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. 

15 Lawson Road Winchester MA 01890

Winchester, MA15 Lawson Road

Price$2,999,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72777864

  • Single Family Detached
  • Village East Hill
  • Bathroom 5
  • Rooms 13
  • Bedrooms 5

This tastefully updated home is exquisitely renovated with 6 fireplaces. The first floor includes sun room with 3 walls of windows, library or second home office, expansive fireplace living and dining rooms which flow to the front to back kitchen and equally large gas fireplace family room with work area and table area for hours of entertainment and mudroom. The second floor has a privately situated double door master suite with sitting room, and walk in closet. It is further complimented by 3 additional generously sized bedrooms, full family bath with double vanity & a cathedral ceiling with 2 skylights home office or 6th bedroom with half bath. The third floor retreat includes a spacious bedroom with 2 skylights, walk in & cedar closets & a full bath. Flexibility abounds with a finished & heated room above the 2 car garage - great for either another office or workout studio. The large 27,299 square foot lot features nightscape lighting, a large patio and great yard.

Listed by Anne Spry of Barrett Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 Myopia Road Winchester MA 01890

Winchester, MA65 Myopia Road

Price$2,599,999

Est. Mortgage: $/month

MLS Number 72775321

  • Single Family Detached
  • Bathroom 5
  • Rooms 14
  • Bedrooms 4
  • Acreage 0.9

A stately Colonial set atop Myopia Hill in one of Boston's most desired suburbs, 65 Myopia Road is a tranquil & immaculate estate well adapted to modern family living. Beyond the grand entry foyer are graciously scaled living & entertaining rooms with oversized windows highlighting beautiful views of the private outdoors. These include the double height living/family room with impressive stone fireplace, chef's kitchen with vaulted breakfast nook, & formal dining room with elegant fireplace. The home's 4 generous bedrooms are all located on the 2nd level. The Master suite is breathtaking with spacious walk-in closet and luxurious bath. Additional features of this residence include the 2nd floor mezzanine game room, home gym, expansive outdoor mahogany deck, & heated outdoor pool. This home is only 9 miles north of Boston, accessible to the commuter rail to North Station, within ½ mile +/- of Ambrose School, & within close proximity to all the shops & restaurants of downtown Winchester.

Listed by Mark Doherty of Campion & Company Fine Homes Real Estate

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 Everett Avenue Winchester MA 01890

Winchester, MA34 Everett Avenue

Price$2,599,000

Est. Mortgage: $/month

Open House

MLS Number 72793009

  • Single Family Detached
  • Next Open House: Sun 03/7 12:00 pm. to 3:00 pm.
  • Village Lake
  • Bathroom 4
  • Rooms 11

Old world beauty and detailing are perfectly preserved throughout this home that sits majestically above the upper Mystic Lake on desirable Everett Avenue. Enjoy watching the sunrise every morning over the water from your private deck or sunroom, take in the wildlife, and enjoy a swim or kayak ride at your leisure. This home presents an unbelievable opportunity for equity as it is priced well below neighborhood and appraised value. It's an incredible palette and opportunity; waiting for your own inspiration and design. This house is a beauty as-is, but once you put your personal stamp on it, you'll have one of the most valuable homes in town. You couldn't ask for a better location with your own lake views, and easy access to the commuter rail, schools, town center and parks. 6 bedrooms, 2 home offices and a 2 car garage.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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2 Edgewater Place Winchester MA 01890

Winchester, MA2 Edgewater Place

Price$2,299,000

Est. Mortgage: $/month

Open House

MLS Number 72793471

  • Single Family Detached
  • Next Open House: Sat 03/6 12:00 pm. to 1:30 pm.
  • Bathroom 5
  • Rooms 10
  • Bedrooms 4

This gorgeous expanded 3 level ranch is sure to impress! This Royal Barry Wills designed home is set just off Everett Ave in a cul-de-sac near Mystic Lakes. Recently renovated by top design/build team offering over the top finishes and every amenity! 4 oversized bedrooms each with gorgeous private baths. The expansive first floor offers state of the art kitchen with custom cabinetry, Thermador appliances, gas range, double fridge & double ovens; inviting family room adj. to kitchen with cathedral ceilings, sliders to deck. Dining offers 2 great areas for entertaining, stunning living room w/fplc, bay window, office/study and sunroom great for gym. Upper floor offers two bedroom suites, custom built ins, lower level offers 2 additional bedrooms, master with fireplace, spa like bath, radiant heat floors, custom walk in closet, laundry, storage. New cedar shake roof, Pella windows, new electrical, heat, A/C, custom closets, control 4 whole house wifi, in wall speakers, alarm & cameras!

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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27 Gershon Way Winchester MA 01890

Winchester, MA27 Gershon Way, Unit 27

Price$2,050,000

Est. Mortgage: $/month

MLS Number 72757101

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

ONLY 3 HOMES REMAIN out of 29! Designed by national, award-winning architect Gary Snider. Live surrounded by luxurious finishes, soaring ceilings, hardwood throughout & plenty of natural sunlight. This open concept plan boasts a 1st floor master suite with tray ceiling, a super-sized walk-in closet and luxurious en suite bath. The eat in kitchen is adorned with ceiling height cabinets, quartz countertops and top of the line stainless steel appliance package featuring Sub*Zero, Bosch, Wolf... The dining room has a stately coffered ceiling, bay window and sliders to a private, covered deck. The flex room can be a home office or studio for your beloved hobbies. 1st floor also features a powder room, mudroom and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath, a library and a large open loft for movie watching or game night. The icing on the cake: attached 2 Car garage with electric car charging station AND a 1,500 SF Walkout basement! MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

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%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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1 Stonefield Circle Winchester MA 01890

Winchester, MA1 Stonefield Circle

Price$1,849,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72725701

  • Single Family Detached
  • Bathroom 5
  • Rooms 14
  • Bedrooms 5
  • Acreage 0.25

NEW PRICE! Amazing value ~ Must see this modern 2005 farmhouse w/ oversized 2 car attached garage and wrap around farmers porch! Completely renovated and expanded by top local builder, this home is located across from the flats area in desirable Stonefield Estates cul-de-sac. This beautiful sprawling home boasts a grand yet very livable first floor with high end chefs kitchen, first floor office/ family room, beautiful dining room and front to back living room with floor to ceiling windows, access to deck / side yard and fireplace. Second floor offers 4 large bedrooms w/ 3 baths .. second floor laundry and study room. The master is beautiful with cathedral ceilings, walk in closet & custom designer bath. Finished third floor offers great space for guests/ additional office or nanny quarters! Lower level game room/ family room / gym with add'l bath. Curb appeal doesn't get much better! Enjoy all of the modern amenities along with the old world charm this special home offers!

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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248 Forest Street Winchester MA 01890
Active With Contract

MLS Number 72770374

  • Single Family Detached
  • Bathroom 5
  • Rooms 11
  • Bedrooms 5
  • Acreage 0.87

~NEW CONSTRUCTION IN WINCHESTER~ Here you will enjoy a tremendous location with convenient access to the Middlesex Fells, Rt 93 while also being located in the popular Muraco School District. Set on a large parcel over 37,000 sf offering a unique scenic setting with wooded views. This 11 room 5 bed, 4.5 bath Colonial built by a prominent local builder has it all! Four fully finished floors provide plenty of space for the whole family plus comfortable space for guests, in-laws and flexible areas for working from home. A gorgeous kitchen with full recessed cabinetry,GE Monogram appliances, 36" oven with exhaust hood and an upgraded island with builtin microwave and opens to a fireplaced family room with sliders to a large deck overlooking a landscaped yard with pleasant views. The finished basement is complete with a full bath and separate storage area. The 3rd floor has a large recreation room a 5th bedroom and a full bath.

Listed by The Synergy Group and Paul Cirignano of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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6-8 Richardson Street Winchester MA 01890

Winchester, MA6-8 Richardson Street

Price$1,500,000

Est. Mortgage: $/month

Open House

MLS Number 72782963

  • Multi-Family 2 Family
  • Next Open House: Sun 03/7 2:00 pm. to 3:00 pm.
  • Total Parking Spaces 2
  • Year Built 2020
  • Bathroom 4

The search for a perfect investment opportunity is over with this meticulously remodeled multi family home located in desirable Winchester. A short distance to the commuter train and a bustling downtown with quaint coffee shops, restaurants and shopping. Boasting 3,615 sq. ft of living area, 4 bedrooms and 4 full bathrooms, modern open concept main living areas and hardwood floors throughout. High ceiling dining rooms designed with architectural details. Fireplaces in each living room, perfect for chilly evenings! Both units have in-units laundry. Deeded parking spaces and charming private manicured garden areas and rooftop terrace with exceptional views of Winchester! Property has been virtually staged.

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

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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25 Gershon Way Winchester MA 01890

Winchester, MA25 Gershon Way, Unit 25

Price$1,475,000

Est. Mortgage: $/month

MLS Number 72725070

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

This fabulous townhome bordering the woods was designed by national, award-winning, architect Gary Snider. Imagine luxurious finishes throughout: 10'+ ceilings, hardwood floors and plenty of natural light. This open concept plan has a 1st floor master suite with oversized walk-in closets and a great bathroom. The kitchen is adorned with ceiling height cabinets, Quartz countertops & island, a spacious pantry + top of the line SS appliance package. The dining room features a beautiful coffered ceiling. Just beyond, the room opens up to a 22' ceiling in the dramatic living room featuring a floor to ceiling fireplace. Abutting the covered porch, a wall of windows pours sunlight into this home. The 1st floor flex room can be a home office, a library or studio for your beloved hobbies. 1st floor also features a powder rm and laundry. Upstairs you'll find 2 additional spacious EN SUITE bedrooms and a bright open loft. 2 Car garage with electric car charging station.*MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 72672238

  • Condo or Co-op
  • Next Open House: Sun 03/7 10:30 am. to 12:00 pm.
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,580

NEW Construction in Town Center. MOVE IN READY, PH Home with split bedrooms and two separate balconies. This Penthouse is the largest unit at Allegro and a one of a kind floor plan that spans the entire back of the building and offers 2 master suites, half bath, 2 car parking spaces and 2 decks overlooking picturesque Vine St. It has a beautiful, open concept layout with bedrooms flocking on either side of the living room. Allegro Winchester is a boutique style building consisting of 11 unique homes in an intimate setting off the beaten path yet steps from restaurants, shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; gas heating & cooling; elevator access to garage parking & additional storage room. Your dream home at Allegro is ready for you now, scheduled your appointment today.

Listed by Janice Dumont of Advisors Living - Back Bay

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$
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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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8-10 Winter Street Winchester MA 01890

Winchester, MA8-10 Winter Street

Price$1,399,000

Est. Mortgage: $/month

MLS Number 72791661

  • Multi-Family Duplex
  • Total Parking Spaces 10
  • Year Built 1881
  • Bathroom 6
  • Full Bath 4

OUTSTANDING DUPLEX IN WINCHESTER!!! Two-Family DUPLEX Style Home on EXTRA LARGE LOT loads of parking. THIS HOME HAS BEEN COMPLETELY RENOVATED , EVERYTHING IS BRAND NEW ! Close to Winchester's FINEST Restaurants and Shops, Commuter Rail, MBTA & Newly Renovated Winchester High School. EASY access to 93, 95 & Route 3. Each unit has three bedrooms with 2 1/2 baths. New cabinets with granite countertops, all newer windows, flooring, roof, heating & electric ! Each side has private patio in the back. HUGE driveway with parking for at least 10 CARS. QUIET STREET & NEIGHBORHOOD. Close to brand new Tri-town bike path and highly sought after schools. Perfect investment for owner occupant or investor! Easy conversion to condo. Lots of privacy.

Listed by Mark Sullivan of T.A. Sullivan Agency Inc.

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$
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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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37 Cambridge Street Winchester MA 01890

Winchester, MA37 Cambridge Street

Price$1,350,000

Est. Mortgage: $/month

Open House

MLS Number 72771272

  • Single Family Detached
  • Next Open House: Sat 03/6 11:00 am. to 1:00 pm.
  • Bathroom 4
  • Rooms 11
  • Bedrooms 4

This contemporary colonial in desirable Winchester is simply beautiful! A 2005 addition transformed this traditional home into a show-stopping open floor plan with soaring walls of windows across the back of the home. Breathtaking views of majestic pine trees provide a natural canopy over a spacious deck with lovely gardens beyond. Long sight lines flow across a modern kitchen/dining area with 2 pantries, island, quartzite counters, & new stainless-steel appliances. A living room w/built-ins & mudroom w/ a one-car attached garage complete the first floor. The second-floor owner's suite features a dramatic vaulted ceiling, tall windows with treetop views, a study & walk-in closet. 3 additional large bedrooms, 2 full baths, laundry & an office complete this floor. Lower level is partially finished w/playroom, wet bar & full bath. Lots of flex-areas everywhere! Numerous amenities & critical updates-see attached. Great transportation access to Alewife & Boston. Ambrose Elementary.

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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