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

r=13-24
241 Cross Winchester MA 01890

Winchester, MA241 Cross

Price$775,000

Est. Mortgage: $/month

MLS Number 73004215

  • Land
  • Acreage 0.18
  • Zoning RG

Attention contractors, builders, and DIY enthusiasts! Looking for a hidden gem in Winchester with many possibilities. Property is in the RG zone and is a conforming lot with adequate frontage on both Cross Street and Pine Grove Park. A spacious flat corner lot with expandable potential. Home could have a major addition or second floor added - or could be replaced, tear down, with a new conforming single family structure. See site plan in paper clip.

Listed by Danielle Storella and Bill Caci of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

171 Swanton Street Winchester MA 01890
Contingent

MLS Number 73004031

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,600
  • High School Whs

Move in Ready! Freshly painted with many updates including new hardwood floors. This END UNIT has an extra family room. Only end units have this bonus space. The first floor open floor plan offers updated kitchen with granite counter's,stainless appliances and a large pantry. The Living room area has a wood burning fireplace, skylight nook,and access to a private patio which is a stones throw to the pool. The 2nd floor has a well proportioned primary suite with ample closet space, plus a fully updated bathroom. The second bedroom has generous storage with an oversized closet. There is a second full bath on this level. Central air and laundry are in unit. One carport covered space plus a tandem second spot close to your door. A private storage room is behind the garage. Enjoy the pool, tennis and the clubhouse. Easy access to Winchester Center, the commuter rail, schools, library, shopping and restaurants. Welcome Home to the ease of condo living.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

115 Washington Street Winchester MA 01890

MLS Number 73003534

  • Condo
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 842
  • High School Winchester High

Welcome to easy living! This is the home you’ve been looking for. There’s nothing to do but move right in and enjoy this meticulously maintained home. This beautifully updated one bedroom and one bathroom condo will take your breath away. The newly renovated gorgeous center island kitchen opens up to a bright living and dining room area. This home boasts of all new windows, kitchen appliances, heat pump, water heater, refinished hardwood floors, & recessed dimmable lighting. California closets have been added in both closets in the bedroom, laundry room and entryway to provide ample storage. Walk in laundry room with extra storage is a bonus! Enjoy the convenient location to the commuter rail, library, town restaurants, & shops.

Listed by Paula R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

108 Arlington Street Winchester MA 01890

Winchester, MA108 Arlington Street

Price$1,125,000

Est. Mortgage: $/month

MLS Number 73003234

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,235
  • High School Whs

Lovely home in delightful Ambrose neighborhood. Move right in to this immaculate cape with two bedrooms on the first floor and an office. Third bedroom is located on the second floor. The first floor also includes the living room with a fireplace and dining room. Front to back Family room is located right off the updated kitchen with granite and stainless steel appliances. The second floor has one bedroom and a large additional room waiting to be finished. The lower level has a family rec room with a fireplace, full bath, bonus room and additional storage. Private rear yard with deck is the perfect place to relax this summer. House includes landscaped yard and an attached garage. Come enjoy all Winchester has to offer this summer!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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 Jefferson Road Winchester MA 01890

Winchester, MA25 Jefferson Road

Price$1,600,000

Est. Mortgage: $/month

MLS Number 72999074

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,839

Charming, spacious & inviting 3 bedroom, 3.5 bath ranch in much loved neighborhood . A welcoming entry foyer with sky lite leads to a large living room with fireplace. Entertain in the formal dining room with wainscoting or dine informally in the kitchen with granite counters and movable island or the 4 season sunroom over looking beautiful gardens, deck & patio. The den with fireplace also leads to front and rear patios plus a 2 car garage. The primary bedroom with private bath and 2nd bedroom and bath are situated off the foyer along with a paneled home office. The 3rd bedroom is on the second floor to the rear of the home and has its own private bathroom. The partially finished lower level features a family room with fireplace, large open second area which can accommodate a pool/ping pong table, a workshop area, laundry area and half bath. Other features include hardwood floors, crown moldings, central AC, loads of storage, plenty of windows for an abundance natural light.

Listed by Karen Piedra of Realty Executives Boston West

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

102 Pond Street Winchester MA 01890

Winchester, MA102 Pond Street

Price$1,175,000

Est. Mortgage: $/month

Contingent

MLS Number 73002599

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,573
  • High School Winchester High

Completely renovated "smart" colonial within walking distance of Lynch elementary school! With seasonal views of Winter Pond, this beautiful sunny home boasts Jerome Bailey Foster design. Aesthetics & function are beautifully combined in the lovely kitchen with cherry cabinets, granite countertops, high-end appliances, breakfast bar, pantry & gas cooking. First floor layout is designed for entertaining, with family room open to the bluestone patio and an amazing backyard offering extensive landscaping, fruit trees, perennials, garden house and firepit. First floor office is ideal for working from home. 3rd floor playroom, 1st floor laundry, den, high ceilings on all floors, recessed lights, French doors, solar panels, 5-zone ducted/ductless mini-split A/C, spray foam insulation, all new roofs, central vacuum, motorized blinds, CAT6 wiring, wall/ceiling speakers, 6-zone sprinkler system, oversized 2-car heated garage wired for EV charger, and much more. This is a truly exceptional home!

Listed by Seeme Moreira of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

241 Cross Winchester MA 01890

Winchester, MA241 Cross

Price$775,000

Est. Mortgage: $/month

MLS Number 73002145

  • Residential
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 828
  • High School Whs

Attention contractors, builders, and DIY enthusiasts! Looking for a hidden gem in Winchester with many possibilities. Convenient one-floor living in this ranch style home which features a galley kitchen, dining room, fireplaced living room, 2 bedrooms, 1 bath, heated sun porch, and a one car garage. Spacious corner lot with expandable potential. This could be a great starter home in Winchester, or an opportunity to make it your own. Take advantage of all that Winchester has to offer award-winning schools, Middlesex Fells, bike path, and easy access to Boston.

Listed by Danielle Storella and Bill Caci of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

7 Conant Road Winchester MA 01890
Open House

MLS Number 73002096

  • Condo
  • Next Open House: Sat 07/9 12:00 pm. to 1:30 pm.
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,236

Awesome opportunity to own a meticulously maintained, one level living 2-BR 2-Bath in the sought after “The Willows” condominium! This south-facing, spacious corner unit boasts an open floor plan with living room, dining room and updated kitchen with tiled back-splash, granite counter-tops, garbage disposal, light fixtures and brand new stainless steel appliances. Sliding door access to the large balcony overlooking the quiet, fenced back common areas. 2 large bedrooms including a master suite with master bath and walk-in closet. Gas fireplace, central AC, efficient gas heating, in-unit laundry, and 2 parking. Enjoy the professionally managed complex amenities: an exterior heated pool and a luxury clubhouse with a fitness room and a full kitchen, and all that the great Winchester community has to offer!

Listed by Wei Fu and Yuan Guo of Phoenix Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

45 Winford Way Winchester MA 01890

Winchester, MA45 Winford Way

Price$839,000

Est. Mortgage: $/month

Contingent

MLS Number 73002067

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,456
  • High School Whs

Welcome to 45 Winford Way, a beautiful full dormered Cape overlooking the Fells on the Winchester/Medford border that gives you the best of both worlds! Cozy up next to the fireplace in the first floor living room, or sit down for a family dinner in the dining room, with its built-in cabinet. Coming out from the kitchen, you’ll find yourself in the three season sunroom- bright, spacious, and perfect for enjoying a book w/ your coffee in the morning sun. An additional bedroom on the first floor provides tons of versatility- exercise room, office, media room – whatever your heart desires! The second floor features 3 more bedrooms and a family bath. Moving back downstairs, the basement features a family room, an office, laundry and exterior access to the sizeable backyard. Winchester schools, Medford trash pickup.

Listed by Anne Spry of Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

5 Squire Road Winchester MA 01890

Winchester, MA5 Squire Road

Price$1,950,000

Est. Mortgage: $/month

Open House

MLS Number 72999744

  • Residential
  • Next Open House: Sun 07/10 1:00 pm. to 3:00 pm.
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,696

Prepare to fall in love w/this luxurious 6-bedroom dream home. Modern, open layout, perfect for today’s lifestyle. Comfortably work at home, entertain, & spend time w/family. Picture windows throughout-welcoming sunlight each day. Gourmet kitchen w/beautiful stone countertops, oversized island, & Viking appliances. Family rm features shiplap fireplace & leads to composite deck, while lg den leads you to a beautiful stone patio. Lg master suite features walk-in closet, dbl vanity, & lg tile shower w/bench. 2nd-level boasts 4 generous BR’s w/custom closets, 2 are walk-in. 2nd bath w/dbl vanity & laundry area complete 2nd Flr. Lower level offers full-size windows, 5th bed, & 3/4 bath, perfect for in-law or nanny, along w/rec room/home gym & lg mudroom w/garage access. Beautiful yard w/sprinkler system, flower beds & privacy fencing complete this oasis. Nestled in a pretty, quiet, community in premier school district w/easy access to all Winchester, Lexington, & Burlington have to offer

Listed by The Laura Baliestiero Team, Laura Baliestiero and Barry Dyment of Coldwell Banker Realty - Concord

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

4 Norwood Street Winchester MA 01890

Winchester, MA4 Norwood Street

Price$1,399,000

Est. Mortgage: $/month

MLS Number 73000824

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,847
  • High School Whs

HISTORIC HOME & WALK TO TOWN! Spectacular location with plenty of vintage characteristics like the floor to ceiling windows and original hardwood flooring. Generous kitchen with breakfast nook and door with access to the deck, perfect for a grilling. Separate dining and living rooms with plentiful natural light. Home office on the 1st floor with attached 3/4 bath. The 2nd level boasts three bedrooms plus a bathroom. Spacious backyard with mature trees and plenty of space in which to play catch or let the pooch run around. Walk to nearby shops, restaurants, banks and boutiques or the weekly Farmer's Market on the Common. Avoid expensive gas prices and city parking, with the convenience of the commuter rail at your fingertips, a 15-20 minute ride into Boston's North Station.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

19 Cedar Street Winchester MA 01890

Winchester, MA19 Cedar Street, Unit 19

Price$1,199,999

Est. Mortgage: $/month

Open House

MLS Number 73000515

  • Condo
  • Next Open House: Sun 07/10 12:00 pm. to 2:00 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,460

Come see this beautiful 2400 square feet two unit complex townhouse in lovely Winchester. Built in 2011. This home is on 3 levels plus the basement. It has 4 bedrooms and 3.5 bathrooms. The 1st floor is open plan with the living room, dinning room, kitchen and half bathroom. From the 1st floor you have access to the basement, double garage and patio doors to the back yard. The kitchen is Stainless and Granite. The home has high ceilings, beautiful wood trim moldings, fire place and hardwood floors throughout the house.The 2nd floor has the master bedroom, master bathroom and a walk in closet. The 2 other bedrooms and bathroom are also on the 2nd floor. The 3rd floor has a lovely walk up finished attic suite with a bedroom and a full bathroom.

Listed by Fintan Doherty of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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. MLSPIN 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.