Winchester, MA Homes

/39
$1,449,000
- 3 Beds
- 2.5 Baths
- 2,282 Sq Ft
20 Fletcher St Unit 20, Winchester, MA 01890

Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication

Kim Covino Compass

20 Fletcher St Unit 20, Winchester, MA 01890
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/13
$2,680 per month
- 2 Beds
- 1 Bath
- 606 Sq Ft
- Condo for Rent
200 Swanton St Unit 239, Winchester, MA 01890

Enjoy scenic water views from this beautifully updated second-floor condo, perfectly situated overlooking the pond. This two-bedroom unit features an inviting open-concept layout that flows seamlessly onto a spacious private balcony—ideal for relaxing or entertaining outdoors. Generous closet space is found throughout the home, with additional storage available on the lower level. One dedicated

Joan Powell

Advisors Living - Merrimac

(781) 818-0292

200 Swanton St Unit 239, Winchester, MA 01890
/39
$4,650,000 Sold May 01, 2025
- 7,779 Sq Ft
- $598/SF
- 5 Days On Market
- 5 Beds
- 7 Baths
- Built 1915
19 Rangeley Rd, Winchester, MA 01890

A treasure. That's how this residence is viewed, throughout town, throughout the decades. One family had the vision to bring this cherished home back to life with a renovation that bestowed the best of everything. On Rangeley Road, gentle rolling lawns fold softly into a private, winding road. Gorgeous architecture graces every lot and ancient oaks stand sentry. Located just steps to the town

Nancy Pallotta Advisors Living - Winchester

19 Rangeley Rd, Winchester, MA 01890

/39
Est $2,248,156 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,539 Sq Ft
38 Winthrop Street Extension, Winchester, MA 01890

38 Winthrop Street Extension, Winchester, MA 01890

/41
$2,899,000 Open Sat 12PM - 1PM
- 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
/14
$1,900 per month
- 1 Bath
- 350 Sq Ft
- Condo for Rent
200 Swanton St Unit 704, Winchester, MA 01890

Studio Apartment for Rent – Parkview Condominiums, Winchester, MAWelcome to Parkview Condominiums. This spacious studio apartment offers comfort, convenience, and a scenic setting overlooking the Parkview duck pond.Studio | 1 BathPrivate balcony with peaceful viewsOutdoor pool and landscaped groundsOff-street parking includedUtilities Included: Heat, Hot Water, Electricity, Air

Joan Powell

Advisors Living - Merrimac

(781) 730-6882

200 Swanton St Unit 704, Winchester, MA 01890
/36
$1,600,000 Sold Apr 30, 2025
- 2,809 Sq Ft
- $570/SF
- 7 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2004
24 Water St, Winchester, MA 01890

Discover the warmth and charm of this inviting New England Colonial, newly built in 2004. This sun-filled home features three bedrooms, 3.5 bathrooms, and a flexible floor plan. First floor features a large family room, dining room, updated kitchen with SS appliances, abundant custom cabinetry, a half bath, mudroom, and a separate living room. Second floor offers a sizable primary suite with a

Domingo Medina Coldwell Banker Realty - Lexington

24 Water St, Winchester, MA 01890

/33
Est $1,709,511 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,254 Sq Ft
20 Graystone Cir Unit 20, Winchester, MA 01890

20 Graystone Cir Unit 20, Winchester, MA 01890

/42
$2,250,000
- 5 Beds
- 3.5 Baths
- 3,719 Sq Ft
17 Harrison St, Winchester, MA 01890

Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized

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

17 Harrison St, Winchester, MA 01890
/19
$2,500 per month
- 2 Beds
- 1 Bath
- 750 Sq Ft
- Condo for Rent
834 Main St Unit 834 Main Street, Winchester, MA 01890

Quaint, historic property with off street parking on well manicured lot.

834 Main St Unit 834 Main Street, Winchester, MA 01890
/30
$1,200,000 Sold Apr 30, 2025
- 2,060 Sq Ft
- $583/SF
- 8 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1926
36 Lebanon St, Winchester, MA 01890

Nicely updated home in desirable Muraco district! This home has been meticulously maintained & features many recent updates including newer windows, central air conditioning & updated systems. Enjoy the sun drenched spaces from the spacious living room w/ fplc & bay window to the charming dining room w/ china cabinet, sunny eat-in kitchen, office, plus 3 season porch & 1/2 bath complete the first

Kim Covino Compass

36 Lebanon St, Winchester, MA 01890

/42
Est $1,140,381 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,522 Sq Ft
284 Cross St Unit A, Winchester, MA 01890

284 Cross St Unit A, Winchester, MA 01890

/13
$2,999,999
- 5 Beds
- 4.5 Baths
- 5,716 Sq Ft
3 Abby Rd, Winchester, MA 01890

Welcome to your dream home! This brand-new, meticulously crafted residence offers the perfect blend of luxury & comfort in Winchester’s newest neighborhood. Boasting 4 beds & 4.5 designer baths, every detail has been thoughtfully curated. The chef’s kitchen boasts custom cabinetry, professional-grade appliances & island — ideal for both everyday living & elegant entertaining. The adjoining dining

Philip Vita Compass

3 Abby Rd, Winchester, MA 01890
/11
$3,850 per month
- 3 Beds
- 2 Baths
- 1,451 Sq Ft
- Condo for Rent
50 Lake St Unit F, Winchester, MA 01890

This beautiful 3-bedroom, 2-bathroom condo is perfectly situated close to downtown Winchester, offering the ideal blend of suburban tranquility and urban convenience. This condo combines the best of both worlds – a peaceful, beautifully landscaped setting with the convenience of being close to all that Winchester has to offer. Off-street, assigned parking, ample storage and in-unit laundry

Ryan Clunan Campion & Company Fine Homes Real Estate

50 Lake St Unit F, Winchester, MA 01890
/42
$2,420,000 Sold Apr 25, 2025
- 4,173 Sq Ft
- $580/SF
- 8 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1914
48 Wedgemere Ave, Winchester, MA 01890

This elegant 1914 Revival home combines timeless charm w/ exceptional architectural details. Located on a highly sought-after, picturesque street in "The Flats," this 5-bedroom, 4 1/2 half-bath residence offers spacious living throughout. The main floor boasts a formal living room w/ built-in bookcases & fireplace, a grand dining room, & a kitchen w/ two impressive butler’s pantries. Inviting

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

48 Wedgemere Ave, Winchester, MA 01890

/41
Est $2,829,234 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

/41
$2,599,000
- 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
/11
$2,200 per month
- 1 Bed
- 1 Bath
- 606 Sq Ft
- Condo for Rent
253 Swanton St Unit 428, Winchester, MA 01890

1 bed and 1 bath located in Winchester Highlands. Easy access to downtown and public transportation!

253 Swanton St Unit 428, Winchester, MA 01890
/20
$1,200,000 Sold Apr 23, 2025
- 1,638 Sq Ft
- $733/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 1954
19 Laurel Hill Ln, Winchester, MA 01890

Nestled in a desirable neighborhood, this home offers the opportunity to embrace the timeless elegance of the mid-century era. Lovingly maintained in its original condition, the ranch style provides the coveted option for one-level living. Enter the main level into the fireplaced living room, with large picture window and hardwood floors. Adjacent to the kitchen is the dining room with hardwood

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

19 Laurel Hill Ln, Winchester, MA 01890

/42
Est $2,666,201 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
$1,995,000
- 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
/18
$4,500 per month
- 4 Beds
- 1.5 Baths
- 1,630 Sq Ft
- House for Rent
488 Washington St, Winchester, MA 01890

Charming, updated Colonial filled with character. This beautiful home features an updated kitchen that is bright and open and offers granite counter tops, stainless steel appliances, frameless maple cabinets & recessed lights. Updated bathrooms. Hardwood floors throughout the 1st & 2nd floors. Access the stone and granite patio through French doors in the dining room. The patio is fenced in and

Matthew Pierce True North Realty

488 Washington St, Winchester, MA 01890
/42
$2,500,000 Sold Apr 18, 2025
- 3,851 Sq Ft
- $649/SF
- 4 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1936
7 Rangeley Rd, Winchester, MA 01890

**OFFER ACCEPTED/ OH CANCELED* Delightful home in Rangeley Estates, just outside Winchester Center! Featuring 5 bedrooms & 4.5 baths; 2 primary bedroom options w/ en-suite baths. A unique layout w/ a California vibe w/open airy spaces perfect for modern day living & just steps from the vibrant downtown. Enjoy easy access to Train, schools, shops, coffee, dining & more, while being tucked away in

Kim Covino Compass

7 Rangeley Rd, Winchester, MA 01890

/25
Est $1,337,106 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
$2,950,000
- 6 Beds
- 7 Baths
- 6,968 Sq Ft
14 Nassau Dr, Winchester, MA 01890

Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

Weidong Li WINN Real Estate & Consulting

14 Nassau Dr, Winchester, MA 01890
/4
$1,900 per month
- 1 Bed
- 1 Bath
- 9,999 Sq Ft
- Condo for Rent
200 Swanton St Unit 3, Winchester, MA 01890

In-unit laundry, 1 parking space included, heat and hot water included.

200 Swanton St Unit 3, Winchester, MA 01890
/42
$1,815,000 Sold Apr 15, 2025
- 2,810 Sq Ft
- $646/SF
- 8 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1935
29 Allen Rd, Winchester, MA 01890

This expanded 4-bedroom, 2.5-bath colonial is a true gem in the heart of a serene Lincoln School neighborhood. Impeccably maintained by the same family for over 40 years, this home has been thoughtfully updated w/ modern comforts, incl. AC throughout. The 1st floor features a remodeled kitchen w/ stainless steel appliances, granite countertops & breakfast bar, flowing into a spacious family room

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

29 Allen Rd, Winchester, MA 01890

/33
Est $1,488,212 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

/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
/12
$3,000 per month
- 3 Beds
- 1.5 Baths
- 1,452 Sq Ft
- Apartment for Rent
11 Bradford Rd Unit 11`, Winchester, MA 01890

Bright & Sunny 3 bedroom, 1.5 bathroom, hardwood floor throughout townhome with 3 level living. it features living room, eat-in kitchen and half bath on the 1st floor, 3 bedroom with a full bath on the 2nd floor, recently finished basement that could be family room, office, or playroom, washer/dryer located in this level. Spacious backyard outdoor space for private use. It's great friendly and

Wei Wang WW Real Estate LLC

11 Bradford Rd Unit 11`, Winchester, MA 01890
/41
$2,350,000 Sold Apr 15, 2025
- 4,273 Sq Ft
- $550/SF
- 7 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1910
5 Pine St, Winchester, MA 01890

This recently renovated Victorian blends historic charm with modern luxury in a prime in-town location-minutes to the shops, Common, train and Wedge Pond. Step into the central hall showcasing elegant woodwork, high ceilings, and gleaming floors. The new kitchen features high-end appliances, a butler’s pantry, and dining banquette. Entertain in the sun-drenched dining room with a marble fireplace

Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

5 Pine St, Winchester, MA 01890

/33
Est $1,400,165 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

/24
$1,099,000 Pending
- 3 Beds
- 3.5 Baths
- 2,290 Sq Ft
160 Swanton St Unit 160, Winchester, MA 01890

Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

Monte Marrocco Coldwell Banker Realty - Lexington

160 Swanton St Unit 160, Winchester, MA 01890
/2
$3,300 per month
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
- Apartment for Rent
16 Richardson St Unit 18, Winchester, MA 01890

3 bedroom 2 bathroom colonial style duplex house in the center of Winchester for rent. Colonial style with spacious living room and kitchen room on the first floor. Second floor master bedroom has an office/exercise room attached. Full basement provides tons of storage spaces. Walking distance to schools, shops, bus stop and commuter rail station. Big backyard provides a great private space for

Weidong Li WINN Real Estate & Consulting

16 Richardson St Unit 18, Winchester, MA 01890
/39
$2,224,000 Sold Apr 11, 2025
- 3,487 Sq Ft
- $638/SF
- 8 Days On Market
- 6 Beds
- 2.5 Baths
- Built 1910
5 Woodside Rd, Winchester, MA 01890

Introducing a captivating waterside home on a gorgeous 34,000 sf lot, located in a top location w/ expansive frontage on Little Winter Pond. This 6-bedroom, 2.5-bathroom home offers unparalleled access to the picturesque pond for activities such as ice skating, fishing, kayaking, & more. The home’s interior is highlighted by high ceilings, hardwood floors & an original fireplace for cozy winter

Kim Covino Compass

5 Woodside Rd, Winchester, MA 01890

/42
Est $1,507,357 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,760 Sq Ft
27 Thornberry Rd, Winchester, MA 01890

27 Thornberry Rd, Winchester, MA 01890

/34
$2,199,900 Pending
- 4 Beds
- 3.5 Baths
- 3,039 Sq Ft
11 Chesterford Rd E, Winchester, MA 01890

Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly

Joseph Pollack Redfin Corp.

11 Chesterford Rd E, Winchester, MA 01890
/25
$4,300 per month
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
- Apartment for Rent
67 Church St, Winchester, MA 01890

Enjoy this beautiful renovated home right outside Winchester center! Direct entry unit completely updated all new with gorgeous kitchen & bath, hardwood floors, new heating system with central air, new windows, electric, very high ceilings, washer & dryer in unit, 2 car parking driveway in rear, exclusive patio area great for grilling! beautifully finished lower level offers a large room/

Kim Covino Compass

67 Church St, Winchester, MA 01890
/38
$2,600,000 Sold Apr 08, 2025
- 4,323 Sq Ft
- $601/SF
- 7 Days On Market
- 6 Beds
- 4.5 Baths
- Built 1929
30 Swan Rd, Winchester, MA 01890

Discover the prestige of owning a home at 30 Swan Road, a distinguished Tudor-style residence on one of Winchester's most esteemed streets. Offering magnificent grounds and an impressive brick exterior complemented by a slate roof, this property sets the tone for the elegance within. It's perfect for a buyer looking to add sweat equity or a contractor seeking a rewarding project. Upon entering,

Jay Noble Compass

30 Swan Rd, Winchester, MA 01890

/42
Est $1,423,610 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

Showing Results 1 - 40, Page 1 of 18

Massachusetts Winchester

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 23 days on the market compared to the national average of 48 days. The average sale price for homes in Winchester, MA over the last 12 months is $1,651,681, up 14% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)

$1,570,000

Median Single Family Price

$1,890,000

Median Townhouse Price

$1,511,250

Median 2 Bedroom Price

$758,500

Median 1 Bedroom Price

$370,000

Average Price Per Sq Ft

$542

Number of Homes for Sale

Last 12 months Home Sales

239

Months of Supply

2.10

Median List Price

$1,624,000

Median Discount From 1st List Price

Median Home Sale Price YoY Change

16%

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