Winchester MA Homes for Sale

Winchester, Massachusetts is a quiet bedroom community located 8 miles north of Boston. Winchester is a family-friendly community that is perfect for raising a family. There are several well-maintained parks in town as well as several bodies of water. 

Check out single family homes for sale in Winchester, MA. Search through hundreds of listings to find the right real estate for you. Save your favorites when you register with us, and you can get email updates when similar properties that match your criteria are posted. Contact us for more information!

37 Swanton Street Winchester MA 01890

Winchester, MA37 Swanton Street

Price$719,900

Est. Mortgage: $/month

MLS Number 72794118

  • Single Family Attached
  • Bathroom 2
  • Rooms 6
  • Bedrooms 4
  • Acreage 0.53

Charming townhouse condo with the feel of a single family (No HOA fees!) - centrally located near all that Winchester has to offer! Walking distance to schools. Private fenced-in backyard patio. Office potential for working from home. High ceilings & numerous upgrades on 3 finished levels from the kitchen & bathroom updates to the newer furnace & AC. The oversized eat-in-kitchen, perfect for entertaining, has granite, Stainless Steel, center island, refinished cabinets, large pantry & new wood-look porcelain tiles & recessed lighting. Bright and airy family room. Notice the beautiful details in the 2nd floor bedrooms with cozy window seats, wide-plank hdwd floors & double closets. Spacious spa-like bath w/jet tub, glass enclosed tiled shower, granite & skylight. Even more space on the 3rd floor w/2 more rooms perfect for office space, exercise room or addl bedrms. Full basement w/W&D & storage. I-93/95 & train to Boston nearby! Move-in ready! All of this & Winchester schools too!

Listed by Kerry Ciapciak of Patriot Property Advisors, LLC - Walpole

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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

Active With Contract

MLS Number 72793471

  • Single Family Detached
  • Bathroom 5
  • Rooms 10
  • Bedrooms 4
  • Acreage 0.39

*OPEN HOUSE SUNDAY CANCELLED, 3/7 *Seller accepted offer* 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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38 Sargent Road Winchester MA 01890

Winchester, MA38 Sargent Road

Price$999,900

Est. Mortgage: $/month

MLS Number 72793749

  • Single Family Detached
  • Bathroom 2
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.14

Charming East Side Colonial home offering 8 rooms, 3/4 bedrooms with a great floor plan! Impeccably maintained with hardwood floors throughout, first floor features a sunny living room with picture window and fireplace, formal dining, family room or 4th bedroom, full bath & spacious eat in kitchen with gas cooking overlooking great fenced in rear and side yard. Second floor with oversized front to back master bedroom with space for future master bath, two additional spacious corner bedrooms with ample closets, and full hall bath. Lower level offers laundry, playroom, storage and access to 1 car garage. Updated systems, this home is simply perfect! Top East side location in Lincoln school district, close to the town center, Wedgemere train station, schools, restaurants, shops.. enjoy all Winchester has to offer while living in this wonderful home!

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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34 Everett Avenue Winchester MA 01890

Winchester, MA34 Everett Avenue

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72793009

  • Single Family Detached
  • Village Lake
  • Bathroom 4
  • Rooms 11
  • Bedrooms 6

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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119 Wildwood Street Winchester MA 01890

Winchester, MA119 Wildwood Street

Price$1,025,000

Est. Mortgage: $/month

MLS Number 72792334

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.23

Welcome to this meticulously maintained and updated Colonial home. Get ready to be met by gleaming hardwood floors, fresh paint, updated tiled kitchen and baths, 4 plus bedrooms and 3 spacious floors of living. Close to schools, parks, commuter rail and shopping. 4 heating zones, 2 cooling zones and 3 sprinkler system zones make maintaining a gorgeous yard and comfortable easy living possible. The office, or fifth bedroom, on the first floor has access to the heated sunroom/mudroom offering a warm sun filled break between Zoom meetings. This home has been well cared for by the same caring family for over 30 years and it shows as you turn every corner. Cozy up on cold nights next to the fireplace and enjoy entertaining guests in the formal dining room. This home has so much to offer and is just waiting for the next owner to bring in their personal touches. Offers due Monday at 3pm

Listed by Jaclyn Wells of EXIT Realty Beatrice Associates

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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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197 Mystic Valley Parkway Winchester MA 01890

MLS Number 72791619

  • Single Family Detached
  • Bathroom 3
  • Rooms 12
  • Bedrooms 4
  • Acreage 0.12

This wonderful four bedroom home is set back from the street and offers easy access to Winchester Center, commuter rail, Lincoln Elementary School, and the Middlesex Fells. The first floor features a comfortable living room with a bay window, fireplace, and an adjoining sunroom. The cozy family room flows into the dining room. A large, light-filled eat-in kitchen opens to the brick patio and small garage. A half bathroom and laundry complete the first level. A beautiful staircase winds to the second floor with its four bedrooms and two full bathrooms. The second floor hallway is a beautiful space that gracefully connects the bedrooms and the stairway to the third level. The finished third floor has two rooms - a perfect get-a-way for family or guests, and room to work or learn from home. Other notable features include central air conditioning and updated systems, hardwood floors, and a spacious basement. Come experience this unique opportunity to live near the heart of Winchester.

Listed by Rob Ramsdell 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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11 Watson Place Winchester MA 01890

Winchester, MA11 Watson Place

Price$699,900

Est. Mortgage: $/month

MLS Number 72791284

  • Single Family Detached
  • Bathroom 2
  • Rooms 7
  • Bedrooms 4
  • Acreage 0.11

Located on a street less traveled along with few other homes. Through the enclosed front porch and passing the sitting room and the living room, you will be pleased to find a first floor Master suite with a full bathroom. You will notice all the natural woodwork, replacement windows and the crown molding that this home has to offer. Enjoy grilling on the oversized deck with built-in benches during the upcoming Spring and Summer.

Listed by Sal Dipinto and Nancy O'Herron 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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376 Highland Avenue Winchester MA 01890

Winchester, MA376 Highland Avenue

Price$969,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72790735

  • Single Family Detached
  • Bathroom 2
  • Rooms 8
  • Bedrooms 3
  • Acreage 0.17

Charming East Hill Cape conveniently located within walking distance to commuter rail, schools, playground, Fells Reservation, and the beautiful Winchester Center. Gracious front-to-back living room, with abundant natural light, is well appointed with a wood-burning stove to contend with NE winters. The heated sun room functions as a 1st floor home office allowing for easy outdoor access between Zoom meetings. Cooking enthusiasts will be pleased to find gas cooking in the updated kitchen with granite counters, newer stainless steel appliances, recessed lights, & eco-friendly Marmoleum flooring. This lovely home features a large Master Bedroom with walk-in closet, spacious Mud Room, generous Den/Playroom in the lower level, beautiful hardwood floors, custom built-ins, 200-amp electric service, new oil tank, 1-car garage, and much more. Situated on a corner lot with attractive landscaping, patio, stone wall, and fenced yard. Pride of ownership abounds in this well maintained home!

Listed by Seeme Moreira of Coldwell Banker Realty - Winchester

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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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33 Cambridge Street Winchester MA 01890

Winchester, MA33 Cambridge Street

Price$1,225,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72787293

  • Single Family Detached
  • Bathroom 3
  • Rooms 10
  • Bedrooms 5
  • Acreage 0.26

Welcome to this spacious elegant colonial home located between Winchester Boat Club and Winchester Country Club! This home offers magnificent views of Mystic Lake from the fenced in backyard. 5 Bedrooms with 2.5 baths and 2,421 sq. ft. of living space. Welcoming living room with a fireplace and a dining room featuring hardwood floors and custom window treatments. The kitchen has ample storage with a pantry, granite countertops, breakfast bar, updated stainless steel appliances and radiant flooring. Exterior access to the outdoor deck makes this a perfect location for entertaining. 1st floor bedroom with a full bathroom. Upper level has a master bedroom and 3 additional bedrooms with a full bathroom. Lower level is finished with a play area or home office and a family room and 2nd fireplace perfect for a cozy movie night! Updated washer and dryer too! This home has all that you have been looking for!

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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524 S Border Road Winchester MA 01890

Winchester, MA524 S Border Road

Price$929,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72786396

  • Single Family Detached
  • Bathroom 2
  • Rooms 7
  • Bedrooms 3
  • Acreage 0.48

This spacious three bedroom Ranch-Style home with central air conditioning is situated on a corner lot. Upon entering the house you will notice the beautiful fireplace located in the formal living room which is complete with a bow window, hardwood floors and stained glass windows. From the kitchen you have a direct view to a bright family room with a cathedral ceiling, a second lovely fireplace and overlooking the backyard. For the outdoor enthusiasts there is easy access to walking trails in the Middlesex Fells Reservation. Easy access to Route 93 in one direction and Winchester Center in the other direction.

Listed by Sal Dipinto and Nancy O'Herron 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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38 Middlesex Street Winchester MA 01890

Winchester, MA38 Middlesex Street

Price$1,149,000

Est. Mortgage: $/month

MLS Number 72780099

  • Single Family Attached
  • Bathroom 4
  • Rooms 7
  • Bedrooms 4
  • Acreage 0.25

Don't miss this opportunity to live in this stylish 4 Bedroom 3.5 Bath NEW CONSTRUCTION townhouse with the feel of a single family, featuring a great first floor master suite with spa like bath! Custom designed and built by top local developer, conveniently located in a great neighborhood near the town center with tennis courts and wedge pond beach close by. Soaring ceilings in the family room, gas fireplace, hardwood floors, sliders to private deck, great kitchen with quartz countertops, & high end appliances ~ second floor with two large bedrooms, full bath, laundry, and loft/ lounge area. Lower level offers a private suite with full bath and walk in closet, great for family room, in law, au pair or in home office! plenty of storage, & exclusive use yards and driveways for each unit. Call today for a private showing!

Listed by Kim Covino of Compass

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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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36 Middlesex Street Winchester MA 01890

Winchester, MA36 Middlesex Street

Price$1,149,000

Est. Mortgage: $/month

MLS Number 72780077

  • Single Family Attached
  • Bathroom 4
  • Rooms 7
  • Bedrooms 4
  • Acreage 0.25

Don't miss this opportunity to live in this stylish 4 Bedroom 3.5 Bath NEW CONSTRUCTION town home with the feel of a single family, featuring a great first floor master suite with spa like bath! Custom designed and built by top local developer, conveniently located in a great neighborhood near the town center with tennis courts and wedge pond beach close by. Soaring ceilings in the family room, gas fireplace, hardwood floors, sliders to private deck, great kitchen with quartz countertops, & high end appliances ~ second floor with two large bedrooms, full bath, laundry, and loft/ lounge area. Lower level offers a private suite with full bath and walk in closet, great for family room, in law, au pair or in home office! plenty of storage, & exclusive use yards and driveways for each unit. Call today for a private showing!

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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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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$
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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

MLS Number 72771272

  • Single Family Detached
  • Bathroom 4
  • Rooms 11
  • Bedrooms 4
  • Acreage 0.23

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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$
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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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2 Greeley Road Winchester MA 01890

Winchester, MA2 Greeley Road

Price$1,095,000

Est. Mortgage: $/month

MLS Number 72740553

  • Single Family Detached
  • Bathroom 2
  • Rooms 7
  • Bedrooms 3
  • Acreage 0.15

Do not miss this bright, move in ready home close to all Winchester has to offer! Recently landscaped yard and walkways welcome you as you enter into the light filled foyer. The main floor has an open, updated kitchen with stainless appliances and plenty of room for a dining or sitting area. A mudroom with built-ins, updated bath, living & dining rooms as well as a screened porch complete the main floor. Upstairs there are 3 good sized bedrooms, a full bath, plenty of storage and access to the 3rd floor bonus room. Enjoy the private fenced yard complete with a new brick walkway out front as well as a patio in the back. The yard has been completely hydroseeded. New roof in spring of 2020. This home is not to be missed!

Listed by Patricia Bruso of Coldwell Banker Realty - Concord

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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

$
$
%
$/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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