Winchester Homes for Sale

Winchester, Massachusetts is 8 miles north of Boston. Winchester is child-friendly and home to lakes, parks, and trails. Winchester keeps its public spaces well maintained. Winchester is a family-friendly bedroom community. 

Discover Winchester Real Estate

As you search through listings please be sure to contact us with any questions or to schedule a viewing. Register on the site to save your favorite listings and to receive email notifications when similar listings come to market.

You may also be interested in viewing homes for sale in
Arlington | Belmont | Cambridge | Waltham | Woburn

15 Myopia Road, Winchester, MA

Price$998,000

Est. Mortgage: $/month

Open House

MLS Number 72170037

  • Single Family
  • Next Open House: Thu 25th 4:00 pm - 6:00 pm
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1970

Perched proudly on coveted Myopia Hill with seasonal water views of the Mystic Lakes,you will enter and be charmed by the calming ambiance of this home. Inside it feels as if you are looking out through the trees. Bright and light are two words that describe this open floor plan, contemporary home sitting on a cul-de sac. The bus to Alewife is at the bottom of the street and it's a relaxing ride to Boston on the commuter rail . In close proximity to the Winchester Boat Club and the Winchester Country Club this convenient location is only 1/2 mile from the Ambrose Elementary School and just over a mile to Winchester's picturesque downtown area with shops, restaurants, and entertainment galore.. Welcome Home to Myopia Hill.

Listed by Singer & Stokes of William Raveis R.E. & Home Services

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

1 Nassau Drive, Winchester, Ma 01890

MLS Number 72169545

  • Rental
  • Date Available 07/01/2017
  • Bathroom 1

Furnished 2 BR in-law apt with all utilities in a beautiful home in Winchester. This spacious 1000+sqft includes all utilities, cable TV, and Wifi . It is on the first floor of a multilevel contemporary house in Winchester, just 8 miles outside of Boston. The European style bathroom was completely redone and expanded in January 2017 with the addition of a tiled shower. Bright open floor plan with living area, dining area, and a kitchen area with stainless steel appliances. Large 2 bedrooms with great closet. It has it's own washer and dryer, kitchen ware and linen. It also has private entrance and off street parking. Must see!

Listed by Ides Miller of Coldwell Banker Residential Brokerage - Winchester

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

34 Clark Street, Winchester, MA 01890

MLS Number 72169956

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2

Great Condo Alternative / Single Family - Opportunity to own in Winchester! Pretty as a picture! White picket fence encloses charming front porch leading to sunny 2 bedroom, 1 ½ bath home. Perfect for the first time home owner. Located on a quiet, dead end street. Short walk to elementary, middle and high schools, shopping, restaurants and commuter rail. Commute to Boston via easily accessible train or easy highway access, only 10 miles from this wonderful town. First floor features cozy living room with hard wood floors and plenty of natural light, eat in kitchen with white cabinets and ½ bath. Second floor features 2 bedrooms with wood floors and many built-ins for plenty of storage. Full bath features a tub/shower and beadboard walls. Living area & bedrooms have been freshly painted. Laundry hook-ups and added storage in the basement. Nice fenced-in yard with large paver patio, outside shed for storage, off street tandem parking. Must see property in a great community!

Listed by Anne Marie Hannon of C. Brendan Noonan & Co.

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

57 Charles Street, Winchester, Ma 01890

MLS Number 72168507

  • Rental
  • Date Available 07/01/2017
  • Bathroom 2

Very well maintained townhouse condominium on a quiet cul de sac in family friendly neighborhood. Hardwood floors; gorgeous brand new kitchen, dining room opens out to deck and nice flat private back yard. Half bath on 1st floor. 2nd floor has 3 bedrooms and full bath. Finished basement includes big family room; office/den; full bath, and storage. Available July 1st. No pets/no smoking

Listed by Diane Plunkett and Sheri O'Connor of Plunkett Properties

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

54 Harvard Street, Winchester, Ma 01890
Open House

MLS Number 72167719

  • Rental
  • Next Open House: Thu 1st 12:00 pm - 2:00 pm
  • Date Available 06/15/2017
  • Bathroom 2

Enjoy living in this renovated Townhouse on desirable Harvard st. Impeccable and Convenient! Easy access to 93 and 95, short distance to the town center, commuter rail, and short distance to Elementary,Middle,and High Schools. This unit offers 3 bedrooms and 2 full baths,extra office space, private patio, and private entrance in the lower unit of the Townhouse on a corner lot. Unit comes with washer/dryer, two off street parking spots, and plenty of street parking.

Listed by Christopher Carlson of Bay State Realty Group, Inc.

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

30 Kenwin Road, Winchester, MA

MLS Number 72168150

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1951
  • Parking Spaces 4

Discover this attractive Colonial in the popular Muraco School District! It is the first home built by Winchester's Paul J. Whitney and the quality of his influence and guidance are evident throughout. With custom millwork, built-in cabinets, bookshelves, hardwood floors, Harvey replacement windows and a playroom in the basement with large desks to do homework, this house has a lot to offer. Another local craftsman named Larry England deserves credit for the gorgeous, cherry cabinets in the kitchen. For buyers new to this area, Leonard Field is five minutes away and features two tennis courts plus plenty of room for outdoor play. Also close by is the Winchester Hospital, the Middlesex Fells Reservation, Muraco School and major commuting routes. Definitely a golden opportunity to own a lovely home!

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

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

95 Ridge, Winchester, Ma 01890

MLS Number 72168277

  • Rental
  • Bathroom 4

PERFECT west side location! Only minutes to the new (2015) Vincent Owen elementary school. Spacious wonderfully maintained 4 Bedroom 3.5 Bath Colonial. Nicely set back off of Ridge St. Handy circular driveway. Attached 2 Car Garage. Fenced .46 acre yard offers privacy, lush green grass and pleasant plantings. Covered entryway. Mudroom w bench. Impressive bright Kitchen has cherry wood cabinetry, granite counters & stainless steel appliances. Pretty dining nook w multiple windows overlooks yard. There is a dining room & living room w French doors and a family room with fireplace. Master Suite consists of an arched room with two walk-in closets - plus an Office with built-in desk and spiral staircase. The Master Bath has a jacuzzi tub, updated walk-in shower and two vanities w new faucets. The Family Bath has tw granite vanity w 2 sinks. The freshly painted finished basement offers 2 rooms w new flooring & a cedar closet. C/Air. Washer/Dryer. Hardwood floors-no carpets!

Listed by Cynthia Conroy of William Raveis R.E. & Home Services

Barrett Sotheby's International Realty - Lincoln
152 Lincoln Road
Lincoln MA, 01773
Office: 781-259-4040

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

65 NELSON Street, Winchester, MA

Price$589,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72167838

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Year Built 1902
  • Parking Spaces 2

Classic, circa 1900, colonial style home on a lovely, tree-lined street in walking distance to Winchester’s quaint town center, schools, library & commuter rail station. Easy access to I-93, I-95 & 7 mile ride to Boston. This residence boasts a circular flow of 6 rooms, 3 bedrooms & 1 bath on 2 floors with hardwood floors; high ceilings; a sunny eat-in- kitchen & a walk up attic that can be finished to add additional living area. A few of the amenities of this home are a 4 year old heating system with direct hot water (no tank), 15 year old roof, 2 car off street parking, low maintenance vinyl exterior & basement storage. A special home in a friendly, welcoming neighborhood. With a bit of updating this home is a perfect condo alternative with a very low maintenance yard. This home is being sold "as is".

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

171 Swanton Street, Winchester, MA 01890

MLS Number 72167613

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2

First time home buyers or looking to downsize! The highly regarded Village Townhouses in Winchester are located within 1 mile of the MBTA station and offer advantage of the back patio, manicured landscape, in-ground swimming pool, clubhouse and tennis court. Level one of this townhouse features a tiled kitchen with stainless appliances and granite countertops, a separate dining room, half-bath, ample storage, and front-to-back spacious living room with wood burning fireplace, skylight and river views. The second floor offers a spacious master bedroom with walk in closet and attached full bath, a generous second bedroom and an in-unit washer/dryer. An additional room which could be used as a third bath, office, or playroom. Additional features include: Single Zone Central AC and heat, covered carport for 2 vehicles and extra storage unit near carport. OPEN HOUSE SUN (11-2) AND MON EVE (5:30-7:30).. PLEASE SUBMIT ALL OFFERS BY TUES 8:00 PM... ALL OFFERS WILL BE REVIEWED AT THAT TIME.

Listed by Dave White of OwnerEntry.com

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

194 Washington Street, Winchester, MA 01890
Active With Contract

MLS Number 72166806

  • Condo or Co-op
  • Bedrooms 5
  • Bathroom 2

Wow! Attached single is super close to town, trains, schools and shops! You'll love the old-world charm that abounds here, melded with modern amenities in one fabulous home. Gorgeous antique hardwood floors shine throughout, highlighting the open layout of the first floor as well as the bedrooms above. Kitchen features granite counters, stainless stove and dishwasher as well as stool-height breakfast bar. 5 bedrooms, mudroom, lovely enclosed rear patio plus ample basement storage, rear garage and oversized 2-car driveway in front offers so much for the price. Fabulous rental history for investors, or a super family home close to everything. Offers reviewed 5/23, Tuesday evening.

Listed by Nancy S. Pallotta of RE/MAX Leading Edge

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

10 Winthrop Street, Winchester, MA

Price$949,500

Est. Mortgage: $/month

MLS Number 72166896

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1852
  • Parking Spaces 2

Take advantage of this Great opportunity in Lincoln School District. Exquisite residence near Winchester town center. Spacious rooms, updated by a sought after local builder. Spacious open kitchen and dining room, 6 burner Viking gas range and upscale appliances , great center island. Britt and sunny. Fireplace living room on first floor. Radiant Heat , Central Air conditioning on 2nd and 3rd Floor. 3 bedroom + office on second floor. 2 bedrooms on third. This is an attached townhouse but lives and feels like a single family home. Lovely gardens with yard exclusive use to this unit. Stroll to Town Center, all schools, library, train, shops, and restaurants. Don't miss out, a must!

Listed by Dorothea Feffer of Coldwell Banker Residential Brokerage - Winchester

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

54 Myopia Road, Winchester, MA

Price$3,175,000

Est. Mortgage: $/month

MLS Number 72166793

  • Single Family
  • Bedrooms 6
  • Bathroom 7
  • Year Built 2000
  • Parking Spaces 6

Decorative wrought iron gates open to a carriage driveway and reveal the spectacular mature gardens that create the estate setting for this Colonial Revival masterpiece. Set upon Myopia Hill, among homes of similar architectural distinction, it is difficult to imagine that such privacy can be available so close to the town of Winchester and within striking distance of the city of Boston. This family-friendly neighborhood provides ease of access to all Winchester offers: fine schools, children’s activities and clubs, boat club, beach, golf course, and the community’s Wright Locke Farm, to name a few. This home is resplendent in architectural detail, both inside and out. The floor plan was designed with a principal goal – to be first and foremost a family home designed around a central core dedicated to a large open plan kitchen and a generously proportioned family room. To the rear a large patio overlooks lawns for children’s activities and a woodland wonderland for exploration.

Listed by Jonathan Radford of Coldwell Banker Residential Brokerage - Boston - Newbury St.

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 2017
* 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

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.