Winchester, MA Homes

/38
$2,795,000
- 4 Beds
- 4.5 Baths
- 5,233 Sq Ft
18 Middlesex St, Winchester, MA 01890

A masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of-the-art amenities.Step into a grand foyer, where a striking curved staircase sets the stage for the home’s sophisticated ambiance. Expansive living and entertaining spaces flow seamlessly, featuring soaring ceilings, custom millwork, and exquisite finishes. The Bespoke

Candice Macoul Luxury Living Real Estate

18 Middlesex St, Winchester, MA 01890
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/41
$6,900 total monthly price
- 4 Beds
- 4 Baths
- 4,650 Sq Ft
- House for Rent
31 Coolidge Rd, Winchester, MA 01890

A grand home with a perfect mix of serenity and entertaining spaces. The main level has endless possibilities with its ability to provide cozy living areas and also an open concept with great flow. Fully equipped modern kitchen with tons of storage and island, Formal dining room with custom built ins, french doors to separate or open up spaces, front to back fireplace between the massive family

Sheri O'Connor Plunkett Properties

31 Coolidge Rd, Winchester, MA 01890
/31
$1,050,000 Sold Oct 22, 2025
- 1,296 Sq Ft
- $810/SF
- 9 Days On Market
- 2 Beds
- 2 Baths
- Built 2021
36 Elmwood Ave Unit 4, Winchester, MA 01890

Welcome to this stunning 2-bedroom, 2-bathroom condo, built in 2021 and being offered by its original owner. Perfectly situated in the center of Winchester, this home is designed for effortless one-level living and offers the best of modern convenience and timeless style with an open and airy floor plan with oversized windows which fill the space with natural light. The gourmet kitchen flows

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

36 Elmwood Ave Unit 4, Winchester, MA 01890

/32
Est $1,635,093 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,622 Sq Ft
104 Thornberry Rd, Winchester, MA 01890

104 Thornberry Rd, Winchester, MA 01890

/42
$1,999,000 Open Sat 12PM - 1:30PM
- 5 Beds
- 3.5 Baths
- 6,232 Sq Ft
5 Azalea Rd, Winchester, MA 01890

NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and

Anthony Marino The Marino Group Collection

5 Azalea Rd, Winchester, MA 01890
/33
$5,500 total monthly price
- 5 Beds
- 4.5 Baths
- 4,000 Sq Ft
- Apartment for Rent
378 Washington St Unit 378, Winchester, MA 01890

A rare find! Newer construction rental home/ attached single family/ featuring 5 bedrooms & 4 baths over 4 finished levels, close to Winchester center and Muraco Elementary School. This great home features large spacious rooms, a sunny granite kitchen w/ maple cabinets, hardwood floors/ open concept w/ family room & a gas fireplace w/ sliders that lead to a spacious deck overlooking a fenced in

Kim Covino Compass

378 Washington St Unit 378, Winchester, MA 01890
/24
$2,155,000 Sold Oct 21, 2025
- 3,186 Sq Ft
- $676/SF
- 1 Day On Market
- 3 Beds
- 4.5 Baths
- Built 1988
7 Wainwright Rd Unit 13, Winchester, MA 01890

Stunning townhouse with 3 bedrooms and 4.5 bathrooms, meticulously renovated with high-end, designer finishes. The sun-drenched living room features 13 ft. ceilings, 5-in. oak floors, custom built-in book shelves, and a double-sided marble-surround fireplace that flows seamlessly to the brand-new gourmet chef’s kitchen. The kitchen is a showpiece with a Sub-Zero fridge, Thermador range, Acadia

Isabella Bruno William Raveis R.E. & Home Services

7 Wainwright Rd Unit 13, Winchester, MA 01890

/39
Est $1,858,825 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,046 Sq Ft
73 Thornberry Rd, Winchester, MA 01890

73 Thornberry Rd, Winchester, MA 01890

/42
$1,975,000
- 6 Beds
- 3.5 Baths
- 3,521 Sq Ft
19 Glengarry Rd, Winchester, MA 01890

A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic

Kim Covino Compass

19 Glengarry Rd, Winchester, MA 01890
/29
$3,200 total monthly price
- 2 Beds
- 1.5 Baths
- 896 Sq Ft
- Apartment for Rent
40 Dunster Ln Unit 1, Winchester, MA 01890

Welcome to this charming, sun-filled 2-bed, 2-bath home in the heart of Winchester. With nearly 900 sq. ft. of living space, it blends classic New England charm with modern convenience. The house comes fully furnished—down to the silverware, linens, and décor—so you can simply unpack and relax. Enjoy hardwood floors, a bright living room, a modern kitchen with upgraded counters, and a private

William Dynan Keller Williams Realty Evolution

40 Dunster Ln Unit 1, Winchester, MA 01890
/30
$900,000 Sold Oct 20, 2025
- 1,843 Sq Ft
- $488/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1984
171 Swanton St Unit 5, Winchester, MA 01890

Charming townhouse located at The Village, one of Winchester’s most sought-after and impeccably maintained communities, offers 1,843sf of living space. Featuring 3 generously sized bedrooms with full-height ceilings, and 2.5 updated bathrooms, it is one of the largest homes in the community. The home is flooded with natural light thanks to its end-unit position, windows on three sides, and a

Jonathan Radford Coldwell Banker Realty - Boston

171 Swanton St Unit 5, Winchester, MA 01890

/35
Est $1,802,968 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,224 Sq Ft
22 Berkshire Dr, Winchester, MA 01890

22 Berkshire Dr, Winchester, MA 01890

/42
$1,869,000 Open Sat 12PM - 1PM
- 5 Beds
- 3.5 Baths
- 3,294 Sq Ft
20 Grove Place, Winchester, MA 01890

From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

Andersen Group Realty Keller Williams Realty Boston Northwest

20 Grove Place, Winchester, MA 01890
/15
$2,400 total monthly price
- 2 Beds
- 1 Bath
- 950 Sq Ft
- Apartment for Rent
343 Washington St Unit 343, Winchester, MA 01890

Sunny 2-Bedroom in Winchester! Beautifully maintained 5-room apartment featuring 2 bedrooms, 1 bath, and parking for 2 cars. This first-floor unit offers gleaming hardwood floors throughout, a bright kitchen with dishwasher and spacious pantry, and a dining room with built-in cabinet and charming chandelier. Two generously sized bedrooms with closets, a full bath, and both front (enclosed) and

Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

343 Washington St Unit 343, Winchester, MA 01890
/38
$1,651,000 Sold Oct 17, 2025
- 2,368 Sq Ft
- $697/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 1951
4 Oakland Cir, Winchester, MA 01890

Welcome to 4 Oakland Circle, a spacious home tucked away on a desirable cul-de-sac in Winchester. Thoughtfully designed with oversized rooms and a versatile layout, this residence provides comfort and flexibility for a variety of lifestyles. The main level features expansive living and dining areas along with a 1st floor primary bedroom option that opens onto a private deck, plus a dedicated home

Surabhi Rathi Redfin Corp.

4 Oakland Cir, Winchester, MA 01890

/42
Est $2,287,291 Not Listed For Sale
- 5 Beds
- 4 Baths
- 4,620 Sq Ft
5 Partridge Ln, Winchester, MA 01890

5 Partridge Ln, Winchester, MA 01890

/40
$2,000,000 Open Sun 11:30AM - 12:30PM
- 6 Beds
- 3.5 Baths
- 4,696 Sq Ft
5 Squire Rd, Winchester, MA 01890

Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

Alina Wang Coldwell Banker Realty - Lexington

5 Squire Rd, Winchester, MA 01890
/29
$7,150 total monthly price
- 3 Beds
- 3.5 Baths
- 3,218 Sq Ft
- House for Rent
29 Wainwright Rd, Winchester, MA 01890

Experience refined New England living in this elegant single-family home in Winchester, Massachusetts—an enclave of luxury just eight miles north of Boston and minutes to Cambridge. This light-filled, impeccably maintained residence blends sophistication and comfort with open living and entertaining spaces. The gourmet kitchen with stainless steel appliances and granite countertops flows into a

Helen Stefan Gibson Sotheby's International Realty

29 Wainwright Rd, Winchester, MA 01890
/42
$1,900,000 Sold Oct 17, 2025
- 3,413 Sq Ft
- $557/SF
- 12 Days On Market
- 7 Beds
- 2.5 Baths
- Built 1890
2 Lagrange St, Winchester, MA 01890

EXQUISITE 12 ROOM, 7 BEDROOMS, 2 STUNNING FIREPLACES, 2.5 BATH QUEEN ANNE VICTORIAN! Easy Stroll to Center of Town. Hear the Church Bells Strike the Hour. Delightfully Quiet Street with a Family Orientated Community. Beautiful Morning and Evening Sun. During the Day the Huge Sun Deck off the Kitchen with a SPACIOUS AWNING is both Shady and Warm. Multi Outdoor Opportunities for Living including a

Alison Lules-Cuccio Don Baker Real Estate

2 Lagrange St, Winchester, MA 01890

/40
Est $2,138,393 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 4,532 Sq Ft
89 Thornberry Rd, Winchester, MA 01890

89 Thornberry Rd, Winchester, MA 01890

/40
$2,100,000 Pending
- 6 Beds
- 5.5 Baths
- 5,791 Sq Ft
58 Bacon St, Winchester, MA 01890

Welcome to 58 Bacon Street—a perfect blend of classic charm and modern comforts. The main level features a front-to-back fireplaced living room, sunroom, formal dining room, and a stunning 2024 kitchen renovation with custom cabinetry, quartz island, and high-end stainless appliances, opening to a bright family room. Upstairs offers flexible space with dual primary suite options (one with

Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

58 Bacon St, Winchester, MA 01890
/34
$11,000 total monthly price
- 6 Beds
- 4.5 Baths
- 5,000 Sq Ft
- House for Rent
52 N Border Rd Unit 52, Winchester, MA 01890

Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home has 6 bedrooms, and 5 bathrooms. The stunning foyer welcomes you to the sprawling first floor. The custom work throughout each sun filled room is exquisite. Gourmet kitchen with top of the line appliances. Generous sized rooms to entertain guests. A private home office with built

Dylan Archambault Archambault Real Estate

52 N Border Rd Unit 52, Winchester, MA 01890
/40
$3,242,250 Sold Oct 17, 2025
- 5,250 Sq Ft
- $618/SF
- 25 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1870
4 Norwood St, Winchester, MA 01890

Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor

Mark Donnellan Gibson Sotheby's International Realty

4 Norwood St, Winchester, MA 01890

/40
Est $2,116,906 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,344 Sq Ft
3 Berkshire Dr, Winchester, MA 01890

3 Berkshire Dr, Winchester, MA 01890

/42
$1,999,000 Pending
- 4 Beds
- 3.5 Baths
- 4,731 Sq Ft
6 Samoset Rd, Winchester, MA 01890

Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up

Anne Spry Barrett Sotheby's International Realty

6 Samoset Rd, Winchester, MA 01890
/8
$2,000 total monthly price
- 1 Bed
- 1 Bath
- 613 Sq Ft
- Condo for Rent
200 Swanton St Unit 713, Winchester, MA 01890

Spacious top floor 1 bedroom with private deck with stunning pond views. Convenient location to public transportation, shopping and restaurants. Heat, hot water and electricity included. Laundry and extra storage in the building. 1 parking spot. No smoking and no pets.

Brunna Henrique Keller Williams Realty Boston-Metro | Back Bay

200 Swanton St Unit 713, Winchester, MA 01890
/31
$1,700,000 Sold Oct 16, 2025
- 2,718 Sq Ft
- $625/SF
- 6 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1910
77 Washington St, Winchester, MA 01890

This isn’t just a house — it’s a front-row seat to the good life, where you can walk to shops, schools, cafes, restaurants, and everything the town has to offer! This 5-bedroom, 3.5-bath Victorian sits proudly in the heart of Winchester Center, in the highly coveted Lincoln School district. Original hardwood floors, soaring ceilings, and stunning architectural details give this home its timeless

Nancy Pallotta Gibson Sotheby's International Realty

77 Washington St, Winchester, MA 01890

/11
Est $1,333,096 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,218 Sq Ft
233 High St, Winchester, MA 01890

233 High St, Winchester, MA 01890

/42
$2,299,000 Open Sat 12PM - 1:30PM
- 3 Beds
- 2.5 Baths
- 3,953 Sq Ft
19 Gershon Way Unit 1, Winchester, MA 01890

Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

Philip Vita Compass

19 Gershon Way Unit 1, Winchester, MA 01890
/19
$8,000 total monthly price
- 4 Beds
- 3 Baths
- 2,666 Sq Ft
- House for Rent
10 Hillcrest Pkwy, Winchester, MA 01890

An elegant property on one of Winchester's most beautiful residential side streets, facing the Middlesex Fells, with breathtaking seasonal views of the reservoir. Feels like a wooded retreat! Features 4 BR, 3 full BA; granite & stainless kitchen; a huge open-concept living area with 10ft+ ceilings, grand fireplace & wet bar; secluded screened patio, deck. Hardwood floors, designer light fixtures.

Robyn Bonnett Coldwell Banker Realty - Lexington

10 Hillcrest Pkwy, Winchester, MA 01890
/39
$2,050,000 Sold Oct 15, 2025
- 3,716 Sq Ft
- $552/SF
- 2 Days On Market
- 4 Beds
- 5 Baths
- Built 1931
64 Westland Ave, Winchester, MA 01890

Open Houses Cancelled. Elegant 1930s Colonial boasts charming architectural features, 4 bedrooms, a recent addition & gorgeous top-of-the-line designer kitchen! The heart of the home is the open concept kitchen, which boasts Wolf & Sub-Zero appliances. The front foyer welcomes you to a grand living room with a fireplace, plus a pair of French doors opening to the most charming screen porch. The

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

64 Westland Ave, Winchester, MA 01890

/40
Est $1,336,407 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,430 Sq Ft
134 Johnson Rd, Winchester, MA 01890

134 Johnson Rd, Winchester, MA 01890

/34
$1,230,000 Open Sat 12PM - 1:30PM
- 2 Beds
- 2 Baths
- 1,342 Sq Ft
36 Elmwood Ave Unit 2, Winchester, MA 01890

Welcome to unit # 2 at Allegro, an ELEVATOR building, built in 2021. Containing 11 units. This building is comfortable, quiet, and modern. Just set back far enough to be out of the traffic. Easy one-level living with an open concept, living room, dining room, and kitchen that all flow seamlessly together. The primary bedroom has its own 3⁄4 bathroom with a full bathroom for the rest of the

Charles Ginsberg Coldwell Banker Realty - Lexington

36 Elmwood Ave Unit 2, Winchester, MA 01890
/8
$2,350 total monthly price
- 2 Beds
- 1 Bath
- 700 Sq Ft
- Condo for Rent
6 Skillings Rd Unit 2, Winchester, MA 01890

Great two bedroom with hardwood floors, super sunny, updated kitchen and bath, in unit laundry, central A/C, good size bedrooms, one off street parking spot. Great location. 9/1 move in no pets.

Kristen Day RE/MAX Realty Plus

6 Skillings Rd Unit 2, Winchester, MA 01890
/24
$1,165,000 Sold Oct 14, 2025
- 2,458 Sq Ft
- $474/SF
- 43 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1958
59 Johnson Rd, Winchester, MA 01890

Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and

Angela Zhang Greatland Real Estate LLC

59 Johnson Rd, Winchester, MA 01890

/42
Est $1,675,707 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,361 Sq Ft
7 Wainwright Rd Unit 98, Winchester, MA 01890

7 Wainwright Rd Unit 98, Winchester, MA 01890

/16
$799,999 Open Thu 5PM - 6:30PM
- 2 Beds
- 2 Baths
- 1,240 Sq Ft
666 Main St Unit 312, Winchester, MA 01890

Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry hook-ups, garage parking,

Walace Nogueira

666 Main St Unit 312, Winchester, MA 01890
/41
$7,500 total monthly price
- 5 Beds
- 3.5 Baths
- 3,474 Sq Ft
- House for Rent
211 Forest St, Winchester, MA 01890

FURNISHED ONLY 1,2 or 3 MONTH WINTER RENTAL. If you’ve been thinking of a kitchen renovation or addition but dread the chaos of construction, or maybe you're visiting one of our world renowned hospitals, our stunning 5-bedroom, 3.5-bathroom, 3,500-square-foot home in the coveted Muraco school district is available for a 3-month winter rental (January through March) while my family snowbirds in

Michael Gilbert Stuart St James, Inc.

211 Forest St, Winchester, MA 01890
/42
$2,862,500 Sold Oct 10, 2025
- 5,238 Sq Ft
- $546/SF
- 6 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1915
54 Wedgemere Ave, Winchester, MA 01890

Exceptional value, prime living in this stunning home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive backyard featuring gorgeous

Kim Covino Compass

54 Wedgemere Ave, Winchester, MA 01890

/33
Est $1,901,935 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,327 Sq Ft
7 Wainwright Rd Unit 72, Winchester, MA 01890

7 Wainwright Rd Unit 72, Winchester, MA 01890

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Massachusetts Middlesex County Winchester

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