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 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

32 Everett Avenue Winchester MA 01890

Price$3,949,000

Est. Mortgage: $/month

MLS Number 72467279

  • Single Family
  • Garage 4
  • Parking Spaces 3
  • Village Mystic Lake
  • Year Built 1906

Every morning you could wake up to a rising sun over a quiet lake, nestled in privacy. This exclusive setting offers an unprecedented 304 feet of lake frontage, with a main house and detached office. This home underwent a massive renovation which restored all the original detail and woodwork to its glory. Grand scale to each room, with one lovelier than the next. Huge kitchen has a full dining area and connects to a family/homework room. The formal living and dining rooms delight with fireplaces and stunning tiger and quarter-sawn oak detailing. There is a receiving hall and staircase that just wows, and upstairs, escape to your master suite with a fireplaced sitting room, large WIC with burled wood builtins, and a master bath done in hand-selected rare green onyx. Full nanny suite on the third, plus a delightful artists studio/7th BR. Sprawling basement level with gym, media, wine and billiards rooms. 4 car garage holds 6! Walk to town, trains. This is a very rare opportunity.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

6 Harrison Street Winchester MA 01890

Price$3,295,000

Est. Mortgage: $/month

Open House

MLS Number 72466644

  • Single Family
  • Next Open House: Sun 24th 1:00 pm - 2:00 pm
  • Garage 3
  • Parking Spaces 4
  • Village The Flats

New construction colonial will take your breath away! Entryway opens up to an open concept layout: Family room w/ gas fireplace, dining room, living room, grand kitchen, office, mudroom w/ built-ins & 1.5 baths. The kitchen features an oversized island w/ White Rhino counters, Wolf double oven w/ grill, griddle, custom hood & pot filler, 54" sub zero fridge/freezer, 2 sinks, 2 dishwashers & pantry. Sliders open up to a patio & expansive lawn. 2nd floor features the grand master suite plus 3 additional bedrooms, all w/ ensuite bathrooms & walk-in closets. Master includes dramatic vaulted ceilings, cupola, attached sitting room, oversized celebrity style closet & master bathroom w/ soaking tub, rain shower & marble floors. The 3rd floor has 2 bedrooms & 1 full bathroom. Finished lower level w/ sunken media room, cable/internet setup, central vac & sitting room w/ full bathroom. Additional features: oversized laundry room; heated floors in full bathrooms; heated oversized 3-car garage.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

8 Eugene Drive Winchester MA 01890

Price$939,900

Est. Mortgage: $/month

MLS Number 72465657

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1994
  • Full Bath 2

Welcome to this bright and sunny, center entrance colonial. From the moment you enter the large foyer, you will enjoy the circular flow of an easy floorplan. Formal living room with built-in shelving expands easily into the dining room for excellent entertaining.The eat-in kitchen opens to the spacious wood burning fireplaced family room, all with views of the backyard. The first floor is complete with laundry, half bath. Second floor boasts private front to back master suite with large walk-in closet and full master bath with jacuzzi tub privately separated from other bedrooms. Three additional ample bedrooms and family bath complete this floor. The spacious finished lower level offers great flexibility and easy entry into the 2 car under garage. Updates include granite counters, new carpeting, hardwood floors and interior painting. The expansive deck and back yard play structure allows for great outdoor entertainment. Move in time to enjoy the central a/c this summer!

Listed by Anne Spry and Ratthapoom Asdornvuttikrai of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

6 FAIRFIELD Place Winchester MA 01890

Price$1,850,000

Est. Mortgage: $/month

MLS Number 72465453

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2016
  • Full Bath 4

Stunning newer construction tucked away in a quiet neighborhood yet steps to town center, The Flats, schools, pond, tennis courts & train. A residence that was custom built in 2016 & offers over 4,500 sq ft of luxurious living on 4 levels; 5 large sunny bedrooms & 4 full baths. An inviting floor plan for all family members to enjoy with a blend of formal & informal spaces such as dining & living rooms; large 3rd fl playroom with full bath; exquisite oversized kitchen/family room that has direct access to paver patio & fenced in rear yard~ perfect for kids & pets; grand master suite & a finished lower level that is perfect for out or town guests or au pair suite. Amenities include hardwood floors; multi zone gas heating & cooking; attached garage; generous storage & so much more. Truly an urban oasis 7 miles from the Boston city line.

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

195 Cambridge Street Winchester MA 01890

Price$1,200,000

Est. Mortgage: $/month

MLS Number 72465456

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 1820
  • Full Bath 3

Welcome to the Wyman House! This historic home offers a spacious and welcoming atmosphere both inside and out. Generations have enjoyed get togethers in the large sun-filled family room featuring a working fireplace and beehive oven. The extremely functional eat-in kitchen is fully applianced and overlooks the large and private fenced-in back yard. Original wood flooring in the formal dining room, living room and family room. The beautiful circular staircase is located at the front of the house with a second set of stairs off the kitchen area. First floor laundry. Two of the five bedrooms have fireplaces and all have wood flooring. Walk-up attic. Detached two car garage and plenty of off street parking. Back yard has mature plantings, garden area and a shed.

Listed by Cory Gracie of Dimacale & Gracie Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

196 Highland Avenue Winchester MA 01890

Price$1,199,900

Est. Mortgage: $/month

MLS Number 72465407

  • Single Family
  • Garage 1
  • Parking Spaces 2
  • Year Built 1900
  • Full Bath 2

Enjoy this classic Colonial perched on high, adjacent to the Fells Reservation. From the front porch to the private backyard patio and indoor heated Endless Pool with Jacuzzi jets in a separate heated building, you will enjoy the outside living as much as the home. Upon entering, you feel you have arrived home. The turn-of-the-century oval window front door and staircase represent a bygone era. The spacious mudroom entrance opens into a large kitchen with dining area and marble counters, gas fireplace family room with built-ins, and a first-floor office which transitions nicely into the formal living room and dining room. The privately located master bedroom suite with beamed cathedral ceiling is a true retreat. Two additional bedrooms and a family bath complete the second floor. The skylit third floor has both a study and bedroom to have some getaway time. This home is the perfect blend of space and comfort.

Listed by Anne Spry and Ides Figueiredo of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

8 Gershon Way Winchester MA 01890

Price$1,400,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72464290

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 9' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage. A short drive to downtown Winchester and only 7 miles from Boston

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

15 Bonad Road Winchester MA 01890

Price$929,000

Est. Mortgage: $/month

MLS Number 72465058

  • Single Family
  • Garage 1
  • Parking Spaces 2
  • Year Built 1930
  • Full Bath 2

Welcome to Winchester! Introducing an original Jerome Bailey Foster cape tastefully decorated straight out of a Pottery Barn catalog and updated with all the modern amenities today's buyers are seeking. Move right into this pristine 3-bedroom cape with high-end finishes including: updated kitchen w/ marble countertops & island, stainless steel appliances, 2 updated full baths, brand new log fireplace and surround sound wiring in the cozy living room, central air, nest thermostat and finished lower level perfect for playroom/media space. Enjoy your morning coffee on the beautiful covered porch off the living room equipped w/ tv-mount and cable hookup. The deck off the kitchen leads out to the picturesque fenced in rear yard featuring professional landscaping, irrigation system, and paver walkways. Recently updated with newer roof, maintenance free cement board siding, gutters & windows. Located minutes from the Muraco school, the Fells hiking trails, parks & major highways!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

10 Wickham Road Winchester MA 01890

Price$985,000

Est. Mortgage: $/month

MLS Number 72464609

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Half Bath 1
  • Year Built 1963

This spacious & updated split-level single-family home has modern updates, great style & flexible space on a beautiful tree-lined street! An open-concept layout means easy flow & comfortable living. The sun-drenched living room w/ large picture window has a gorgeous fireplace focal point. The dining area has sliders & looks out over the patio, backyard w/ stone wall & mature trees. The kitchen is modern & appointed with S/S appliances, granite counters, clean white cabinets, tiled backsplash, & island w/ additional seating. The master has a gorgeous new bathroom w/ double sinks and oversized shower. There is a full bath and 2 additional bedrooms w/ comfortable space. You will love the lower level space w/ fireplace, beamed ceiling, built-ins, 1/2 bath, mudroom space, storage and a lovey laundry area. Enjoy hardwood floors, recessed lighting, 2-car garage, great yard and close proximity to Mystic Lake recreation, Middlesex Fells, Winchester Commuter Rail and Winchester Center.

Listed by Stephen McKenna and Erika Leigh Pereira of Bowes Real Estate Real Living

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

45 Loring Avenue Winchester MA 01890

Price$829,000

Est. Mortgage: $/month

MLS Number 72463152

  • Single Family
  • Garage 1
  • Parking Spaces 2
  • Year Built 1959
  • Full Bath 2

SWEET & COZY SINGLE HOME LOOKING FOR A NEW FAMILY! Located within walking distance to public transportation and McDonald Field. Freshly painted interior, in today's trendy neutral Benjamin Moore colors. New interior light fixtures throughout. Great layout with large fireplaced living room, dining room and kitchen. 3 spacious bedrooms and a full bath on the 1st floor. Basement is finished with 2 large bonus rooms, laundry, a 3/4 bath and access to the garage. Level back yard ready to play catch! Relax with your iPad and lemonade in the sun filled 3-season porch. Kitchen and bathroom are original to the house and ready for a change! Bring your design eye and imagine what "it could be"! Short drive to downtown Winchester where you'll find multiple coffee shops, salons, boutiques and enjoy a 15 minute ride on the commuter rail to Boston's North Station. Easy access to Route 93 and priced to sell!

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

5 Fox Hunt Lane Winchester MA 01890

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72463183

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Half Bath 1
  • Year Built 1982

Understated and unique luxury. This traditional brick colonial opens into an interior of simple, contemporary beauty. Situated on 1.2 acres that border the 13th fairway of the Winchester Country Club, the home's 300-foot elevation affords sweeping views across the Mystic Lake and into East Boston, with brilliant sunrises that change hourly with the light and weather. A large deck and patio invite outside entertaining. Inside, the home mixes traditional and contemporary elements: an expansive living room with custom Butternut woodwork and vaulted ceiling; a kitchen/family room with a gas fireplace; a TV and billiards room; a master bedroom suite with a fireplace and attached office/dressing room. The second floor features two ensuite bedrooms, plus options for additional bedrooms. The walk-out lower level includes an indoor pool, greenhouse, and a fourth bedroom with a separate entrance, bathroom, and sauna.

Listed by Cynthia Houle of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

63 Woodside Road Winchester MA 01890

Price$939,000

Est. Mortgage: $/month

MLS Number 72463303

  • Single Family
  • Parking Spaces 5
  • Year Built 1929
  • Full Bath 2
  • Bathroom 2

Charming colonial in great neighborhood--close to elementary school, playground and Horn Pond trails. This sun-filled home offers generous living space with 9 rooms and a versatile layout. A cherry kitchen with granite counters, island and stainless-steel appliances opens onto a large family room with built-ins and gas fireplace. The first level has a sunny, open floor plan, complete with a traditional living room, generous dining room and heated sunroom. Ideal for entertaining and large gatherings. A mudroom and full bath round out the first floor. Upstairs there are 3 large bedrooms and a smaller 4th room that could be used as an office, nursery or single bedroom. The spacious master has a vaulted ceiling, large closets, and direct access to a bright and cheery full bath. A walk-up attic with great storage space or expansion potential sits on the third floor, and there is a finished “bonus room” in the basement. This beautiful home has been lovingly maintained and is move in ready!

Listed by Barbara Bellotti of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 2019
* 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

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.