Barrett Sotheby's International Realty Logo

Homes for Sale Winchester MA

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 Barrett Sotheby's International Realty 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

380 Highland Avenue Winchester MA 01890

Winchester, MA380 Highland Avenue

Price$1,329,000

Est. Mortgage: $/month

Open House

MLS Number 72982187

  • Single Family Detached
  • Next Open House: Sat 05/21 11:00 am. to 12:00 pm.
  • Bathroom 3
  • Rooms 9
  • Bedrooms 4

Rare opportunity to live on the corner of a private cul-de-sac in East Hill! Just minutes from Winchester Center, downtown shops, restaurants & the commuter rail. Captivating Cape has been updated w/ modern conveniences while still maintaining the integrity & charm of the original home. Beautiful craftsmanship throughout featuring gorgeous hardwood floors, custom built-ins, oversized wood burning fireplace, along w/ a sunny Florida room with access to the outdoor patio. Formal dining room is located near the update chef's kitchen. Kitchen features custom cabinetry, SS appliances, beamed ceiling, ample storage & space to eat-in. A cozy family room completes this level. Spacious main bedroom with custom California closets and ensuite bathroom. Three additional bedrooms and a full bathroom complete the second floor living. Outdoor patio surrounded by flower gardens, storage shed and a newly paved driveway. Move into this fabulous home on one of the most desired streets in Winchester!

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

15 Clark Street Winchester MA 01890

Winchester, MA15 Clark Street

Price$799,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72981918

  • Single Family Attached
  • Bedrooms 3
  • Bathroom 2
  • Rooms 6
  • Square Feet 1,500

OPEN HOUSE TODAY 5/15~12-2 PM This private, dead end street and NEWLY RENOVATED townhome that lives like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 mile to the high school, Wedge Pond, Elliot Park, Borggaard Beach & Splash Park & the Tri-Community bike path,1/2 mile to commuter rail and town center shops and restaurants and 7 miles to Boston! The main floor of this stylish, sun drenched unit with lofty ceiling heights and oak flooring throughout offers a stunning white kitchen with quartz counters, tiled backsplash and high end stainless appliances, living and dining rooms & a large half bath.Upstairs you'll find 3 bedrooms,more lofty ceilings,beautifully restored pine flooring,a laundry closet,a spacious full bath and storage everywhere!All new systems including central air,huge Anderson windows throughout and a full basement.Outside is ready to party with a private,level & usable fenced-in backyard & off street parking for 4 cars!

Listed by Chrisanne Connolly of Wilson Wolfe Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

11 Chesterford Road East Winchester MA 01890

Winchester, MA11 Chesterford Road East

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72981610

  • Single Family Detached
  • Bathroom 4
  • Rooms 9
  • Bedrooms 4
  • Acreage 0.31

Showings begin Friday May 20th. Delightful waterfront home nestled alongside Little Winter pond with fabulous views! This updated contemporary designed home features a stunning entry, vaulted ceilings and walls of windows showcasing the spectacular setting. Updated kitchen w/ adj dining room w/ built in bench flows into the living room w/fplc and family room flooded with natural light w/water views from the many windows & slider to the gorgeous new deck. The main level also offers 3 bedrooms and 2 full baths; awake each morning in the relaxing primary suite w/unsurpassed views, oversized walk-in closet & new bath. The lower level includes a large media room, bedroom, full bath and gym. There are water views from almost every room in this home! The wrap around deck is perfect for enjoying the scenery and for summertime bbq's. There is a lower patio on the water making it easy to canoe/kayak & fish from your own front yard! Enjoy living an active lifestyle in this very special home!

Listed by Kim Covino & Co. Team of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

25 Olde Village Drive Winchester MA 01890

Winchester, MA25 Olde Village Drive

Price$2,285,000

Est. Mortgage: $/month

MLS Number 72980996

  • Single Family Detached
  • Bathroom 5
  • Rooms 12
  • Bedrooms 5
  • Acreage 0.79

Quality, Craftsmanship & Design! Never before offered estate like property with stunning grounds. Custom designed & constructed this home exudes quality & elegance. Superb materials were selected & used throughout. Marble entry with vaulted ceiling & impressive curved stairway. Formal living room w/custom oak flooring in a basket weave pattern, arched doorways & fireplace w/ Portoro marble. Impressive formal dining room. First flr family room finished in rare Wormy Chestnut will be the center of activity w/access to deck & patio. The kitchen boasts custom cabinetry, granite, hardwood & top of the line appliances. Adjacent dining area, half bath, pantry w/ laundry & two car garage. First flr bedroom w/ full bath. The second flr features four bedrooms including front to back master suite w/ dressing rm & full bath. Amazing LL-golf driving range, putting green, pool table, & half bath. The land is stunning w/ gorgeous plantings & fenced court for tennis, basketball or just fun!

Listed by Jodi Winchester, Suzanne Winchester Miller and Jean Winchester of Coldwell Banker Realty - Lexington

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

12 Maxwell Road Winchester MA 01890

Winchester, MA12 Maxwell Road

Price$1,325,000

Est. Mortgage: $/month

MLS Number 72980568

  • Single Family Detached
  • Village Town Center
  • Bedrooms 4
  • Rooms 9
  • Bathroom 3

Queen Anne Victorian nestled in the Heart of Winchester Center - Enchanting house mixed with period details & modern updates. Enjoy living in this sun filled home w/ a cozy Living Room w/ french doors & built-ins which opens to a large fire-placed Dining Room w/ built-in china cabinet & a dazzling chandelier. Updated kitchen with SS appliances, granite countertops and large bay window with lots of cabinets. You will love outdoor living at its best with a spacious deck for dining alfresco, family hangouts and entertaining. Deck overlooks a beautiful fenced back yard complete w/ swing set. 4 BDR's & 2.5 baths provide generous living spaces. Large Primary BDRM w/ period bay windows & double closets. 3rd flr has 4th DBR and office space w/ attic storage. Full walkout Bonus RM in lower level w/ a gorgeous enclosed screened-in porch. Great living spaces inside & out. Don't miss this special home in a sought-after neighborhood. Walk to ALL schools, train and town center. 8 miles to Boston!

Listed by Leigh Ventura of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

12 Keenan Drive Winchester MA 01890

MLS Number 72981263

  • Single Family Detached
  • Rooms 11
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,000

Impressive 4 bed, 3 and 1/2 bath colonial located in the popular Muraco School District on cul-de-sac with easy access to Rt 93. Great layout for todays living. Enter through front foyer with high ceiling & French doors to den with custom shelving for a perfect home office. Formal living room and dining room plus eat-in kitchen with granite counters and gas oven open to family room w/cathedral ceiling and wood burning fireplace with french doors to large rear deck overlooking private yard with mature landscaping. Laundry room and pantry right off kitchen with direct access to 2 car garage, plus parking for 4 additional cars in the driveway. Double sinks in 2nd floor full bath. Large primary bedroom suite with walk in closet, reading nook & spacious primary bathroom with double sinks, whirlpool tub and walk in shower. Exceptional walk out lower level, with full bath perfect for in-laws, au-pair, teen suite & home gym. Open houses Sat/Sun 12:00-1:30 offers reviewed Wed May 18th 2:00pm

Listed by The Synergy Group and Louis Cirignano of The Synergy Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

15 Clark Street Winchester MA 01890
Contingent

MLS Number 72980621

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,500

OPEN HOUSE TODAY 5/15~12-2 PM This private, dead end street and NEWLY RENOVATED townhome that lives like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 mile to the high school, Wedge Pond, Elliot Park, Borggaard Beach & Splash Park & the Tri-Community bike path,1/2 mile to commuter rail and town center shops and restaurants and 7 miles to Boston! The main floor of this stylish, sun drenched unit with lofty ceiling heights and oak flooring throughout offers a stunning white kitchen with quartz counters, tiled backsplash and high end stainless appliances, living and dining rooms & a large half bath.Upstairs you'll find 3 bedrooms,more lofty ceilings,beautifully restored pine flooring,a laundry closet,a spacious full bath and storage everywhere!All new systems including central air,huge Anderson windows throughout and a full basement.Outside is ready to party with a private,level & usable fenced-in backyard & off street parking for 4 cars!

Listed by Chrisanne Connolly of Wilson Wolfe Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

9 George Road Winchester MA 01890

Winchester, MA9 George Road, Unit 9

Price$689,900

Est. Mortgage: $/month

Open House

MLS Number 72981321

  • Condo or Co-op
  • Next Open House: Thu 05/19 3:00 pm. to 5:00 pm.
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 968

Extensively rehabbed and updated two story Winchester townhome! Beautiful new kitchen with stainless steel appliances, shaker cabinets with dovetail slow close drawers. LED recessed lights. Harvey insulated dual pane windows. Just refinished gleaming oak hardwood floors. 2 new bathrooms with ceramic tile floors. Large living room with picture window. Bedrooms with double closets and mirrored doors. Huge 20'5 x 10'11 main bedroom. 3 new Mitsubishi ductless mini split systems for cooling as well as a new Advantage cast iron boiler (2017) for hot water baseboard heat. 40 gallon Rheem electric hot water heater (2015). Potential to finish large basement for multiple home offices, family room, media room or home fitness area. Great back yard with masonry patio and large storage shed. Quick closing possible if needed. Near McDonald Field for baseball and tennis, fitness centers, health care facilities and Horn Pond.

Listed by Joseph Bean of Joe Bean Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

20 BELLEVUE Avenue Winchester MA 01890

Winchester, MA20 BELLEVUE Avenue

Price$895,000

Est. Mortgage: $/month

MLS Number 72978810

  • Single Family Detached
  • Bathroom 1
  • Bedrooms 2
  • Rooms 5
  • Square Feet 1,373

This Charming home in a wonderful location, is the opportunity you have been waiting for. Surrounded by large exquisite homes and sited on a large wooded corner lot. Enjoy the peaceful setting all seasons. Keep as is, enlarge this house to your needs, or BUILD YOUR DREAM HOME. SPACIOUS COUNTRY KITCHEN with Cathedral ceiling skylights and deck, is perfect for indoor outdoor entertaining. Additional loft space overlooking kitchen. HARDWOOD FLOORS THROUGH MOST OF THE HOUSE. Media room with WOOD STOVE. FIREPLACE LIVINGROOM. Bonus Finished Lower Level with large closet and extra storage space. IMPECCABLE! Great Investment. MURACO SCHOOL. Easy commute to Boston Or 128/95, only minutes to Rt 93. Close to The Fells. Included in price is lot 0 Eugene Dr. with an additional 0.039 Acres. Parcel ID 13020. BOOK 78065 PAGE 528. BY APPOINMENT ONLY

Listed by Dorothea Feffer of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

8 Sunset Road Winchester MA 01890

Winchester, MA8 Sunset Road

Price$1,299,000

Est. Mortgage: $/month

Price Changed

MLS Number 72978540

  • Single Family Detached
  • Rooms 8
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,029

Hello Winchester! This capacious, 5 bedroom 4 bath home has an open floor plan flooded w/natural light. An entry foyer w/double coat closets flows into a welcoming wood burning fireplaced living room & dining area w/expansive windows to enjoy the backyard view. A sunny kitchen has granite counters, ss appliances, an island for entertaining, & a peninsula overlooking the cozy family room. 2 bedrooms & a full bath - great for guests &/or home offices complete the 1st floor. A 2012 2nd floor addition transformed the home, creating a front to back primary suite w/walk in closets, double vanity & tiled shower w/glass surround. Two add'l bedrooms, a main bath, & a coveted 2nd floor laundry room w/sink complete this floor. The finished lower level has a bonus room, full bath, & oodles of storage. The mahogany front porch is a cheerful place for morning coffee, while the ample backyard deck is perfect for summer grilling. Many updates! Convenient to 93, 128, & the Fells Res. Muraco School!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

10 Sheffield Road Winchester MA 01890

Winchester, MA10 Sheffield Road

Price$3,699,000

Est. Mortgage: $/month

MLS Number 72978329

  • Single Family Detached
  • Bathroom 6
  • Rooms 12
  • Bedrooms 7
  • Acreage 0.28

Refined, elegant and turnkey, this Colonial Revival is on one of Winchester's premier streets. Steps to train, town, and the desirable Ambrose school. Designed for entertaining, working from home and multi-generational, family life, the 1st floor features a beautifully functional, customized chef's kitchen, spacious living room, family room, dining room, a half bath, & mud room. The 2nd floor boasts a luxurious master suite w/ walk-in closets & large master bath/jacuzzi, plus 2 additional bedrooms & updated bathroom. The 3rd floor includes 3 large bedrooms, walk-ins & other large closets, plus 2 full bathrooms, currently configured w/ large studio/office & spacious study with lovely views of the Sheffield/Everett neighborhood. Fully finished basement with wet bar & wine cellar. New two-car garage, storage shed, patio/deck & sizeable lot. Renovations include kitchen extension, deck, wrap around porch, HVAC, windows, top grade electric & IT wiring, beautiful wood flooring, and more!

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk A QuestionMore Details

20 Lorena Road Winchester MA 01890

Winchester, MA20 Lorena Road

Price$3,399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72977765

  • Single Family Detached
  • Rooms 14
  • Bathroom 7
  • Bedrooms 6
  • Acreage 0.27

Majestic 6 bedroom, 7 bathroom custom built home in top location! From the moment you step inside, you will feel the unsurpassed quality of this grand home built by top local builder. A welcoming front porch & foyer flow into the formal living room & into the beautiful formal dining room. The stunning eat in kitchen boasts custom cabinetry, top of the line appliances, dual dishwashers and a large marble island. The family room showcases a wall of windows overlooking picturesque yard w/coffered ceilings, gas fireplace & gorgeous hardwood floors; the first floor also has a home office or 7th bed and full bath. The second level has 4 generously sized bedrooms w/ walk in closets & private baths; the primary bedroom having a foyer, dual walk in closets & a spa like bathroom. The top floor offers a large media room, 2 additional beds, a full bath & storage. The basement has a playroom, gym area, full bath and spacious mudroom, direct to the 3 car garage! Perfect yard for entertaining!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 TourAsk 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.