orient Heights. A short walk to The Orient Heights MBTA Station AND The Beach. Close to Logan Airport. Close to shopping, dining and more. Photos and Video coming soon. Text Listing Agent to see the property today before it hits the open market in two weeks! Any 1031 Exhange buyers looking to sell their old Multi Famliy and move into a brand new one? There are grants, tax credits City, State and Federal programs for owner occupant first time home buyer's out there. Tired of renting? Become the landlord. Looking for yo

$1,790,000

7 beds6 baths3,517 sq ft

5,000 sq ft lot • 3 parking spots • Built 2026

806 Saratoga, Boston, MA 02128

ABOUT THIS HOME
Luxury Home for sale in Winthrop, MA:
Welcome to 106 Barnes Ave an exceptional 3-family opportunity in East Boston’s desirable Orient Heights neighborhood. Ideal for investors or owner-occupants, this property offers spacious units. The first-floor lower level unit features 3-bedrooms, recently renovated updates that features an open-concept kitchen with an electric stove, wall oven, spacious living room and a full bath. The second-floor unit offers 3 bedrooms hardwood floors, kitchen, 1 full bath, in unit-washer/dryer. The third-floor unit features 3- bedrooms, kitchen with granite countertops, shaker cabinetry, tile backsplash, generous dining area, 2 full baths, including a beautiful bath with a glass-enclosed shower a

$1,349,900

8 beds4 baths3,977 sq ft

Wall oven • Open concept kitchen • Shaker cabinetry

106 Barnes Ave, East Boston, MA 02128

Property at 207 Gladstone St, East Boston, MA 02128, 5 beds, 2 baths

$1,100,000

5 beds2 baths2,390 sq ft

207 Gladstone St, East Boston, MA 02128

Property at 92+96 Waldemar, East Boston, MA 02128, 4 beds, 2.5 baths

$899,999

4 beds2.5 baths2,038 sq ft

92+96 Waldemar, East Boston, MA 02128

Property at 126 Leyden St, East Boston, MA 02128, 6 beds, 1 bath

$895,000

6 beds1 bath3,000 sq ft

126 Leyden St, East Boston, MA 02128

Property at 198 Byron St, East Boston, MA 02128, 3 beds, 2 baths

$1,150,000

3 beds2 baths2,385 sq ft

198 Byron St, East Boston, MA 02128

Property at 20 Nancia St, East Boston, MA 02128, 4 beds, 2 baths

$1,200,000

4 beds2 baths1,188 sq ft

20 Nancia St, East Boston, MA 02128

Luxury Homes for Sale in Winthrop

There are currently 19 luxury homes for sale in Winthrop at a median listing price of $629K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winthrop stay on the market for 58 days and receive 1 offers. Popular neighborhoods include Logan Airport / Jeffries Point, East Boston, Beachmont, Orient Heights, and Jeffries Point. This map is refreshed with the newest listings in Winthrop every 15 minutes.

In the past month, 12 homes have been sold in Winthrop. In addition to houses in Winthrop, there were also 54 condos, 4 townhouses, and 10 multi-family units for sale in Winthrop last month. Find your dream home in Winthrop using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winthrop are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winthrop. Our Winthrop real estate stats and trends will give you more information about home buying and selling trends in Winthrop. If you're looking to sell your home in the Winthrop area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winthrop with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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