Winchester Homes for Sale

Winchester, Massachusetts is a quiet, bedroom community conveniently located just 8 miles north of Boston. Winchester is home to several lakes and parks. Winchester is a family-friendly community that is home to several well-maintained parks, several lakes, and lots of trails.

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Browse all homes for sale in Winchester, Massachusetts below. Contact us to schedule a showing or if you have any questions. Create an account to save your favorite Winchester listings and to receive email notifications when similar properties become available. 

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7 Forest Circle Winchester MA 01890
Open House

MLS Number 72591125

  • Single Family
  • Next Open House: Sun 23rd 1:00 pm - 2:30 pm
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6

Look no further! This hidden gem could be the perfect home for you! Sited on a large lot off of a small side street and at the end of a tree-lined driveway, this charming house appears! Nicely maintained inside and out, the versatile floor plan is perfect for the buyer who wants privacy and ample space. Whether it is a large family or an individual who needs a separate work area, this home could be the perfect solution. The large master suite has a fabulous bathroom plus laundry facilities This home has what every buyer wants---hardwood floors, high ceilings, a wood-burning fireplace, large country kitchen, ample bedrooms and more! If you enjoy gardening and outdoor living, this beautiful, large lot is the perfect place to have those wonderful flower and vegetable gardens. Don't miss the over-sized two car garage which has room for storage and work space. Located near access roads to Routes 28, 93 and 128, commuting North or South, this home is a great find!

Listed by Nancy O'Herron of Coldwell Banker Residential Brokerage - Winchester

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Wainwright Road Winchester MA 01890
Open House

MLS Number 72614966

  • Condo or Co-op
  • Next Open House: Sun 23rd 1:00 pm - 2:30 pm
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,297

Inviting Ledges condo with a fabulous floor plan.This bright sunny home is an A unit which consists of kitchen in front and large dining room and fireplace living room. There is a master suite on first floor and a den or small bedroom and full bath on this level. The second floor has a bedroom with full bath and loft area. The basement is finished with a large family room and bedroom and bath and small kitchen area and ample storage space..This condo has a great location close to the clubhouse and pool. Live in a beautiful condo that has been lovingly maintained and enjoy the wooded serenity of The Ledges.

Listed by Nannette Shanahan of Better Homes and Gardens Real Estate - The Shanahan Group

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%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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35 Forest Circle Winchester MA 01890

Winchester, MA35 Forest Circle

Price$1,099,000

Est. Mortgage: $/month

Open House

MLS Number 72596363

  • Single Family
  • Next Open House: Sat 22nd 1:00 pm - 3:00 pm
  • Garage 1
  • Parking Spaces 2
  • Total Parking Spaces 3

Move right into this Highly desirable town of Winchester. This Warm Luxurious Renovated Single-Family Home recently added a 2nd floor. It has a total of 5 Bedrooms, 3 bathrooms and 3 fireplaces to cozy up to on those cold snowy winter nights. The home is situated on a tree lined street in an incredibly friendly and safe neighborhood with beautiful trails and parks nearby. You will be 10 miles from the Heart of Boston and less than a mile from The Gingerbread Construction Co., which has the best over-sized muffins you will ever taste! This home is extremely well constructed from frame to windows/doors to the insulation and more. It comes with a 1 car garage with parking in the driveway and a Beautifully Landscaped yard with several Terraces, a Patio to enjoy and relax after a long day at work. This is an Unbelievable House at an Unbelievable Price! We look forward to seeing you there!

Listed by Joanne Vanstry and Jack Lister of Berkshire Hathaway HomeServices Verani Realty

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Dix Street Winchester MA 01890

Winchester, MA15 Dix Street, Unit 9

Price$1,080,000

Est. Mortgage: $/month

MLS Number 72557325

  • Condo or Co-op
  • Bedrooms 1
  • Bathroom 2
  • Square Feet 1,275
  • Waterfront

Luxury living on the top floor at FIFTEEN DIX STREET. One level living with elevator access from heated garage with 2 exclusive use parking spots. This is the place to be for LOCATION, LOCATION, LOCATION AND GARAGE PARKING!!! Open floor plan features hardwood flooring, large windows, and an unbelievable amount of storage space. Kitchen features large marble topped island with counter seating, gas range and Sub Zero refrigerator. Bedroom has ample storage space, view of Wedge Pond and large en-suite bathroom with laundry. Office also has full en-suite bathroom. Elegant layout with quality details throughout. Addl'l storage in garage. Live in town with easy access to commuter rail, shops, restaurants and services. Enjoy everything this great community has to offer: Middlesex Fells Reservation, Wright-Locke Farm, annual community events, Saturday Farmer's Market, a vibrant arts community and more!

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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36 Elmwood Avenue Winchester MA 01890
Open House

MLS Number 72575935

  • Condo or Co-op
  • Next Open House: Sat 22nd 11:00 am - 1:00 pm
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,269

NEW CONSTRUCTION IN TOWN CENTER! Introducing allegro Winchester: a boutique style building consisting of 11 unique units in an intimate setting off the beaten path yet steps from market shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; well appointed master suite; multi zone gas heating & cooling; elevator access to garage parking; balcony or patio private outdoor space & additional storage room. Sq foot starts at 1,072 & largest unit is 1,580. Pre construction pricing in effect now!

Listed by Nancy Ciampa McLaughlin of Advisors Living - Back Bay

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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65 Thornberry Road Winchester MA 01890

Winchester, MA65 Thornberry Road

Price$1,050,000

Est. Mortgage: $/month

Open House

MLS Number 72622016

  • Single Family
  • Next Open House: Sat 22nd 12:00 pm - 1:30 pm
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8

Single level living at its best! Picturesque four bed room, two-and-a-half bath updated ranch with attached two car garage on a lovely, landscaped half-acre lot. Cathedral-ceiling kitchen with center island seating, granite counters, and stainless appliances. Open plan living room and dining room. Cozy family room with fireplace. Sun room with wall of windows overlooking the backyard. Master suite with cathedral ceiling, two custom-built walk-in closets, and a beautifully updated private bath. Four zone gas heat and central air. Pella windows, sprinkler system, and fully insulated basement, attic, and walls. Loads of basement storage. Three decks, circular stone patio, stone walls, and a fire pit, all in the expansive backyard. Just move in and enjoy!

Listed by Rebecca Brennan of Better Homes and Gardens Real Estate - The Shanahan Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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192 Highland Avenue Winchester MA 01890

Winchester, MA192 Highland Avenue

Price$999,000

Est. Mortgage: $/month

MLS Number 72622066

  • Single Family
  • Parking Spaces 6
  • Total Parking Spaces 6
  • Year Built 1888
  • Full Bath 2

Three bedroom, two bath Antique Farmhouse with over half an acre of land in the Muraco School District. It is a nature lover's dream set back from the road with a terraced backyard overlooking The Middlesex Fells. First floor has an updated open kitchen and family room, large pantry, full bath, dining room, living room, and heated sunroom. Second floor has three bedrooms, a full bath, and an office. The third floor has two bonus rooms with electric baseboard heat. The interior, front steps, and back deck have been freshly painted. Convenient to town, library, shops, restaurants, commuter rail, and miles and miles of trails in the Middlesex Fells. Welcome home!

Listed by Rebecca Brennan of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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34 Oneida Road Winchester MA 01890

Winchester, MA34 Oneida Road

Price$989,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72616554

  • Single Family
  • Garage 1
  • Parking Spaces 2
  • Total Parking Spaces 3
  • Year Built 1930

This tremendous center entrance colonial home in the Ambrose school district packs a powerful punch. First floor with a front to back fireplace living room offers great light and leads to both a family room and small office for quiet moments. The updated kitchen with built-in table leads to a formal dining room and opens to a large deck and spacious flat back yard that overlooks the Ambrose school grounds. The second floor features a front to back master bedroom with a private bath & radiant heat and a walk in closet, and is complemented by two generously sized bedrooms and an additional updated full bath with radiant heated floor. Walk up attic, and basement with walk out access to the yard offer plenty of storage space and great potential. Offers due Tuesday, Feb 11 by 11am

Listed by Anne Spry and Stephanie Mcgowan of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Amberwood Drive Winchester MA 01890

Winchester, MA7 Amberwood Drive

Price$985,900

Est. Mortgage: $/month

MLS Number 72618720

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • Year Built 1972

Pride of ownership in this charming Split-Level home.The oversized Foyer has abundant light & ceramic tiled flooring.The LR is expansive & accented with a wood burning fireplace & large bay window.An oversized opening to the formal DR with wainscoting is perfect for entertaining.The Kitchen has been updated with SS appliances & granite. Adjacent to the kitchen is a wonderful family room with large bay window & sliders to the Azek deck. Steps away is an 18' flagstone patio surrounded by mature plantings and ultimate privacy. The main level of the home has a master BR with double closets and access to a private bathroom.Two additional BR's, a second bath plus private bathing area complete this area. The first floor is a wonderful surprise hosting two additional BR's, a 3rd bath and laundry. There is a second fireplaced family room/recreation room plus office area and an oversized direct entry two car garage. All this plus hardwood floors, newer windows, central AC.

Listed by Suzanne Winchester Miller of Coldwell Banker Residential Brokerage - Lexington

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

36 Elmwood Avenue Winchester MA 01890
Open House

MLS Number 72575934

  • Condo or Co-op
  • Next Open House: Sat 22nd 11:00 am - 1:00 pm
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,072

NEW CONSTRUCTION IN TOWN CENTER! Introducing allegro Winchester: a boutique style building consisting of 11 unique units in an intimate setting off the beaten path yet steps from market shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; well appointed master suite; multi zone gas heating & cooling; elevator access to garage parking; balcony or patio private outdoor space & additional storage room. Sq foot starts at 1,072 & largest unit is 1,580. Pre construction pricing in effect now!

Listed by Nancy Ciampa McLaughlin of Advisors Living - Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

29 Thornberry Road Winchester MA 01890

Winchester, MA29 Thornberry Road

Price$949,000

Est. Mortgage: $/month

Open House

MLS Number 72621788

  • Single Family
  • Next Open House: Sat 22nd 12:00 pm - 1:30 pm
  • Garage 1
  • Parking Spaces 4
  • Total Parking Spaces 5

West Side Location, Vinson Owen Elementary School. Curb appeal, yes, BUT you can not tell from the street the amount of living space offered by this 3-4 bedroom, 2 1/2 Bath Mid Century Ranch. Updated granite/stainless steel kitchen opens to vaulted ceiling family room with wood burning stove and sliders to spacious deck Open living room with fireplace and Dining room with access to screen porch. Great flow one level living, lots of additional sunlit lower level space for playroom, fitness, workshop, office, Guest/au pair /bedroom with bath. Versatile floor plan open to many changes.

Listed by Peggy Otis and Ann Norberg of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

7 Wainwright Road Winchester MA 01890
Open House

MLS Number 72590085

  • Condo or Co-op
  • Next Open House: Sun 23rd 1:00 pm - 2:30 pm
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,918

Welcome to The Ledges! This C unit is located in a private wooded setting with a deck off the rear. This well-maintained unit has a first-floor master suite and an updated kitchen with breakfast nook overlooking the sunny courtyard. Lovely hardwood floors in dining and living room. Two additional bedrooms and a bath are on the second level. Potential to finish out lower level with ample storage .This is a perfect opportunity to afford The Ledges and enjoy the Clubhouse , pool, tennis courts and the beauty and serenity of this desirable location. In addition the roof and 4 skylights have just been replaced.

Listed by Nannette Shanahan of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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