$3,299,000
$100K PRICE DROP
- 7 Beds
- 7.5 Baths
- 7,226 Sq Ft
1 Plymouth Rd, Winchester, MA 01890
George Sarkis Douglas Elliman Real Estate - The Sarkis Team
9,200
Winchester, MA Homes
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1 Plymouth Rd, Winchester, MA 01890
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$4,950 Per Month
- 5 Beds
- 2 Baths
- 2,174 Sq Ft
- Apartment for Rent
79 Bacon St Unit 79, Winchester, MA 01890
79 Bacon St Unit 79, Winchester, MA 01890Welcome to this spacious 3-story Colonial, where timeless curb appeal meets modern living. A bluestone path invites you to the main entry, setting the tone for a home designed for both comfort and sophistication. Inside, expansive living and dining rooms showcase wood trim and custom built-ins, while hardwood floors and oversized replacement windows flood the space with natural light. The heart
Gayle Winters Compass
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$1,525,000
Sold Sep 12, 20255 Thornton Rd, Winchester, MA 01890
- 4 Beds
- 3.5 Baths
- 2,755 Sq Ft
- Built 1929
Last Sold Summary
- 12% Below List Price
- $554/SF
- 30 Days On Market
Current Estimated Value $1,787,828
Last Listing Agent Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group
5 Thornton Rd, Winchester, MA 01890 -
Est $1,135,855
Not Listed For Sale322 Cambridge St, Winchester, MA 01890
- 4 Beds
- 2 Baths
- 2,172 Sq Ft
- Built 1985
Last Sold Summary
- 6 Days On Market
Last Listing Agent Joanne McDonnell McDonnell Real Estate Group, LLC
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$1,750,000
Pending- 3 Beds
- 2.5 Baths
- 2,833 Sq Ft
18 Graystone Cir Unit 18, Winchester, MA 01890
18 Graystone Cir Unit 18, Winchester, MA 01890Kim Covino Compass
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$3,400 Per Month
- 3 Beds
- 1.5 Baths
- Apartment for Rent
5 Quigley Ct Unit 5, Winchester, MA 01890
5 Quigley Ct Unit 5, Winchester, MA 01890Great opportunity to rent this spacious 3-bedroom duplex offering three levels of living space, tucked away on a quiet dead-end street. Freshly painted throughout, the unit features new flooring, an updated kitchen equipped with a stove, dishwasher, and refrigerator, three generously sized bedrooms, and 1.5 bathrooms. The basement offers additional storage space, with a washer and dryer available
Anna Mean AC Realty
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$3,150,000
Sold May 28, 2026257 High St, Winchester, MA 01890
- 5 Beds
- 7 Baths
- 7,101 Sq Ft
- Built 1994
Last Sold Summary
- 3% Below List Price
- $444/SF
- 2 Days On Market
Current Estimated Value $3,118,023
Last Listing Agent Kim Covino Compass
257 High St, Winchester, MA 01890 -
Est $2,000,869
Not Listed For Sale40 Wainwright Rd, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 2,853 Sq Ft
- Built 1992
Last Sold Summary
- 7 Days On Market
Last Listing Agent Kim Covino Compass
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$1,899,000
Open Sat 12PM - 1:30PM- 5 Beds
- 3.5 Baths
- 3,210 Sq Ft
79 Grove St, Winchester, MA 01890
79 Grove St, Winchester, MA 01890Pirani & Wile Group Gibson Sotheby's International Realty
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$2,950 Per Month
- 2 Beds
- 1 Bath
- 833 Sq Ft
- Condo for Rent
200 Swanton St Unit 705, Winchester, MA 01890
200 Swanton St Unit 705, Winchester, MA 01890All utilities included (heat, hot water, and electricity) in this top-floor 2-bedroom, 1-bath condo with stunning views over the treetops and duck pond. Its 7th-floor perch offers exceptional privacy, quiet, and floor-to-ceiling, south-facing windows that fill the home with natural light. One cat allowed. The kitchen and bath were fully renovated several years ago, and the entire unit has been
Noha Soliman Leading Edge Real Estate
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$1,730,000
Sold Jul 24, 2026307 Cross St, Winchester, MA 01890
- 5 Beds
- 5 Baths
- 3,500 Sq Ft
- Built 1986
Last Sold Summary
- 2% Above List Price
- $494/SF
- 6 Days On Market
Current Estimated Value $1,678,133
Last Listing Agent Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group
307 Cross St, Winchester, MA 01890 -
Est $2,816,240
Not Listed For Sale19 Socrates Way, Winchester, MA 01890
- 5 Beds
- 6 Baths
- 5,678 Sq Ft
- Built 1994
Last Sold Summary
- 12 Days On Market
Last Listing Agent Lucille Murray Gibson Sotheby's International Realty
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$1,350,000
- 4 Beds
- 3 Baths
- 2,690 Sq Ft
423 Washington St, Winchester, MA 01890
423 Washington St, Winchester, MA 01890Danielle Fleming MA Properties
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$4,200 Per Month
- 2 Beds
- 2 Baths
- 1,707 Sq Ft
- Condo for Rent
10 Winchester Place Unit 102, Winchester, MA 01890
10 Winchester Place Unit 102, Winchester, MA 01890Spacious and sunny corner unit condo at Winchester Place - Beautifully appointed unit with custom stenciled paint, "gold" dining room ceiling, living room with custom built-ins (including 2 desks) and gas fireplace, hardwood flooring throughout, new kitchen appliances, large walk in closet in main bedroom; oversized shower and large soaking tub in main bathroom which was recently renovated.
Diane Plunkett Plunkett Properties
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$1,850,000
Sold Jan 15, 202677A Brooks St, Winchester, MA 01890
- 6 Beds
- 3.5 Baths
- 4,122 Sq Ft
- Built 1890
Last Sold Summary
- 19% Below List Price
- $449/SF
- 35 Days On Market
Current Estimated Value $1,997,994
Last Listing Agent Anne Spry Barrett Sotheby's International Realty
77A Brooks St, Winchester, MA 01890 -
Est $1,560,744
Not Listed For Sale21 Johnson Rd, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 2,814 Sq Ft
- Built 1970
Last Sold Summary
- 5 Days On Market
Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest
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$2,799,000
$51K PRICE DROP- 6 Beds
- 7 Baths
- 6,968 Sq Ft
14 Nassau Dr, Winchester, MA 01890
14 Nassau Dr, Winchester, MA 01890Weidong Li WINN Real Estate & Consulting
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$3,500 Per Month
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
- Apartment for Rent
28 East St, Winchester, MA 01890
28 East St, Winchester, MA 01890Spacious and well-maintained 3-bedroom, 2-bath townhouse featuring three levels of living space, with a large private yard and a storage shed. Enjoy hardwood floors throughout, a fully equipped kitchen with stainless steel appliances, and a finished basement with laundry and abundant storage space. The property includes 4 off-street parking spaces on a paved driveway. Conveniently located with an
Jennifer Zhao HMW Real Estate, LLC
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$703,000
Sold Jun 16, 2026115 Washington St Unit 2A, Winchester, MA 01890
- 2 Beds
- 1 Bath
- 1,029 Sq Ft
- Built 1988
Last Sold Summary
- 3% Below List Price
- $683/SF
- 36 Days On Market
Current Estimated Value $708,797
Last Listing Agent Kim Covino Compass
115 Washington St Unit 2A, Winchester, MA 01890 -
Est $2,303,255
Not Listed For Sale9 Amberwood Dr, Winchester, MA 01890
- 5 Beds
- 4.5 Baths
- 4,257 Sq Ft
- Built 2021
Last Sold Summary
- 195 Days On Market
Last Listing Agent Nicholas Gatto Better Homes and Gardens Real Estate - The Shanahan Group
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$1,125,000
Pending- 5 Beds
- 2.5 Baths
- 2,391 Sq Ft
8-10 Oak St, Winchester, MA 01890
8-10 Oak St, Winchester, MA 01890Paul Cirignano The Synergy Group
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$13,000 Per Month
- 6 Beds
- 5.5 Baths
- 6,400 Sq Ft
- House for Rent
52 N Border Rd, Winchester, MA 01890
52 N Border Rd, Winchester, MA 01890Grand and masterfully crafted, this exceptional residence sits on a private road abutting the Fells conservation land, offering rare privacy and natural surroundings. The spacious home features 6 bedrooms and 6 bathrooms, beginning with a stunning foyer that opens to a sprawling first floor. Sun-filled rooms showcase exquisite custom craftsmanship throughout. The gourmet kitchen is equipped with
Dylan Archambault The Archambault Group
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$1,936,000
Sold Jun 23, 20262 Gershon Way Unit 2, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 2,306 Sq Ft
- Built 2019
Last Sold Summary
- 2% Above List Price
- $840/SF
- 7 Days On Market
Current Estimated Value $1,902,667
Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington
2 Gershon Way Unit 2, Winchester, MA 01890 -
Est $2,434,116
Not Listed For Sale5 Pilgrim Dr, Winchester, MA 01890
- 6 Beds
- 3.5 Baths
- 4,138 Sq Ft
- Built 1962
Last Sold Summary
- 5 Days On Market
Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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$888,000
$12K PRICE DROP- 4 Beds
- 2 Baths
- 2,083 Sq Ft
84 Oak St, Winchester, MA 01890
84 Oak St, Winchester, MA 01890John Magazzu Charlesgate Realty Group LLC
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$3,700 Per Month
- 4 Beds
- 2 Baths
- 1,967 Sq Ft
- Apartment for Rent
10-12 Webster St Unit 1, Winchester, MA 01890
10-12 Webster St Unit 1, Winchester, MA 01890Spacious 4-bedroom, 2-bath apartment available for immediate occupancy in a two-family home just minutes from Winchester Center. Please note: This is NOT a single-family home. This unique unit occupies the entire first floor and finished lower level. The main level features hardwood floors throughout, a living room, dining room, two spacious bedrooms, a full bath, and an eat-in kitchen with a new
Ryan Kelly Real Broker MA, LLC
-
$1,700,000
Sold Jun 29, 202629 Pilgrim Dr, Winchester, MA 01890
- 5 Beds
- 3 Baths
- 3,271 Sq Ft
- Built 1963
Last Sold Summary
- 3% Below List Price
- $520/SF
- 20 Days On Market
Current Estimated Value $1,737,516
Last Listing Agent Anne Spry Barrett Sotheby's International Realty
29 Pilgrim Dr, Winchester, MA 01890 -
Est $1,434,908
Not Listed For Sale16 Johnson Rd, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 3,142 Sq Ft
- Built 1958
Last Sold Summary
- 6 Days On Market
Last Listing Agent Anne Spry Barrett Sotheby's International Realty
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$1,699,000
Pending- 4 Beds
- 3 Baths
- 2,707 Sq Ft
11 Carriage Ln, Winchester, MA 01890
11 Carriage Ln, Winchester, MA 01890Kim Covino Compass
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$3,200 Per Month
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Apartment for Rent
63-65 Harvard St Unit 2, Winchester, MA 01890
63-65 Harvard St Unit 2, Winchester, MA 01890Three bedrooms and an office in this two floor, second floor unit in Winchester. Open kitchen with pantry, spacious living room. Two bedrooms on this main level. Upstairs two more rooms. Two full baths and laundry in the basement. One car garage parking and plenty of space for several cars. Shareable backyard. All of this in the Muraco School District.
Beth Sager Group Keller Williams Realty Boston Northwest
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$2,155,000
Sold Oct 21, 20257 Wainwright Rd Unit 13, Winchester, MA 01890
- 3 Beds
- 4.5 Baths
- 3,186 Sq Ft
- Built 1988
Last Sold Summary
- $676/SF
- 1 Day On Market
Current Estimated Value $1,856,310
Last Listing Agent Isabella Bruno William Raveis R.E. & Home Services
7 Wainwright Rd Unit 13, Winchester, MA 01890 -
Est $1,912,567
Not Listed For Sale19 Johnson Rd, Winchester, MA 01890
- 5 Beds
- 3.5 Baths
- 4,318 Sq Ft
- Built 1956
Last Sold Summary
- 7 Days On Market
Last Listing Agent Philip Vita Compass
-
$1,125,000
Pending- 5 Beds
- 2.5 Baths
- 2,391 Sq Ft
8 Oak St Unit 10, Winchester, MA 01890
8 Oak St Unit 10, Winchester, MA 01890Paul Cirignano The Synergy Group
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$6,000 Per Month
- 3 Beds
- 2 Baths
- 3,500 Sq Ft
- House for Rent
31 Fells Rd, Winchester, MA 01890
31 Fells Rd, Winchester, MA 01890Available SHORT TERM rental through October 2025 with flexible lease options. Prime location on desirable Fells Road with easy access to Middlesex Fells trails and conservation land. This charming home sits on a beautiful lot and offers a spacious first floor featuring a large family room, updated kitchen, and a den or optional first floor bedroom. Enjoy the screened porch overlooking the private
Kim Covino Compass
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$888,000
Sold Jun 08, 20269 Governors Ave Unit 2, Winchester, MA 01890
- 3 Beds
- 1.5 Baths
- 1,799 Sq Ft
- Built 1903
Last Sold Summary
- 1% Below List Price
- $494/SF
- 6 Days On Market
Current Estimated Value $883,967
Last Listing Agent Philip Vita Compass
9 Governors Ave Unit 2, Winchester, MA 01890 -
Est $2,007,321
Not Listed For Sale1 Saint Augustine Ct, Winchester, MA 01890
- 4 Beds
- 4 Baths
- 3,818 Sq Ft
- Built 1967
Last Sold Summary
- 0 Days On Market
Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
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$849,000
- 3 Beds
- 1.5 Baths
- 1,340 Sq Ft
15 Clark St Unit 17, Winchester, MA 01890
15 Clark St Unit 17, Winchester, MA 01890Jeffrey Hsu Coldwell Banker Realty - Milton
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$6,500 Per Month
- 3 Beds
- 3 Baths
- 2,443 Sq Ft
- House for Rent
25 Berkshire Dr, Winchester, MA 01890
25 Berkshire Dr, Winchester, MA 01890This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail
Nadia Mounsif McCaul & Mounsif Real Estate Group LLC
-
$3,100,000
Sold Jul 15, 202627 Everett Ave, Winchester, MA 01890
- 6 Beds
- 5.5 Baths
- 7,431 Sq Ft
- Built 1905
Last Sold Summary
- 14% Below List Price
- $417/SF
- 118 Days On Market
Current Estimated Value $3,249,259
Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
27 Everett Ave, Winchester, MA 01890 -
Est $1,944,465
Not Listed For Sale8 Olde Lyme Rd, Winchester, MA 01890
- 5 Beds
- 3.5 Baths
- 4,603 Sq Ft
- Built 1960
Last Sold Summary
- 2 Days On Market
Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
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