Homes in Winchester MA

Winchester MA offers excellent access to metropolitan Boston making it a popular place to live. Single family homes are a sound solution to living eight miles from Boston. View frequently updated Winchester MA real estate listings below. You might also be interested in viewing all Arlington Area homes for sale.

Tour Single Family Homes in Winchester MA

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15 Sargent Road Winchester MA 01890

Winchester, MA15 Sargent Road

Price$1,299,000

Est. Mortgage: $/month

Open House

MLS Number 72899111

  • Single Family Detached
  • Next Open House: Sat 09/25 12:00 pm. to 1:30 pm.
  • Village East hill
  • Bathroom 3
  • Rooms 9

Lovingly maintained East side colonial in top location offering 9 rooms, 4 bedrooms 2.5 baths plus office and family room! This spacious home features high ceilings w/ 3 finished levels & offers a great floor plan with lots of natural sunlight. Enter through the beautiful foyer flowing to the living room with hardwood floors & charming fireplace, sunny family room surrounded by windows overlooking private yard, a formal dining room with built ins, spacious kitchen and first floor half bath compete the main level. The second floor offers three large bedrooms including a spacious 2 room master suite with sleeping area, full bath, two closets and an amazing adjacent sunroom. The third floor has two rooms/ one bedroom and a perfect home office space or optional 5th bedroom. An attached garage under and back patio complete this home. Minutes to Wedgemere train station, downtown Winchester and schools; add your personal touch and move right in! Lincoln Elementary. OFFERS DUE MONDAY AT 3PM

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 Cambridge Street Winchester MA 01890

Winchester, MA376 Cambridge Street

Price$1,006,893

Est. Mortgage: $/month

Open House

MLS Number 72897497

  • Single Family Detached
  • Next Open House: Sat 09/25 11:00 am. to 1:00 pm.
  • Rooms 6
  • Bathroom 3
  • Bedrooms 3

First time on the market this home is ready for its second owner! This home has been meticulously maintained and loved over the years. You will find well cared for original hardwood flooring throughout, along with original tiling to include Italian ceramic tiles. The open living room has a custom Mahogany mantel on the wood-burning fireplace and polished limestone hearth. The dining room has a large picture window for viewing the mature detailed landscaping. The eat-in kitchen leads to the rear yard & a spacious patio for outside entertaining & landscaping that must be seen to be appreciated. The lower level has a large family room complete with another wood-burning fireplace, ¾ bath, laundry room & direct access to the two-car garage. In the garage, you will find a cold storage room that has been filled with many homemade wines, sauces & more. Being centrally located to many great shopping experiences, major highways & T stations make this a commuters dream. Agent related to Sellers.

Listed by Catharine Bray and Michael Petrowski of Keller Williams Coastal Realty

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 Chestnut Street Winchester MA 01890

Winchester, MA12 Chestnut Street

Price$1,499,000

Est. Mortgage: $/month

Open House

MLS Number 72898196

  • Single Family Detached
  • Next Open House: Sat 09/25 11:00 am. to 12:30 pm.
  • Bathroom 3
  • Rooms 9
  • Bedrooms 4

Welcome to Winchester! A gorgeous Colonial located on upper Chestnut Street. Walking distance to the Lincoln Elementary School and McCall Middle School. This feature-rich home with beautiful woodwork expands approximately 3,500 sq/ft and is situated on over a quarter-acre lot. Enter the foyer with original hardwood floors that flow nicely into a sitting room, family room, and formal dining room. Off the spacious eat-in kitchen, an open concept living area is complete with a projector and drop-down screen to watch football in a theater-like setting. On the second floor, you will find three spacious bedrooms and a smaller room perfect for a home office. The master features a separate room that could double as an office, nursery, or amazing walk-in closet. A finished 3rd floor provides bonus space for a playroom, home gym, or hobby room. There is more! An amazing backyard awaits for BBQs and a spacious garage and plentiful parking to boot! Do not miss this opportunity!

Listed by Nick Lento Group and David Beeching of Coldwell Banker Realty - Arlington

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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23 Lawson Road Winchester MA 01890

Winchester, MA23 Lawson Road

Price$1,559,000

Est. Mortgage: $/month

Open House

MLS Number 72898281

  • Single Family Detached
  • Next Open House: Sat 09/25 11:30 am. to 1:00 pm.
  • Village Near center
  • Rooms 6
  • Bathroom 3

Welcome to this picture perfect Cape filled with character and charm in TOP location close to the town center and schools.This sweet home home is perfect for the buyer looking to downsize or for a buyer or builder looking to expand. A beautiful sunlit foyer welcomes you & flows into a large family room with lots of windows and natural light, featuring an oversized fireplace and custom built-ins. A formal living room and dining room are joined by French doors. A lovely kitchen awaits with views of the picturesque yard & patio through the oversized windows. A full bath, mudroom and attached garage with direct access complete this floor. The second floor has a full rear dormer creating space for two generously sized bedrooms/ three rooms; the master consists of two rooms and works nicely as adj. home office space. The lower level offers a third bedroom, full bath and laundry. Plenty of storage throughout, Central A/C. This home is situated on a beautiful lot with an abundance of privacy!

Listed by Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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60 Emerson Road Winchester MA 01890

Winchester, MA60 Emerson Road

Price$1,600,000

Est. Mortgage: $/month

Open House

MLS Number 72896521

  • Single Family Detached
  • Next Open House: Sun 09/26 1:30 pm. to 3:00 pm.
  • Village West Side
  • Bathroom 3
  • Rooms 9

Welcome to this tastefully remodeled 4/5 bed home nestled into the hillside at the end of desirable Emerson Road! Enjoy the backyard oasis filled with peach and apple trees, nice lawn area and new deck perfect for outdoor entertaining. Enter the home through the welcoming foyer and fall in love with the sunny open floor plan. The spacious european designed kitchen offers an oversized island w/ seating, high end appliances with an abundance of storage & breakfast area w/ picture window. A formal dining room, sunny living room w/ historic fireplace & family room/ or 5th bed with a full bath and a laundry room complete the first level. The second floor offers 4 bedrooms w/ 2 bathrooms; a fabulous master suite w/ updated full bath and custom walk in closet, and an office/homework space w/ built in desks. Finished lower level with family room, fireplace, fun kids play area and plenty of storage. 2 car attached garage, central AC, all new windows & updated systems. Move right in and enjoy!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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18 Berkshire Drive Winchester MA 01890

Winchester, MA18 Berkshire Drive

Price$1,090,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72895354

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Square Feet 2,626

This beautiful hardwood floored multi-level home has unlimited potential with its ample space and prime location on the West Side of Winchester. With its expansive bay window and fireplace, the living room offers a serene view of the neighborhood from the comfort of your couch or through the dining room. The dining room opens up to the enclosed porch w/ its 3 walls of windows that showcase the natural beauty of the wooded backyard. The spacious master bedroom includes an en-suite master bath and large walk-in closet. The 3 other bedrooms each feature double closets and offer plenty of opportunity. The lower level family room has direct access to the two car garage, laundry room, and basement. Offers due by 10am, Monday, 9/20.

Listed by Anne Spry of Barrett Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 Ginn Road Winchester MA 01890

Winchester, MA34 Ginn Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72894624

  • Single Family Detached
  • Bathroom 5
  • Bedrooms 5
  • Rooms 15
  • Acreage 0.39

COOK THANKSGIVING DINNER IN YOUR BRAND NEW KITCHEN! New construction home with an estimated completion date of November 2021. Local master builder brings another winning design to Winchester. Showing off both vertical & horizontal siding and featuring a metal roof over the front porch. This home will be loaded with high tech bells and whistles for modern conveniences. Just shy of 6,000 square feet, there's plenty of space for the family to spread out on 4 different floors. The phenomenal master wing boasts a sitting-library-dressing room with gas fireplace, a separate bedroom with soaring ceilings, a to-die-for walk in closet and gorgeous bathroom. Start your day with a workout in your downstairs gym. Multiple locations to set up a home office. There's even a secondary master suite on the 1st floor, perfect for overnight guests. The hardscape features spectacular stone work including a fire pit for those up coming cooler evenings. 2-Car garage and ample parking.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 Westland Avenue Winchester MA 01890

Winchester, MA8 Westland Avenue

Price$1,700,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72894282

  • Single Family Detached
  • Bathroom 3
  • Rooms 11
  • Bedrooms 4
  • Acreage 0.34

Sumptuously landscaped modern colonial radiates an ambiance of comfortable elegance throughout: high ceilings, gleaming hardwood floors, 3 fireplaces, & a spacious, versatile floor plan for everyday living & entertaining. The sensational living room has soaring ceilings, walls of windows, & an impressive wood burning fireplace. The large sun-splashed eat-in kitchen features custom cabinetry, peninsula seating, granite counters, ss appliances, & a vaulted ceiling w/skylight. The kitchen is open to the sunroom, & a circular flow connects all 1st floor rooms including a formal dining room, office, & half bath. 2nd floor has 4 bedrooms, 2 full baths, & features a primary bedroom w/cathedral ceilings, dramatic windows & fireplace. Lower level has a finished media/game room & playroom. Exterior amenities: a 2-tiered deck, koi pond, & treehouse. Two-car detached garage w/storage. Ambrose Elementary location; close to Winchester center w/two commuter rail stops. Welcome to your forever home!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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19 Hancock Street Winchester MA 01890
Open House

MLS Number 72893699

  • Single Family Detached
  • Next Open House: Sun 09/26 2:00 pm. to 3:30 pm.
  • Bathroom 2
  • Bedrooms 5
  • Rooms 11

Attention investors and owner occupants! This Classic two family with craftsman details is located on quiet street in Winchester Highlands with 15,000 sf lot, could easily be converted to a single family. Walking distance to The Fells Reservation, perfect for hiking, biking, or walking your dog. Close proximity to downtown Winchester with shops, restaurants, Commuter Rail and more. First floor unit, 2 bed, 1 bath. Second floor unit, 3 bed, 1 bath. Both units feature sunny living rooms, large formal dining rooms, and hardwood floors throughout. The second floor could be converted to 4-5 bedrooms. Front covered porch and large rear deck, plus immense side yard offers potential for expansion. Includes giant driveway that can comfortably fit 6 cars, plus 2 garage spaces. ~Open House Sunday Sept 26th 2:00-3:30pm~

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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 Forest Street Winchester MA 01890

Winchester, MA119 Forest Street

Price$2,349,000

Est. Mortgage: $/month

Open House

MLS Number 72893561

  • Single Family Detached
  • Next Open House: Sun 09/26 11:30 am. to 1:00 pm.
  • Village Fells area
  • Bathroom 6
  • Rooms 12

Must see this fabulous +/- 6000 sf Colonial farmhouse! This newly constructed 5 bed, 4 full, 2 half bath home by premiere local builder is one of a kind & offers space & style that will impress! With the frontage on Bell Road, the location offers an abundance of privacy and side street access. From the moment you enter you will feel the quality & appreciate the beautiful craftsmanship; features include a stunning kitchen w/quartz counters, wide plank oak flooring, oversized island, Viking appliances w/ 48" fridge, 6 burner gas range along with a wet bar w/wine fridge & walk in pantry! Adjacent family room w/fplc, formal dining room, living room & stunning office w/ walls of windows, Amazing master suite w/ spa like bath, soaking tub & oversized marble shower. 4 additional spacious bedrooms /2 en-suite, 2 car garage w/2 charging outlets, direct entry to mudroom w/ bench, bead board trim & cubbies. Great lower level Media/Game/Home Gym. In wall speakers & smart locks, Don't miss!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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