Winchester, MA Homes

/38
$1,500,000
- 4 Beds
- 3 Baths
- 2,897 Sq Ft
195 Mystic Valley Pkwy, Winchester, MA 01890

Lovely brick home just up the road from EVERYTHING!!! Commuter Rail, Library, Schools, Shopping, Restaurants, Town Hall. Less than 9 miles to Boston! So close to the Middlesex Fells and the Tri-Community Greenway. Location, location, location - CHECK! Now the structure...classic brick home built to stand the test of time with BIG IMPROVEMENTS. Grand front to back living room with fireplace leads

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

195 Mystic Valley Pkwy, Winchester, MA 01890
/42
$8,000 per month
- 5 Beds
- 3.5 Baths
- 3,700 Sq Ft
- House for Rent
271 Washington St Unit 1, Winchester, MA 01890

Walk to town and schools from this spacious 11 room, 5 bedroom, 3.5 bath home! Open floor plan and high ceilings. Bonus rooms/ home office space. Delightful and bright sun porch. New kitchen with classic white cabinetry and quartz countertops. Two car attached garage and mud room. New heating and central air. Ample off street parking. Available July 1, 2025

Julia Marino Archambault Real Estate

271 Washington St Unit 1, Winchester, MA 01890
/42
$2,900,000 Sold Mar 07, 2025
- 4,400 Sq Ft
- $659/SF
- 67 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1917
64 Wildwood St, Winchester, MA 01890

Exquisitely restored brick Colonial situated in the sought-after Flats neighborhood of Winchester. Boasting refinished hardwood floors, beautiful moldings and trim, and high ceilings throughout, no detail has been overlooked in this meticulous renovation. The gourmet kitchen, featuring high end appliances, is perfect for culinary enthusiasts, while the formal dining room, complete w/ wood-burning

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

64 Wildwood St, Winchester, MA 01890

/4
Est $2,915,025 Not Listed For Sale
- 6 Beds
- 7 Baths
- 6,500 Sq Ft
136 Ridge St, Winchester, MA 01890

136 Ridge St, Winchester, MA 01890

/31
$385,000
- 1 Bed
- 1 Bath
- 613 Sq Ft
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
/13
$4,500 per month
- 3 Beds
- 1.5 Baths
- 1,657 Sq Ft
- House for Rent
17 Russell Rd, Winchester, MA 01890

Single-family home with 3 bedrooms and 1.5 baths. Move in date: 6/1/2025. Tenant pays all utilities (gas, heat, electricity, cold/hot water and trash disposal). Lead Paint: Certified Treated. No pets allowed. Laundry in the unit. Move-in costs: First month's rent, one month's rent as a security deposit, and one month's rent as a broker fee.

KoKo Kwan Kwan Realty Inc.

17 Russell Rd, Winchester, MA 01890
/42
$1,600,000 Sold Mar 03, 2025
- 2,075 Sq Ft
- $771/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1900
410 Main St, Winchester, MA 01890

Charming, updated carriage house on a private lot, where form meets function in an in-town location. The expansive living room with a fireplace and beam ceiling offers flexibility for dual purposes or a single use. The impressive kitchen boasts a timeless style with a coffee bar, an eat-in breakfast nook, & a convenient peninsula with a six burner stove and Thermador oven. Positioned by a bay

Anne Spry Barrett Sotheby's International Realty

410 Main St, Winchester, MA 01890

/36
Est $1,360,874 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,823 Sq Ft
7 Wainwright Rd Unit 88, Winchester, MA 01890

7 Wainwright Rd Unit 88, Winchester, MA 01890

/37
$1,399,000
- 3 Beds
- 2 Baths
- 1,884 Sq Ft
147 Highland Ave, Winchester, MA 01890

Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you with a spacious living room w fplc that flows seamlessly into a sun-drenched updated kitchen featuring stainless steel

Kim Covino Compass

147 Highland Ave, Winchester, MA 01890
/11
$2,200 per month
- 1 Bed
- 1 Bath
- 606 Sq Ft
- Condo for Rent
200 Swanton St Unit 428, Winchester, MA 01890

Bright and sunny 1 bedroom and 1 bathroom condo in Winchester Park View. close to shopping, restaurants, town Center and walking to commuter train. Easy access to all major highways. Rental fee Including heat, electricity, hot water and a lot of more... Available 06/01.

Wei Wang WW Real Estate LLC

200 Swanton St Unit 428, 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 $1,658,517 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,327 Sq Ft
7 Wainwright Rd Unit 72, Winchester, MA 01890

7 Wainwright Rd Unit 72, Winchester, MA 01890

/32
$749,900
- 3 Beds
- 1.5 Baths
- 1,931 Sq Ft
235 Cross St, Winchester, MA 01890

Lovingly cared for by its original owners for nearly 70 years, this charming ranch-style home rests proudly on a desirable corner lot in a welcoming, established neighborhood. Offering 3 comfortable bedrooms, 1.5 bathrooms, and two fireplaces, the home is filled with warmth, character, and exciting potential for new owners to make it their own. The yard comes alive each spring with vibrant

Melanie Lentini Leading Edge Real Estate

235 Cross St, Winchester, MA 01890
/36
$11,000 per month
- 6 Beds
- 4.5 Baths
- 6,500 Sq Ft
- House for Rent
52 N Border Rd, Winchester, MA 01890

Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home has 6 bedrooms, and 5 bathrooms. The stunning foyer welcomes you to the sprawling first floor. The custom work throughout each sun filled room is exquisite. Gourmet kitchen with top of the line appliances. Generous sized rooms to entertain guests. A private home office with built

Julia Marino Archambault Real Estate

52 N Border Rd, Winchester, MA 01890
/42
$2,825,000 Sold Feb 25, 2025
- 5,850 Sq Ft
- $483/SF
- 8 Days On Market
- 5 Beds
- 6 Baths
- Built 2018
16 Wickham Rd, Winchester, MA 01890

Tucked away on a quiet sought after neighborhood, just steps away from the Wedgemere Station and Winchester Center, this meticulously maintained 5-bedroom home built in 2018 perfectly blends modern design with refined details, including beautiful coffered ceilings, wainscoting, chair rails, and crown moulding. The 1st floor offers a formal living room, a spacious family room with a fireplace, a

Rodrigo Serrano Leading Edge Real Estate

16 Wickham Rd, Winchester, MA 01890

/38
Est $1,574,436 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

/42
$1,199,000
- 3 Beds
- 1.5 Baths
- 1,906 Sq Ft
44 Forest St, Winchester, MA 01890

This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living

Kim Covino Compass

44 Forest St, Winchester, MA 01890
/36
$5,000 per month
- 3 Beds
- 1.5 Baths
- 2,364 Sq Ft
- House for Rent
27 Ledyard Rd Unit SF, Winchester, MA 01890

SHORT TERM RENTAL - Oversized cape with hardwood floors throughout. Large front to back living room with working fireplace, built in bookcases and cabinets and lots of natural light. Formal dining room with built in china cabinet and French door leading to spacious 3-season porch. Kitchen has all new stainless steel appliances and access to side porch for relaxing with morning coffee or

Diane Plunkett Plunkett Properties

27 Ledyard Rd Unit SF, Winchester, MA 01890
/36
$630,000 Sold Feb 25, 2025
- 1,160 Sq Ft
- $543/SF
- 137 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
666 Main St Unit LV2, Winchester, MA 01890

Welcome to 666 Main Street, Unit LV2, Winchester. This beautiful well maintained 2 bedroom, 2 bathroom condominium on the desirable ground level, features a Private Entrance & a Walk Out Patio w/ Wedge Pond views. Enjoy the close distance of all that Winchester Centre has to offer; shops, restaurants, commuter rail & more. Enjoy an updated kitchen w/ stainless appliances & peninsula, separate

Katie DiVirgilio

666 Main St Unit LV2, Winchester, MA 01890

/39
Est $1,691,762 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

/37
$1,899,000
- 5 Beds
- 3.5 Baths
- 3,478 Sq Ft
10 Olde Lyme Rd, Winchester, MA 01890

PRICE IMPROVEMENT.Beautifully updated 5 bed, 3.5 bath Colonial on Winchester's West Side with over 3400 sq ft of living space located on a quiet cul-de-sac in the coveted Vinson-Owen school district. Set on an 18,000 sq ft lot abutting Sucker Brook conservation area and walking trails. This home offers privacy, space and natural beauty. The main level features a spacious layout with an

Darryl Brian RE/MAX Bentley's

10 Olde Lyme Rd, Winchester, MA 01890
/8
$2,500 per month
- 1 Bed
- 1.5 Baths
- 800 Sq Ft
- Apartment for Rent
253 Swanton St Unit Rear, Winchester, MA 01890

Enjoy this beautifully renovated 1 bedroom, 1.5 bathroom comfortable living area only minutes away from downtown Winchester, pubic schools, T-Station, commuter rail, restaurants, and shopping. A beautiful custom kitchen featuring mahogany countertops, Subzero and Wolfe appliances opens up to a family room complete with impeccable finishes. Escape downstairs to a large spacious bedroom complete

Rachel Ventresca Greater Metropolitan R. E.

253 Swanton St Unit Rear, 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

/42
Est $1,809,729 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

/34
$1,499,900
- 5 Beds
- 2 Baths
- 3,033 Sq Ft
7 Thornberry Rd, Winchester, MA 01890

Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighborhood. 15 minutes to Downtown Boston. 5 bedrooms, 2 full baths, Living, Dining PLUS family room & 2nd finished room ( play or office) ground level room heated & A/C walk access to outdoor deck & fire pit. Open concept kitchen area. Hardwood floors, 2 fireplace, 2 garage space,

salim chowdhury TAJ Mahal Realty LLC

7 Thornberry Rd, Winchester, MA 01890
/40
$2,532,000 Sold Feb 18, 2025
- 6,300 Sq Ft
- $402/SF
- 28 Days On Market
- 6 Beds
- 6.5 Baths
- Built 2024
20 Bellevue Ave, Winchester, MA 01890

Exquisite 6-bed, 6.5-bath residence offers 6,300 sq ft of sophisticated design and luxurious features. The chef’s kitchen boasts dual islands, quartz countertops, Viking appliances, and a sunny breakfast nook perfect for entertaining. The family room with a gas fireplace opens to a deck and landscaped yard for seamless indoor-outdoor living. The first floor includes a guest bedroom or office with

Monte Marrocco Coldwell Banker Realty - Lexington

20 Bellevue Ave, Winchester, MA 01890

/41
Est $1,739,242 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,246 Sq Ft
8 Wainwright Rd, Winchester, MA 01890

8 Wainwright Rd, Winchester, MA 01890

/42
$1,650,000
- 3 Beds
- 2.5 Baths
- 2,605 Sq Ft
14 Hillside Ave, Winchester, MA 01890

Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps from Town Center! This property has been lovingly owned & maintained by the same family for 70+ years and is now ready for new owners. Prepare to fall in love with the charm and period details of this circa 1870 historic home, the first house built on Hillside Ave. The 1st floor

Seeme Moreira Coldwell Banker Realty - Lexington

14 Hillside Ave, Winchester, MA 01890
/34
$1,020,000 Sold Feb 14, 2025
- 1,470 Sq Ft
- $694/SF
- 4 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1965
28 Bellevue Ave, Winchester, MA 01890

Nestled at the end of a peaceful cul-de-sac in Winchester, this charming 3-bedroom, 1.5-bath home is a must-see. Recently updated with fresh paint, modern flooring, stylish lighting fixtures, and updated stainless steel appliances in the kitchen, it blends comfort with convenience. The living room features a cozy wood-burning fireplace, perfect for chilly evenings. The walk-out basement offers

Gayle Winters Compass

28 Bellevue Ave, Winchester, MA 01890

/42
Est $2,523,080 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

/41
$2,450,000
- 5 Beds
- 5 Baths
- 3,940 Sq Ft
17 Wagon Wheel Rd, Winchester, MA 01890

Enjoy breathtaking Boston skyline views from nearly every room of this meticulously maintained home, offering the ultimate private retreat for peace and tranquility. The owners have thoughtfully upgraded the property, including a 2020 expansion that added an en-suite with a private bathroom and enlarged the open-concept kitchen. With 5 bedrooms and 5 bathrooms, including four en-suites, this home

Dream Team Dreamega International Realty LLC

17 Wagon Wheel Rd, Winchester, MA 01890
/20
$660,000 Sold Feb 12, 2025
- 1,160 Sq Ft
- $569/SF
- 63 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
666 Main St Unit L3, Winchester, MA 01890

Welcome to 666 Main St Unit L3- Ground level 2 Bedroom Unit with Sliders to Patio overlooking Wedge Pond-Kitchen Totally Updated with Custom Cabinets and Quartz Countertop and Back Splash. Stainless Steel Appliances- Fire Place Living Room with Hardwood Floors-Spacious Dining Area with Hardwood Floors- Open Concept-Master Bedroom with Full Bath, Walk in Closet and Hardwood Floors-2nd Bedroom with

Steven Petrello Century 21 North East

666 Main St Unit L3, Winchester, MA 01890

/38
Est $1,808,688 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

/41
$3,599,000
- 6 Beds
- 5.5 Baths
- 7,431 Sq Ft
27 Everett Ave, Winchester, MA 01890

Completely renovated in 2023/2024! This is one of the most distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. This residence combines the magnificence of early 1900s architecture with today's modern amenities., this home features hallmark architectural details including Tudor-style balusters and high ceilings. Large rooms, coffered ceilings, original crown

Nancy Pallotta Advisors Living - Winchester

27 Everett Ave, Winchester, MA 01890
/25
$1,450,000 Sold Feb 10, 2025
- 2,632 Sq Ft
- $551/SF
- 3 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1911
48 Water St Unit 50, Winchester, MA 01890

Embrace elegance and convenience with this exquisite townhouse that's been meticulously designed. This residence presents a generous 4-bedroom, 3.5-bathroom, ample space for relaxation and entertainment across its three expansive levels. The heart of this home is the open floor plan, where natural light cascades over fine finishes that align with the rhythm of your daily life. Culinary

Chris Kostopoulos Keller Williams Realty

48 Water St Unit 50, Winchester, MA 01890

/27
Est $1,560,884 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
3 Amberwood Dr, Winchester, MA 01890

3 Amberwood 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
/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

/36
Est $2,227,895 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

/4
$3,799,900
- 7 Beds
- 7.5 Baths
- 7,429 Sq Ft
11 Viking Rd, Winchester, MA 01890

Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

The McLaren D'Agostino Team Compass

11 Viking Rd, Winchester, MA 01890

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