Middlesex, MA Homes

/42
$1,600,000 Sold Mar 03, 2025
- 2,075 Sq Ft
- $771/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1900
410 Main St, Winchester, MA 01890

Charming, updated carriage house on a private lot, where form meets function in an in-town location. The expansive living room with a fireplace and beam ceiling offers flexibility for dual purposes or a single use. The impressive kitchen boasts a timeless style with a coffee bar, an eat-in breakfast nook, & a convenient peninsula with a six burner stove and Thermador oven. Positioned by a bay

Anne Spry Barrett Sotheby's International Realty

410 Main St, Winchester, MA 01890

/42
Est $2,450,896 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,775 Sq Ft
76 Yale St, Winchester, MA 01890

76 Yale St, Winchester, MA 01890

/27
$1,200,000 Sold Feb 28, 2025
- 3,350 Sq Ft
- $358/SF
- 183 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1989
7 Wainwright Rd Unit 22, Winchester, MA 01890

Now is the time to make a move! Step into a sophisticated lifestyle as you enter through a charming courtyard into this elegant condo. The beautifully updated kitchen is a standout, featuring granite countertops, cherry cabinetry, and premium new stainless steel appliances—a chef’s dream come true. The open-concept layout is perfect for modern living, with a dining area flowing into the inviting

DeWolfe Group Gibson Sotheby's International Realty

7 Wainwright Rd Unit 22, Winchester, MA 01890

/36
Est $3,621,355 Not Listed For Sale
- 6 Beds
- 6 Baths
- 6,073 Sq Ft
25 Dartmouth St, Winchester, MA 01890

25 Dartmouth St, Winchester, MA 01890

/42
$2,825,000 Sold Feb 25, 2025
- 5,850 Sq Ft
- $483/SF
- 8 Days On Market
- 5 Beds
- 6 Baths
- Built 2018
16 Wickham Rd, Winchester, MA 01890

Tucked away on a quiet sought after neighborhood, just steps away from the Wedgemere Station and Winchester Center, this meticulously maintained 5-bedroom home built in 2018 perfectly blends modern design with refined details, including beautiful coffered ceilings, wainscoting, chair rails, and crown moulding. The 1st floor offers a formal living room, a spacious family room with a fireplace, a

Rodrigo Serrano Leading Edge Real Estate

16 Wickham Rd, Winchester, MA 01890

/32
Est $1,950,508 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,350 Sq Ft
57 Wildwood St, Winchester, MA 01890

57 Wildwood St, Winchester, MA 01890

/36
$630,000 Sold Feb 25, 2025
- 1,160 Sq Ft
- $543/SF
- 137 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
666 Main St Unit LV2, Winchester, MA 01890

Welcome to 666 Main Street, Unit LV2, Winchester. This beautiful well maintained 2 bedroom, 2 bathroom condominium on the desirable ground level, features a Private Entrance & a Walk Out Patio w/ Wedge Pond views. Enjoy the close distance of all that Winchester Centre has to offer; shops, restaurants, commuter rail & more. Enjoy an updated kitchen w/ stainless appliances & peninsula, separate

Katie DiVirgilio RE/MAX 360

666 Main St Unit LV2, Winchester, MA 01890

/42
Est $2,007,191 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,003 Sq Ft
12 Woodside Rd, Winchester, MA 01890

12 Woodside Rd, Winchester, MA 01890

/42
$2,025,000 Sold Feb 21, 2025
- 4,997 Sq Ft
- $405/SF
- 8 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1975
23 Olde Village Dr, Winchester, MA 01890

Welcome to this exceptional one floor living ranch-style home, a true haven for both luxury living and car enthusiasts. Nestled among towering trees, this expansive property offers the perfect balance of privacy and beauty, with a stunning 4-car garage designed to accommodate your prized vehicles, ample storage space, workshop, home gym or additional living space. With a grand, welcoming entrance

Andersen Group Realty Keller Williams Realty Boston Northwest

23 Olde Village Dr, Winchester, MA 01890

/42
Est $1,519,227 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,562 Sq Ft
32 Woodside Rd, Winchester, MA 01890

32 Woodside Rd, Winchester, MA 01890

/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

/32
Est $1,344,507 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,894 Sq Ft
114 Pond St, Winchester, MA 01890

114 Pond 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

/40
Est $1,264,902 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,919 Sq Ft
94 Pond St, Winchester, MA 01890

94 Pond St, Winchester, MA 01890

/20
$660,000 Sold Feb 12, 2025
- 1,160 Sq Ft
- $569/SF
- 63 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
666 Main St Unit L3, Winchester, MA 01890

Welcome to 666 Main St Unit L3- Ground level 2 Bedroom Unit with Sliders to Patio overlooking Wedge Pond-Kitchen Totally Updated with Custom Cabinets and Quartz Countertop and Back Splash. Stainless Steel Appliances- Fire Place Living Room with Hardwood Floors-Spacious Dining Area with Hardwood Floors- Open Concept-Master Bedroom with Full Bath, Walk in Closet and Hardwood Floors-2nd Bedroom with

Steven Petrello Century 21 North East

666 Main St Unit L3, Winchester, MA 01890

/42
Est $3,237,940 Not Listed For Sale
- 5 Beds
- 5 Baths
- 4,550 Sq Ft
47 Wedgemere Ave, Winchester, MA 01890

47 Wedgemere Ave, Winchester, MA 01890

/25
$1,450,000 Sold Feb 10, 2025
- 2,632 Sq Ft
- $551/SF
- 3 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1911
48 Water St Unit 50, Winchester, MA 01890

Embrace elegance and convenience with this exquisite townhouse that's been meticulously designed. This residence presents a generous 4-bedroom, 3.5-bathroom, ample space for relaxation and entertainment across its three expansive levels. The heart of this home is the open floor plan, where natural light cascades over fine finishes that align with the rhythm of your daily life. Culinary

Chris Kostopoulos Keller Williams Realty

48 Water St Unit 50, Winchester, MA 01890

/37
Est $2,274,129 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,696 Sq Ft
21 Foxcroft Rd, Winchester, MA 01890

21 Foxcroft Rd, Winchester, MA 01890

/38
$1,650,000 Sold Jan 30, 2025
- 2,376 Sq Ft
- $694/SF
- 30 Days On Market
- 3 Beds
- 4 Baths
- Built 1927
36 Oneida Rd, Winchester, MA 01890

TOTAL RENOVATION! Thoughtfully crafted to create a warm and inviting abode. Step inside to discover the completely reimagined first floor with an open concept dining room, sitting room, and show-stopping brand new kitchen with a center island, and a slider leading to a patio, ideal for alfresco dining and entertaining. The first floor also hosts a versatile family room with access to a private

Philip Vita Compass

36 Oneida Rd, Winchester, MA 01890

/39
Est $2,261,004 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 4,605 Sq Ft
61 Oxford St, Winchester, MA 01890

61 Oxford St, Winchester, MA 01890

/42
$2,799,000 Sold Jan 30, 2025
- 4,324 Sq Ft
- $647/SF
- 68 Days On Market
- 5 Beds
- 6 Baths
- Built 1938
16 Ardley Place, Winchester, MA 01890

Beautiful & magnificent, this colonial single family offers a perfect blend of timeless elegance and contemporary amenities. Situated at the end of a serene cul-de-sac & private hilltop oasis just minutes from the new Lynch Elementary School opening in 2025. Enjoy proximity to Horn Pond recreation areas & seasonal views of Winter Pond. Featuring 5 Bed,4 Full baths, 2-half with 2 ensuites plus a

Ann Norberg Coldwell Banker Realty - Lexington

16 Ardley Place, Winchester, MA 01890

/42
Est $2,721,938 Not Listed For Sale
- 7 Beds
- 3.5 Baths
- 5,616 Sq Ft
49 Oxford St, Winchester, MA 01890

49 Oxford St, Winchester, MA 01890

/38
$1,900,000 Sold Jan 29, 2025
- 3,611 Sq Ft
- $526/SF
- 50 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1984
11 Plymouth Rd, Winchester, MA 01890

OPEN HOUSE SUNDAY 11/17 11:30-1:00pm. Magnificent Brick Colonial, perfectly situated at the end of a quite dead-end street, abutting conservation that offers unmatched privacy and tranquility. The gorgeous, spacious foyer leads into the beautiful front to back living room with a warm and inviting fireplace. The well-appointed dining room with custom built-in China cabinet is perfect for large

Darryl Brian RE/MAX Bentley's

11 Plymouth Rd, Winchester, MA 01890

/24
Est $2,272,072 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,516 Sq Ft
38 Cabot St, Winchester, MA 01890

38 Cabot St, Winchester, MA 01890

/33
$642,000 Sold Jan 28, 2025
- 1,752 Sq Ft
- $366/SF
- 56 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1880
20 Hancock St, Winchester, MA 01890

Welcome to Winchester ! This townhouse with large shared backyard is located on lovely tree lined street . The front porch welcomes you as you can sit and watch the world go by. First floor has living room, dining room and kitchen with laundry. Half bath completes the first floor. Three bedrooms and full bath upstairs. One bedroom is a pass through. Back stairway to half of full size attic is off

Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

20 Hancock St, Winchester, MA 01890

/42
Est $1,884,701 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,131 Sq Ft
39 Wildwood St, Winchester, MA 01890

39 Wildwood St, Winchester, MA 01890

/38
$2,199,000 Sold Jan 27, 2025
- 3,431 Sq Ft
- $641/SF
- 21 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
11 Alden Ln, Winchester, MA 01890

This stunning new 4 Bed 3.5 BA home in Winchester’s sought-after East Side is a must see! The first floor boasts a dramatic contemporary design with high ceilings and designer finishes with oversized windows drawing attention to the setting w/ large rear yard & oversized deck, great for entertaining and family enjoyment.The open airy layout features a great entry w/ mud room, high-end kitchen

Kim Covino Compass

11 Alden Ln, Winchester, MA 01890

/40
Est $2,682,071 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,347 Sq Ft
10 Cabot St, Winchester, MA 01890

10 Cabot St, Winchester, MA 01890

/30
$2,050,000 Sold Jan 24, 2025
- 3,450 Sq Ft
- $594/SF
- 89 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1953
9 South Gateway, Winchester, MA 01890

Completely renovated colonial style home on a quiet cul-de-sac within walking distance to downtown Winchester! This home features 5 bedrooms, 3.5 bathrooms and an attached 2 car garage. The first floor offers kitchen, dining, living room and den/study. The flexible first floor also has a bedroom with en suite bath and an office/additional bedroom. Completing the first floor are a half bath

Mark Donnellan Advisors Living - Winchester

9 South Gateway, Winchester, MA 01890

/41
Est $3,027,869 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,263 Sq Ft
30 Wedgemere Ave, Winchester, MA 01890

30 Wedgemere Ave, Winchester, MA 01890

/42
$1,517,500 Sold Jan 09, 2025
- 3,091 Sq Ft
- $491/SF
- 7 Days On Market
- 6 Beds
- 3 Baths
- Built 1957
14 Henry St, Winchester, MA 01890

Incredible value! Don’t miss this 6 BR, 3 full bathroom expanded colonial w/ over 3,000 square feet of living space tucked away in a charming Vinson Owen School neighborhood. This expansive home features an open concept, eat-in kitchen/family room w/ granite countertops, double ovens, large island, recessed lighting & cozy family room. The sunny kitchen also opens to a private backyard w/ stone

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

14 Henry St, Winchester, MA 01890

/33
Est $1,704,944 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,938 Sq Ft
133 Cambridge St, Winchester, MA 01890

133 Cambridge St, 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

/31
Not Listed For Sale
- 7 Beds
- 5.5 Baths
- 4,636 Sq Ft
127 Church St, Winchester, MA 01890

127 Church St, Winchester, MA 01890

/32
$1,080,000 Sold Jan 08, 2025
- 3,220 Sq Ft
- $335/SF
- 105 Days On Market
- 5 Beds
- 2.5 Baths
- Built 1900
89 Mystic Valley Pkwy, Winchester, MA 01890

Price Adjustment to Assessed Value!! Victorian townhome in fabulous downtown location! Ideally situated in close proximity to trains, schools, restaurants and everything Winchester Center has to offer! Front porch welcomes you into this lovingly cared for home blending old world charm with modern amenities. First floor features high ceilings, beautiful hardwood flooring, fireplaced living room

Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

89 Mystic Valley Pkwy, Winchester, MA 01890

/42
Est $1,487,774 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,863 Sq Ft
62 Bacon St, Winchester, MA 01890

62 Bacon St, Winchester, MA 01890

/33
$1,542,500 Sold Jan 07, 2025
- 3,588 Sq Ft
- $430/SF
- 62 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2011
58 Graystone Cir Unit 58, Winchester, MA 01890

Discover this like-new three bedroom, 3.5 bathroom property, originally purchased as a model unit with numerous high-end upgrades and impeccably maintained since. Soaring ceilings in the first-floor family room create a bright, airy space perfect for entertaining. The open-concept layout seamlessly flows from the designer kitchen area through to dining room and living room, with french doors to

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

58 Graystone Cir Unit 58, Winchester, MA 01890

/35
Est $1,459,283 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,430 Sq Ft
97 Cambridge St, Winchester, MA 01890

97 Cambridge 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

/37
Est $1,890,998 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,436 Sq Ft
111 Cambridge St, Winchester, MA 01890

111 Cambridge St, Winchester, MA 01890

Showing Results 321 - 360, Page 9 of 18

Massachusetts Middlesex County Winchester

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

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

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