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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19 Gershon Way Winchester MA 01890

Winchester, MA19 Gershon Way, Unit 19

Price$1,550,000

Est. Mortgage: $/month

Open House

MLS Number 72709846

  • Condo or Co-op
  • Next Open House: Sat 08/15 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

WINCHESTER'S 1ST 55+ COMMUNITY! Designed by national, award-winning, architect Gary Snider. 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. 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.***MODEL HOME OPEN DAILY 11-4PM***

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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1A Ledgewood Road Winchester MA 01890

Winchester, MA1A Ledgewood Road

Price$3,495,000

Est. Mortgage: $/month

MLS Number 72710089

  • Single Family
  • Garage 3
  • Parking Spaces 6
  • Total Parking Spaces 9
  • MLS Status New

Developer saved the best for last at Winchester's new French Hill luxury home development. Exquisite details abound inside and outside in this masterpiece estate in one of Winchester's most desirable neighborhoods! Five-six Bedrooms, six and one-half Baths, include luxurious Master Suite complete with Sitting Room and two walk-in closets. Enormous Kitchen with two islands, premiere stainless and paneled gas appliances and Butler's Pantry. Over-sized bluestone Deck with perennial border overlooks lush grounds, setting the perfect scene for entertaining and relaxing. Deep 3-car Garage, outfitted Mudroom and 1st floor Office Suite. Gracious front porch, and shingled exterior, with fieldstone detail. Enjoy a scenic stroll into both Winchester's charming downtown and the “Fells,” with acres of hiking and mountain biking trails. Walk to the commuter rail, playgrounds and schools. Sited on an exquisite parcel - perfect for a swimming pool - just 11 minutes to downtown Boston!

Listed by Elizabeth P. Crampton of Coldwell Banker Residential Brokerage - Lexington

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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86 Middlesex Street Winchester MA 01890

Winchester, MA86 Middlesex Street

Price$675,000

Est. Mortgage: $/month

Open House

MLS Number 72709018

  • Single Family
  • Next Open House: Sat 08/15 1:00 pm. to 2:30 pm.
  • Parking Spaces 2
  • Total Parking Spaces 2
  • MLS Status New

Home Sweet Home! 86 Middlesex St is a lovingly maintained home, featuring gorgeous oak flooring throughout and a great open floor plan. An updated kitchen with stainless appliances, granite counters and plenty of space for cooking opens to a sunny dining room, ready to fit a big table. The family room has great space for hanging out with wireless ready recess lighting and built in speakers and opens to an office area with sliders out to the yard. The second floor offers two large bedrooms and one full bathroom, updated with modern fixtures and lots of storage space. Unfinished basement provides laundry, additional storage and ample ceiling height for your home gym! Lots of smart home tech including Nest thermostats, smoke detectors and door lock. Enjoy the outdoors in a private, fenced in yard with patio, shed and plenty of space for gardening or play. Or, venture out to nearby schools, Winchester town center, Tri-Community Greenway and Horn Pond. Perfection!

Listed by Karen S. Garrett of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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185 Cross Street Winchester MA 01890

Winchester, MA185 Cross Street

Price$1,599,000

Est. Mortgage: $/month

Open House

MLS Number 72708352

  • Single Family
  • Next Open House: Sat 08/15 12:00 pm. to 1:00 pm.
  • Garage 2
  • Parking Spaces 2
  • Total Parking Spaces 4

Prepare to be stunned when you step into this impeccably designed, luxury home! This custom Colonial, newly built in 2016, boasts 4 finished levels! An open concept first floor features a chef's kitchen with island seating, custom cabinetry and high end appliances. You'll love the fireplace and built-in shelving in the sun-filled family room, as well as convenient home office and 1st fl bath. The 2nd fl offers 3 bedrooms, including a gorgeous master with shower & soaking tub and huge walk-in closet! Entertain often? Get ready to walk back in time--push the 3rd fl bookcase to reveal a hidden speakeasy with rich leather walls and bar that features a copper sink and ice fridge! There's even more: another full bed and bath in the finished basement, along with a custom wine room and kitchenette. There's an attached garage & fenced yard with beautiful patio and garden. Close to Rte. 93 and Fells reservation. You simply MUST SEE this gem of a home!

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: 2.96% last updated on Aug 13, 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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22 Baldwin Street Winchester MA 01890

Winchester, MA22 Baldwin Street

Price$699,900

Est. Mortgage: $/month

Open House

MLS Number 72707874

  • Single Family
  • Next Open House: Sat 08/15 11:30 am. to 1:30 pm.
  • Parking Spaces 4
  • Total Parking Spaces 4
  • MLS Status New

Meticulously cared for by the same family for a half century and its pride speaks loudly for itself. This sound and charming HOME sits on an extremely level 9500 sq ft lot affording its new owner a myriad of options in both indoor and outdoor future living options. Located on a small dead end provides that community feel and a limited amount of traffic. Tall mature plantings provide privacy for outdoor activities and entertaining. Inside you will find well maintained hardwood on both levels, a spotless kitchen with gas stove, a generous living room, and a dining room featuring an impressive built in cabinet. Den off of kitchen offers wood burning fireplace and full bath with its own heating zone. Second floor is where you will find three bedrooms and a full bath. Finished room in basement provides additional space. Easy access to major transportation routes and walking distance to downtown with its diverse options for shopping, dining, as well as one of Winchester's two commuter rails.

Listed by REthink39 Group and Philip Massa of LAER Realty Partners

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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3 Oneida Circle Winchester MA 01890

Winchester, MA3 Oneida Circle

Price$799,900

Est. Mortgage: $/month

MLS Number 72707325

  • Single Family
  • Garage 1
  • Parking Spaces 3
  • Total Parking Spaces 4
  • MLS Status Active

Location can't be beat! This charming Colonial is situated in the coveted Ambrose Elementary School neighborhood. Plenty of natural light streams through and offers a cheery feel to this solid home. Features of this home include high ceilings, hardwood flooring, 3 large bedrooms, 1.5 bath, a one car garage and a wonderfully private backyard. First floor includes a large living room with hardwood flooring and a fireplace flanked with built-in bookshelves, dining room with corner cabinet. This much loved home is ready for its new owner to refresh and enjoy! Offers due Saturday, August 15th by 5 p.m.

Listed by Stephanie Mcgowan of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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372 Cambridge Street Winchester MA 01890

Winchester, MA372 Cambridge Street

Price$749,999

Est. Mortgage: $/month

Open House

MLS Number 72706984

  • Single Family
  • Next Open House: Sat 08/15 12:00 pm. to 1:30 pm.
  • Parking Spaces 3
  • Total Parking Spaces 3
  • MLS Status Active

Discreetly set back from the road is this TWO OWNER hidden treasure! As you approach you will be immediately greeted by an oversized and secluded courtyard. Surrounded by lush greenery, you will truly feel like you're relaxing in your own private retreat every day. Morning coffee, or your evening dinner, will be enjoyed tenfold here! The main level of this property is where you will find the open concept living room and kitchen. A beautiful brick wood burning fireplace is the focal point of this space which also boasts an eat-in dining area. With treetop views from every window you'll feel tranquil energy from each room in 372 Cambridge Street. On the upper level you will find 3 bedrooms, and your first full bath. This bath has been beautifully renovated with current tile, frameless glass shower door, and stone countertops. As you make your way down a level you'll find 2 additional bedrooms, a play room, and another tastefully renovated full bath. Located in the desirable VO district!

Listed by Vita Realty Group and Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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11 Trinity Road Winchester MA 01890

Winchester, MA11 Trinity Road

Price$1,199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72706409

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

Welcome to Winchester! Never before offered to the public - this spacious multi-level home offers sprawling grounds, oversized living space and the opportunity to customize and renovate to make this your own!! Located on cul-de-sac in desirable Vinsen Owen neighborhood - this 4 bed 2.5 bath home has been meticulously maintained by the same family for over 50+ years. The main level offers a cozy living room w/ FP & oversized windows, dining room and eat-in kitchen with direct access to the yard/patio. Four oversized bedrooms with a master suite equipped with walk-in closet and full bath. The lower level features 2-car attached, mudroom/laundry area, family room and half bath. Located minutes from Wright-Locke Farm, Whipple Hill, Winchester Country Club and Turkey Hill hiking trails this home is a must see!!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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24 Surrey Road Winchester MA 01890

Winchester, MA24 Surrey Road

Price$1,699,999

Est. Mortgage: $/month

Open House

MLS Number 72706012

  • Single Family
  • Next Open House: Sat 08/15 12:00 pm. to 1:30 pm.
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6

This may seem like your typical split-level home from the exterior but my, oh, my, would you be WRONG! As you enter a dramatic foyer with stunning crystal orbital chandelier will lead you to the living room with cathedral ceilings and floor to ceiling ledger stone fireplace. To say this section of the home is impressive would be an understatement! But it gets better from there; the dining room offers majestic views of the Boston city skyline. The beautifully renovated kitchen with eat-in area boasts a stainless farmers sink and Bosch appliances including a 36" induction cooktop. Three bedrooms, including the master suite, are also found on this level. Access to the rear deck and a stunning spa-like bathroom with body sprays, linear drain, and steam shower are just a few of this masters special features. The lower level has an expansive family room, play room, bed #4, a full bath, kitchenette, and access to the 2 car garage. Quite possibly the in-law you've been searching for! Come see!

Listed by Vita Realty Group and Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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29 Dunster Lane Winchester MA 01890

Winchester, MA29 Dunster Lane

Price$1,749,000

Est. Mortgage: $/month

Open House

MLS Number 72704942

  • Single Family
  • Next Open House: Sun 08/16 2:00 pm. to 3:00 pm.
  • Parking Spaces 7
  • Total Parking Spaces 7
  • MLS Status Active

Come experience the peace & casual elegance unique to this residence! Meant for a family seeking a lifetime of precious memories & located on a quiet street. This inviting home offers all the bells & whistles today's savvy buyer seeks. Lovingly designed with 5 bedrooms (3 of which are "en-suite"), boasting 5.5 bathrooms & many heated floors. Ideal for entertaining friends & family, featuring a true Chef's kitchen & an open concept great room with fireplace & espresso bar. Plenty of space for all to enjoy, including a stunning back yard for playing catch with Rover-the-dog! Several rooms could be dedicated as an art studio or home office to accommodate your working demands. Around the corner from Wright Locke Farm for strawberry picking with the children. Dreaming of your own private roof deck ? A place to soak up some rays, host a BBQ, observe the starry nights through a telescope? Look no further! A short drive to bustling downtown Winchester featuring many coffee shops & boutiques.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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32 Cambridge Street Winchester MA 01890

Winchester, MA32 Cambridge Street

Price$999,000

Est. Mortgage: $/month

Open House

MLS Number 72705066

  • Single Family
  • Next Open House: Sun 08/16 2:00 pm. to 3:00 pm.
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8

Looking to live in the idyllic Winchester community? Now you can! This charming move-in ready ranch is located just a short drive to the highly acclaimed Ambrose Elementary School, Winchester Boat Club and golf course. Featuring hardwood floors throughout its spacious open concept layout on the main floor, a beautiful kitchen with recessed lighting, granite countertops and an incredible island, this home has a modern touch while still maintaining its exquisite original design. Separated by beautiful French doors, an inviting living with fireplace plus a large family room with soaring cathedral ceilings offer beautiful spaces for relaxation and intimate gatherings. Finished lower level with additional bedroom and bath perfect for in-laws or an au pair suite. Two car garage, plenty of off-street parking and a beautiful deck and patio overlooking a peaceful and private backyard. This home truly has it all!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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17 Squire Road Winchester MA 01890

Winchester, MA17 Squire Road

Price$1,255,000

Est. Mortgage: $/month

MLS Number 72704513

  • Single Family
  • Parking Spaces 5
  • Total Parking Spaces 5
  • MLS Status Active
  • Village Winchester Estates

Bright & beautifully renovated home with a unique 4-level-open-layout. The inviting entry foyer leads to the primary bedroom suite with double closets & private bath. Spacious main level has a fully applianced kitchen with cherry cabinetry, granite counters & breakfast bar that opens to the dining & living rooms, a perfect layout for easy living or entertaining. The upper level offers 3 large bedrooms, full bath with linen closet & has hardwood floors throughout. There is excellent easily accessible attic storage in two locations. The lower level offers a rec room & office area with glass doors leading to the multi-level patio. The 1/2 acre lot has multiple perennial plantings, offering privacy & space for expansion. Close to Winchester Swim & Tennis Club, Wright Locke Farm & the Vinson-Owen elementary school, shopping, the commuter rail, easy highway access, and all the wonderful things that Winchester has to offer.

Listed by Carol Fontana of RE/MAX Andrew Realty Services

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 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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