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. 

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11 Gershon Way Winchester MA 01890

Winchester, MA11 Gershon Way, Unit 11

Price$1,450,000

Est. Mortgage: $/month

MLS Number 72575806

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

WINCHESTER'S 1ST 55+ COMMUNITY! 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 10' 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 with a hot cider. The dining room has a beautiful coffered ceiling and 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: 3.33% last updated on Apr 2, 2020
* 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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15 Gershon Way Winchester MA 01890

Winchester, MA15 Gershon Way, Unit 15

Price$1,450,000

Est. Mortgage: $/month

MLS Number 72618537

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,549

WINCHESTER'S 1ST 55+ COMMUNITY! 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 10' 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 with a hot cider. The dining room has a beautiful coffered ceiling and 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: 3.33% last updated on Apr 2, 2020
* 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

18 Gershon Way Winchester MA 01890

Winchester, MA18 Gershon Way, Unit 18

Price$1,375,000

Est. Mortgage: $/month

MLS Number 72623280

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,549

WINCHESTER'S 1ST 55+ COMMUNITY! 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 10' 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 with a hot cider. The dining room has a beautiful coffered ceiling and 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: 3.33% last updated on Apr 2, 2020
* 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

49 Amberwood Drive Winchester MA 01890

Winchester, MA49 Amberwood Drive

Price$1,349,000

Est. Mortgage: $/month

MLS Number 72623259

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

BEAUTIFUL CONTEMPORARY HOME IN WINCHESTER'S DESIRABLE WEST SIDE! Meticulously maintained, recently painted in a neutral BM color PLUS freshly sanded and stained hardwood floors! Nothing to do but move in. This gorgeous home, on a very quiet street, has an inviting layout featuring a 1st floor master suite with exceptional ceiling height. The kitchen has a breakfast nook, an open concept family room, with adjacent laundry and full bathroom. The dining room, living room combination make up the rest of this floor. Upstairs are 3 large bedrooms with ample closet space, a full bathroom and bonus room which could be an office. The exterior features a deck and stone stairs leading to 2 other levels with exceptional views. WITHIN WALKING DISTANCE TO THE 3 YEAR OLD VINSON OWEN SCHOOL! A short drive to downtown Winchester where you'll be greeted with plentiful restaurants, boutiques, coffee shops and the commuter rail to North Station. Easy access to major highways and just 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: 3.33% last updated on Apr 2, 2020
* 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

MLS Number 72575937

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,482
  • Complex Allegro

NEW CONSTRUCTION IN TOWN CENTER! Introducing allegro Winchester: a boutique style building consisting of 11 unique units in an intimate setting off the beaten path yet steps from market shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; well appointed master suite; multi zone gas heating & cooling; elevator access to garage parking; balcony or patio private outdoor space & additional storage room. Sq foot starts at 1,072 & largest unit is 1,580. Pre construction pricing in effect now!

Listed by Nancy Ciampa McLaughlin of Advisors Living - Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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57 Grove Street Winchester MA 01890

Winchester, MA57 Grove Street

Price$1,259,900

Est. Mortgage: $/month

MLS Number 72635009

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

Open Concept colonial in meticulous condition with an eye for detail throughout. New kitchen and Family Room additions in the last 5 years. Gourmet kitchen with Viking Appliances, granite, SS, and center island with pendant lighting, Family room with separate mini split system, cathedral ceilings, over sized windows make this a treat to read, relax or entertain. Hardwood floors adorn the entire home, fireplaces in the living room and lower level family room which is perfect for extended family and includes separate laundry room and hobby room to enjoy your crafts. 3 spacious bedrooms and gorgeous master bathroom plus 2.5 additional baths throughout the home. 200 AMP electric service, 6 zone heating, Direct hot water, plus 2 stall garage, lovely grounds with mature plantings throughout.

Listed by John Demers of First Choice Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 Farrow Street Winchester MA 01890

Winchester, MA30 Farrow Street

Price$1,249,000

Est. Mortgage: $/month

MLS Number 72625142

  • Single Family
  • Garage 2
  • Parking Spaces 3
  • Total Parking Spaces 5
  • MLS Status Active

COMPLETELY RENOVATED SINGLE FAMILY HOME!!! Set on a quiet street, within the Lynch School district, this spacious 5 bed, 3.5 bath house is in need of a family to share its life with. 12' ceilings throughout the 1st floor with an open concept floor plan. The huge living room is perfect for lounging, watching the game or snuggling up with a good read. Host your next party in the oversized dining room. Generous kitchen with large dining area allows you to be part of the conversation while preparing a drink for your guests. Adorned with stainless appliances, Quartz counters & a door that leads to an exterior deck overlooking the backyard for throwing the ball around. The 2nd floor has a master suite (WIC & spacious bathroom) & two additional bedrooms that share a Jack & Jill bathroom. The 3rd floor has 2 bedrooms & 3/4 bath, a perfect hideaway for teenagers. A short drive to downtown bustling with coffee houses, boutiques & the commuter rail to Boston.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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$1,200,000

Est. Mortgage: $/month

MLS Number 72625527

  • Multi-Family 2 Family - 2 Units Side by Side
  • Total Parking Spaces 8
  • MLS Status ACT
  • Year Built 1881
  • Bathroom 6

OUTSTANDING DUPLEX IN WINCHESTER!!! Two-Family DUPLEX Style Home on EXTRA LARGE LOT with TWO driveways.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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 Bacon Street Winchester MA 01890

Winchester, MA57 Bacon Street

Price$1,199,000

Est. Mortgage: $/month

MLS Number 72626892

  • Single Family
  • Garage 2
  • Parking Spaces 2
  • Total Parking Spaces 4
  • MLS Status Active

Welcome to Winchester! Move right-in to this nicely updated single family home with huge fenced in back yard, close to Winchester center, Ginn field, and Wedgemere train station direct to North Station!! This bright and sunny split entry home features a main level with updated eat-in kitchen w/ quartz countertops, formal dining room, living room with wood burning FP, Master BR with stylish new tiled bath, two additional spacious beds and add'l large renovated full hall bath. Newly refinished hardwood floors, Lower level features great family room loaded with windows, stone fireplace, updated half bathroom, direct access to 2-car attached garage and an abundance of storage space! Ambrose elementary school, new roof, central A/C...enjoy easy living in this great home & take advantage of all Winchester has to offer with this great home at an unbeatable price! Move right in and enjoy!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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216 Cross Street Winchester MA 01890

Winchester, MA216 Cross Street, Unit 1

Price$1,100,000

Est. Mortgage: $/month

MLS Number 72625317

  • Condo or Co-op
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,000

ONLY ONE left! Enjoy maintenance free,new construction townhouse w/ 4 levels of living space.First floor open concept living rm,dining rm,kitchen,family rm w/ gas fireplace w/ 9' ceilings & crown molding open to maint. free deck, also 1st fl. half bath.Kitchen has soft-close white shaker cabinets, marble counters w/island, stainless appliances w/5 burner gas stove, fridge & undercabinet microwave. 2nd level: 2 spacious bedrms. w/ lg. 2-sink shared bath, master BR suite w/2 person walk-in tiled shower, walk-in closet, 2nd fl. laundry room w/tile fl. 3rd fl level: lg.rm complete w/full bath& tiled fl, plenty of closet & storage space:use for a 2nd master or au pair suite, playroom or office! All floors are solid oak w/dk. walnut stain, bathrm flrs are high-end tile w/sleek quartz counters. Finished basement is the perfect playrm, office, gym open to 2 car garage. Radon & irrigation systems in place,home will be HERS rated for move. Well landscaped lot w/ beautiful stonework & priv fence.

Listed by Dave White of OwnerEntry.com

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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35 Forest Circle Winchester MA 01890

Winchester, MA35 Forest Circle

Price$1,092,500

Est. Mortgage: $/month

MLS Number 72596363

  • Single Family
  • Garage 1
  • Parking Spaces 2
  • Total Parking Spaces 3
  • MLS Status Active

Move right into this Highly desirable town of Winchester. This Warm Luxurious Renovated Single-Family Home recently added a 2nd floor. It has a total of 5 Bedrooms, 3 bathrooms and 3 fireplaces to cozy up to on those cold snowy winter nights. The home is situated on a tree lined street in an incredibly friendly and safe neighborhood with beautiful trails and parks nearby. You will be 10 miles from the Heart of Boston and less than a mile from The Gingerbread Construction Co., which has the best over-sized muffins you will ever taste! This home is extremely well constructed from frame to windows/doors to the insulation and more. It comes with a 1 car garage with parking in the driveway and a Beautifully Landscaped yard with several Terraces, a Patio to enjoy and relax after a long day at work. This is an Unbelievable House at an Unbelievable Price! We look forward to seeing you there!

Listed by Joanne Vanstry and Jack Lister of Berkshire Hathaway HomeServices Verani Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

36 Elmwood Avenue Winchester MA 01890

MLS Number 72575935

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,269
  • Complex Allegro

NEW CONSTRUCTION IN TOWN CENTER! Introducing allegro Winchester: a boutique style building consisting of 11 unique units in an intimate setting off the beaten path yet steps from market shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; well appointed master suite; multi zone gas heating & cooling; elevator access to garage parking; balcony or patio private outdoor space & additional storage room. Sq foot starts at 1,072 & largest unit is 1,580. Pre construction pricing in effect now!

Listed by Nancy Ciampa McLaughlin of Advisors Living - Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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

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