Winchester, MA Homes

/39
$1,500,000
- 5 Beds
- 3.5 Baths
- 3,362 Sq Ft
38 Salem St Unit 40, Winchester, MA 01890

A rare opportunity to enjoy easy, yet refined living in Winchester, this well-maintained newer construction home offers 4-5 bedrooms and 3 1⁄2 baths with a thoughtfully designed open floor plan. The main level features a spacious living area, eat-in kitchen with granite countertops, stainless steel appliances and pantry, along with a 1⁄2 bath and practical mudroom for everyday ease. Upstairs,

Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

38 Salem St Unit 40, Winchester, MA 01890
/39
$1,425,000 Sold Dec 01, 2025

102 Hillcrest Pkwy, Winchester, MA 01890
- 4 Beds
- 2 Baths
- 1,755 Sq Ft
- Built 1939
Last Sold Summary
- 19% Above List Price
- $812/SF
- 4 Days On Market
Current Estimated Value $1,374,749

Last Listing Agent Curtis Howe Howe Realty Group

102 Hillcrest Pkwy, Winchester, MA 01890

/26
Est $1,174,871 Not Listed For Sale

75 Dunster Ln, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 1,826 Sq Ft
- Built 1928
75 Dunster Ln, Winchester, MA 01890

Last Sold Summary
- 21% Above List Price
- $531/SF
- 15 Days On Market
- Last Sold Price $970,000
- Aug 11, 2023
Last Listing Agent Adriano Varano Keller Williams Realty

/9
$379,900
- 1 Bed
- 1 Bath
- 606 Sq Ft
200 Swanton St Unit 318, Winchester, MA 01890

Beautifully renovated oversized one-bedroom condo at Parkview Condominium featuring an open floor plan and private balcony overlooking a serene Japanese garden and duck pond. Spacious primary bedroom offers room for a king-size bed and includes a walk-in closet. Updated kitchen, bathroom, and flooring provide years of low-maintenance living. Amenities include swimming pool, cabana, picnic

Mike Huang Lewis & Joyce Real Estate

200 Swanton St Unit 318, 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

/42
Est $3,085,565 Not Listed For Sale

222 High St, Winchester, MA 01890
- 5 Beds
- 4.5 Baths
- 5,676 Sq Ft
- Built 2006
222 High St, Winchester, MA 01890

Last Sold Summary
- 8% Above List Price
- $504/SF
- 0 Days On Market
- Last Sold Price $2,860,000
- Aug 31, 2023
Last Listing Agent Gayle Winters Compass

/41
$1,799,000
- 4 Beds
- 2.5 Baths
- 2,818 Sq Ft
12 Cox Rd, Winchester, MA 01890

Fabulous 11 room, 4 bedroom Colonial set on a beautiful lot on Winchester’s west side. The first floor offers a bright and sunny, open concept kitchen and family room which creates the perfect space for everyday living and entertaining which leads to a mud room, laundry, and home office . Completing the first floor is half bath off kitchen, a dining room and a front to back, fireplaced, living

Darryl Brian RE/MAX Bentley's

12 Cox Rd, Winchester, MA 01890
/36
$519,000 Sold Oct 08, 2025

115 Washington St Unit 3D, Winchester, MA 01890
- 1 Bed
- 1.5 Baths
- 769 Sq Ft
- Built 1988
Last Sold Summary
- $675/SF
- 5 Days On Market
Current Estimated Value $523,660

Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

115 Washington St Unit 3D, Winchester, MA 01890

/30
Est $922,819 Not Listed For Sale

62 Edward Dr, Winchester, MA 01890
- 2 Beds
- 2.5 Baths
- 1,857 Sq Ft
- Built 1985
62 Edward Dr, Winchester, MA 01890

Last Sold Summary
- 3% Above List Price
- $485/SF
- 6 Days On Market
- Last Sold Price $900,000
- Nov 21, 2024
Last Listing Agent Melissa Perrone Better Homes and Gardens Real Estate - The Shanahan Group

/39
$1,099,000 Pending
- 3 Beds
- 1.5 Baths
- 1,973 Sq Ft
15 East St, Winchester, MA 01890

Move in ready & nicely remodeled ranch on a fabulous 10K fenced lot! This 3-4bedroom, 2 full bath home w/full lower level including office, family room/bedroom & full bath offers a sunny, functional layout w/ tasteful updates throughout.The main living spaces flow seamlessly, highlighted by a newer eat-in kitchen w/ access to deck & great yard; perfect for indoor/outdoor living & entertaining.

Kim Covino Compass

15 East St, Winchester, MA 01890
/30
$1,207,500 Sold Jul 24, 2025

18 Brookside Ave, Winchester, MA 01890
- 3 Beds
- 1.5 Baths
- 1,573 Sq Ft
- Built 1910
Last Sold Summary
- 1% Above List Price
- $768/SF
- 20 Days On Market
Current Estimated Value $1,190,603

Last Listing Agent Kim Covino Compass

18 Brookside Ave, Winchester, MA 01890

/27
Est $1,059,932 Not Listed For Sale

46 Edward Dr, Winchester, MA 01890
- 3 Beds
- 3.5 Baths
- 2,859 Sq Ft
- Built 1985
46 Edward Dr, Winchester, MA 01890

Last Sold Summary
- 15% Above List Price
- $324/SF
- 8 Days On Market
- Last Sold Price $925,000
- Nov 20, 2023
Last Listing Agent Sam Zhu Keller Williams Realty

/26
$649,000 Pending
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
2 George Rd Unit 2, Winchester, MA 01890

Inviting 3 Bed 2 bath townhouse situated on one of the largest lots in the neighborhood offering a perfect blend of space and natural light. This home is in great condition with hardwood floors and an updated kitchen with direct access to the yard. The living room with picture window flows into an open concept dining area. Upstairs find three bedrooms and a full updated bath. The finished lower

Kim Covino Compass

2 George Rd Unit 2, Winchester, MA 01890
/35
$1,375,000 Sold Jan 23, 2026

32 Oak St, Winchester, MA 01890
- 4 Beds
- 3 Baths
- 2,652 Sq Ft
- Built 1963
Last Sold Summary
- 2% Above List Price
- $518/SF
- 6 Days On Market
Current Estimated Value $1,351,535

Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

32 Oak St, Winchester, MA 01890

/36
Est $975,813 Not Listed For Sale

55 Edward Dr, Winchester, MA 01890
- 3 Beds
- 3.5 Baths
- 2,568 Sq Ft
- Built 1987
55 Edward Dr, Winchester, MA 01890

Last Sold Summary
- $380/SF
- 6 Days On Market
- Last Sold Price $975,000
- Sep 16, 2024
Last Listing Agent Anne Spry Barrett Sotheby's International Realty

/30
$364,900
- 1 Bed
- 1 Bath
- 613 Sq Ft
200 Swanton St Unit 717, Winchester, MA 01890

Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for

Cameron Moniz Coldwell Banker Realty - Lexington

200 Swanton St Unit 717, 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

/42
Est $1,112,184 Not Listed For Sale

41 Edward Dr, Winchester, MA 01890
- 3 Beds
- 3.5 Baths
- 2,738 Sq Ft
- Built 1985
41 Edward Dr, Winchester, MA 01890

Last Sold Summary
- 26% Above List Price
- $323/SF
- 17 Days On Market
- Last Sold Price $885,000
- Aug 01, 2023
Last Listing Agent Beth Sager Group Keller Williams Realty Boston Northwest

/41
$929,900
- 4 Beds
- 2 Baths
- 1,938 Sq Ft
380 Cross St, Winchester, MA 01890

This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a nice place for family to congregate and get to

Rajive Dogra Coldwell Banker Realty - Lexington

380 Cross St, 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

/38
Est $1,050,154 Not Listed For Sale

34 Edward Dr, Winchester, MA 01890
- 3 Beds
- 3.5 Baths
- 2,754 Sq Ft
- Built 1985
34 Edward Dr, Winchester, MA 01890

Last Sold Summary
- 11% Above List Price
- $345/SF
- 6 Days On Market
- Last Sold Price $950,000
- Apr 23, 2024
Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

/42
$2,299,000 Pending
- 5 Beds
- 3.5 Baths
- 4,822 Sq Ft
216 Highland Ave, Winchester, MA 01890

Welcome to this fully updated 5 BR, 3.5 BA Victorian showcasing elegant period detail throughout, including intricate woodwork, moldings, high ceilings & hardwood floors. The main level features a gourmet eat-in kitchen w/ quartz island & high-end stainless appliances, opening to a custom butler’s pantry w/ additional oven, sink & wine chiller. A sun-filled family room w/French doors leads to the

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

216 Highland Ave, 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

/37
Est $910,267 Not Listed For Sale

47 Edward Dr, Winchester, MA 01890
- 2 Beds
- 2 Baths
- 1,920 Sq Ft
- Built 1985
47 Edward Dr, Winchester, MA 01890

Last Sold Summary
- 25% Above List Price
- $379/SF
- 7 Days On Market
- Last Sold Price $727,500
- Jan 05, 2024
Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

/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
/4
$700,000 Sold Apr 28, 2026

20 Charles Rd, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 1,317 Sq Ft
- Built 1962
Last Sold Summary
- 8% Above List Price
- $532/SF
- 8 Days On Market
Current Estimated Value $650,387

Last Listing Agent Wei Wenny Fu Phoenix Real Estate

20 Charles Rd, Winchester, MA 01890

/31
Est $1,818,912 Not Listed For Sale

56 Ridge St, Winchester, MA 01890
- 4 Beds
- 4 Baths
- 4,028 Sq Ft
- Built 1973
56 Ridge St, Winchester, MA 01890

Last Sold Summary
- 14% Above List Price
- $397/SF
- 5 Days On Market
- Last Sold Price $1,600,000
- May 31, 2023
Last Listing Agent Philip Vita Compass

/31
$1,300,000 Pending
- 3 Beds
- 3.5 Baths
- 2,803 Sq Ft
7 Wainwright Rd Unit 30, Winchester, MA 01890

This three bedroom condo in Winchester offers 2025 kitchen and bath updates with a thoughtfully designed, expansive layout across multiple levels. Hardwood floors span the first level with a den and open living and dining area ideal for everyday living and entertaining. The second floor features a generous primary suite with walk-in glass shower and stackable laundry, plus an additional bedroom

Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

7 Wainwright Rd Unit 30, 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

/23
Est $968,549 Not Listed For Sale

12 James St, Winchester, MA 01890
- 3 Beds
- 1.5 Baths
- 1,548 Sq Ft
- Built 1950
12 James St, Winchester, MA 01890

Last Sold Summary
- 14% Above List Price
- $548/SF
- 25 Days On Market
- Last Sold Price $849,000
- Jul 25, 2023
Last Listing Agent Gigi Nguyen Harmony Hill Realty LLC

/33
$1,150,000
- 5 Beds
- 3 Baths
- 2,186 Sq Ft
63-65 Harvard St, Winchester, MA 01890

Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home.

Beth Sager Group Keller Williams Realty Boston Northwest

63-65 Harvard St, 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

/42
Est $995,505 Not Listed For Sale

25 Henry St, Winchester, MA 01890
- 5 Beds
- 4.5 Baths
- 3,890 Sq Ft
- Built 2021
25 Henry St, Winchester, MA 01890

Last Sold Summary
- 34% Below List Price
- $388/SF
- 3 Days On Market
- Last Sold Price $1,510,000
- Jan 24, 2024
Last Listing Agent Karima Alami Compass

/39
$400,000
- 2 Beds
- 1 Bath
- 810 Sq Ft
200 Swanton St Unit T35, Winchester, MA 01890

SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of

Nuri Tirana Tirana Real Estate Group

200 Swanton St Unit T35, 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

/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
- Oct 25, 2023
Last Listing Agent Alison Socha Leading Edge Real Estate

/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 $2,162,346

Last Listing Agent Kim Covino Compass

14 Grove St, Winchester, MA 01890

/42
Est $1,385,161 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
- 9% Below List Price
- $491/SF
- 7 Days On Market
- Last Sold Price $1,517,500
- Jan 09, 2025
Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

/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

/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
- Aug 24, 2023
Last Listing Agent Ruth Gagne Barrett Sotheby's International Realty

Showing Results 161 - 200, Page 5 of 18

Massachusetts Middlesex County Winchester

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

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

Winchester, MA Homes

Real Estate & Homes