Winchester, MA Homes

/39
$3,599,000
- 6 Beds
- 4.5 Baths
- 5,876 Sq Ft
5 Stratford Rd, Winchester, MA 01890

This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

Kim Covino Compass

5 Stratford Rd, Winchester, MA 01890
/23
$4,395 per month
- 3 Beds
- 2.5 Baths
- 1,823 Sq Ft
- Condo for Rent
171 Swanton St Unit 63, Winchester, MA 01890

Welcome to the Village at Winchester!Experience comfortable living in this spacious 1,800 sq ft townhome nestled in a professionally managed 80-unit complex. This beautiful 3-bedroom, 2.5-bath home features hardwood floors, a cozy fireplace in the living room, and a bright dining area with a skylight that opens to a private patio—perfect for relaxing and entertaining.Additional highlights include

Gary Vrotsos Coldwell Banker Realty - Cambridge

171 Swanton St Unit 63, Winchester, MA 01890
/13
$680,000 Sold May 15, 2025
- 968 Sq Ft
- $702/SF
- 12 Days On Market
- 2 Beds
- 2 Baths
- Built 1963
15 Charles Rd, Winchester, MA 01890

Rarely available 2 bedrooms 2 bathrooms townhouse at The Residences in Winchester! Here is your chance to move into a wonderful community. This unit has a private level large back yard, where you can have your own garden area. First floor features a living room-dining room and kitchen. Second floor has two bedrooms and two baths ( Master bedroom has a 3/4 bath). Recently renovated and freshly

Beiping Zhao Jack Gately Real Estate, LLC

15 Charles Rd, Winchester, MA 01890

/42
Est $2,226,527 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,124 Sq Ft
9 Buckman Dr, Winchester, MA 01890

9 Buckman Dr, Winchester, MA 01890

/41
$1,349,000 Open Sun 1PM - 2:30PM
- 3 Beds
- 1.5 Baths
- 3,335 Sq Ft
10 Girard Rd, Winchester, MA 01890

Unleash Your Vision in Winchester’s Coveted West Side! Don't miss this rare chance to transform this Mid-Century Modern ranch on a generous 15,024 square foot idyllic lot in one of Winchester’s most desirable neighborhoods. Whether you renovate, expand, or enjoy this home as it is, this 3-bed, 1.5-bath home offers endless potential. Nestled on a quiet, tree-lined street abutting conservation land

Joanne Sexeny Coldwell Banker Realty - Lexington

10 Girard Rd, Winchester, MA 01890
/39
$10,000 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
/42
$2,200,000 Sold May 09, 2025
- 4,097 Sq Ft
- $537/SF
- 24 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1939
88 Arlington St, Winchester, MA 01890

Welcome to this warm & inviting home nestled amidst the serene landscapes of the Winchester Country Club. A Royal Barry Wills design, showcasing 5-beds, 3.5-baths, w/4 fireplaces & attached direct entry 2 car garage! This home has w/ an abundance of charm in every room; the spacious living areas are warm and inviting & flooded with natural light, showcasing original woodwork & oversized wood

Kim Covino Compass

88 Arlington St, Winchester, MA 01890

/42
Est $1,920,005 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
3 Bigelow Ave, Winchester, MA 01890

3 Bigelow Ave, Winchester, MA 01890

/29
$1,799,999
- 3 Beds
- 2.5 Baths
- 3,002 Sq Ft
44 Amberwood Dr, Winchester, MA 01890

Incredibly well maintained, nicely updated 3-4 bedroom Colonial in a wonderful neighborhood in desirable VO School district! The first floor has an oversized kitchen w/cherry cabinets, all granite counters & breakfast bar that opens to a great room with FP and a recently added family room w/vaulted ceiling, computer cubby and 10' slider to a deck overlooking a beautiful landscaped yard & 2

Hudson Santana Keller Williams Realty Boston Northwest

44 Amberwood Dr, 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
/39
$3,199,000 Sold May 09, 2025
- 6,694 Sq Ft
- $478/SF
- 9 Days On Market
- 7 Beds
- 5 Baths
- Built 1880
12 Prospect St, Winchester, MA 01890

Exuding elegant luxury, this fully renovated Victorian boasts a carriage house and extraordinary grounds, in one of Winchester’s most coveted neighborhoods! A show-stopping chef's kitchen boasts state-of-the-art Thermador appliances, wine tower, 42'' fridge, a 6-burner gas range, a quartzite island with seating for 4, & a breakfast nook overlooking a beautifully landscaped large yard with rock

Nancy Pallotta Advisors Living - Winchester

12 Prospect St, Winchester, MA 01890

/42
Est $2,194,951 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,256 Sq Ft
15 Pilgrim Dr, Winchester, MA 01890

15 Pilgrim Dr, Winchester, MA 01890

/40
$1,199,900
- 4 Beds
- 2.5 Baths
- 2,302 Sq Ft
518 Washington St, Winchester, MA 01890

Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry.

Rodrigo Serrano Leading Edge Real Estate

518 Washington 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
/15
$1,088,000 Sold May 08, 2025
- 2,172 Sq Ft
- $501/SF
- 6 Days On Market
- 4 Beds
- 2 Baths
- Built 1985
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 RE/MAX Real Estate Center

322 Cambridge St, Winchester, MA 01890

/40
Est $1,436,673 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,142 Sq Ft
16 Johnson Rd, Winchester, MA 01890

16 Johnson Rd, Winchester, MA 01890

/42
$2,899,000 Open Sun 12PM - 1PM
- 7 Beds
- 5.5 Baths
- 5,864 Sq Ft
10 Sheffield Rd, Winchester, MA 01890

This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

Andersen Group Realty Keller Williams Realty Boston Northwest

10 Sheffield Rd, Winchester, MA 01890
/38
$2,850,000 Sold May 07, 2025
- 5,044 Sq Ft
- $565/SF
- 5 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2025
22 Standish Ln, Winchester, MA 01890

This distinguished residence, built by premier local developer, represents the pinnacle of elegant living! Soaring ~9' ceilings & pristine hardwood floors set an impressive tone in this meticulously crafted new construction offering 4 levels of refined living space. The eye-catching foyer ushers guests into a realm of sophisticated design, where premium finishes & high-end appliances elevate

Michaela Mahtani Leading Edge Real Estate

22 Standish Ln, Winchester, MA 01890

/33
Est $1,993,043 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,603 Sq Ft
8 Olde Lyme Rd, Winchester, MA 01890

8 Olde Lyme Rd, Winchester, MA 01890

/37
$859,000
- 2 Beds
- 1 Bath
- 1,123 Sq Ft
22 Grove Place Unit 4, Winchester, MA 01890

Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect opportunity to enjoy the lovely town of Winchester and keep costs down. Near Symmes corner, downtown Winchester & Wedgemere train station, this wonderful 2 bedroom, 1 bathroom end unit lives and feels like a single home with windows on all three sides. The kitchen offers a

Kim Covino Compass

22 Grove Place Unit 4, Winchester, MA 01890
/27
$975,000 Sold May 07, 2025
- 2,873 Sq Ft
- $339/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1958
18 Pine Grove Park, Winchester, MA 01890

Beautifully maintained one owner Cape, 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 terrific location. Three bedrooms, two full baths, with a bonus room offer flexibility and space to make it your own. Gleaming hardwood floors throughout, with built-ins in

Michele Forester EXIT Premier Real Estate

18 Pine Grove Park, Winchester, MA 01890

/42
Est $2,430,910 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,473 Sq Ft
239 Ridge St, Winchester, MA 01890

239 Ridge St, Winchester, MA 01890

/38
$3,249,000 Open Sun 11:30AM - 12:30PM
- 6 Beds
- 6.5 Baths
- 6,028 Sq Ft
44 Cabot St, Winchester, MA 01890

Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

Andersen Group Realty Keller Williams Realty Boston Northwest

44 Cabot St, Winchester, MA 01890
/20
$2,398,000 Sold May 06, 2025
- 4,468 Sq Ft
- $537/SF
- 26 Days On Market
- 5 Beds
- 4 Baths
- Built 1937
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 RE/MAX Real Estate Center

74 Hillcrest Pkwy, Winchester, MA 01890

/26
Est $1,165,599 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,826 Sq Ft
75 Dunster Ln, Winchester, MA 01890

75 Dunster Ln, Winchester, MA 01890

/34
$959,000 Open Sun 10:30AM - 12PM
- 3 Beds
- 1 Bath
- 1,425 Sq Ft
571 Washington St, Winchester, MA 01890

Welcome to this beautifully maintained 3-bedroom home just moments from vibrant Winchester Center. Ideal for commuters with quick access to I-95 and I-93, this home blends charm, comfort, and convenience. The updated kitchen features quartz countertops and generous cabinetry—perfect for cooking and gathering. Light-filled living spaces offer a warm, welcoming feel throughout. Unwind on the

Ryan Wilson Keller Williams Realty

571 Washington St, Winchester, MA 01890
/36
$730,000 Sold May 01, 2025
- 1,393 Sq Ft
- $524/SF
- 7 Days On Market
- 2 Beds
- 1 Bath
- Built 1890
21 Shepard Ct, Winchester, MA 01890

Welcome to 21 Shepard Court, a beautifully renovated townhouse nestled in a quiet cul-de-sac. This 2+ bedroom, 1-bathroom home offers four levels of living space with modern upgrades & timeless charm. Renovated features: The main level boasts a high-end kitchen with new quartz countertops stainless steel appliances, custom cabinetry, & eat in island. The bathroom has been fully upgraded with

Abe Guillen Encore Realty

21 Shepard Ct, Winchester, MA 01890

/42
Est $3,219,589 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 5,676 Sq Ft
222 High St, Winchester, MA 01890

222 High St, Winchester, MA 01890

/37
$3,475,000 Open Sun 12PM - 1:30PM
- 5 Beds
- 3.5 Baths
- 5,632 Sq Ft
80 Arlington St, Winchester, MA 01890

This stunning Royal Barry Wills colonial estate, with 11 rooms, 5 bedrooms and 3.5 baths, is nestled alongside the 4th green of the exclusive Winchester Country Club. Take in views from the sun-splashed eat-in kitchen, complete w/ granite island, custom wood cabinetry, and a generous seating area. Unwind by the fireplace in the richly paneled study. Access the expansive wrap around patio from the

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

80 Arlington St, 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

/27
Est $1,059,337 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,859 Sq Ft
46 Edward Dr, Winchester, MA 01890

46 Edward Dr, Winchester, MA 01890

/42
$3,099,000
- 6 Beds
- 3.5 Baths
- 5,238 Sq Ft
54 Wedgemere Ave, Winchester, MA 01890

Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive back yard featuring

Kim Covino Compass

54 Wedgemere Ave, 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

/42
Est $1,034,119 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,738 Sq Ft
41 Edward Dr, Winchester, MA 01890

41 Edward Dr, Winchester, MA 01890

/37
$1,329,000 Open Sun 1:30PM - 2:30PM
- 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
/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

/38
Est $1,051,700 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,754 Sq Ft
34 Edward Dr, Winchester, MA 01890

34 Edward Dr, 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
/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

/34
Est $1,061,958 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,859 Sq Ft
36 Edward Dr, Winchester, MA 01890

36 Edward Dr, Winchester, MA 01890

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