Winchester MA Real Estate & Homes for Sale

43 Properties Found

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Beds:
4
Baths:
4.00
Sq.Ft.:
3,286
Status:
Active
MLS#:
73537676
Type:
Single Family
Lot size:
1.23 Acres
Year built:
1989
Courtesy: Barrett Sotheby's International Realty 781-729-7900
View additional info

ADDITIONAL INFORMATION

Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless appliances, an island, and a sunny window seat. A main-level primary suite with deck access, two walk-in closets, and a spa-like bath provides a calm retreat. Additional bedrooms offer flexibility for rest, work, or guests, while the full walk-out unfinished lower level—with abundant windows and slider—adds exceptional potential for an ADU, future living area, studio, or recreation space. Updated efficient heat pump heating and cooling, an oversized attached garage, professional landscaping, stone walls, sprinklers, and a cul-de-sac setting complete this distinctive property.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,145
Status:
Active
MLS#:
73534894
Type:
Condo
Year built:
1987
Courtesy: Better Homes and Gardens Real Estate - The Shanahan Group 781-729-9030
View additional info

ADDITIONAL INFORMATION

Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub. Spacious single floor living! Plus an upper floor with a loft office space overlooking the living room, and an attractive 2d bedroom suite. The unfinished walk-out basement offers significant room to expand. Landscaping, exterior maintenance, snow removal all done for you while you enjoy the association clubhouse, outdoor pool, tennis court and walking trails in the adjacent Sucker Brook Conservation area. Just minutes from Boston via car or train from charming Winchester Center with its coffee shops, restaurants and outdoor summer dining, pharmacies, and Whole Foods Market all near.

Open House:

Sunday, 8/9 10:00-11:00AM

More Open House Info >

Beds:
5
Baths:
4.00
Sq.Ft.:
5,083
Status:
Active
MLS#:
73525195
Type:
Single Family
Lot size:
0.49 Acres
Year built:
2025
Courtesy: Keller Williams Realty Boston Northwest 781-862-2800
View additional info

ADDITIONAL INFORMATION

Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient laundry add flexibility for guests or multigenerational living. Upstairs, the luxurious master retreat boasts a cozy gas fireplace, expansive walk-in closet, and spa-like bath, followed by another bedroom with an ensuite bath, and two additional bedrooms sharing a Jack and Jill bath. A finished basement provides versatile space for a gym, media room, or playroom. Enjoy a charming front porch, private back deck, durable Hardy Plank exterior, and attached two-car garage. Exceptional craftsmanship and timeless curb appeal make this a must-see home! Located within the Winchester School District

Beds:
2
Baths:
1.00
Sq.Ft.:
822
Status:
Active
MLS#:
73524262
Type:
Condo
Year built:
1966
Courtesy: REMAX Andrew Realty Services 781-395-7676
View additional info

ADDITIONAL INFORMATION

Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and flexibility for comfortable living. The living area opens to scenic views overlooking the duck pond and professionally maintained grounds, creating a peaceful setting to enjoy year-round. The building offers secure card-entry access, ample resident parking, and guest parking area off Swanton Street. The HOA includes heat, hot water, electricity,AC, and access to the in-ground pool, providing exceptional value and convenience. Unit comes with 1 storage unit in basement.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,235
Status:
Active
MLS#:
73519082
Type:
Single Family
Subdivision:
Middlesex / downtown
Lot size:
0.15 Acres
Year built:
1864
Courtesy: Compass 781-219-0313
View additional info

ADDITIONAL INFORMATION

Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

Beds:
4
Baths:
5.00
Sq.Ft.:
5,233
Status:
Active
MLS#:
73518621
Type:
Single Family
Lot size:
0.25 Acres
Year built:
2004
Courtesy: Luxury Living Real Estate 617-227-7007
View additional info

ADDITIONAL INFORMATION

This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate. A lifestyle of luxury/convenience steps away from town, commuter rail, school and walking trails.

Open House:

Sunday, 8/9 10:00-11:30AM

More Open House Info >

Beds:
3
Baths:
4.00
Sq.Ft.:
2,420
Status:
Active
MLS#:
73513572
Type:
Condo
Year built:
1890
Courtesy: Leading Edge Real Estate 781-979-0100
View additional info

ADDITIONAL INFORMATION

Experience the best of Winchester with a home that pairs exceptional value with an unbeatable location. Just moments from Winchester Center, enjoy a low-maintenance lifestyle within walking distance of downtown, the commuter rail, and all three school levels. This townhouse-style condo lives like a single-family home, offering space, flow, and flexibility across four finished levels. The open main level seamlessly connects the kitchen, dining, and living areas, highlighted by coffered ceilings, wainscoting, and a beautifully renovated kitchen with stainless steel appliances and modern finishes. Upstairs, the front-to-back primary suite features custom closets and a spa-inspired bath with a soaking tub and glass shower. The finished lower level provides the perfect flex space for a home office, media room, fitness area, or playroom. Complete with two deeded parking spaces, this is effortless living in one of Winchester's most desirable locations.

Beds:
5
Baths:
6.00
Sq.Ft.:
6,500
Status:
Active
MLS#:
73513501
Type:
Single Family
Lot size:
0.24 Acres
Year built:
2025
Courtesy: Rise Signature Homes 617-383-5659
View additional info

ADDITIONAL INFORMATION

Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef's kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and dining areas, while the oversized pantry completes the space. Three bedrooms including the primary suite feature en suite baths, with two offering spacious walk-in closets. The primary suite provides a spa-inspired bath and a generous walk-in closet. The expansive lower level, with ceiling heights over 10 ft, offers flexible space for an au pair, media room, gym, or additional living area. Designed by Salt and Stone Co., with a two-car garage. Seller is offering a backyard improvement credit at closing toward landscaping, hardscape, or outdoor living features of the buyer's choice. Prime location

Beds:
7
Baths:
8.00
Sq.Ft.:
8,540
Status:
Active
MLS#:
73502853
Type:
Single Family
Lot size:
0.46 Acres
Year built:
2009
Courtesy: Compass 781-219-0313
View additional info

ADDITIONAL INFORMATION

Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz countertops, oversized island, 2 dishwashers & butler’s pantry w/ice maker & wine fridge flowing into formal DR & LR plus a fireplaced FMRM overlooking a meticulously maintained yard. Each oversized bedroom offers an en-suite bath, sitting area & walk-in closet, providing comfort & privacy throughout. The 1st flr includes a private office w/wet bar plus a lavish bedroom wing ideal for guests or multi-generational living. The 3rd floor suite features a full BA & 2 closets, while the finished lower level adds media/game/gym areas w/access to stunning heated pool, complimented by lush outdoor landscape

Beds:
4
Baths:
3.00
Sq.Ft.:
3,123
Status:
Active
MLS#:
73502658
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1904
Courtesy: Gibson Sotheby's International Realty 781-648-3500
View additional info

ADDITIONAL INFORMATION

Set in one of Winchester’s most coveted neighborhoods, this distinguished Robert Coit-designed residence seamlessly blends timeless architecture with exceptional modern living. Rich in original detail and brimming with character, this 4-bedroom, 2.5-bath home is a true testament to enduring craftsmanship. Gracious living spaces are anchored by three fireplaces, creating warmth and elegance throughout. The expansive kitchen is a showpiece—generous in scale and thoughtfully designed for both everyday living and entertaining. A cypress-paneled den with a fireplace is located on the first floor. The top floor offers 1 room with sink and a large open gallery space, perfect for a home office. Outside, the property unfolds into spectacular, professionally curated gardens and lush landscaping, offering a private oasis that changes beautifully with the seasons. There is a full unfinished basement for additional space. Large welcoming front porch, close to the center and top-rated schools.

Beds:
1
Baths:
1.00
Sq.Ft.:
613
Status:
Active
MLS#:
73500952
Type:
Condo
Year built:
1966
Courtesy: Coldwell Banker Realty - Lexington 781-862-2600
View additional info

ADDITIONAL INFORMATION

Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for dining and entertaining. Large living room with a glass slider leading to a private balcony overlooking a view of beautifully landscaped grounds. Unit also includes 1 parking space, storage space in the basement, and on-site laundry room. Condo fee includes; heat. hot water, electric, A/C, water/sewer, landscape, & snow removal. Other amenities include gated entry, on-site management, plus the swimming pool with picnic/BBQ area. minutes away from town center, shops, restaurants, bus stop, & the commuter rail t-stop. Close to outdoor trails, major highways, and easy access to the city of Boston

Beds:
6
Baths:
7.00
Sq.Ft.:
6,968
Status:
Active
MLS#:
73500890
Type:
Single Family
Lot size:
0.43 Acres
Year built:
2002
Courtesy: WINN Real Estate & Consulting 617-306-0648
View additional info

ADDITIONAL INFORMATION

Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.

Beds:
7
Baths:
8.00
Sq.Ft.:
7,226
Status:
Active
MLS#:
73498293
Type:
Single Family
Lot size:
0.43 Acres
Year built:
2025
Courtesy: Douglas Elliman Real Estate - The Sarkis Team 617-875-4950
View additional info

ADDITIONAL INFORMATION

Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to accommodate today's evolving lifestyle. At the heart of the home is a stunning chef's kitchen that flows seamlessly into a fireplaced family room with soaring cathedral ceilings, creating an inviting space for both everyday living and entertaining.What truly sets this property apart is its versatility. A private two-bedroom au pair offers its own living area, office, wet bar, and full bath ideal for extended family, guests, or live-in support. A finished lower level provides valuable additional living and recreation space.Just moments from Mullen Field, and everything Winchester has to offer

Beds:
2
Baths:
2.00
Sq.Ft.:
1,365
Status:
Active
MLS#:
73497739
Type:
Condo
Year built:
1983
Courtesy: Better Homes and Gardens Real Estate - The Shanahan Group 781-729-9030
View additional info

ADDITIONAL INFORMATION

Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal chandeliers & wall sconces. The thoughtfully renovated kitchen features granite countertops, custom cabinetry, stainless steel appliances, & opens to a stylish butler’s pantry complete w/wine fridge, sink, & in-unit washer/dryer. Upstairs, both bedrooms offer HW flooring, updated lighting, & skylight w/shade. Bathrooms have been tastefully updated. Additional highlights include updated electrical, gas line connection, & integrated sound wiring.Includes one car garage, an additional outdoor parking space & basement storage w/bonus cedar closet.Turnkey home near town center, shops & commuter rail. Some photos are virtually staged.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,938
Status:
Active
MLS#:
73498603
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1939
Courtesy: Coldwell Banker Realty - Lexington 781-862-2600
View additional info

ADDITIONAL INFORMATION

This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a nice place for family to congregate and get to gather. The living room, graced with crown molding, offers a welcoming space for relaxation and entertainment. The home features four bedrooms and two full bathrooms, providing ample space for a comfortable lifestyle. The inclusion of a walk-in closet adds a practical and desirable element, offering generous storage and organization. Please come and visit this fine home close to shops, highways and schools!

Open House:

Sunday, 8/9 12:00-2:00PM

More Open House Info >

Beds:
2
Baths:
1.00
Sq.Ft.:
810
Status:
Active
MLS#:
73496844
Type:
Condo
Year built:
1966
Courtesy: Tirana Real Estate Group 857-891-1453
View additional info

ADDITIONAL INFORMATION

SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of closet spaces. Private storage space and laundry in the building. In ground pool and beautiful out door spaces. One off street parking space and huge guest parking lot. Easy access to Rte. I95, Rte. I93, "T" and Boston. Walking distance to shopping, Winchester town center and many more. HEAT , HOT WATER AND ELECTRICITY ARE INCLUDED IN THE CONDOMINIUM FEE. EASY TO SHOW! OPEN HOUSE ON SATURDAY 11: 00 -- 1:00 PM AND SUNDAY 12:00--1:30 PM OFFERS DEADLINE : MONDAY APRIL 20, 2026

Beds:
5
Baths:
4.00
Sq.Ft.:
5,006
Status:
Active
MLS#:
73496396
Type:
Single Family
Subdivision:
Cox Road / High St Extension neighborhood
Lot size:
0.46 Acres
Year built:
1992
Courtesy: Compass 781-219-0313
View additional info

ADDITIONAL INFORMATION

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

Beds:
6
Baths:
6.00
Sq.Ft.:
6,100
Status:
Active
MLS#:
73482275
Type:
Single Family
Subdivision:
West side
Lot size:
0.26 Acres
Year built:
2026
Courtesy: Compass 781-219-0313
View additional info

ADDITIONAL INFORMATION

Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer kitchen w/vaulted ceilings, skylights, oversized island, sliders to large deck & a fire-placed family room, along with formal living and dining rooms & a FIRST FLOOR bedroom suite! The 2nd floor offers 4 generous BR's including a luxurious primary suite, 2 additional full baths & convenient second floor laundry. The above grade/ walk-out lower level adds exceptional flexibility w/ *Au- pair or In-law suite* media room, home office, exercise room, bedroom & full bath Enjoy all the area has to offer including restaurants, shops, schools, train to Boston, Bike-paths & more! 7 miles from Boston

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Andrea D. Conner, License 1?0?0?0?1?8?8, Xome Inc., License 9622, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. Copyright © 2026 MLS Property Information Network, Inc. All rights reserved.



Winchester Real Estate

Winchester is located in Massachusetts. Winchester, Massachusetts has a population of 22,875. Winchester is more family-centric than the surrounding county with 48.34% of the households containing married families with children. The county average for households married with children is 35.9%.

The median household income in Winchester, Massachusetts is $184,844. The median household income for the surrounding county is $111,790 compared to the national median of $69,021. The median age of people living in Winchester is 42.4 years.

Winchester Weather

The average high temperature in July is 82.3 degrees, with an average low temperature in January of 19 degrees. The average rainfall is approximately 46.9 inches per year, with 52.7 inches of snow per year.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $1,561,000
    12.9%
    change since last quarter
  • # Active listings

    45
    30-day change

Winchester Schools and Demographics

Education near Winchester, MA

City County
High School Graduates 97.52 93.57
College Degree - 2 year 3.07 5.86
College Degree - 4 year 75.47 57.77
Graduate Degree 28.51 19.76
Expenditures per Student 23,560 23,560
Students per Teacher 12 12

Elementary Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Ambrose Elementary School KG - 05 458 13.5 01890
Brackett KG - 05 497 16.3 02476
Brooks School PK - 05 534 13.2 02155
Christopher Columbus PK - 05 471 11.8 02155
Clyde Reeves PK - 05 512 15.7 01801
Cyrus E Dallin KG - 05 456 15.4 02476
Daniel P Hurld KG - 05 217 14.5 01801
Goodyear Elementary School KG - 05 322 12.8 01801
Hardy KG - 05 392 16.4 02474
John A Bishop KG - 05 415 16.8 02474
John J McGlynn Elementary School PK - 05 559 13.2 02155
Lincoln Elementary School KG - 05 408 13.1 01890
Linscott-Rumford KG - 05 213 13.9 01801
Lynch Elementary School PK - 05 524 12.6 01890
Malcolm White KG - 05 336 14.7 01801
Mary D Altavesta KG - 05 235 10.8 01801
Menotomy Preschool PK - PK 57 9.5 02476
Milton Fuller Roberts PK - 05 576 13.2 02155
Muraco Elementary School KG - 05 406 12.6 01890
Shamrock PK - 05 350 13.2 01801
Thompson KG - 05 392 16 02474
Vinson-Owen Elementary School KG - 05 427 13.5 01890
Wyman KG - 05 189 13.5 01801

Middle Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Daniel L Joyce Middle School 06 - 08 528 10.6 01801
John F Kennedy Middle School 06 - 08 527 11.7 01801
John J. McGlynn Middle School 06 - 08 476 9.7 02155
Madeleine Dugger Andrews 06 - 08 494 11.5 02155
McCall Middle School 06 - 08 1,073 14.1 01890
Ottoson Middle School 06 - 08 1,107 12.7 02476

High Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Arlington High School 09 - 12 1,217 13.8 02476
Curtis-Tufts 09 - 12 22 5 02155
Medford High School 09 - 12 1,176 12 02155
Winchester High School 09 - 12 1,209 14.1 01890
Woburn High 09 - 12 1,332 13.8 01801

Demographics near Winchester, MA

City County
Neighborhood Type Suburban
Population 22,875 1,623,411
Population Density 3,793 1,985
Median Age 42.4 38.5
People per Household 2.8 2.5
Median Household Income 184,844 111,790
Average Income per Capita 90,356 58,399

Real estate near Winchester