Winchester, MA Homes

/31
$940,000 Sold Mar 14, 2025
- 2,418 Sq Ft
- $389/SF
- 8 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1985
60 Edward Dr Unit 60, Winchester, MA 01890

Welcome to this move in ready townhouse in Pepper Hill Estates! Enjoy easy living with this stunning open concept home boasting a newer eat-in kitchen, spacious dining room & oversized living room with a wood burning fireplace and floor to ceiling windows that are flooded w/natural light. This main floor also has great closet space, a half bath and a beautiful rear deck to enjoy. The 2nd level

Kim Covino Compass

60 Edward Dr Unit 60, Winchester, MA 01890

/40
Est $1,397,344 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,456 Sq Ft
25 Lockeland Rd, Winchester, MA 01890

25 Lockeland Rd, Winchester, MA 01890

/5
$2,899,000 New Construction
- 5 Beds
- 5.5 Baths
- 4,627 Sq Ft
11 Taft Dr, Winchester, MA 01890

Luxury and location converge in this stunning 5-bedroom, 5.5-bathroom home nestled in one of Winchester’s most coveted Westside neighborhoods. Beautifully rehabbed and thoughtfully expanded, this turnkey residence offers over 4,600 sq. ft. of refined living space, just steps from Ambrose School, one block from the Alewife bus stop, & a short ½-mile stroll to the commuter rail. Every detail has

Monte Marrocco Coldwell Banker Realty - Lexington

11 Taft Dr, Winchester, MA 01890
/42
$2,200,000 Sold Mar 07, 2025
- 3,676 Sq Ft
- $598/SF
- 12 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1940
6 Ardley Place, Winchester, MA 01890

Tucked away on a dead-end street, 6 Ardley Place blends classic character with modern comforts. Beautifully expanded with a complete renovation & redesign in 2013, this home offers a warm & inviting atmosphere w/elegant finishes throughout. The heart of the home is a stunning chef’s kitchen, featuring a 10 foot walnut island, Viking gas stove, beautiful cabinetry, & flows into the family room

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

6 Ardley Place, Winchester, MA 01890

/37
Est $2,182,530 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,209 Sq Ft
4 Mayflower Rd, Winchester, MA 01890

4 Mayflower Rd, Winchester, MA 01890

/38
$2,499,000 Open Sun 11AM - 12PM
- 7 Beds
- 5.5 Baths
- 4,829 Sq Ft
89 Wildwood St, Winchester, MA 01890

Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

Monte Marrocco Coldwell Banker Realty - Lexington

89 Wildwood St, Winchester, MA 01890
/42
$2,900,000 Sold Mar 07, 2025
- 4,400 Sq Ft
- $659/SF
- 67 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1917
64 Wildwood St, Winchester, MA 01890

Exquisitely restored brick Colonial situated in the sought-after Flats neighborhood of Winchester. Boasting refinished hardwood floors, beautiful moldings and trim, and high ceilings throughout, no detail has been overlooked in this meticulous renovation. The gourmet kitchen, featuring high end appliances, is perfect for culinary enthusiasts, while the formal dining room, complete w/ wood-burning

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

64 Wildwood St, Winchester, MA 01890

/40
Est $1,802,104 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,744 Sq Ft
20 Mayflower Rd, Winchester, MA 01890

20 Mayflower Rd, Winchester, MA 01890

/42
$3,895,000 Pending
- 7 Beds
- 8 Baths
- 7,587 Sq Ft
25 Wedgemere Ave, Winchester, MA 01890

Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7

Prestige Homes Realty Team Prestige Homes Real Estate, LLC

25 Wedgemere Ave, Winchester, MA 01890
/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

/36
Est $1,668,008 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,190 Sq Ft
43 Mayflower Rd, Winchester, MA 01890

43 Mayflower Rd, Winchester, MA 01890

/33
$1,769,000 Pending
- 5 Beds
- 3.5 Baths
- 3,478 Sq Ft
10 Olde Lyme Rd, Winchester, MA 01890

Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state.

Darryl Brian RE/MAX Bentley's

10 Olde Lyme Rd, 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

/41
Est $2,223,066 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,372 Sq Ft
36 Mayflower Rd, Winchester, MA 01890

36 Mayflower Rd, Winchester, MA 01890

/42
$1,775,000 Pending
- 5 Beds
- 3.5 Baths
- 3,150 Sq Ft
19 Pilgrim Dr, Winchester, MA 01890

Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –

Gorfinkle Group eXp Realty

19 Pilgrim Dr, 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

/42
Est $3,102,982 Not Listed For Sale
- 6 Beds
- 5 Baths
- 4,805 Sq Ft
53 Hutchinson Rd, Winchester, MA 01890

53 Hutchinson 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
/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

/33
Est $1,328,901 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,636 Sq Ft
132 Cambridge St, Winchester, MA 01890

132 Cambridge St, Winchester, MA 01890

/34
$689,000 Pending
- 2 Beds
- 2 Baths
- 1,160 Sq Ft
7 Conant Rd Unit 23, Winchester, MA 01890

Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts’ top-rated school districts. Located in the desirable Lynch Elementary district, which will open a brand-new school building this fall. This move-in ready home has just been freshly painted, with brand-new kitchen appliances and new carpeting throughout. The open-concept living and dining area

Xin Cui Hooli Homes Boston

7 Conant Rd Unit 23, 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

/40
Est $2,813,734 Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,051 Sq Ft
50 Emerson Rd, Winchester, MA 01890

50 Emerson Rd, Winchester, MA 01890

/39
$960,000 Pending
- 2 Beds
- 2 Baths
- 1,540 Sq Ft
6 Francis Circuit Unit 6, Winchester, MA 01890

Submerge yourself in historic elegance in this meticulously detailed Victorian home, brimming with classic design. Located on one of Winchester’s most serene and desirable cul-de-sacs, this stunning gem overflows with rich architectural details. Inside, you'll find three stately fireplaces, two oversized pocket doors, exquisite antique leaded light fixtures, stained glass, gleaming hardwood

Katherine Waters-Clark Compass

6 Francis Circuit Unit 6, 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

/37
Est $1,847,640 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,689 Sq Ft
36 Robinhood Rd, Winchester, MA 01890

36 Robinhood Rd, Winchester, MA 01890

/40
$1,625,000 Pending
- 3 Beds
- 3.5 Baths
- 4,228 Sq Ft
7 Wainwright Rd Unit 55, Winchester, MA 01890

Welcome to The Ledges—an exceptional custom-designed “E” style end-unit townhouse offering over 10 rooms of refined living space and a distinctive layout found in no other unit. Thoughtfully maintained and tastefully updated, this residence features an expansive open floor plan with cathedral ceilings, elegant crown molding, and a gourmet chef’s kitchen equipped with premium appliances. The first

Ngoc Anh Goldstein Leading Edge Real Estate

7 Wainwright Rd Unit 55, 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

/33
Est $1,519,590 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,920 Sq Ft
10 Albamont Rd, Winchester, MA 01890

10 Albamont Rd, Winchester, MA 01890

/36
$999,000 Pending
- 4 Beds
- 2.5 Baths
- 2,335 Sq Ft
163 Main St, Winchester, MA 01890

Charming multi-level home in close proximity to Winchester Center, public transit, Lincoln Elementary, and McCall. The main level offers an open floor plan with beautiful hardwood floors, bay windows, a skylit eat-in kitchen, and abundant natural light. Perfect for entertaining, the living and dining rooms flow seamlessly to a spacious yard, relaxing patio, and mature gardens. The top floor

Andersen Group Realty Keller Williams Realty Boston Northwest

163 Main 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

/27
Est $1,374,423 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,413 Sq Ft
12 Albamont Rd, Winchester, MA 01890

12 Albamont Rd, Winchester, MA 01890

/40
$1,458,000 Pending
- 4 Beds
- 2.5 Baths
- 2,470 Sq Ft
35 Rumford St Unit 35, Winchester, MA 01890

This sun-filled 2012 townhouse, with its spacious layout, backyard oasis & attached garage, lives like a single-family home. Spend weekends lounging on the private deck, unwinding under the pergola, or playing on the lush, fenced lawn. Inside, the inviting open layout is made for gathering—whether around the gas fireplace on cozy evenings or at the kitchen island while entertaining friends. High

Elena Langlois Compass

35 Rumford St Unit 35, 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 $1,457,542 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,597 Sq Ft
22 Albamont Rd, Winchester, MA 01890

22 Albamont Rd, Winchester, MA 01890

/19
$1,799,000 Pending
- 4 Beds
- 3.5 Baths
- 3,784 Sq Ft
109 Thornberry Rd, Winchester, MA 01890

Ideally located in one of Winchester’s most desirable neighborhoods, this classic Colonial blends timeless design with thoughtful updates. At the heart of the home, the beautifully updated kitchen features a generous center island, opening to a spacious family room with a slider leading to a large deck overlooking the expansive, level backyard - perfect for summer entertaining. Just off the

Andrew Martini Compass

109 Thornberry 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

/13
Est $1,560,287 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,290 Sq Ft
26 New Meadows Rd, Winchester, MA 01890

26 New Meadows Rd, Winchester, MA 01890

/39
$2,299,000 Pending
- 4 Beds
- 3.5 Baths
- 3,896 Sq Ft
4 Fairfield Place, Winchester, MA 01890

NEWER CONSTRUCTION 4 bed 3.5 bath colonial located in a great neighborhood right outside Winchester center! Enjoy all the area has to offer just outside your door including restaurants, shops, schools, train to Boston, the Tri-Community bike path, Horn Pond, Packer tennis courts & Wedge pond! This warm and welcoming, gently lived in home showcases 3900sf of space on 3 levels with 4 large

Kim Covino Compass

4 Fairfield Place, 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

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Massachusetts Winchester

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