Winchester Highlands Homes

/40
$2,532,000 Sold Feb 18, 2025
- 6,300 Sq Ft
- $402/SF
- 28 Days On Market
- 6 Beds
- 6.5 Baths
- Built 2024
20 Bellevue Ave, Winchester, MA 01890

Exquisite 6-bed, 6.5-bath residence offers 6,300 sq ft of sophisticated design and luxurious features. The chef’s kitchen boasts dual islands, quartz countertops, Viking appliances, and a sunny breakfast nook perfect for entertaining. The family room with a gas fireplace opens to a deck and landscaped yard for seamless indoor-outdoor living. The first floor includes a guest bedroom or office with

Monte Marrocco Coldwell Banker Realty - Lexington

20 Bellevue Ave, Winchester, MA 01890
Selling your home? Sell it faster and for more with a Homes.com Boost.
Get a Boost

/38
Est $1,243,034 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,681 Sq Ft
32 Nathaniel Rd, Winchester, MA 01890

32 Nathaniel Rd, Winchester, MA 01890

/40
$1,199,900 Pending
- 4 Beds
- 2.5 Baths
- 2,302 Sq Ft
518 Washington St, Winchester, MA 01890

Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry.

Rodrigo Serrano Leading Edge Real Estate

518 Washington St, Winchester, MA 01890
/34
$1,020,000 Sold Feb 14, 2025
- 1,470 Sq Ft
- $694/SF
- 4 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1965
28 Bellevue Ave, Winchester, MA 01890

Nestled at the end of a peaceful cul-de-sac in Winchester, this charming 3-bedroom, 1.5-bath home is a must-see. Recently updated with fresh paint, modern flooring, stylish lighting fixtures, and updated stainless steel appliances in the kitchen, it blends comfort with convenience. The living room features a cozy wood-burning fireplace, perfect for chilly evenings. The walk-out basement offers

Gayle Winters Compass

28 Bellevue Ave, Winchester, MA 01890

/42
Est $2,216,000 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,634 Sq Ft
15 Tufts Rd, Winchester, MA 01890

15 Tufts Rd, Winchester, MA 01890

/41
$2,599,000 Pending
- 4 Beds
- 4.5 Baths
- 5,501 Sq Ft
15 Churchill Rd, Winchester, MA 01890

Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor

Kim Covino Compass

15 Churchill Rd, Winchester, MA 01890
/42
$1,130,000 Sold Jan 08, 2025
- 1,883 Sq Ft
- $600/SF
- 21 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1948
6 Governors Ave, Winchester, MA 01890

Welcome to this impeccably maintained & beautifully updated Colonial on large lot near the town center. This home blends charm w/ modern convenience, featuring 3 spacious bedrooms & 1.5 baths w/ a great floor plan. The first level features a sun-drenched living room that flows into an inviting dining room; updated kitchen overlooks the rear yard & is equipped w/ ample storage, stainless steel

Kim Covino Compass

6 Governors Ave, Winchester, MA 01890

/24
Est $1,228,007 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,139 Sq Ft
32 Tufts Rd, Winchester, MA 01890

32 Tufts Rd, Winchester, MA 01890

/29
$1,345,000 Pending
- 3 Beds
- 2 Baths
- 2,238 Sq Ft
49 Lincoln St, Winchester, MA 01890

Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking

Vantage Point Team William Raveis R.E. & Home Services

49 Lincoln St, Winchester, MA 01890
/21
$425,000 Sold Jan 03, 2025
- 758 Sq Ft
- $561/SF
- 9 Days On Market
- 1 Bed
- 1 Bath
- Built 1982
64 Highland Ave Unit 18, Winchester, MA 01890

DON'T MISS THIS ONE! Ideal location at Waterfield Square - This spacious one bedroom is a diamond-in-the-rough waiting for your upgrades. High ceilings and huge windows bring in lots of sun and light. Open floor plan. Lots of closet space. Washer & Dryer in unit. Deeded parking, basement storage, tennis court, picnic area with grill, fire pit, located across from the North Reservoir and

Diane Plunkett Plunkett Properties

64 Highland Ave Unit 18, Winchester, MA 01890

/34
Est $1,077,136 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,918 Sq Ft
5 Bates Rd, Winchester, MA 01890

5 Bates Rd, Winchester, MA 01890

/30
$1,199,000 Pending
- 3 Beds
- 1.5 Baths
- 1,573 Sq Ft
18 Brookside Ave, Winchester, MA 01890

Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to a bright bow front living room w/ high ceilings, that flows into the dining room & beautifully updated kitchen w/ stainless appliances & custom cabinetry w/ generous counter space. Off the kitchen, there’s a half bath and a bonus room—great as an office, playroom, or casual

Kim Covino Compass

18 Brookside Ave, Winchester, MA 01890
/39
$1,450,000 Sold Dec 26, 2024
- 1,969 Sq Ft
- $736/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1950
37 Tufts Rd, Winchester, MA 01890

Beautifully renovated home with open concept main living area including elegantly updated kitchen with quartz countertops, professional grade range and wine refrigerator. Primary suite includes cathedral ceilings and oversized (8' high) sliders opening up to private balcony with views of Leonard Pond. His and hers closets and private bath with double sinks and radiant heat make this the perfect

Amanda Armstrong Compass

37 Tufts Rd, Winchester, MA 01890

/35
Est $1,253,714 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,565 Sq Ft
63 Irving St, Winchester, MA 01890

63 Irving St, Winchester, MA 01890

/34
$1,071,000 Sold Dec 05, 2024
- 2,186 Sq Ft
- $490/SF
- 8 Days On Market
- 5 Beds
- 3 Baths
- Built 1880
63-65 Harvard St, Winchester, MA 01890

Discover this rare multi-family gem in a highly desirable Winchester neighborhood, offering endless possibilities for savvy investors, owner-occupants, or multi-generational living. Situated on a large, flat, private lot with a detached two-car garage and ample off-street parking, this home perfectly balances charm, function, and convenience. The first-floor unit includes two bedrooms, a bright

Nancy Pallotta Advisors Living - Winchester

63-65 Harvard St, Winchester, MA 01890

/35
Est $898,723 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,252 Sq Ft
42 Irving St, Winchester, MA 01890

42 Irving St, Winchester, MA 01890

/42
$2,375,000 Sold Dec 02, 2024
- 5,279 Sq Ft
- $450/SF
- 7 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2014
7 Bellevue Ave, Winchester, MA 01890

Exceptionally designed & meticulously maintained 2015 Contemporary Colonial. Elegant farmers porch welcomes you into a magnificent layout w/ exquisite mouldings, wainscotting, oak hardwoods, custom fixtures/millwork, & plantation shutters. Spectacular, open-concept main level boasts dual island, granite/stainless chef’s kitchen w/ 2 ovens, butler’s pantry, built-in buffet, walk-in pantry, &

Cam Chesley Keller Williams Realty Boston-Metro | Back Bay

7 Bellevue Ave, Winchester, MA 01890

/34
Est $1,135,630 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,477 Sq Ft
30 Irving St Unit 32, Winchester, MA 01890

30 Irving St Unit 32, Winchester, MA 01890

/30
$1,050,000 Sold Nov 21, 2024
- 2,136 Sq Ft
- $492/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1926
359-361 Washington St, Winchester, MA 01890

Welcome to this well-maintained two-unit multi-family home, perfect for investors or owner-occupants seeking a spacious living arrangement with rental income potential. Each unit boasts two well apportioned bedrooms and dedicated in-home office areas, ideal for today’s work-from-home lifestyle. Enjoy the convenience of off-street parking along with two garage bays, ensuring easy access for you

Anne Spry Barrett Sotheby's International Realty

359-361 Washington St, Winchester, MA 01890

/39
Est $1,091,962 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,065 Sq Ft
29 Harvard St, Winchester, MA 01890

29 Harvard St, Winchester, MA 01890

/41
$1,800,000 Sold Nov 18, 2024
- 3,866 Sq Ft
- $466/SF
- 5 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1905
118 Forest St, Winchester, MA 01890

This thoughtfully updated home combines historic charm and modern style. The oversized, beautifully landscaped lot showcases established plantings, charming stone paths, and terraced gardens - the perfect oasis for relaxing family time and outdoor entertaining. Inside, the hub of this 5 BR, 3,5 BA home is the large, open-concept kitchen and family room, featuring a cathedral ceiling, gas

Jay Smith Brad Hutchinson Real Estate

118 Forest St, Winchester, MA 01890

/33
Est $981,083 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,770 Sq Ft
316 Washington St, Winchester, MA 01890

316 Washington St, Winchester, MA 01890

/33
$1,700,000 Sold Oct 18, 2024
- 3,061 Sq Ft
- $555/SF
- 26 Days On Market
- 4 Beds
- 5 Baths
- Built 1937
25 Englewood Rd, Winchester, MA 01890

Exquisitely renovated down to the studs and close to completion w/ over 3,000 sq ft in a great neighborhood! The home offers 4 Bedrooms + Loft, 3 full and 2 half baths w/ designer tile, 6"wide hardwood floors on all 3 living levels. First floor has an open floor plan and great flow for entertaining. Large eat-in Kitchen with island, Quartz counters and SS appliances. Stepdown to a huge living

Lisa Simmons William Raveis R.E. & Home Services

25 Englewood Rd, Winchester, MA 01890

/26
Est $1,164,420 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,886 Sq Ft
11 Swanton St, Winchester, MA 01890

11 Swanton St, Winchester, MA 01890

/33
$1,198,000 Sold Oct 02, 2024
- 2,250 Sq Ft
- $532/SF
- 28 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
70 Harvard St Unit 70, Winchester, MA 01890

Your wait is over! Brand New Townhouse with a stylish flair has just been completed and is ready for YOU to call it HOME! Located just minutes away from all the amenities in Winchester and major highways. This flexible use floor plan offers an open floor plan on the 1st floor with a spacious well appointed kitchen, dining area, living room, mudroom and half bath. The 2nd floor features the

Bill Copithorne Keller Williams Realty Boston Northwest

70 Harvard St Unit 70, Winchester, MA 01890

/18
Est $999,433 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,152 Sq Ft
22 Chester St, Winchester, MA 01890

22 Chester St, Winchester, MA 01890

/30
$1,210,000 Sold Aug 21, 2024
- 2,181 Sq Ft
- $555/SF
- 81 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
68 Harvard St, Winchester, MA 01890

A Brand New Townhouse with a modern stylish feel has just been completed and is ready for a new owner to make it their Home! Located just minutes away from all the amenities in Winchester Center you could not ask for a more convenient location. You will be wowed as you cross the farmer's porch into the well designed open 1st floor that features a custom FP in the living room, built-in bench

Bill Copithorne Keller Williams Realty Boston Northwest

68 Harvard St, Winchester, MA 01890

/25
Est $1,013,126 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,236 Sq Ft
101 Harvard St, Winchester, MA 01890

101 Harvard St, Winchester, MA 01890

/38
$1,875,000 Sold Aug 06, 2024
- 4,234 Sq Ft
- $443/SF
- 5 Days On Market
- 5 Beds
- 5 Baths
- Built 1900
25 Marion St, Winchester, MA 01890

Welcome to your sprawling retreat nestled on an expansive lot, offering unparalleled versatility for recreation and relaxation. This magnificent property boasts 27,952 square feet lot with an inground pool. Whether you're hosting barbecues by the cabana, or enjoying a morning swim, this outdoor oasis offers endless possibilities for lifelong memories. The 4,234 square foot home, proudly owned and

Anne Spry Barrett Sotheby's International Realty

25 Marion St, Winchester, MA 01890

/19
Est $860,456 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,292 Sq Ft
18 Olive St, Winchester, MA 01890

18 Olive St, Winchester, MA 01890

/36
$1,150,000 Sold Aug 06, 2024
- 1,875 Sq Ft
- $613/SF
- 26 Days On Market
- 3 Beds
- 2 Baths
- Built 1930
19 Kenwin Rd, Winchester, MA 01890

Aah, the beautiful summer weather is here. We wait all year for this, and the level yard at 19 Kenwin Rd is sunny and lush and ready for you to enjoy your outdoor living. Sited on more than a quarter acre, this 9-room 3-bed 2-bath colonial is located just a mile to vibrant Winchester Center, and one block to Middlesex Fells Reservation, a 2,575 acre natural haven. The main floor has 5 rooms

Judy Weinberg Leading Edge Real Estate

19 Kenwin Rd, Winchester, MA 01890

/10
Est $1,635,921 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,050 Sq Ft
30 Florence St, Winchester, MA 01890

30 Florence St, Winchester, MA 01890

/38
$1,150,000 Sold Jul 26, 2024
- 2,217 Sq Ft
- $519/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1960
6 Nathaniel Rd, Winchester, MA 01890

Lovingly maintained family home on a gorgeous oversized lot with beautiful perennial gardens, and an abundance of privacy bound by beautiful mature landscape. This custom built 4 bedroom home is awaiting your personal touch. Create the home of your dreams with this extraordinarily spacious layout featuring a rear family room addition plus glass enclosed heated sunroom overlooking the beautiful

Kim Covino Compass

6 Nathaniel Rd, Winchester, MA 01890

/41
Est $2,576,569 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,583 Sq Ft
148 Highland Ave, Winchester, MA 01890

148 Highland Ave, Winchester, MA 01890

/42
Est $786,318 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,547 Sq Ft
6 Park Ave Unit A, Winchester, MA 01890

6 Park Ave Unit A, Winchester, MA 01890

/42
Est $1,745,795 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,803 Sq Ft
33 Fells Rd, Winchester, MA 01890

33 Fells Rd, Winchester, MA 01890

/42
Est $2,320,547 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,814 Sq Ft
46 Fells Rd, Winchester, MA 01890

46 Fells Rd, Winchester, MA 01890

/38
Est $1,442,887 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,914 Sq Ft
22 Fells Rd, Winchester, MA 01890

22 Fells Rd, Winchester, MA 01890

/41
Est $1,222,933 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,175 Sq Ft
39 Lebanon St, Winchester, MA 01890

39 Lebanon St, Winchester, MA 01890

/42
Est $1,924,902 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,175 Sq Ft
18 Stone Ave, Winchester, MA 01890

18 Stone Ave, Winchester, MA 01890

Showing Results 41 - 80, Page 2 of 18

Massachusetts Winchester Winchester Highlands

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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