Homes in ZIP Code 01890

/42
$3,537,000
- 7 Beds
- 7.5 Baths
- 8,540 Sq Ft
37 Mayflower Rd, Winchester, MA 01890

Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

Kim Covino Compass

37 Mayflower Rd, Winchester, MA 01890
/22
$2,400,000 Sold Dec 18, 2025

19 Laurel Hill Ln, Winchester, MA 01890
- 5 Beds
- 4.5 Baths
- 3,700 Sq Ft
- Built 1954
Last Sold Summary
- 4% Below List Price
- $649/SF
- 3 Days On Market
Current Estimated Value $2,407,336

Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

19 Laurel Hill Ln, Winchester, MA 01890

/26
Est $857,084 Not Listed For Sale

28 Henry St, Winchester, MA 01890
- 2 Beds
- 1 Bath
- 1,279 Sq Ft
- Built 1942
28 Henry St, Winchester, MA 01890

Last Sold Summary
- 20% Above List Price
- $559/SF
- 5 Days On Market
Last Sold Price $715,000

Last Listing Agent Alison Socha Leading Edge Real Estate

/35
$2,395,000 Open Sun 12PM - 1:30PM
- 3 Beds
- 3.5 Baths
- 4,087 Sq Ft
15 Gershon Way Unit 15, Winchester, MA 01890

Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual

Moira Lown Coldwell Banker Realty - Wellesley

15 Gershon Way Unit 15, Winchester, MA 01890
/32
$1,250,000 Sold Jun 30, 2025

80 Harvard St, Winchester, MA 01890
- 4 Beds
- 2 Baths
- 2,759 Sq Ft
- Built 1973
Last Sold Summary
- 4% Above List Price
- $453/SF
- 6 Days On Market
Current Estimated Value $1,291,783

Last Listing Agent Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

80 Harvard St, Winchester, MA 01890

/42
Est $1,420,894 Not Listed For Sale

14 Henry St, Winchester, MA 01890
- 6 Beds
- 3 Baths
- 3,091 Sq Ft
- Built 1957
14 Henry St, Winchester, MA 01890

Last Sold Summary
- 6% Below List Price
- $491/SF
- 7 Days On Market
Last Sold Price $1,517,500

Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

/25
$999,000 Pending
- 4 Beds
- 2 Baths
- 1,552 Sq Ft
76 Woodside Rd, Winchester, MA 01890

Welcome to this charming 4-bedroom, 2-bath home in desirable Winchester. Ideally located in one of the town’s most sought-after neighborhoods, this well-maintained residence offers the perfect blend of classic character and everyday comfort. The home features a bright and inviting layout with generous living spaces, hardwood floors, bookshelves and windows seats. The kitchen flows seamlessly into

Michael Pierce Mystic Properties Real Estate

76 Woodside Rd, Winchester, MA 01890
/42
$2,450,000 Sold Dec 16, 2025

30 Prospect St, Winchester, MA 01890
- 4 Beds
- 3 Baths
- 2,519 Sq Ft
- Built 1934
Last Sold Summary
- 17% Above List Price
- $973/SF
- 3 Days On Market
Current Estimated Value $2,253,239

Last Listing Agent Karima Alami Compass

30 Prospect St, Winchester, MA 01890

/20
Est $1,089,149 Not Listed For Sale

14 Locke St, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 1,432 Sq Ft
- Built 1910
14 Locke St, Winchester, MA 01890

Last Sold Summary
- 13% Above List Price
- $670/SF
- 35 Days On Market
Last Sold Price $960,000

Last Listing Agent Ruth Gagne Barrett Sotheby's International Realty

/2
$359,900 Pending
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
20 Arthur St, Winchester, MA 01890

Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

Dan O'Connell LAER Realty Partners

20 Arthur St, Winchester, MA 01890
/16
$1,050,000 Sold Jul 11, 2025

61 Westland Ave, Winchester, MA 01890
- 4 Beds
- 2 Baths
- 2,621 Sq Ft
- Built 1952
Last Sold Summary
- 16% Below List Price
- $401/SF
- 48 Days On Market
Current Estimated Value $1,712,003

Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

61 Westland Ave, Winchester, MA 01890

/17
Est $1,947,875 Not Listed For Sale

21 Dunster Ln, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 3,578 Sq Ft
- Built 1950
21 Dunster Ln, Winchester, MA 01890

Last Sold Summary
- 3% Below List Price
- $559/SF
- 9 Days On Market
Last Sold Price $2,000,000

Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

/16
$2,799,000
- 5 Beds
- 4 Baths
- 5,083 Sq Ft
53 Winford Way, Winchester, MA 01890

Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

Andersen Group Realty Keller Williams Realty Boston Northwest

53 Winford Way, Winchester, MA 01890
/40
$1,100,000 Sold Sep 12, 2025

5 Cutting St, Winchester, MA 01890
- 3 Beds
- 1.5 Baths
- 1,414 Sq Ft
- Built 1900
Last Sold Summary
- 2% Above List Price
- $778/SF
- 8 Days On Market
Current Estimated Value $1,109,150

Last Listing Agent Oliver Koester Compass

5 Cutting St, Winchester, MA 01890

/38
Est $1,234,471 Not Listed For Sale

18 Ridge St, Winchester, MA 01890
- 5 Beds
- 1.5 Baths
- 2,383 Sq Ft
- Built 1840
18 Ridge St, Winchester, MA 01890

Last Sold Summary
- 18% Above List Price
- $441/SF
- 15 Days On Market
Last Sold Price $1,050,000

Last Listing Agent Gayle Winters Compass

/34
$1,095,000 Pending
- 5 Beds
- 2 Baths
- 2,331 Sq Ft
149 Horn Pond Brook Rd, Winchester, MA 01890

Picture-perfect Cape Cod single family home on a corner lot across the street from the brand new Lynch Elementary School. This special residence is much larger than it looks & has 4–5 spacious bedrooms across two levels & two full baths on each floor. Such space offers versatility with 2 beds on main level & 3 bedrooms on the upper floor. The sun-filled living room flows nicely to a charming

Nancy McLaughlin Redfin Corp.

149 Horn Pond Brook Rd, Winchester, MA 01890
/37
$665,000 Sold Nov 14, 2025

7 Conant Rd Unit 20, Winchester, MA 01890
- 2 Beds
- 2 Baths
- 1,168 Sq Ft
- Built 2000
Last Sold Summary
- 8% Below List Price
- $569/SF
- 124 Days On Market
Current Estimated Value $673,544

Last Listing Agent Brian Woods Woods Properties Inc.

7 Conant Rd Unit 20, Winchester, MA 01890

/40
Est $2,368,607 Not Listed For Sale

280 High St, Winchester, MA 01890
- 6 Beds
- 5 Baths
- 6,259 Sq Ft
- Built 1976
280 High St, Winchester, MA 01890

Last Sold Summary
- 20% Above List Price
- $316/SF
- 136 Days On Market
Last Sold Price $1,980,000

Last Listing Agent Anthony Marino The Marino Group Collection

/26
$1,499,999
- 6 Beds
- 3 Baths
- 2,658 Sq Ft
65 High St, Winchester, MA 01890

Fantastic! The best value in Winchester in a desired neighborhood. The sunny first floor flows nicely from room to room, with hardwood floors in the living areas and a hallway leading to the 3 original bedrooms. Ideal for an office, guests, or visiting in-laws. A screen porch and patio off the dining room ideal for al fresco dining. The generous second-floor renovation features a full bath with

Anna Jung K Stadium Realty INC

65 High St, Winchester, MA 01890
/42
$2,111,000 Sold Jun 05, 2025

14 Grove St, Winchester, MA 01890
- 5 Beds
- 4 Baths
- 4,744 Sq Ft
- Built 1922
Last Sold Summary
- 8% Above List Price
- $445/SF
- 6 Days On Market
Current Estimated Value $2,162,518

Last Listing Agent Kim Covino Compass

14 Grove St, Winchester, MA 01890

/42
Est $2,067,887 Not Listed For Sale

23 Olde Village Dr, Winchester, MA 01890
- 3 Beds
- 3.5 Baths
- 4,997 Sq Ft
- Built 1975
23 Olde Village Dr, Winchester, MA 01890

Last Sold Summary
- 2% Above List Price
- $405/SF
- 8 Days On Market
Last Sold Price $2,025,000

Last Listing Agent Ngoc Anh Goldstein Leading Edge Real Estate

/37
$1,524,000
- 4 Beds
- 2.5 Baths
- 3,380 Sq Ft
34 Robinhood Rd, Winchester, MA 01890

This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main

Janet Halloran RE/MAX Real Estate Center

34 Robinhood Rd, Winchester, MA 01890
/42
$4,450,000 Sold Oct 24, 2025

20 Foxcroft Rd, Winchester, MA 01890
- 5 Beds
- 7 Baths
- 7,679 Sq Ft
- Built 1937
Last Sold Summary
- 1% Above List Price
- $580/SF
- 1 Day On Market
Last Listing Agent Carolyn Walsh Better Homes and Gardens Real Estate - The Shanahan Group

20 Foxcroft Rd, Winchester, MA 01890

/38
Est $1,648,420 Not Listed For Sale

31 Girard Rd, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 3,158 Sq Ft
- Built 1975
31 Girard Rd, Winchester, MA 01890

Last Sold Summary
- $522/SF
- 6 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Philip Vita Compass

/37
$1,799,000 Pending
- 4 Beds
- 2.5 Baths
- 2,910 Sq Ft
58 Jefferson Rd, Winchester, MA 01890

This well-maintained colonial is tucked at the end of a cul-de-sac in a very desirable neighborhood. Upon entering, the bright foyer with hardwood floors opens to a spacious front to back living room. The formal dining room leads to the eat in kitchen, perfect for entertaining and gatherings. Just off the kitchen the family room features a stone fireplace and sliding doors leading to the deck and

Stephanie Macfarland Wilson Wolfe Real Estate

58 Jefferson Rd, Winchester, MA 01890
/36
$1,945,000 Sold Sep 16, 2025

20 Grayson Rd, Winchester, MA 01890
- 5 Beds
- 4.5 Baths
- 3,825 Sq Ft
- Built 2025
Last Sold Summary
- 2% Above List Price
- $508/SF
- 7 Days On Market
Current Estimated Value $1,895,414

Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

20 Grayson Rd, Winchester, MA 01890

/40
Est $2,045,016 Not Listed For Sale

99 Ridge St, Winchester, MA 01890
- 5 Beds
- 3.5 Baths
- 4,567 Sq Ft
- Built 2004
99 Ridge St, Winchester, MA 01890

Last Sold Summary
- 7% Above List Price
- $418/SF
- 4 Days On Market
Last Sold Price $1,910,000

Last Listing Agent Doug Hills Compass

/35
$1,060,000 Pending
- 5 Beds
- 2.5 Baths
- 2,849 Sq Ft
62 Richardson St, Winchester, MA 01890

Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly situated on a large corner lot. Venture into Unit 1 through the all seasons porch. The kitchen offers ample cabinet space, center island, & breakfast nook. Two bedrooms on level 1, both w/ ample closet storage. Full bath w/

Frank Ventresca Strategy Street

62 Richardson St, Winchester, MA 01890
/42
$3,745,000 Sold Aug 08, 2025

25 Wedgemere Ave, Winchester, MA 01890
- 7 Beds
- 8 Baths
- 7,587 Sq Ft
- Built 2010
Last Sold Summary
- 6% Below List Price
- $494/SF
- 44 Days On Market
Current Estimated Value $3,933,190

Last Listing Agent Prestige Homes Realty Team Prestige Homes Real Estate, LLC

25 Wedgemere Ave, Winchester, MA 01890

/42
Est $1,245,518 Not Listed For Sale

119 Ridge St, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 2,542 Sq Ft
- Built 1956
119 Ridge St, Winchester, MA 01890

Last Sold Summary
- 22% Above List Price
- $403/SF
- 31 Days On Market
Last Sold Price $1,025,000

Last Listing Agent Charles Jolin Keller Williams Realty

/13
$3,199,000 Pending
- 6 Beds
- 7 Baths
- 5,709 Sq Ft
39 Town Way, Winchester, MA 01890

Discover all this gorgeous new construction home in top East Side location will offer! Designed with today’s lifestyle in mind, this home features a flexible open floor plan perfect for entertaining & everyday living / A great opportunity for you to customize the finishes & bring your vision to life! First floor offers a mudroom, half bath, office/living room, bedroom w/ full bath & a stunning

Kim Covino Compass

39 Town Way, Winchester, MA 01890
/31
$1,965,000 Sold Jan 27, 2026

46 Church St, Winchester, MA 01890
- 4 Beds
- 3.5 Baths
- 3,475 Sq Ft
- Built 1960
Last Sold Summary
- 2% Below List Price
- $565/SF
- 13 Days On Market
Current Estimated Value $1,968,427

Last Listing Agent Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

46 Church St, Winchester, MA 01890

/41
Est $3,841,638 Not Listed For Sale

11 Viking Rd, Winchester, MA 01890
- 5 Beds
- 4.5 Baths
- 4,322 Sq Ft
- Built 1980
11 Viking Rd, Winchester, MA 01890

Last Sold Summary
- 159% Above List Price
- $344/SF
- 9 Days On Market
Last Sold Price $1,485,000

Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

/32
$722,500 Pending
- 2 Beds
- 2.5 Baths
- 1,596 Sq Ft
171 Swanton St Unit 73, Winchester, MA 01890

Welcome to The Village in Winchester! This picturesque 80-unit condominium community is set along conservation land and the Aberjona River. Unit 73 is a spacious, 2-bedroom, 2.5-bath end-unit townhouse with rare offering of a first floor bonus room; den, home office, bedroom, you decide! The first floor also offers a living room with skylight and fireplace, kitchen, dining room, half bath and

John and Maria Reilly JMR Real Estate Group LLC

171 Swanton St Unit 73, Winchester, MA 01890
/28
$710,000 Sold Sep 10, 2025

666 Main St Unit 206, Winchester, MA 01890
- 2 Beds
- 2 Baths
- 1,170 Sq Ft
- Built 1982
Last Sold Summary
- 2% Below List Price
- $607/SF
- 50 Days On Market
Current Estimated Value $709,665

Last Listing Agent Sveta Vakhitova Berkshire Hathaway HomeServices Warren Residential

666 Main St Unit 206, Winchester, MA 01890

/40
Est $1,358,625 Not Listed For Sale

25 Lockeland Rd, Winchester, MA 01890
- 3 Beds
- 3 Baths
- 2,456 Sq Ft
- Built 1954
25 Lockeland Rd, Winchester, MA 01890

Last Sold Summary
- 10% Above List Price
- $501/SF
- 12 Days On Market
Last Sold Price $1,230,000

Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

/42
$3,299,000
- 5 Beds
- 4 Baths
- 4,028 Sq Ft
10 Dartmouth St, Winchester, MA 01890

Winchester's premiere location! This stunning waterfront gem is perfectly situated on Winter Pond, offering over 80 feet of direct water frontage with expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this property presents a rare opportunity to enjoy water activities such as kayaking, paddleboarding, fishing, ice skating and hockey all

Kim Covino Compass

10 Dartmouth St, Winchester, MA 01890
/35
$1,100,000 Sold Jun 27, 2025

63 Church St, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 3,157 Sq Ft
- Built 1866
Last Sold Summary
- 24% Below List Price
- $348/SF
- 20 Days On Market
Current Estimated Value $1,158,542

Last Listing Agent Nancy McLaughlin Redfin Corp.

63 Church St, Winchester, MA 01890

/42
Est $1,929,491 Not Listed For Sale

7 Plymouth Rd, Winchester, MA 01890
- 4 Beds
- 4 Baths
- 2,770 Sq Ft
- Built 1959
7 Plymouth Rd, Winchester, MA 01890

Last Sold Summary
- 8% Below List Price
- $756/SF
- 0 Days On Market
Last Sold Price $2,095,000

Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

/40
$2,895,000 Sold Oct 30, 2025

6 Abby Rd, Winchester, MA 01890
- 5 Beds
- 4.5 Baths
- 5,716 Sq Ft
- Built 2025
Last Sold Summary
- 3% Below List Price
- $506/SF
- 28 Days On Market
Last Listing Agent Philip Vita Compass

6 Abby Rd, Winchester, MA 01890

Showing Results 161 - 200, Page 5 of 18

Massachusetts Middlesex County Winchester 01890

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