Winchester, MA Homes

/42
$1,755,000 Sold Dec 10, 2024
- 2,886 Sq Ft
- $608/SF
- 7 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1911
19 Warren St, Winchester, MA 01890

Step into this beautifully designed 3-bedroom, 3-bathroom single-family home located in the sought-after Flats of Winchester. Nestled in a wonderful neighborhood, this home offers a perfect blend of charm and modern living. The spacious living room with a cozy fireplace flows seamlessly into a bright sunroom, filling the space with natural light. The eat-in kitchen is equipped with stainless

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

19 Warren St, Winchester, MA 01890

/41
Est $2,043,689 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,730 Sq Ft
2 Tanglewood Ln, Winchester, MA 01890

2 Tanglewood Ln, Winchester, MA 01890

/40
$1,375,000 Pending
- 3 Beds
- 2 Baths
- 3,406 Sq Ft
7 Hutchinson Rd, Winchester, MA 01890

A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l

Kim Covino Compass

7 Hutchinson Rd, Winchester, MA 01890
/40
$1,225,000 Sold Dec 09, 2024
- 3,350 Sq Ft
- $366/SF
- 27 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1988
7 Wainwright Rd Unit 29, Winchester, MA 01890

Imagine arriving home to peace & serenity at The Ledges, a hilltop oasis on Winchester's West side. This tranquil retreat offers carefree living & your private sanctuary. Relax in the fireplace living room, sliders to your private deck & expansive views. The main bedroom en suite, is conveniently located on the first floor. Second level finds a loft, skylit bonus room perfect for a home office,

Joanne Sexeny Coldwell Banker Realty - Lexington

7 Wainwright Rd Unit 29, Winchester, MA 01890

/34
Est $2,724,450 Not Listed For Sale
- 5 Beds
- 5 Baths
- 7,235 Sq Ft
25 Olde Village Dr, Winchester, MA 01890

25 Olde Village Dr, Winchester, MA 01890

/11
$1,269,000 Pending
- 3 Beds
- 3.5 Baths
- 2,136 Sq Ft
158 Swanton St Unit 160, Winchester, MA 01890

Welcome to 158 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

158 Swanton St Unit 160, Winchester, MA 01890
/34
$1,071,000 Sold Dec 05, 2024
- 2,186 Sq Ft
- $490/SF
- 8 Days On Market
- 5 Beds
- 3 Baths
- Built 1880
63-65 Harvard St, Winchester, MA 01890

Discover this rare multi-family gem in a highly desirable Winchester neighborhood, offering endless possibilities for savvy investors, owner-occupants, or multi-generational living. Situated on a large, flat, private lot with a detached two-car garage and ample off-street parking, this home perfectly balances charm, function, and convenience. The first-floor unit includes two bedrooms, a bright

Nancy Pallotta Advisors Living - Winchester

63-65 Harvard St, Winchester, MA 01890

/22
Est $2,686,111 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,333 Sq Ft
18 Olde Village Dr, Winchester, MA 01890

18 Olde Village Dr, 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
/42
$2,900,000 Sold Dec 03, 2024
- 4,215 Sq Ft
- $688/SF
- 32 Days On Market
- 4 Beds
- 5 Baths
- Built 1917
27 Cabot St, Winchester, MA 01890

Meticulously renovated home in desirable Winchester Flats! Set on a tranquil corner lot surrounded by mature trees, less than a mile from schools, Winchester Center, and commuter rail, this exquisite four-level Tudor offers the perfect blend of modern elegance and classic charm. The main level showcases 2 inviting family rooms adorned with fireplace and integrated sound system, gourmet kitchen

The McLaren D'Agostino Team Compass

27 Cabot St, Winchester, MA 01890

/40
Est $1,357,519 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,456 Sq Ft
25 Lockeland Rd, Winchester, MA 01890

25 Lockeland Rd, 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
/37
$2,899,999 Sold Dec 03, 2024
- 7,242 Sq Ft
- $400/SF
- 8 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2010
50 Lorena Rd, Winchester, MA 01890

Stunning cedar shingle Colonial home nestled in sought-after East Hill. As you step inside, you are greeted by an elegant foyer leading to a chef's kitchen with center island, pantry, granite counters, SS appliances and a sun-filled dining area.The kitchen seamlessly flows to a stone deck, perfect for grilling and alfresco dining. Large family room wrapped with windows featuring a stone

Leigh Ventura Compass

50 Lorena Rd, Winchester, MA 01890

/37
Est $2,178,050 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,209 Sq Ft
4 Mayflower Rd, Winchester, MA 01890

4 Mayflower Rd, Winchester, MA 01890

/32
$1,199,000 Pending
- 4 Beds
- 2 Baths
- 2,759 Sq Ft
80 Harvard St, Winchester, MA 01890

Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3 bedrooms and a bathroom.

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

80 Harvard St, Winchester, MA 01890
/38
$3,800,000 Sold Dec 03, 2024
- 5,500 Sq Ft
- $691/SF
- 47 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1951
25 Ledgewood Rd, Winchester, MA 01890

Nestled on 1.1 acres in Winchester, this fully custom renovated home is truly a hidden gem. The property is well secluded from the main road, offering a tranquil retreat. Transformed in 2024, this home features 5 spacious beds, 4.5 baths and custom spaces throughout. The grand kitchen, with white oak accents, is a culinary centerpiece. The light-filled family room has expansive windows and a

Mark Donnellan Advisors Living - Winchester

25 Ledgewood Rd, Winchester, MA 01890

/40
Est $1,812,148 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,744 Sq Ft
20 Mayflower Rd, Winchester, MA 01890

20 Mayflower Rd, Winchester, MA 01890

/26
$1,149,000 Pending
- 3 Beds
- 2 Baths
- 1,646 Sq Ft
7 Indian Hill Rd, Winchester, MA 01890

This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood floors, a gas fireplace, and arched doorways add character and warmth to the space. The well-equipped kitchen features granite countertops, glass-front cabinetry and access to a side deck for al fresco dining. Three bright bedrooms and a

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

7 Indian Hill Rd, Winchester, MA 01890
/19
$377,000 Sold Dec 02, 2024
- 634 Sq Ft
- $595/SF
- 5 Days On Market
- 1 Bed
- 1 Bath
- Built 1966
200 Swanton St Unit T26, Winchester, MA 01890

Ideal for first-time homeowners, down-sizers, or investors. Desirable private/direct-entry terrace level 1BD, 1BA condo overlooking scenic duck ponds and lush landscape at The Parkview, Winchester’s iconic Midcentury Modern building. With 634 Sq. Ft. this unit offers ample space for dining, living & bedroom area with a large walk in closet! Association amenities include a pool for hot summer

Gretchen Chingris Metropolitan Boston Real Estate, LLC

200 Swanton St Unit T26, Winchester, MA 01890

/41
Est $2,167,944 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,372 Sq Ft
36 Mayflower Rd, Winchester, MA 01890

36 Mayflower Rd, Winchester, MA 01890

/34
$2,499,000 Pending
- 4 Beds
- 3.5 Baths
- 5,218 Sq Ft
31 Lawson Rd, Winchester, MA 01890

Welcome to this gracious Colonial, seamlessly blending traditional charm with modern amenities, perfect for today’s lifestyle. Located in one of Winchester’s most desirable neighborhoods, you’ll enjoy easy access to top-rated schools, the commuter rail, and downtown. This home showcases deep moldings along w/ a stunning kitchen that naturally flows into the living/dining area & family room,

Monte Marrocco Coldwell Banker Realty - Lexington

31 Lawson Rd, Winchester, MA 01890
/42
$2,375,000 Sold Dec 02, 2024
- 5,279 Sq Ft
- $450/SF
- 7 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2014
7 Bellevue Ave, Winchester, MA 01890

Exceptionally designed & meticulously maintained 2015 Contemporary Colonial. Elegant farmers porch welcomes you into a magnificent layout w/ exquisite mouldings, wainscotting, oak hardwoods, custom fixtures/millwork, & plantation shutters. Spectacular, open-concept main level boasts dual island, granite/stainless chef’s kitchen w/ 2 ovens, butler’s pantry, built-in buffet, walk-in pantry, &

Cam Chesley Keller Williams Realty Boston-Metro | Back Bay

7 Bellevue Ave, Winchester, MA 01890

/42
Est $3,158,970 Not Listed For Sale
- 6 Beds
- 5 Baths
- 4,805 Sq Ft
53 Hutchinson Rd, Winchester, MA 01890

53 Hutchinson Rd, Winchester, MA 01890

/41
$1,499,000 Pending
- 4 Beds
- 3.5 Baths
- 4,214 Sq Ft
7 Wainwright Rd Unit 117, Winchester, MA 01890

Welcome to the largest unit at The Ledges! This stunning F unit boasts soaring ceilings and an expansive open floor plan, perfect for entertaining or relaxing in style. Custom decorated in a perfect, custom Palm Beach vibe, but easy to change if you don't love it. Sunlight floods the large formal living room, with an attached deck, bifurcated by a gas fireplace that leads to the dining room. A

Nancy Pallotta Advisors Living - Winchester

7 Wainwright Rd Unit 117, Winchester, MA 01890
/34
$1,580,000 Sold Nov 29, 2024
- 2,650 Sq Ft
- $596/SF
- 26 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1900
78 Middlesex St, Winchester, MA 01890

Amazing transformation of a Classic Colonial carefully reimagined for today's busy lifestyle. Living room with gas fireplace opens to the family room, oversized hi-end kitchen with island, stainless & granite, dining room with sliders to the yard with a stone patio for outside entertaining, a mud room & 1/2 bath. Upstairs has a primary bedroom suite, bath with 2 separate vanities, walk-in custom

Marjie and Phil Advisors Living - Arlington

78 Middlesex St, Winchester, MA 01890

/33
Est $1,278,191 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,636 Sq Ft
132 Cambridge St, Winchester, MA 01890

132 Cambridge St, Winchester, MA 01890

/42
$2,749,000 Pending
- 6 Beds
- 6 Baths
- 5,263 Sq Ft
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
/4
$1,650,000 Sold Nov 22, 2024
- 2,000 Sq Ft
- $825/SF
- 11 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1935
40 Foxcroft Rd, Winchester, MA 01890

Garrison Colonial nestled in the highly desirable Flats neighborhood of Winchester! This 3-bedroom, 2.5-bath home offers plenty of potential, with additional space in the walk-up attic and a large backyard. Classic brick fireplaces in first floor living room and in basement. With the existing 2,000 sq. ft., this home is ready for a complete renovation and expansion, giving you the opportunity to

Monte Marrocco Coldwell Banker Realty - Lexington

40 Foxcroft Rd, Winchester, MA 01890

/42
Est $2,096,486 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,259 Sq Ft
5 Dawes Ave, Winchester, MA 01890

5 Dawes Ave, Winchester, MA 01890

/42
$1,324,000 Pending
- 3 Beds
- 3.5 Baths
- 2,792 Sq Ft
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
/38
$1,300,000 Sold Nov 22, 2024
- 3,122 Sq Ft
- $416/SF
- 111 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
14 Pine Grove Park Unit 14, Winchester, MA 01890

Welcome to this newly constructed luxurious 4-bedroom, 3.5-bathroom townhome spanning four levels of exquisite living space! Step through the charming covered porch into the striking open floor plan. The elegant living room boasts expansive windows, custom fireplace wall and hardwood floors. The showstopper kitchen dazzles with gorgeous white cabinetry accented by gold details, quartz countertops

Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

14 Pine Grove Park Unit 14, Winchester, MA 01890

/40
Est $2,738,691 Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,051 Sq Ft
50 Emerson Rd, Winchester, MA 01890

50 Emerson Rd, Winchester, MA 01890

/15
$925,000 Pending
- 4 Beds
- 2 Baths
- 2,172 Sq Ft
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
/30
$900,000 Sold Nov 21, 2024
- 1,857 Sq Ft
- $485/SF
- 6 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1985
62 Edward Dr, Winchester, MA 01890

Welcome to 62 Edward Drive in the sought-after Pepper Hill Estates. This spacious townhouse-style condo features two bedrooms and a versatile bonus room on the lower level, perfect for a home office, guest space, or playroom. The well-maintained home boasts an open living and dining area filled with natural light and a beautiful fireplace. The updated kitchen includes granite countertops, newer

Melissa Perrone Better Homes and Gardens Real Estate - The Shanahan Group

62 Edward Dr, Winchester, MA 01890

/37
Est $1,869,591 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,689 Sq Ft
36 Robinhood Rd, Winchester, MA 01890

36 Robinhood Rd, Winchester, MA 01890

/41
$2,900,000 Pending
- 4 Beds
- 4 Baths
- 4,325 Sq Ft
45 Brooks St, Winchester, MA 01890

Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4BD 4 BA home offering a classic exterior with a stunning "must see" interior; featuring formal spaces great for entertaining blended w/casual living areas both inside & out w/ walls of floor to ceiling windows capturing the elements of

Kim Covino Compass

45 Brooks St, Winchester, MA 01890
/30
$1,050,000 Sold Nov 21, 2024
- 2,136 Sq Ft
- $492/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1926
359-361 Washington St, Winchester, MA 01890

Welcome to this well-maintained two-unit multi-family home, perfect for investors or owner-occupants seeking a spacious living arrangement with rental income potential. Each unit boasts two well apportioned bedrooms and dedicated in-home office areas, ideal for today’s work-from-home lifestyle. Enjoy the convenience of off-street parking along with two garage bays, ensuring easy access for you

Anne Spry Barrett Sotheby's International Realty

359-361 Washington St, Winchester, MA 01890

/33
Est $1,509,460 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,920 Sq Ft
10 Albamont Rd, Winchester, MA 01890

10 Albamont Rd, Winchester, MA 01890

/42
$3,199,000 Pending
- 5 Beds
- 5 Baths
- 4,279 Sq Ft
51 Wedgemere Ave, Winchester, MA 01890

Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-placed foyer welcomes you into the home, enhanced by a new chefs kitchen w/ 10' island, custom cabinetry, & adjacent family room overlooking yard. With four floors of beautifully finished spaces, there's room for every lifestyle need. Enjoy

Kim Covino Compass

51 Wedgemere Ave, Winchester, MA 01890
/42
$2,200,000 Sold Nov 21, 2024
- 3,969 Sq Ft
- $554/SF
- 6 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1865
7 Herrick St, Winchester, MA 01890

Step into a world of timeless elegance in this beautifully preserved home, where classic architectural details seamlessly blend with modern comfort. The inviting front porch welcomes you. Inside, high ceilings complement a living room w/beamed ceilings & custom built-ins, a gracious dining room, & a light-filled, eat-in kitchen. The cozy family room offers a charming window seat. A quaint stone

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

7 Herrick St, Winchester, MA 01890

Showing Results 201 - 240, Page 6 of 18

Massachusetts Winchester

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage