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
/33
$6,800 per month
- 4 Beds
- 3.5 Baths
- 2,800 Sq Ft
- Apartment for Rent
37 Rumford St Unit 37, Winchester, MA 01890

This 4-bed,3.5-bath custom-designed and built in 2012 townhouse feels like a single family. Step onto the welcoming farmer’s porch into an open, airy layout with natural light streaming through large windows. It features gleaming wood floors and a chef’s kitchen with stainless steel appliances, granite countertops, custom cabinets, and a beautifully designed kitchen island. Living room has a

Alina Wang Coldwell Banker Realty - Lexington

37 Rumford St Unit 37, Winchester, MA 01890
/37
$1,450,000 Sold May 30, 2025
- 3,763 Sq Ft
- $385/SF
- 34 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1988
7 Wainwright Rd Unit 8, Winchester, MA 01890

Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large

Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

7 Wainwright Rd Unit 8, Winchester, MA 01890

/38
Est $1,591,156 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,368 Sq Ft
7 Wainwright Rd Unit 39, Winchester, MA 01890

7 Wainwright Rd Unit 39, Winchester, MA 01890

/28
$1,299,000 Pending
- 3 Beds
- 2.5 Baths
- 2,705 Sq Ft
261 Cambridge St Unit 261 G, Winchester, MA 01890

Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms,

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

261 Cambridge St Unit 261 G, Winchester, MA 01890
/16
$2,700 per month
- 2 Beds
- 1 Bath
- 822 Sq Ft
- Condo for Rent
200 Swanton St Unit 205, Winchester, MA 01890

Sunny & Bright 2-Bedroom Condo in Winchester Park View – Available 09/01. Enjoy comfortable living in this updated and sunny 2-bedroom, 1-bathroom condo featuring: Modern kitchen and bathroom. Private balcony. Heat, electricity, hot water, and more included in rent. 2 parking spaces. Ground maintenance and trash removal included. Conveniently located near shopping, restaurants, and Winchester

Wei Wang WW Real Estate LLC

200 Swanton St Unit 205, Winchester, MA 01890
/25
$1,881,900 Sold May 30, 2025
- 3,488 Sq Ft
- $540/SF
- 34 Days On Market
- 4 Beds
- 4 Baths
- Built 1980
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

/39
Est $1,705,272 Not Listed For Sale
- 2 Beds
- 4 Baths
- 3,655 Sq Ft
7 Wainwright Rd Unit 37, Winchester, MA 01890

7 Wainwright Rd Unit 37, 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
/12
$2,100 per month
- 1 Bed
- 1 Bath
- 602 Sq Ft
- Condo for Rent
200 Swanton St Unit L25, Winchester, MA 01890

The sought after Parkview Condominium! Prime Winchester Location ! Living room with glass sliders to balcony overlooking a calming landscaped wildlife garden and pond with ducks & swans. Rent includes heat, cold & hot water, electricity and 1 gated parking space! Amenities: swimming pool and on-site laundry facilities! No pets. No smoking of any substance. Professionally management on-site.

Ai Cheng Goh Z. Realty

200 Swanton St Unit L25, Winchester, MA 01890
/42
$1,558,000 Sold May 29, 2025
- 2,792 Sq Ft
- $558/SF
- 9 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1993
24 Eugene Dr, Winchester, MA 01890

Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layout plus amenities like central air, 1st floor laundry room, direct indoor access to a 2-car garage, and delightful wooded back yard are more outstanding details. The kitchen & family room at the back of the house will be everyone’s favorite gathering spot. The eat-in kitchen

Andrea O'Reilly Keller Williams Realty Evolution

24 Eugene Dr, Winchester, MA 01890

/42
Est $1,822,284 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,901 Sq Ft
7 Wainwright Rd Unit 5, Winchester, MA 01890

7 Wainwright Rd Unit 5, Winchester, MA 01890

/41
$799,900 Open Sun 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,441 Sq Ft
9 Emerson Ct, Winchester, MA 01890

Looking for the ideal first home or a peaceful place to settle into your next chapter? This charming 3-bedroom, 2-bath home, nestled at the end of a quiet dead-end street, was completely remodeled in 2009. Step inside to a warm and welcoming space with a practical layout—everything you need without the fuss. Whether you're just getting started or looking to simplify, this move-in-ready home is a

Rodrigo Serrano Leading Edge Real Estate

9 Emerson Ct, Winchester, MA 01890
/12
$3,000 per month
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
- Apartment for Rent
17 Irving St Unit 3, Winchester, MA 01890

Great opportunity to live close to Winchester Center.Available June 1st this 2nd floor unit features a large deck before entering kitchen. Kitchen has been completely done over new floors, cabinets and all new appliances, living room, bedroom and full bath. Next level, has two bedrooms, bath with shower. All hardwood floors and many windows. Tenant is responsible for Gas, Electric and Cable.

Robin Griffiths J. Mulkerin Realty

17 Irving St Unit 3, Winchester, MA 01890
/31
$948,000 Sold May 29, 2025
- 1,469 Sq Ft
- $645/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1928
79 Sylvester Ave, Winchester, MA 01890

Discover where form meets function in this beautifully maintained home, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a quintessential location. Thoughtfully updated, the kitchen, exterior, and bedrooms reflect pride of ownership, showcasing care and attention

Anne Spry Barrett Sotheby's International Realty

79 Sylvester Ave, Winchester, MA 01890

/41
Est $1,642,024 Not Listed For Sale
- 2 Beds
- 4 Baths
- 5,564 Sq Ft
7 Wainwright Rd Unit 41, Winchester, MA 01890

7 Wainwright Rd Unit 41, Winchester, MA 01890

/38
$1,699,000 Open Sun 12PM - 1:30PM
- 5 Beds
- 4 Baths
- 2,853 Sq Ft
32 Oneida Rd, Winchester, MA 01890

Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

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

32 Oneida Rd, Winchester, MA 01890
/18
$7,000 per month
- 4 Beds
- 2.5 Baths
- 2,800 Sq Ft
- Apartment for Rent
72 Holland St Unit 72, Winchester, MA 01890

Welcome to your dream home in the heart of Winchester! This beautifully built 2021 townhouse offers the perfect blend of modern style, comfort, and convenience, featuring 4 spacious bedrooms, 2.5 sleek bathrooms, and bright open-concept living areas. Located just steps from Winchester High School and within walking distance to the town center and public library, you’ll enjoy easy access to

Haosheng Zhang Phoenix Real Estate Partners, LLC

72 Holland St Unit 72, Winchester, MA 01890
/31
$380,000 Sold May 23, 2025
- 613 Sq Ft
- $620/SF
- 15 Days On Market
- 1 Bed
- 1 Bath
- Built 1966
200 Swanton St Unit 722, Winchester, MA 01890

Top-Floor Penthouse Condo with Scenic Views at Parkview Condominiums Move right into this beautifully updated 1-bedroom, 1-bath top-floor unit at the highly desirable Parkview Condominiums in Winchester. Centrally located on the 7th floor, this penthouse offers stunning treetop and pond views from your private balcony—perfect for enjoying peaceful moments all year round. Inside, you'll find a

Yang Liu Weston Realty LLC

200 Swanton St Unit 722, Winchester, MA 01890

/42
Est $2,067,524 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,853 Sq Ft
40 Wainwright Rd, Winchester, MA 01890

40 Wainwright Rd, Winchester, MA 01890

/27
$625,000 Open Sun 12:30PM - 1:30PM
- 2 Beds
- 1.5 Baths
- 1,554 Sq Ft
50 Lake St Unit B, Winchester, MA 01890

A well-maintained 2-bed, 1.5-bath townhouse-style condo offering scenic views of Wedge Pond. The main level features hardwood floors, a spacious living area, half bath, and a kitchen with granite countertops and stainless steel appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides versatile space for a family room, home office, or gym. Additional highlights

Andersen Group Realty Keller Williams Realty Boston Northwest

50 Lake St Unit B, 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
/33
$1,785,000 Sold May 22, 2025
- 2,848 Sq Ft
- $627/SF
- 13 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1968
85 Thornberry Rd, Winchester, MA 01890

Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,000 sqft lot with professional landscaping. The living room features a charming wood-burning fireplace, while the sun-filled formal dining room is centered with an elegant chandelier. The kitchen has granite countertops, stainless steel appliances, and an adjacent eat-in area

Diane Basemera Coldwell Banker Realty - Newton

85 Thornberry Rd, Winchester, MA 01890

/42
Est $2,832,848 Not Listed For Sale
- 5 Beds
- 6 Baths
- 5,678 Sq Ft
19 Socrates Way, Winchester, MA 01890

19 Socrates Way, Winchester, MA 01890

/42
$4,250,000
- 5 Beds
- 3.5 Baths
- 4,484 Sq Ft
9 Lakeview Terrace, Winchester, MA 01890

LAKEFRONT! Nestled on the serene shore of Mystic Lake just 7 miles from Boston, this extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room! Located in one of Winchester’s most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and

Kim Covino Compass

9 Lakeview Terrace, Winchester, MA 01890
/9
$1,650 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
$2,750,000 Sold May 19, 2025
- 5,263 Sq Ft
- $523/SF
- 12 Days On Market
- 6 Beds
- 6 Baths
- Built 1920
35 Lawson Rd, Winchester, MA 01890

Welcome 35 Lawson where elegance meets modern luxury in this exquisite 6-bedroom 4F, 2H bathroom residence. A stunning marble mudroom welcomes you into the home w/ heated floors leading into fabulous new custom kitchen featuring a large dining island, inset cabinets, Wolf/Sub-Zero appliances (2 dishwashers, 2 ovens/ steam oven, 2 fridge drawers) a sleek gas fireplace, built-in banquette & direct

Kim Covino Compass

35 Lawson Rd, Winchester, MA 01890

/42
Est $2,666,250 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 5,713 Sq Ft
40 Amberwood Dr, Winchester, MA 01890

40 Amberwood Dr, Winchester, MA 01890

/29
$1,345,000 Open Sun 12PM - 1:30PM
- 3 Beds
- 2 Baths
- 2,238 Sq Ft
49 Lincoln St, Winchester, MA 01890

Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking

Vantage Point Team William Raveis R.E. & Home Services

49 Lincoln St, 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
$2,499,000 Sold May 19, 2025
- 4,270 Sq Ft
- $585/SF
- 0 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2024
50 Winford Way, Winchester, MA 01890

Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace, open dining leads to sitting room & out to a deck

Kim Covino Compass

50 Winford Way, Winchester, MA 01890

/38
Est $1,837,255 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 4,008 Sq Ft
45 Amberwood Dr, Winchester, MA 01890

45 Amberwood Dr, Winchester, MA 01890

/38
$1,099,000 Open Sun 11:30AM - 1PM
- 3 Beds
- 2 Baths
- 1,536 Sq Ft
8 Garfield Ave, Winchester, MA 01890

Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a brand new custom built cottage, blends timeless charm with modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace, while the formal dining room is perfect for gatherings. A bright

Kim Covino Compass

8 Garfield Ave, Winchester, MA 01890
/38
$8,900 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
/38
$2,600,000 Sold May 19, 2025
- 4,060 Sq Ft
- $640/SF
- 88 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1912
3 Lagrange St, Winchester, MA 01890

Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting foyer welcomes you from a wrap-around porch into an open yet intimate layout connecting the kitchen, dining, and family rooms. A mudroom with marble checkered flooring and a walk-in pantry with a beverage fridge add practical luxury.

Mark Donnellan Advisors Living - Winchester

3 Lagrange St, Winchester, MA 01890

/36
Est $2,295,926 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,257 Sq Ft
9 Amberwood Dr, Winchester, MA 01890

9 Amberwood Dr, Winchester, MA 01890

/36
$1,349,900 Open Sun 12PM - 1:30PM
- 5 Beds
- 2 Baths
- 1,706 Sq Ft
35 Harvard St, Winchester, MA 01890

Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

Joanne Mulkerin J. Mulkerin Realty

35 Harvard 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
$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

/38
Est $1,798,061 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,218 Sq Ft
27 Amberwood Dr, Winchester, MA 01890

27 Amberwood Dr, Winchester, MA 01890

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