Winchester, MA Homes

/39
$1,149,000 Pending
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
83 Canal St Unit 85, Winchester, MA 01890

This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary

Mary O'Hagan Barrett Sotheby's International Realty

83 Canal St Unit 85, 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
/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

/35
Est $1,594,509 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

/42
$1,949,000 Pending
- 5 Beds
- 4 Baths
- 4,744 Sq Ft
14 Grove St, Winchester, MA 01890

Located just outside the town center near Brooks neighborhood & the train to Boston! This spacious home has it all! Situated on a lovely level lot w/ 2 car garage & private yard, this updated move in ready home boasts an abundance of space w/ideal layout & large sun drenched eat in kitchen with skylights & bay window, adjacent family room, living room w/ fplc, formal dining, office, laundry & 2

Kim Covino Compass

14 Grove St, Winchester, MA 01890
/9
$1,800 per month
- 1 Bath
- 394 Sq Ft
- Condo for Rent
200 Swanton St Unit 502, Winchester, MA 01890

This rental is SHORT TERM and comes fully furnished. Sparkling, recently renovated studio with amazing views of a beautifully landscaped garden and pond. White cabinet kitchen features stainless steel appliances, tiled backsplash and a marble top peninsula with seating.The main area has hardwood floors and glass sliders out to a good sized balcony, letting in plenty of natural light. In the hall

Susan Murie Aikenhead Real Estate, Inc.

200 Swanton St Unit 502, Winchester, MA 01890
/42
$682,000 Sold Mar 28, 2025
- 1,196 Sq Ft
- $570/SF
- 68 Days On Market
- 2 Beds
- 2 Baths
- Built 2000
7 Conant Rd Unit 24, Winchester, MA 01890

A rare opportunity to live at the Willows in Winchester. Fabulous corner unit on 2nd floor w/ open concept living and dining area features gorgeous hardwood floors. You will be impressed w/ the updated kitchen featuring solid granite counters, stainless steel sink and appliances, new carpeting and paint added in the bedrooms 1 year ago. New paint in dining room and closets. Gas fireplace for the

Paul Bettencourt Beaudoin & Associates, REALTOR®

7 Conant Rd Unit 24, 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

/42
$2,050,000 Pending
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
57 Jefferson Rd, Winchester, MA 01890

Situated on a picturesque corner lot, this exceptional home is nestled in a very desirable neighborhood! Step into a light-filled, open-concept 1st floor, where a soaring beamed ceiling enhances the inviting ambiance. The living room boasts built-in shelves, while the kitchen impresses w/timeless white cabinetry, soapstone counters, SS appliances, large island, & pantry. The dining area, warmed

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

57 Jefferson Rd, Winchester, MA 01890
/14
$3,600 per month
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
- Apartment for Rent
38 Florence St Unit 40, Winchester, MA 01890

3-Bed / 2 Full-bath apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this three-bedroom and two-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless appliances. Two bright generous bedrooms are with high ceiling and fans on the second floor.

Weidong Li WINN Real Estate & Consulting

38 Florence St Unit 40, Winchester, MA 01890
/42
$3,665,000 Sold Mar 27, 2025
- 5,768 Sq Ft
- $635/SF
- 1 Day On Market
- 5 Beds
- 4.5 Baths
- Built 1895
6 Lakeview Rd, Winchester, MA 01890

Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town’s most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Reconstructed and designed by RENEW, a company committed to blending historical integrity with modern amenities, paying meticulous attention to every

Kim Covino Compass

6 Lakeview Rd, Winchester, MA 01890

/32
Est $1,579,531 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,622 Sq Ft
104 Thornberry Rd, Winchester, MA 01890

104 Thornberry Rd, Winchester, MA 01890

/20
$2,398,000 Pending
- 5 Beds
- 4 Baths
- 4,468 Sq Ft
74 Hillcrest Pkwy, Winchester, MA 01890

Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fells Reservation on one of Winchester's most picturesque streets! First floor seamlessly blends living, dining, & kitchen areas. Living room has wood burning fireplace & custom built-in shelves. Dining room offers delightful space for cozy gatherings and the spacious eat-in kitchen

Ann Hogstadius

74 Hillcrest Pkwy, 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
/42
$2,350,000 Sold Mar 24, 2025
- 3,059 Sq Ft
- $768/SF
- 6 Days On Market
- 5 Beds
- 2 Baths
- Built 1940
17 Dix St, Winchester, MA 01890

Prime Waterfront home in downtown Winchester!! Take advantage of this unique opportunity to customize, renovate, expand or rebuild your dream home on this heavenly 1/2 acre lot with gorgeous grounds and expansive frontage on Wedge Pond. The current home was custom built and enjoyed by one family who made unforgettable memories here including skating, swimming, canoeing & sledding right in their

Kim Covino Compass

17 Dix St, Winchester, MA 01890

/34
Est $2,013,303 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

/17
$299,000 Open Fri 11AM - 1PM
- 1 Bed
- 1 Bath
- 450 Sq Ft
200 Swanton St Unit T4, Winchester, MA 01890

Immaculate, recently renovated Jumbo Studio Condominium with a private/direct-entry terrace level. This unit is spacious and bright, featuring a slider that leads to a private patio overlooking scenic duck ponds and lush landscaping. The large eat-in kitchen features white cabinets, with a white tiled backsplash and granite countertops. The bathroom was recently updated with new fixtures,

Michael Masci North Atlantic Realty Group

200 Swanton St Unit T4, Winchester, MA 01890
/38
$11,000 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
/33
$615,000 Sold Mar 24, 2025
- 1,452 Sq Ft
- $424/SF
- 5 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1960
299 Cross St Unit 299, Winchester, MA 01890

Welcome to The Residences at Winchester! A perfect move-in ready single-family alternative without the hassle of yard work. Fantastic chance to own this 2 bedroom 1.5 bathroom gem with beautiful hardwood floors, open concept living/dining/kitchen in Winchester at a budget-friendly price. Why rent when you can own? The finished lower level adds over 400 square feet of extra living area.

Patricia Nunez Redfin Corp.

299 Cross St Unit 299, Winchester, MA 01890

/39
Est $1,841,028 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

/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! W 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 throughout.

Kim Covino Compass

20 Fletcher St Unit 20, Winchester, MA 01890
/18
$5,500 per month
- 4 Beds
- 3.5 Baths
- 2,500 Sq Ft
- Apartment for Rent
48 Spruce St Unit 48, Winchester, MA 01890

Walk to town from this completely renovated 4 bedroom, 3.5 bath, 4 level attached home. Excellent finishes and space. Beautifully appointed open concept kitchen and family room with space for entire family. Three full and one half bathrooms with heated floors. Three levels of finished living space. Clean, partially finished basement for multiple uses. Walk to the High School. Located on a

Julia Marino Archambault Real Estate

48 Spruce St Unit 48, Winchester, MA 01890
/2
$1,650,000 Sold Mar 19, 2025
- 3,381 Sq Ft
- $488/SF
- 14 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1938
5 Alben St, Winchester, MA 01890

Welcome to this charming Colonial, thoughtfully maintained by its owners! Nestled on a peaceful, tree-lined street, this beautifully updated colonial home exudes warmth and character. Featuring a recently updated roof (2022), new triple pane energy efficient windows with transferable lifetime warranty (2018), and fresh interior and exterior paint, this home is move-in ready and full of charm.

Andersen Group Realty Keller Williams Realty Boston Northwest

5 Alben St, Winchester, MA 01890

/35
Est $1,763,402 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
$1,849,000
- 4 Beds
- 5 Baths
- 3,148 Sq Ft
15 Kendall St, Winchester, MA 01890

Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lot with slider to patio & expansive rear yard, this captivating home has an absolutely beautiful setting w/natural stone walls, raised planting beds w/flowering trees, perennials & a spectacular rose garden! Enjoy the lovely farmers porch & desirable layout w/sun-drenched kitchen

Kim Covino Compass

15 Kendall St, Winchester, MA 01890
/42
$9,500 per month
- 6 Beds
- 4.5 Baths
- 3,118 Sq Ft
- House for Rent
23 Jefferson Rd, Winchester, MA 01890

Stunning 6BR/4.5BA Fully Furnished Home w/ Office, Fireplace & Private Patio – Move-In Ready! Spacious and beautifully appointed single-family home featuring 6 bedrooms, 4.5 bathrooms, and a dedicated office—ideal for remote work. Fully furnished with high-end finishes, including a cozy fireplace and a perfect layout for entertaining and everyday living. Gourmet kitchen, large bedrooms, and ample

Andersen Group Realty Keller Williams Realty Boston Northwest

23 Jefferson Rd, Winchester, MA 01890
/42
$3,250,000 Sold Mar 18, 2025
- 4,714 Sq Ft
- $689/SF
- 9 Days On Market
- 6 Beds
- 6 Baths
- Built 1909
23 Everett Ave, Winchester, MA 01890

Talk about curb appeal! This fabulous Colonial home beckons with an amazing front porch overlooking an expansive front yard, proudly perched on a quiet corner in one of the most coveted neighborhoods in town. Well-tended gardens and plants mesh with giant overhanging oak trees making your heart sing. Inside, delight in the quarter-sawn oak walls and floors, huge sunny family room and a dining

Nancy Pallotta Advisors Living - Winchester

23 Everett Ave, Winchester, MA 01890

/42
Est $2,171,981 Not Listed For Sale
- 5 Beds
- 4 Baths
- 4,620 Sq Ft
5 Partridge Ln, Winchester, MA 01890

5 Partridge Ln, Winchester, MA 01890

/33
$1,599,000
- 4 Beds
- 3.5 Baths
- 3,338 Sq Ft
34 Coolidge Rd, Winchester, MA 01890

A chance to update and create your personal design that is located in Winchester's sought after Vinson Owen School district. Set on a impressive massive manicured corner lot that has been maintained since it has been custom built by its original owners. Scenic backyard with a patio off the kitchen that spills on a large private backyard that has an inground pool. Set the stage with a large foyer

Pauline Marino Coldwell Banker Realty - Lexington

34 Coolidge Rd, Winchester, MA 01890
/23
$4,500 per month
- 3 Beds
- 2.5 Baths
- 1,823 Sq Ft
- Condo for Rent
171 Swanton St Unit 63, Winchester, MA 01890

Available at "The Village." End unit with three bedrooms/two and a half bathrooms, attached garage, granite kitchen, skylight dining area, private patio, gas fireplace, primary suite features walk-in closet, spacious second bedroom, in unit laundry area. Close to pool, clubhouse, tennis court. Near Winchester center, schools, commuter rail..and the Fells! Easy access to 93 as well. NEW STAINLESS

Gary Vrotsos Coldwell Banker Realty - Cambridge

171 Swanton St Unit 63, Winchester, MA 01890
/42
$1,670,000 Sold Mar 18, 2025
- 3,224 Sq Ft
- $518/SF
- 59 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1945
9 Robinson Park, Winchester, MA 01890

Classic Colonial 4 bedroom 3+1/2 bath on quiet street overlooking the Mystic Lake. Awaits buyers with vision prepared to renovate. Freshly painted interior gleaming hardwood floors. Gracious front to back fireplaced living room w/custom shelves & built-ins & picture windows. Formal dining room w/2 china closets adjacent to large open eat-in light filled kitchen. French doors to back deck.

Paul Reardon William Raveis R.E. & Home Services

9 Robinson Park, Winchester, MA 01890

/40
Est $2,033,071 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

/19
$734,900
- 2 Beds
- 2.5 Baths
- 1,634 Sq Ft
7 Conant Rd Unit 60, Winchester, MA 01890

Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and Central A/C & heating with Nest

Irene Novia Loka Matahari Real Estate LLC

7 Conant Rd Unit 60, Winchester, MA 01890
/39
$11,000 per month
- 7 Beds
- 3.5 Baths
- 3,300 Sq Ft
- House for Rent
34 Glen Rd, Winchester, MA 01890

TOP location! Beautifully renovated single family colonial in Ambrose elementary district, situated on a gorgeous lot with oversized new 2 car garage, This 6-7 bedroom 3.5 bath home has been tastefully updated & redesigned offering desirable open concept living w/ central air & all new systems. This home features a welcoming front porch, spacious foyer, beautiful custom chefs kitchen w/

Kim Covino Compass

34 Glen 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

/38
Est $1,346,590 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,082 Sq Ft
1 Valleywood Cir, Winchester, MA 01890

1 Valleywood Cir, Winchester, MA 01890

/37
$1,379,000
- 4 Beds
- 2.5 Baths
- 2,388 Sq Ft
26 Ridge St, Winchester, MA 01890

Set on a generous, beautifully landscaped lot, this meticulously maintained home showcases numerous recent upgrades, and offers both comfort and style. The newly renovated kitchen features upscale appliances and custom quartz countertops, perfect for everyday living and entertaining alike.Hardwood floors, two fireplaces, a sunlit living room, and a separate family room create inviting spaces

Dream Team Dreamega International Realty LLC

26 Ridge St, Winchester, MA 01890
/18
$8,000 per month
- 3 Beds
- 2.5 Baths
- 2,900 Sq Ft
- Apartment for Rent
846 Main St Unit 4, Winchester, MA 01890

Top of the Line! Stunning newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2 1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

Anthony Marino The Marino Group Collection

846 Main St Unit 4, 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

/11
Est $1,276,614 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,218 Sq Ft
233 High St, Winchester, MA 01890

233 High St, Winchester, MA 01890

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