West Side Homes

/41
$2,899,000
- 5 Beds
- 4.5 Baths
- 6,904 Sq Ft
11 Fieldstone Dr, Winchester, MA 01890

Stunning 5BD/4.5BA contemporary estate on a private cul-de-sac in Winchester’s most coveted neighborhood. Modern design with soaring two-story ceilings, skylights, wide-plank hardwoods, and a dramatic stone fireplace. Gourmet chef’s kitchen with all-white waterfall island, Sub-Zero appliances, and butler’s pantry. Luxe primary suite with dual walk-in closet, spa bath, and private terrace. Fully

Andersen Group Realty Keller Williams Realty Boston Northwest

11 Fieldstone Dr, Winchester, MA 01890
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/20

$2,650 - $6,710 per month

Sanctuary Winchester West

Studio-3 Beds

416 Cambridge St, Winchester, MA 01890

The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

416 Cambridge St, Winchester, MA 01890
/42
$4,065,000 Sold May 16, 2025
- 7,500 Sq Ft
- $542/SF
- 71 Days On Market
- 6 Beds
- 7.5 Baths
- Built 2025
6 Vinson Cir, Winchester, MA 01890

Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living. Spanning 7,500 sq. ft., this exquisite 6-bedroom, 7.5-bathroom home combines style, comfort, and functionality. Discover an open-concept floor plan bathed in natural light, perfect for entertaining and everyday living. The kitchen features top-of-the-line Wolf appliances,

Peter Kasseris Coldwell Banker Realty - Lexington

6 Vinson Cir, Winchester, MA 01890

/41
Est $3,002,661 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,662 Sq Ft
15 Vinson Cir, Winchester, MA 01890

15 Vinson Cir, Winchester, MA 01890

/40
$1,899,000
- 3 Beds
- 2 Baths
- 2,813 Sq Ft
20 Seneca Rd, Winchester, MA 01890

Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

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

20 Seneca Rd, Winchester, MA 01890
/31
$4,950 per month
- 5 Beds
- 2 Baths
- 2,095 Sq Ft
- House for Rent
137 Ridge St, Winchester, MA 01890

Available 5/1/25! Set in one of Greater Boston’s most sought-after communities, this oversized 5-bed, 2-bath Cape offers the perfect blend of comfort, character, and location. Enjoy light-filled, spacious rooms, gleaming hardwood floors, and insulated windows throughout. The detached 2-bay garage and expansive yard provide exceptional outdoor living, while the screened-in porch is perfect for

Lien Vuong Berkshire Hathaway HomeServices Commonwealth Real Estate

137 Ridge St, Winchester, MA 01890
/15
$1,088,000 Sold May 08, 2025
- 2,172 Sq Ft
- $501/SF
- 6 Days On Market
- 4 Beds
- 2 Baths
- Built 1985
322 Cambridge St, Winchester, MA 01890

Not your average Garrison Colonial! You might not expect the bright, open charm waiting within this inviting 8-room, 3-level home. The stunning main level living room, dining and kitchen area boasts cathedral ceilings, skylights, and a dramatic brick fireplace, creating a sense of space and light. This home features 2 full baths and 4 bedrooms, including 3 with brand-new hardwood floors and a

Joanne McDonnell

322 Cambridge St, Winchester, MA 01890

/42
Est $2,779,160 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 6,265 Sq Ft
228 Ridge St, Winchester, MA 01890

228 Ridge St, Winchester, MA 01890

/40
$2,099,000
- 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
/38
$9,800 per month
- 4 Beds
- 4 Baths
- 4,650 Sq Ft
- House for Rent
31 Coolidge Rd, Winchester, MA 01890

Available now! Welcome to this beautifully renovated and maintained colonial at a very quiet street in a desirable neighborhood with easy commute to schools, Boston, highways and MBTA train stations. The 1st floor offers a foyer with formal dining room and living room in either sides. The kitchen, with island and full breakfast/dining area, flows into a family room that transitions to a private

Carlos Xu Lexwin Realty

31 Coolidge Rd, Winchester, MA 01890
/42
$1,890,000 Sold Mar 28, 2025
- 4,318 Sq Ft
- $438/SF
- 7 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1956
19 Johnson Rd, Winchester, MA 01890

A DESIGNER DREAM! Welcome to 19 Johnson Road, a pristine 5-bedroom colonial-style home located in the highly sought-after Vinson Owen School district! As you enter the home, you are greeted by a stunning curved staircase adorned with molding and a statement-making light fixture. The first level boasts a fireplaced living room, a fireplaced family room, an updated kitchen, and a gorgeous formal

Philip Vita Compass

19 Johnson Rd, Winchester, MA 01890

/40
Est $1,339,673 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,529 Sq Ft
15 Wincrest Dr, Winchester, MA 01890

15 Wincrest Dr, Winchester, MA 01890

/13
$2,449,000
- 4 Beds
- 3.5 Baths
- 4,959 Sq Ft
5 Azalea Rd, Winchester, MA 01890

Exceptional Home nestled in one of Winchester's most desirable West Side Neighborhoods and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room open

Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

5 Azalea Rd, Winchester, MA 01890
/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

/25
Est $1,356,290 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,342 Sq Ft
40 Squire Rd, Winchester, MA 01890

40 Squire Rd, Winchester, MA 01890

/42
$2,650,000
- 4 Beds
- 3 Baths
- 4,276 Sq Ft
8 Tanglewood Ln, Winchester, MA 01890

This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard.

Kim Covino Compass

8 Tanglewood Ln, 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

/33
Est $1,503,133 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,034 Sq Ft
10 Carriage Ln, Winchester, MA 01890

10 Carriage Ln, Winchester, MA 01890

/42
$2,399,000
- 5 Beds
- 3.5 Baths
- 5,077 Sq Ft
276 High St, Winchester, MA 01890

This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a private half-acre lot in a tranquil cul-de-sac, near the Winchester/Lexington border. It’s far from road traffic, offering exceptional privacy. The residence spans four levels, featuring 5 bedrooms, 3.5 bathrooms, and two separate laundry areas. The expansive grounds showcase

Andersen Group Realty Keller Williams Realty Boston Northwest

276 High St, 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

/33
Est $1,417,239 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,968 Sq Ft
16 Carriage Ln, Winchester, MA 01890

16 Carriage Ln, Winchester, MA 01890

/39
$1,999,000 Pending
- 4 Beds
- 4 Baths
- 3,818 Sq Ft
1 Saint Augustine Ct, Winchester, MA 01890

Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and gleaming hardwood floors throughout, it strikes the perfect balance between timeless charm and fresh, move-in-ready style. The front-to-back living room is flooded with natural light—ideal for everything from morning coffee to impromptu

Nancy Pallotta Advisors Living - Winchester

1 Saint Augustine Ct, 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

/42
Est $1,520,844 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,760 Sq Ft
27 Thornberry Rd, Winchester, MA 01890

27 Thornberry Rd, Winchester, MA 01890

/25
$1,899,000 Pending
- 4 Beds
- 4 Baths
- 3,488 Sq Ft
4 Olde Lyme Rd, Winchester, MA 01890

This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace and an open-concept design, this spacious home is bathed in natural beauty. The gourmet kitchen is pristine and boasts high-end appliances, quartz countertops, a prep sink and secondary dishwasher, and a large island—ideal for

Nancy Pallotta Advisors Living - Winchester

4 Olde Lyme Rd, 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

/42
Est $1,438,309 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,125 Sq Ft
47 Thornberry Rd, Winchester, MA 01890

47 Thornberry Rd, Winchester, MA 01890

/37
$1,399,500
- 4 Beds
- 2.5 Baths
- 2,525 Sq Ft
65 Thornberry Rd, Winchester, MA 01890

Beautifully updated 4-bed, 2.5-bath ranch on a landscaped half-acre lot with attached 2-car garage. Enjoy single-level living with an open floor plan, cathedral-ceiling kitchen with granite counters, island seating, and stainless appliances. Living and dining areas flow seamlessly; cozy family room with fireplace. Sunroom with wall of windows overlooks the expansive backyard. Primary suite

Hongmei Wang HMW Real Estate, LLC

65 Thornberry Rd, 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

/35
Est $1,634,897 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,926 Sq Ft
16 Nassau Dr, Winchester, MA 01890

16 Nassau Dr, Winchester, MA 01890

/40
$1,449,000
- 3 Beds
- 4.5 Baths
- 3,186 Sq Ft
7 Wainwright Rd Unit 13, Winchester, MA 01890

Welcome to The Ledges, Winchester’s premier townhouse community! This extraordinary F Style corner unit is truly one of a kind with soaring ceilings, sun-filled spaces, and rare flat backyard space with two decks. A landscaped courtyard leads to a gracious foyer and transitions into an expansive open layout. The chef’s kitchen opens to the dining rm and features ss appliances, granite countertops

Nancy Pallotta Advisors Living - Winchester

7 Wainwright Rd Unit 13, Winchester, MA 01890
/29
$1,335,000 Sold Dec 27, 2024
- 2,245 Sq Ft
- $595/SF
- 117 Days On Market
- 4 Beds
- 2 Baths
- Built 1959
28 Thornberry Rd, Winchester, MA 01890

Welcome to 28 Thornberry! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining,

Shaundize Moosavizadeh Coldwell Banker Realty - Boston

28 Thornberry Rd, Winchester, MA 01890

/36
Est $1,521,024 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,171 Sq Ft
94 Johnson Rd, Winchester, MA 01890

94 Johnson Rd, Winchester, MA 01890

/39
$1,325,000
- 4 Beds
- 3 Baths
- 2,496 Sq Ft
9 Thornberry Rd, Winchester, MA 01890

Nestled on a picturesque lot with lush landscaping and mature trees, 9 Thornberry Road offers a perfect blend of natural beauty and refined living. Sunlight pours into this thoughtfully designed home, featuring an open-concept layout ideal for comfortable living and entertaining. The main level includes a welcoming fireplace, hardwood floors, large living room, dining area, and an updated kitchen

Louise Coakley Better Homes and Gardens Real Estate - The Shanahan Group

9 Thornberry Rd, Winchester, MA 01890
/25
$1,000,000 Sold Dec 19, 2024
- 1,840 Sq Ft
- $543/SF
- 8 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1937
15 Westland Ave, Winchester, MA 01890

A dIamond in the rough!!! Are you a contractor or handy end user looking for a project in sought after WInchester? Look no further than this 1937, 4 bedroom Colonial brimming with potential. The charm of yesteryear shows through with custom built-ins, crown moldings, hardwood flooring and so much more. Full walk out unfinished basement with double soapstone sink and a full walk up attic lends

Libby Rankin Hamill Berkshire Hathaway HomeServices Stephan Real Estate

15 Westland Ave, Winchester, MA 01890

/32
Est $1,616,616 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
$1,699,000
- 3 Beds
- 4 Baths
- 2,646 Sq Ft
50 Johnson Rd, Winchester, MA 01890

One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins.

Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

50 Johnson Rd, Winchester, MA 01890
/38
$1,650,000 Sold Dec 11, 2024
- 3,158 Sq Ft
- $522/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1975
31 Girard Rd, Winchester, MA 01890

Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you’ll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen, seamlessly connected to a bright and airy dining area. This space is perfect for hosting

Philip Vita Compass

31 Girard Rd, Winchester, MA 01890

/34
Est $2,050,192 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,000 Sq Ft
133 Johnson Rd, Winchester, MA 01890

133 Johnson Rd, Winchester, MA 01890

/31
$1,825,000
- 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 $1,825,000! 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

Showing Results 1 - 40, Page 1 of 18

Massachusetts Winchester West Side

Learn more about living in West Side

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 23 days on the market compared to the national average of 48 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,700,000, up 14% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,700,000

Median Single Family Sale Price

$1,905,000

Median Townhouse Sale Price

$1,897,500

Median 2 Bedroom Sale Price

$1,200,000

Average Price Per Sq Ft

$490

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

4.00

Median List Price

$1,737,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

14%

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