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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

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32 Grove Place Winchester MA 01890

Price$649,900

Est. Mortgage: $/month

MLS Number 72496673

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1375

You must step inside to see all the charm of this inviting home located on a dead end street! Surprisingly spacious throughout, this home features many sought after details - high ceilings, crown molding, exposed brick, hardwood floors, recessed lighting, and more! First floor features a gracious floor plan to include an entry foyer, updated kitchen complete with granite counters and SS appliances, lovely dining room, living room with bay window, a fully renovated bath, and a third bedroom option. Retreat upstairs to find two additional bedrooms, each with jack and jill access to a beautifully renovated bathroom w/cathedral ceiling and skylight. The large enclosed front porch offers a great spot to relax in after a long day! Conveniently located just .5 miles to Wedgemere station for commuter rail to Boston. Enjoy living in Winchester with it's top rated schools, vibrant town center, restaurants, shops, farmer's market, and more! Ambrose School district.

Listed by Antonella Nigro of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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2 Marchant Road Winchester MA 01890

Price$1,150,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72496444

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1935
  • Full Bath 2

Move right in to this 4 plus bedroom colonial, substantially renovated inside & out. Located on a cul-de-sac in desired East Hill. This home has been transformed into a perfect layout for busy households starting with a 2 car attached garage, large mudroom, a granite and stainless kitchen with breakfast bar & wall of windows overlooking a large deck & expansive, level backyard. The 1st floor has a pleasing circular flow with a center foyer, dining room, front-to back fireplaced living room, sunroom, & 1/2-bath. The 2nd floor features a new master suite retreat w/bath & huge dressing room (or 5th bedroom/nursery). 3 additional large corner bedrooms, bath, & laundry room complete the 2nd floor. Hardwood floors & built-ins throughout. Finished Lower level family room. Newer roof. Energy-saving features: solar panels, triple pane windows, rigid foam insulation, & cement fiber siding. Only a half mile to Wedgemere Commuter Rail & just a mile to downtown Winchester. Lincoln Elem. School!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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143-145 Cambridge Street Winchester MA 01890

Price$1,250,000

Est. Mortgage: $/month

Price Changed

MLS Number 72496530

  • Multi-Family 2 Family
  • Year Built 1860
  • Bedrooms 5

~New to Market~ Legal 2 Family with 3 car detached garage. Located near the Flats of Winchester is this stately legal 2 family home with a detached 3 car garage and parking for several more vehicles. Built in 1860 this 12 room home has a flexible floor plan which can be used as a legal 2 family, a single family with an in-law or as a single family. The yard is mostly fenced in and beautifully landscaped. The owners unt has a family room with cathedral ceilings 2 fireplaces and a partially finished basement. Newer separate gas heating systems with multiple zones . ~OPEN HOUSE Sunday May 19th 12:00-1:30pm~

Listed by The Synergy Group and David Proch- Wilson of Leading Edge Real Estate

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%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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22 Brooks Street Winchester MA 01890

Price$2,499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72495013

  • Single Family
  • Garage 3
  • Parking Spaces 5
  • Year Built 2003
  • Full Bath 5

Gorgeous colonial w/ modern design and open layout! Grand foyer w/ staircase, chandelier & soaring ceilings welcomes you. Living room w/ fireplace, dining area & outdoor access in back. Enjoy a sprawling open layout in kitchen & family room: oversized center island, granite countertops, stainless steel appliances, convection ovens, cooktop w/ commercial range & breakfast bar; family room w/ vaulted ceilings, skylights, fireplace. Large dining area w/ backyard access. A private office & half bath complete 1st floor. Master suite w/ hardwood floors, fireplace, walk-in closet & spa-like ensuite bath plus 2 addt'l bedrooms, 1 full bath & laundry room on 2nd floor. Head up one more level to find 2 bedrooms w/ ensuite baths & closets separated by a playroom w/ hardwood floors. Finished lower level w/ mudroom, 2 rooms for entertaining & bathroom w/ steam shower. Bose audio system throughout house, 3 car garage, fenced yard w/ deck and direct access to Town Forest hiking and walking trails.

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: 4.07% last updated on May 16, 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.

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171 Swanton Street Winchester MA 01890

Price$599,900

Est. Mortgage: $/month

MLS Number 72494704

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1450

A tremendous value! Welcome home to this fantastic 2 bedroom townhouse. Superb convenient location in desirable Winchester, The Village Condominiums. Completely renovated with beautiful high end finishes! This end unit has been tastefully renovated. Custom wainscoting plasma TV surround, granite kitchen with maple cabinets and all new appliances. Hardwood floors have been installed throughout the home! Nice rear patio with privacy and easy access to the pool, Master suite with private renovated bath, glass tiles and cherry vanity, 2nd floor laundry room, Spacious second bedroom with ADDITIONAL FULL BATH. Scenic location right overlooking a lovely lake with private walking trails Relax and BBQ on your private outdoor patio. This community is professionally managed to the highest standards. Amenities include pool, tennis court and clubhouse. Easy luxury living in a truly peaceful environment. 1 carport space and an additional deeded guest space complete this fantastic offering...

Listed by Jacob Rosenberg of Gibson Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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33 Lockeland Road Winchester MA 01890

Price$1,049,000

Est. Mortgage: $/month

MLS Number 72494416

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1966
  • Full Bath 3

Beautiful Cape home in the heart of Winchester designed for grand entertaining as well as intimate family living. Bright, open living room with floor-to-ceiling bay windows, spacious eat-in kitchen with ample cabinet & storage space, formal dining room, & window-lined sunroom overlooking backyard for ultimate relaxation. Three bedrooms (one with ensuite bath) & full bath complete the first floor. Upstairs, find a luxurious master bedroom with attached oversized, celeb-style walk-in closet, featuring skylight windows & shelving for maximum storage. Enjoy ultimate serenity in attached ensuite bathroom with spa-like tub, standing shower & stacked laundry. Office space right down the hall. Partially-finished lower level contains a large family room with fireplace, office (could also be a media room, playroom or bedroom). Laundry & storage areas plus half bath complete lower level. Additional property features include large front & back yard, driveway, 2-car garage & off-street parking.

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: 4.07% last updated on May 16, 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.

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12 Prospect Street Winchester MA 01890

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72493394

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Village near center
  • Year Built 1880

Spectacular NEW RENOVATION! Must see this breathtaking home with gorgeous kitchen featuring state of the art design with Thermador appliances, full wine tower, 42'' fridge, 6 burner gas range, quartzite island with seating for 4/5 and breakfast nook overlooking beautiful 27.000+ sf lot with perennial plantings and unique stone and shingle 3 car garage/ carriage house. Formal dining room with beautiful woodwork; double crown moldings, wainscoting, 2 chandeliers and bay window seating area. Elegant formal LR with lit built ins and fplc. Family room w/ oversized wood burning fplc, and a wall of windows beaming with sunlight. Enjoy summer evenings on the expansive front porch or on the rear terrace/ & patio with 6 person Jacuzzi offering gorgeous sunset views over Winchester center! This Magnificent home features 7 spacious bedrooms each w/ generous closet space & high ceilings. Pella windows, 400amp electric, 3 zone A/C, irrigation well, 3 car garage. Basement media room MUST SEE!

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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25 Wildwood Street Winchester MA 01890

Price$1,599,000

Est. Mortgage: $/month

MLS Number 72492360

  • Single Family
  • Garage 1
  • Parking Spaces 2
  • Village The Flats
  • Year Built 1886

A true Victorian in the Flats that harkens from Winchester's early days. Built in 1886 for a Boston & Maine railroad executive, this fabulous home showcases everything that makes Victorian architecture so fab: curved walls, high ceilings, nooks and crannies and beautiful woodwork. The kitchen here will inspire the chef in you, it's enormous and leads to a large screened back porch that begs for dinner parties. There's a butlers pantry with a wet bar, beautiful dining room highlighted by a fireplace and a classic double parlor design. Upstairs, 5 BRS are highlighted by a large master with a sweet private deck and lots of closet space and a lovely front bedroom with the classic Victorian curve. Outside, there are numerous areas to entertain or lounge, including a wide front porch, sprawling stone patio and newly landscaped yard. All in a walk to town and school location!

Listed by Nancy S. Pallotta of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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247 Washington Street Winchester MA 01890

Price$469,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72491940

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1400

Townhome living at its finest and a commuters dream! Extensive renovations over time have created a generous open living, dining, and kitchen area that offers a bright and spacious area to entertain. The open concept kitchen features new granite countertops and all new appliances. On the second floor, you'll find two spacious bedrooms and a tiled full bathroom with tub. A staircase leads you to a fabulous master bedroom with cathedral ceiling, skylight, half bathroom plus huge closet space! Beautiful hardwood floors flow throughout the first two levels and carpet in the Master third floor. Partially finished basement with dedicated laundry offers area for family room/play room or office. Condo association has own trash and recycling. Centrally located in Winchester's top-rated school district, minutes from Route 93/95/128 and less than 1 mile to Winchester Center and the Commuter Rail! You will love the convenient access to the Middlesex Fells Reservation! Call listing agent for appt

Listed by Gayle Winters of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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25 Thornberry Road Winchester MA 01890

Price$1,450,000

Est. Mortgage: $/month

MLS Number 72491257

  • Single Family
  • Garage 1
  • Parking Spaces 5
  • Year Built 1959
  • Full Bath 4

Fabulous renovation in this large contemporary home with 5 bedrooms and 4 bathrooms with open floor plan and top of the line finishes. Enter through the mudroom from attached garage or from the gracious front porch. Expansive, open kitchen/dining area with over sized, beautiful island, perfect for entertaining and top of the line appliances. This sunny room opens to a first floor family room and attached home office/guest suite. Lower level offers a large family room with deck overlooking landscaped yard and another guest suite along with plenty of storage space. Large, gracious foyer awaits you on the second floor with three bedrooms including a large master suite with walk-in closet and heated bathroom floor. The third floor offers a perfect loft area and some more storage space. All in a serene setting in the highly sought after Vinson Owen school district.

Listed by Lesley Smith of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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3 Wildwood Street Winchester MA 01890

Price$2,199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72493069

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 1842
  • Full Bath 4

Gorgeous & picture perfect inside and out, this 5 bedroom 4.5 ba home has been completely renovated & expanded by owner/builder featured on "This Old House" TV show! Centrally located to all Winchester has to offer, this inviting Victorian farmhouse located right outside the center, offers a perfect blend of old world charm and modern design with every amenity and feature you can dream of; including floor to ceiling windows in LR, wi-fi operated sprinklers, alarm system and Sonos whole house music system! Custom gourmet kitchen with Thermador appliances, double sinks, island & adj. sitting room/dining area. Patio off kitchen showcases an outdoor living room with stone fireplace, full kitchen w/ built in gas grill, dining area, Jacuzzi and a large, flat private yard with beautiful landscape and perennial gardens. 2 car detached garage with great space above for gym or home office! Master suite with high ceilings & spa like bath, two laundry areas, mudroom, finished bsmt/ media/game rm.

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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.

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57 Winford Way Winchester MA 01890

Price$1,649,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72490128

  • Single Family
  • Garage 2
  • Parking Spaces 5
  • Year Built 2017
  • Full Bath 4

Gorgeous colonial home custom built in 2017! Open floor plan, soaring ceilings, abundant natural light, hardwood floors and recessed lighting throughout. First floor features open layout anchored by a jaw-dropping kitchen - designed by Bespoke of Winchester - complete with BlueStar gas range, Sub-zero fridge and freezer, Bosch dishwasher and wine fridge. A large bedroom with ensuite bath (perfect for in-laws or master suite option!) plus a half bath/powder room complete the first floor. Second floor features grand master suite with celeb-style walk-in closet containing a second washer/dryer hookup and spa-like ensuite bathroom. Two additional bedrooms (each with ensuite bath) and office space also on second floor. An oversized, extra-deep two car garage and double driveway offer ample space for vehicles. The large, private backyard backs up directly to the Fells Reservation for a peaceful, serene space to enjoy nature and gatherings.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 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

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