West Side Homes

/36
$3,600,000
- 6 Beds
- 7 Baths
- 8,866 Sq Ft
20 Amberwood Dr, Winchester, MA 01890

Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

Wei Wang

WW Real Estate LLC

(781) 678-8050

20 Amberwood Dr, Winchester, MA 01890
Explore West Side
/20

$2,628 - $11,296 plus fees

Sanctuary Winchester West

Studio - 3 Beds

416 Cambridge St, Winchester, MA 01890

The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

416 Cambridge St, Winchester, MA 01890
/39
$2,200,000 Sold Jun 30, 2025

1 Saint Augustine Ct, Winchester, MA 01890
- 4 Beds
- 4 Baths
- 3,818 Sq Ft
- Built 1967
Last Sold Summary
- 10% Above List Price
- $576/SF
- 0 Days On Market
Current Estimated Value $2,156,313

Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

1 Saint Augustine Ct, Winchester, MA 01890

/42
Est $1,953,895 Not Listed For Sale

19 Johnson Rd, Winchester, MA 01890
- 5 Beds
- 3.5 Baths
- 4,318 Sq Ft
- Built 1956
19 Johnson Rd, Winchester, MA 01890

Last Sold Summary
- 3% Above List Price
- $438/SF
- 7 Days On Market
Last Sold Price $1,890,000

Last Listing Agent Philip Vita Compass

/42
$958,000 Pending
- 3 Beds
- 2.5 Baths
- 2,082 Sq Ft
15 Edward Dr Unit 15, Winchester, MA 01890

Welcome to the highly sought-after Pepper Hill Estates, ideally situated on a quiet street near Vinson-Owen Elementary School and within walking distance to Wright-Locke Farm and McClennen Park. This Colonial-style home offers a highly desirable and functional layout. The first floor features an open-concept design with a spacious living room, dining area, and a custom-built kitchen by Schrock

Alina Wang

Coldwell Banker Realty - Lexington

(781) 512-7277

15 Edward Dr Unit 15, Winchester, MA 01890
/27
$10,000 per month
- 6 Beds
- 4.5 Baths
- 6,583 Sq Ft
- House for Rent
282 High St, Winchester, MA 01890

Fabulous 6 month rental opportunity with full additional in-law suite with private kitchen, bedroom, bath, and laundry. Very generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and

Anthony Marino The Marino Group Collection

282 High St, Winchester, MA 01890
/42
$1,055,000 Sold Feb 26, 2026

7 Trinity Rd, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 2,130 Sq Ft
- Built 1963
Last Sold Summary
- 11% Below List Price
- $495/SF
- 24 Days On Market
Current Estimated Value $1,138,443

Last Listing Agent Gayle Winters Compass

7 Trinity Rd, Winchester, MA 01890

/42
Est $2,936,744 Not Listed For Sale

228 Ridge St, Winchester, MA 01890
- 5 Beds
- 5.5 Baths
- 6,265 Sq Ft
- Built 2023
228 Ridge St, Winchester, MA 01890

Last Sold Summary
- 18% Above List Price
- $399/SF
- 142 Days On Market
Last Sold Price $2,499,000

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

/10
$3,400,000
- 6 Beds
- 5.5 Baths
- 6,100 Sq Ft
9 Albamont Rd, Winchester, MA 01890

Brand new high end construction in prime Winchester location! Currently under construction w/ completion expected late spring 2026. A thoughtfully designed home with immense curb appeal showcasing stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer

Kim Covino Compass

9 Albamont Rd, Winchester, MA 01890
/11
$3,700 total monthly price
- 2 Beds
- 1 Bath
- 1,300 Sq Ft
- House for Rent
67 Dunster Ln, Winchester, MA 01890

Are you looking for a Beautiful, Updated 2 bedroom with Privacy?Then this 2 bedroom House will be perfect. No neighbors above or below you like a traditional 2 bedroomin a 2-family.This is an adorable stand alone, single family with 2 bedroom, 1 bath(New) with Living room, Dining Room and NEW KITCHEN!!Storage in basement and Laundry hookups.Excellent condition.Front porch

67 Dunster Ln, Winchester, MA 01890
/25
$1,881,900 Sold May 30, 2025

4 Olde Lyme Rd, Winchester, MA 01890
- 4 Beds
- 4 Baths
- 3,488 Sq Ft
- Built 1980
Last Sold Summary
- 1% Below List Price
- $540/SF
- 34 Days On Market
Current Estimated Value $1,881,317

Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

4 Olde Lyme Rd, Winchester, MA 01890

/40
Est $1,323,953 Not Listed For Sale

15 Wincrest Dr, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 2,529 Sq Ft
- Built 1957
15 Wincrest Dr, Winchester, MA 01890

Last Sold Summary
- 5% Above List Price
- $498/SF
- 4 Days On Market
Last Sold Price $1,260,000

Last Listing Agent Kim Covino Compass

/40
$3,250,000 Pending
- 5 Beds
- 7 Baths
- 7,101 Sq Ft
257 High St, Winchester, MA 01890

OPEN HOUSE CANCELLED 4/12 **OFFER ACCEPTED** Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial

Kim Covino Compass

257 High St, Winchester, MA 01890
/42
$1,580,000 Sold Feb 26, 2026

10 Trinity Rd, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 2,112 Sq Ft
- Built 1963
Last Sold Summary
- 11% Above List Price
- $748/SF
- 5 Days On Market
Current Estimated Value $1,516,703

Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

10 Trinity Rd, Winchester, MA 01890

/33
Est $1,376,446 Not Listed For Sale

10 Carriage Ln, Winchester, MA 01890
- 4 Beds
- 3.5 Baths
- 2,034 Sq Ft
- Built 1957
10 Carriage Ln, Winchester, MA 01890

Last Sold Summary
- 3% Below List Price
- $698/SF
- 5 Days On Market
Last Sold Price $1,420,000

Last Listing Agent Peter Kasseris Serhant

/35
$3,399,000
- 7 Beds
- 7.5 Baths
- 7,226 Sq Ft
1 Plymouth Rd, Winchester, MA 01890

Discover a beautifully reimagined home in one of Winchester’s most sought-after neighborhoods, offering exceptional space, comfort, and convenience in a truly prime location. With 7 bedrooms, 7 full baths, and 1 half bath, 1 Plymouth has been thoughtfully expanded and rebuilt with high-end finishes throughout to suit today’s lifestyle. At the heart of the home is a stunning fireplaced family room

George Sarkis Douglas Elliman Real Estate - The Sarkis Team

1 Plymouth Rd, Winchester, MA 01890
/37
$1,390,000 Sold Jul 15, 2025

26 Ridge St, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 2,388 Sq Ft
- Built 1963
Last Sold Summary
- 1% Above List Price
- $582/SF
- 6 Days On Market
Current Estimated Value $1,422,456

Last Listing Agent Dream Team Dreamega International Realty LLC

26 Ridge St, Winchester, MA 01890

/29
Est $1,251,415 Not Listed For Sale

28 Thornberry Rd, Winchester, MA 01890
- 4 Beds
- 2 Baths
- 2,245 Sq Ft
- Built 1959
28 Thornberry Rd, Winchester, MA 01890

Last Sold Summary
- 6% Below List Price
- $595/SF
- 117 Days On Market
Last Sold Price $1,335,000

Last Listing Agent Shaundize Moosavizadeh Coldwell Banker Realty - Boston

/42
$3,499,000
- 5 Beds
- 7.5 Baths
- 6,899 Sq Ft
54 Johnson Rd, Winchester, MA 01890

This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the

Kim Covino Compass

54 Johnson Rd, Winchester, MA 01890
/39
$2,050,000 Sold Oct 15, 2025

64 Westland Ave, Winchester, MA 01890
- 4 Beds
- 5 Baths
- 3,716 Sq Ft
- Built 1931
Last Sold Summary
- $552/SF
- 2 Days On Market
Current Estimated Value $2,014,153

Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

64 Westland Ave, Winchester, MA 01890

/35
Est $1,538,561 Not Listed For Sale

16 Nassau Dr, Winchester, MA 01890
- 4 Beds
- 3.5 Baths
- 2,926 Sq Ft
- Built 1960
16 Nassau Dr, Winchester, MA 01890

Last Sold Summary
- 5% Above List Price
- $499/SF
- 20 Days On Market
Last Sold Price $1,460,000

Last Listing Agent Peter Kasseris Serhant

/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
/38
$1,525,000 Sold Sep 12, 2025

5 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 $1,760,461

Last Listing Agent Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

5 Thornton Rd, Winchester, MA 01890

/32
Est $1,460,711 Not Listed For Sale

104 Thornberry Rd, Winchester, MA 01890
- 4 Beds
- 3 Baths
- 2,622 Sq Ft
- Built 1973
104 Thornberry Rd, Winchester, MA 01890

Last Sold Summary
- 3% Above List Price
- $543/SF
- 4 Days On Market
Last Sold Price $1,425,000

Last Listing Agent Philip Vita Compass

/38
$2,299,000
- 5 Beds
- 3.5 Baths
- 5,006 Sq Ft
276 High St, Winchester, MA 01890

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

Kim Covino Compass

276 High St, Winchester, MA 01890
/42
$1,540,000 Sold Jul 11, 2025

21 Johnson Rd, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 2,814 Sq Ft
- Built 1970
Last Sold Summary
- 1% Above List Price
- $547/SF
- 5 Days On Market
Current Estimated Value $1,540,767

Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

21 Johnson Rd, Winchester, MA 01890

/39
Est $1,786,181 Not Listed For Sale

73 Thornberry Rd, Winchester, MA 01890
- 4 Beds
- 2.5 Baths
- 3,046 Sq Ft
- Built 1966
73 Thornberry Rd, Winchester, MA 01890

Last Sold Summary
- 8% Above List Price
- $543/SF
- 7 Days On Market
Last Sold Price $1,655,000

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

/31
$1,200,000 Pending
- 3 Beds
- 2 Baths
- 2,087 Sq Ft
12 Thornberry Rd, Winchester, MA 01890

Lovingly maintained and tastefully renovated, this spacious three bedroom, two bath ranch with 3 car garage will impress! This remodeled open concept home is set on an oversized 16k lot and features a beautiful kitchen with custom cabinetry & dining island ideal for both every day living and entertaining. The main level also offers an inviting living room with bay window & fireplace, dining room

Kim Covino Compass

12 Thornberry Rd, Winchester, MA 01890
/24
$2,155,000 Sold Oct 21, 2025

7 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 $1,923,907

Last Listing Agent Isabella Bruno William Raveis R.E. & Home Services

7 Wainwright Rd Unit 13, Winchester, MA 01890

/35
Est $1,728,492 Not Listed For Sale

22 Berkshire Dr, Winchester, MA 01890
- 5 Beds
- 3.5 Baths
- 3,224 Sq Ft
- Built 1967
22 Berkshire Dr, Winchester, MA 01890

Last Sold Summary
- 10% Above List Price
- $486/SF
- 3 Days On Market
Last Sold Price $1,568,000

Last Listing Agent Timothy Morgan RE/MAX

/33
$1,899,000
- 3 Beds
- 2.5 Baths
- 2,306 Sq Ft
2 Gershon Way Unit 2, Winchester, MA 01890

Welcome to Winning Farm of Winchester —an award-winning 55+ community and one of Winchester’s most sought-after addresses for effortless, elevated living. This meticulously maintained and lightly lived-in 3-bedroom, 2.5-bath townhome offers 2,306 sq ft of thoughtfully designed living, showcasing fine craftsmanship & timeless finishes throughout. Sun-drenched interiors highlight gorgeous hardwood

Monte Marrocco Coldwell Banker Realty - Lexington

2 Gershon Way Unit 2, Winchester, MA 01890
/41
$2,000,000 Sold Apr 15, 2025

31 Coolidge Rd, Winchester, MA 01890
- 4 Beds
- 4 Baths
- 4,650 Sq Ft
- Built 1980
Last Sold Summary
- 2% Below List Price
- $430/SF
- 11 Days On Market
Current Estimated Value $2,025,981

Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

31 Coolidge Rd, Winchester, MA 01890

/42
Est $2,179,464 Not Listed For Sale

5 Partridge Ln, Winchester, MA 01890
- 5 Beds
- 4 Baths
- 4,620 Sq Ft
- Built 1967
5 Partridge Ln, Winchester, MA 01890

Last Sold Summary
- 10% Above List Price
- $428/SF
- 6 Days On Market
Last Sold Price $1,977,000

Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

/42
$1,749,000
- 5 Beds
- 3 Baths
- 3,271 Sq Ft
29 Pilgrim Dr, Winchester, MA 01890

Beautifully updated home offers generous living spaces & a seamless, open flow. Sun-filled living &dining areas feature hardwood floors, elegant detailing, & a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, & large island that opens to the dining area, which flows into the family

Anne Spry Barrett Sotheby's International Realty

29 Pilgrim Dr, Winchester, MA 01890
/42
$1,550,000 Sold Oct 31, 2025

205 Ridge St, Winchester, MA 01890
- 5 Beds
- 3 Baths
- 2,995 Sq Ft
- Built 1960
Last Sold Summary
- $518/SF
- 5 Days On Market
Current Estimated Value $1,576,590

Last Listing Agent Debby Valdes eXp Realty

205 Ridge St, Winchester, MA 01890

/40
Est $1,997,839 Not Listed For Sale

89 Thornberry Rd, Winchester, MA 01890
- 5 Beds
- 2.5 Baths
- 4,532 Sq Ft
- Built 1964
89 Thornberry Rd, Winchester, MA 01890

Last Sold Summary
- 11% Above List Price
- $397/SF
- 12 Days On Market
Last Sold Price $1,799,000

Last Listing Agent Kim Covino Compass

/42
$1,795,000 Pending
- 3 Beds
- 3 Baths
- 3,182 Sq Ft
114 Johnson Rd, Winchester, MA 01890

Welcome Home to this gracious Colonial set on beautifully manicured grounds in one of Winchester’s most sought-after neighborhoods, known for its vibrant community & top-rated schools. An oversized updated kitchen w/ Corian countertops, double ovens & abundant cabinetry anchors the home, opening to an elegant dining room & inviting formal living room. Lovely hardwood floors thruout add warmth &

Rosemary Kelleher LAER Realty Partners

114 Johnson Rd, 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

/40
Est $1,943,267 Not Listed For Sale

3 Berkshire Dr, Winchester, MA 01890
- 5 Beds
- 2.5 Baths
- 3,344 Sq Ft
- Built 1967
3 Berkshire Dr, Winchester, MA 01890

Last Sold Summary
- 9% Below List Price
- $635/SF
- 4 Days On Market
Last Sold Price $2,125,000

Last Listing Agent Allison Shannon Berkshire Hathaway HomeServices Robert Paul Properties

/23
$1,399,800
- 6 Beds
- 3 Baths
- 2,658 Sq Ft
65 High St, Winchester, MA 01890

Exceptional opportunity in a highly desirable Winchester neighborhood! This spacious 6-bedroom home offers incredible flexibility for today's lifestyle, perfect for multi-generational living, work-from-home setups, or growing households. The sun-filled main level 3-bedrooms feature hardwood floors and a seamless flow, ideal for both everyday living and entertaining. The updated second floor

Anna Jung K Stadium Realty INC

65 High St, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18

Massachusetts Middlesex County Winchester West Side

Learn more about living in West Side

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 21 days on the market compared to the national average of 55 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,650,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,650,000

Median Single Family Sale Price

$1,719,000

Median Townhouse Sale Price

$2,395,000

Average Price Per Sq Ft

$536

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.70

Median List Price

$1,749,950

Median Change From 1st List Price

Median Home Sale Price YoY Change

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