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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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14 Mount Pleasant Street Winchester MA 01890

Winchester, MA14 Mount Pleasant Street

Price$1,699,000

Est. Mortgage: $/month

Open House

MLS Number 72812204

  • Single Family Attached
  • Next Open House: Sun 04/11 1:30 pm. to 3:00 pm.
  • Village Town center location
  • Bathroom 3
  • Rooms 9

Stunning and recently renovated 6 bedroom 2.5 bath home offering top of the line finishes and a highly desirable location right outside the town center! This gorgeous home has been renovated inside and out with only the finest materials, by skilled craftsmen offering grand rooms with original detail, oversized windows, hardwood floors, gas fireplaces & high ceilings. The spacious gourmet eat in kitchen w/ dining area & walls of windows leads to private deck overlooking exclusive yard. The yard has been meticulously maintained with beautiful perennial gardens & stone patio offering a tranquil setting so hard to find this close to town! Second floor offers three generously sized bedrooms with one full bath, third offers three additional bedrooms, laundry and full bath. Full basement, walk out lower level, private driveway. All updated systems, windows, electric, plumbing, siding, roof, central A/C & more. Yard is exclusive to #14. Don't miss this opportunity!

Listed by Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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12 Mount Pleasant Street Winchester MA 01890

Winchester, MA12 Mount Pleasant Street

Price$1,999,000

Est. Mortgage: $/month

Open House

MLS Number 72812251

  • Single Family Attached
  • Next Open House: Sun 04/11 1:30 pm. to 3:00 pm.
  • Bathroom 4
  • Rooms 11
  • Bedrooms 6

RARE FIND! Must see this spectacular turn of the century home completely renovated & restored inside and out! This spacious home offers a prime downtown location with 4 floors of space featuring 5+bedrooms, 3.5 baths complete with private ELEVATOR! This recently renovated custom designed town home lives like a single family and offers all the luxuries todays buyers desire, close to town, shops, schools, train to Boston. Stunning kitchen with cherry cabinets, stainless appliances, dining area flooded with sunlight, and family room with walls of windows overlooking beautifully manicured grounds. Formal LR with gas fireplace and detailed moldings. Spacious Master suite with w/fplc, walk in closet & marble bath w/ soaking tub. Third floor w/ 4 addl. beds and full bath. EXCLUSIVE to this unit is also a 3 CAR GARAGE/ CARRIAGE HOUSE w/ full in-law apartment above. The carriage house is handicapped accessible equipped with chair lift, full bath, laundry, kitchenette, living and bedroom areas.

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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89 Johnson Road Winchester MA 01890

Winchester, MA89 Johnson Road

Price$925,000

Est. Mortgage: $/month

Open House

MLS Number 72811563

  • Single Family Detached
  • Next Open House: Sun 04/11 1:00 pm. to 3:00 pm.
  • Bathroom 3
  • Rooms 10
  • Bedrooms 3

Welcome home to Winchester's highly desirable West Side neighborhood steps away from the award-winning Vinson-Owen Elementary School. A true gem, this immaculate split entry has contemporary style, timeless appeal, and lovely surroundings on a spacious half acre lot. The open concept formal living room is perfect for casual living featuring a fireplace with a floor to ceiling surround and a slider to the front wraparound balcony. Prepare favorite recipes in the sunny and cheerful kitchen with a large bay window and informal dining. A cathedral ceiling defines the inviting sunroom with walls of windows overlooking the huge, private backyard with a patio. The master suite has a sliding door to a private office, large double closets, and full bathroom. Cozy up for movie night in the lower level family room or work comfortably from home with an additional private office and full bathroom. A short drive to Winchester's vibrant downtown area with shopping, dining, and the commuter rail.

Listed by Danielle Fleming of MA Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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53 Henry Street Winchester MA 01890

Winchester, MA53 Henry Street

Price$795,000

Est. Mortgage: $/month

MLS Number 72810304

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

Wonderful opportunity to own in Winchester. Charming Colonial totally renovated in 2005, plus many more recent updates (see attachment). Bright and airy kitchen features stainless steel appliances and granite countertops with custom cabinets. The living room, dining room and kitchen all flow beautifully with gleaming hardwood floors. The sunny family room, with a wall of glass, overlooks a professionally landscaped backyard with a secluded patio. The lower level was recently finished with a marble bath. Baths on all three levels. Four zones of heat and three zones of A/C. All this and much more in the Vinson Owen school district, close to Wright-Locke Farm, McClennon Park and the bus to Alewife. Sit on your front porch or rear deck and enjoy the neighborhood.

Listed by Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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26 Charles Road Winchester MA 01890
Open House

MLS Number 72810099

  • Condo or Co-op
  • Next Open House: Sun 04/11 12:00 pm. to 2:00 pm.
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,002

WONDERFUL OPPORTUNITY TO OWN A DIRECT-ENTRY TOWNHOUSE LOCATED AT CUL-DE-SAC! 3 Levels of living- The Main level features a living room with coat closet, a dining area, bright white kitchen with marble countertop and easy access to a private backyard. The upper floor consists of 3 bedrooms with good size closets, a full bath, and a linen closet. Basement offers potential for a family room, office or gym and has a great storage space with laundry. Rare side-by-side parking for 2 cars (possibly more) and exclusive fenced patio and side yard for privacy are unique features in this unit! Enjoy abundant natural light, and hardwood floors. Possibility for expansion per association rules. A pet friendly association with low condo fee which includes landscaping, water, and trash removal. Great location, top rated schools, close to downtown restaurants, shops, schools, hospital train and commuter routes.

Listed by Lin Zhu of Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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13 Gershon Way Winchester MA 01890

Winchester, MA13 Gershon Way, Unit 13

Price$1,880,000

Est. Mortgage: $/month

Open House

MLS Number 72809921

  • Condo or Co-op
  • Next Open House: Sun 04/11 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,550

Luxurious and sophisticated best describe this new 3 bed, 2.5 bath end unit townhome at Winchester's Winning Farm, a gold medal award winner from NAHB for best 55+ community in the US. The layout offers great flexibility for today's lifestyle with superior quality and charm. The first floor's open concept features living room with gas fireplace and large windows to let in loads of natural light and great views. The dining room has coffered ceiling and door to outside deck. The office/den is accessed through double French doors. The custom chef's kitchen has high-end appliances, quartz countertops, and large island. The 1st fl master suite has walk-in closet with custom shelving, door to outside patio, and bathroom with double vanity, walk-in shower with bench, and separate soaking tub. The second floor has two large bedrooms, full bath with walk-in shower, and loft/open space. There is a two-car attached garage and basement with high ceilings that offers many options for future use.

Listed by Tom Doherty of Gibson Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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15 Chester Street Winchester MA 01890

Winchester, MA15 Chester Street

Price$999,000

Est. Mortgage: $/month

Open House

MLS Number 72810666

  • Single Family Detached
  • Next Open House: Sun 04/11 12:00 pm. to 2:00 pm.
  • Bathroom 2
  • Rooms 7
  • Bedrooms 4

Welcome home! Just over half a mile from the amenities of Winchester Center and the HS, 0.3 miles from Muraco Elementary School, and 0.8 miles from McCall, this colonial home is ideally located. Inside, find an updated and open kitchen and dining room, formal living room, and sunroom with a separate door that makes it a perfect home office. A half bath completes the first level. French doors from the kitchen lead out to a Trex deck and unparalleled backyard that is ideal for entertaining! Surrounding the flat grassy yard, meticulously maintained landscaping offers four-season appeal with a mix of perennials and evergreens, and includes four different types of hydrangeas, beautiful paper birch trees, multicolored rosebushes, and evergreen moonglow magnolia trees, and a professionally installed playground. Back inside, find 4 bedrooms and a full bath upstairs, and a partially finished basement that is an ideal playroom or exercise space. There is nothing left to do but move in and enjoy!

Listed by Caroline Staudt of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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58 Westland Avenue Winchester MA 01890

Winchester, MA58 Westland Avenue

Price$1,195,000

Est. Mortgage: $/month

MLS Number 72809234

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 3
  • Acreage 0.56

This extended Cape home will delight w/ mature landscaping, plentiful storage & expansion potential on a gorgeous corner half-acre lot! Sited on a gentle knoll, the center entrance welcomes you into the front-to-back living room w/ a classic brick fireplace; step through to the 3-season porch to relax in the breeze. Spacious kitchen w/ granite countertops, double ovens & peninsula adjoins the large family room w/ half bath. Upstairs find the master bedroom with 3 closets, 2 additional bedrooms, and an office, all w/ hardwood floors. Prefer another configuration? With two full baths & a flexible floorplan, the upstairs could be arranged into a master suite w/ private bath & sitting/office area or nursery, plus two additional bedrooms. Expansive, southwest-facing bluestone patio with stone wall surround offers vast space to entertain, and so much room to play in the sprawling yard. Close proximity to the Winchester Boat Club, Winchester Country Club, & bus transportation to Alewife.

Listed by Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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20 Kenwin Road Winchester MA 01890

Winchester, MA20 Kenwin Road

Price$999,000

Est. Mortgage: $/month

Open House

MLS Number 72809472

  • Single Family Detached
  • Next Open House: Sun 04/11 11:00 am. to 1:00 pm.
  • Bathroom 3
  • Rooms 7
  • Bedrooms 3

Pride of ownership throughout this meticulously updated and maintained colonial. Located 1/10th mile from Middlesex Fells and 1/2 mile from Muraco School this gracious home welcomes you with a large front porch perfect for enjoying warm evenings. Foyer leads to the sunny living room w/ sparkling hardwoods, built-ins, and fireplace. French doors separate a recently added home office while the dining room flows into the kitchen which overlooks the large level back yard. Custom maple cabinets and stainless steel appliances plus extra storage in adjacent mud room. Upstairs you'll find three bedrooms, including master suite, plus additional full bath. Partially finished basement features family room with additional built-in office space and play area. State of the art water leak prevention system, 2car garage & large level lot offering plenty of room for potential expansion. Roof 2016, appliances 2019, 325 amps electric, fireplace cleaned and inspected annually. Nothing to do but move in!

Listed by Kara Spelman of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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21 Ridgefield Road Winchester MA 01890

Winchester, MA21 Ridgefield Road

Price$2,199,000

Est. Mortgage: $/month

Open House

MLS Number 72808764

  • Single Family Detached
  • Next Open House: Sun 04/11 12:00 pm. to 1:00 pm.
  • Village Town Forest
  • Bathroom 4
  • Rooms 13

Location is everything! This stunning Revival home abutting Town forest land and near downtown offers unparalleled privacy & spectacular views! This spacious home stuns with impeccable old world craftsmanship mixed with sophisticated updates. You'll be wowed by the high ceilings, architectural mastery & stylish design. Grand foyer leads into an expansive living room with fireplace and gorgeous hardwood floors, flowing into a dining room with custom built-ins. Don't miss the cozy family room with dazzling views & additional fireplace! Modern kitchen with granite countertops, stainless steel appliances and two dishwashers. Fully screened-in porch with skylights is an entertainer's dream. Huge master suite complete with en-suite bath, sitting area, fireplace & full bonus room! Another two bedrooms & full bath complete the 2nd floor. Upper level features two more bedrooms, full bath & office. Manicured yard with stone patio and 2 car garage. Simply an exceptional home in a prime location!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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457 Washington Street Winchester MA 01890

Winchester, MA457 Washington Street

Price$679,000

Est. Mortgage: $/month

Open House

MLS Number 72808589

  • Single Family Detached
  • Next Open House: Sun 04/11 2:00 pm. to 3:00 pm.
  • Bathroom 2
  • Rooms 6
  • Bedrooms 2

MUST SEE opportunity to own in Winchester! This inviting two bedroom, and one and one half bath Craftsman style home is situated in a prime location, directly across from Leonard Field and near highly desirable Muraco school and playgrounds. You'll feel its charm as soon as you enter its spacious living room with a gorgeous fireplace. Modern kitchen leads into a formal dining room featuring French doors out into a large, private patio. Finished basement offers ample space for a home office, media area or playroom, as well as an additional half bath. The second floor features two bedrooms and a newly renovated full bath, complete with gorgeous skylight. There are smart features throughout the house, including Nest thermostats, alarms and doorbell. Conveniently located near the Fells Reservation or Tri-Community Greenway. Easy access to Rt. 93, downtown shops, restaurants and commuter transportation. Welcome to Winchester.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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73 Sunset Road Winchester MA 01890

Winchester, MA73 Sunset Road

Price$2,300,000

Est. Mortgage: $/month

Open House

MLS Number 72808584

  • Single Family Detached
  • Next Open House: Sun 04/11 11:00 am. to 1:00 pm.
  • Bathroom 5
  • Rooms 11
  • Bedrooms 5

Better than new! Thoughtfully designed and updated cul-de-sac home with all the details you wish for. Covered front entry leads to gracious, welcoming foyer w/ double closets. To your left, a formal LR or office. To your right, an open, large dining room and powder room. High ceilings expand this sunlit home where the family room, chef's kitchen, sunroom all seem to flow into the gardens. Another large front corner room can be a BR, office or playroom. Upstairs, 5 spacious BRs open to the circular hallway with laundry. Owner's suite has exceptional closets, walk-in shower and jacuzzi tub. Two more baths serve other BRs. Over-sized 2+ car garage leads you to large mudroom, full bath, expansive media/rec room plus a workroom, ample wine cellar and great storage. Home's clever details not found anywhere else. And the real gem: Expansive, very private, must-see garden oasis with bluestone patio, natural stream, koi pond and hot tub. Very convenient to 93, 128, the Fells and more.

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 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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