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Winchester Homes for Sale

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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48 Edward Drive, Winchester, MA 01890

Price$648,888

Est. Mortgage: $/month

Open House

MLS Number 72215448

  • Condo or Co-op
  • Next Open House: Fri 18th 11:00 am - 12:00 pm
  • Bedrooms 2
  • Bathroom 3

COME SEE THIS SPACIOUS NEWLY RENOVATED TOWN HOUSE IN THE DESIRABLE PEPPER HILL ESTATES! All the amenities of Winchester without the work- no more shoveling or yard work. Nearby the newly built Vinson-Owen Elementary School, abuts Whipple Hill conservation & trails and the Wright-Locke Farm. On the main level you will find a brand new granite kitchen with all new appliances leading to a private deck overlooking Whipple Hill. There is new wood flooring throughout this level with an open dining/living room area which is separated by a lovely marble surround wood burning fireplace. On the upper level you will find two very generous bedrooms with endless closets. The master has HIS & HER walk-in closets plus a full bath with jacuzzi tub and separate shower. There is a second full bath with stackable laundry outside and additional closets. All baths have been updated. The lower walk-out level features a very large office, this room could easily be used as a 3rd bedroom.

Listed by Yvonne Logan of RE/MAX Leading Edge

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Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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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396 Main Street, Winchester, MA 01890

Price$639,000

Est. Mortgage: $/month

MLS Number 72214848

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 1

Location, Location, Location!!! Less than a half mile from Winchester Center Commuter Rail Stop, and even closer to Middle School and Lincoln Elementary. This 3 bedroom, 1 bath townhouse with off-street parking and private yard is perfect entry into Winchester. Potential around every corner. Walk up 3rd floor which sits unfinished. Windows on all four sides allowing sunshine to pour in all day long. Inviting front porch, and back deck, this sun filled townhouse should not be missed. Turn this amazing location into your dream townhouse.

Listed by The Gatto Team and Nicholas Gatto of Better Homes and Gardens Real Estate - The Shanahan Group

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Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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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7 Conant Road, Winchester, MA 01890

Price$515,000

Est. Mortgage: $/month

Open House

MLS Number 72214629

  • Condo or Co-op
  • Next Open House: Sat 19th 12:30 pm - 2:00 pm
  • Bedrooms 2
  • Bathroom 3

LUXURY, CONVENIENT LIVING AT ITS BEST! SIMILAR UNIT 2 DOORS DOWN JUST CLOSED for $600K! NEWER, OPEN- CONCEPT townhouse in the finest school district of Winchester. Minutes to town center, commuter rail, and commuter routes. Efficient Open concept kitchen features butler's pantry. Living Room has Gas fireplace to warm up on those brisk winter nights. Deck off the Dining room is ideal for summer cocktails before dinner. Home office & half bath complete first level. Each bedroom upstairs has its own FULL bath. Master Bedroom is very large and has a walk in closet and its own balcony. Open up the slider and feel the Spring & Autumn Breeze. Addt'l Features include In-unit laundry, central air, gas heat & lots of closet space. PLUS bonus deeded storage space in basement. The Willows is a wonderful luxury style complex with club house and swimming pool. An opportunity like clearly won't last.

Listed by Mehr & Brandon Tabassi of RE/MAX Partners

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Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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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226 Cross Street, Winchester, MA 01890

Price$1,200,000

Est. Mortgage: $/month

MLS Number 72214308

  • Condo or Co-op
  • Bedrooms 5
  • Bathroom 4

NEW CONSTRUCTION! HANDSOME ATTACHED SINGLE FAMILY HOME LOOKING FOR A LONG TERM RELATIONSHIP WITH NEW OWNER! Located a short distance to downtown, with plentiful boutiques, restaurants, coffee shops, salons and the commuter rail to Boston. The 1st floor features an integrated floor plan for today's modern lifestyle with an open concept family room and kitchen (perfect for entertaining friends and family). A formal dining room and 1/2 bath complete the first level. Lots of natural light and gleaming hardwood floors throughout. The 2nd floor features a master en suite with walk-in closet and a spa like bathroom. Laundry, 2 additional bedrooms, and a full bath complete the 2nd floor. The 3rd level walk up is home to 2 more bedrooms and a bathroom. The lower level basement can be finished for an additional charge. Nothing to do but move in, decorate, and host your next party in your new home!! Within the Lynch School district, easy access to major highways and only 7 miles from Boston!

Listed by Monte Marrocco, Gayle Winters and Philip Massa of RE/MAX Leading Edge

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Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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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238 High Street, Winchester, MA

Price$2,099,000

Est. Mortgage: $/month

Open House

MLS Number 72214098

  • Single Family
  • Next Open House: Sun 20th 2:00 pm - 3:00 pm
  • Bedrooms 5
  • Bathroom 8
  • Parking Spaces 5

Enjoy residential bliss in this classic colonial home on a lot that affords privacy and tranquility, while not being secluded. Purchased by current owners as new construction in 2008, this home is ideally located in the acclaimed Vinson Owen school district with easy access to Rte. 93 and Boston. This impeccably-landscaped home features lush greenery and mature plantings that are appreciated from every room. Boasting expansive living spaces, chef’s kitchen, intricate detailing, distinctive fireplaces and the finest finishes at every turn, this magnificent residence epitomizes class and style whether you wish to relax casually or entertain grandly. Extra features in this home include security system, oversized 3 car garage, wifi enabled thermostat system, wifi controlled lighting, custom closets in 4 bedrooms, surround sound system in living room and family room, central vacuum, completely wired for cable and internet, and gas fireplaces.

Listed by The Andersen Team and Sven Andersen of RE/MAX Leading Edge

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

20 Hollywood Road, Winchester, MA

Price$1,180,000

Est. Mortgage: $/month

Open House

MLS Number 72215241

  • Single Family
  • Next Open House: Fri 18th 11:30 am - 1:00 pm
  • Bedrooms 3
  • Bathroom 3
  • Parking Spaces 4

Love Winchester? Looking for an amazing place that feels like home right when you walk through the door? Searching for an outstanding yard to entertain and enjoy cookouts? 20 Hollywood Road is the perfect home for you and your family and friends to gather. This inviting colonial home located on a tranquil street in a superb East Hill location offers 3-4 large bedrooms, 2 full and 1 half baths, light-filled family room with vaulted ceiling, skylights and french door slider that leads to your private spacious outdoor space with a large stone patio. Finished lower level offers a huge second family room and a 4th bedroom, which is ideal for a teen or extended family. Walk to train, town center and The Fells, one of the top 5 State Parks in MA. The Fells has over 2,200 acres of walking trails and protected landscape. Hollywood awaits you.

Listed by Lorie Glantz and Alison Kee of RE/MAX Realty Experts

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Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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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4 Ardley Road, Winchester, MA

Price$869,000

Est. Mortgage: $/month

Open House

MLS Number 72213265

  • Single Family
  • Next Open House: Sun 20th 1:00 pm - 2:00 pm
  • Bedrooms 4
  • Bathroom 2
  • Parking Spaces 4

Beautiful Cape style home in Winchester! This exquisite home, expanded by the current owners & freshly painted is move in ready! From the minute you walk into this charming residence, you will instantly feel welcomed with the spacious mudroom & inviting family room containing stunning hardwood floors, built-ins & recessed lighting. The 1st floor has a spectacular flow from the living room into the eat-in kitchen, which contains a slider leading out to the deck & private backyard. Just steps from the kitchen you will find a bedroom & full bath perfect for guests. Entertain in the elegant dining room & cozy living room. The 2nd floor offers 3 bedrooms, inclusive of the spacious master with ample closet space. Just steps down to the lower level, enjoy an incredible media room with wood burning fireplace & game room just off the media room. Within walking distance to Lynch Elementary School & just minutes from downtown Winchester & the commuter rail, make this charming home yours!

Listed by The Andersen Team and Sven Andersen of RE/MAX Leading Edge

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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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7 Wainwright Road, Winchester, MA 01890

Price$1,570,000

Est. Mortgage: $/month

Open House

MLS Number 72213559

  • Condo or Co-op
  • Next Open House: Sat 19th 12:00 pm - 2:00 pm
  • Bedrooms 4
  • Bathroom 4

Absolutely stunning 4 bed, 3.5 bath,4247 sq ft townhouse at The Ledges w/first floor master suite & 2 car garage off mud room. From top to bottom,this F style home has been custom designed & renovated like no other.By removing a wall,they were able to create an open floor plan that stretches from the Chef's kitchen & dining rm, to the beautiful family rm w/floor-to-ceiling windows over looking a private yard, and a view thru gas fireplace that connects to living room.The entire 1st fl has beautiful Brazilian HDWD flrs, rec'd lighting & wall sconces.The kitchen has a gorgeous 10' island,custom cabinetry,Thermador stainless steel appliances w/induction cooktop,microwave drawer,Miele steam oven,bar sink & both leathered & polished granite. Master suite w/gas fireplace in sitting area & gorgeous master bath. Slider off the kitchen leads to patio w/beautiful hardscape, that connect to rear yard & lower gardens. The garden level has full walkout off Great Room and 2 lg bedrms w/steam shower.

Listed by David Hayes of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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

90 Thornberry Road, Winchester, MA

Price$1,050,000

Est. Mortgage: $/month

Open House

MLS Number 72213545

  • Single Family
  • Next Open House: Sat 19th 1:30 pm - 3:00 pm
  • Bedrooms 5
  • Bathroom 3
  • Parking Spaces 4

Spacious and gracious! This lovely home is located on a beautiful lot in the Vinson-Owen School District. The main level features good sized rooms with hardwood floors in each room, including the kitchen. Adjacent to the dining-room is a screened porch for alfresco dining and relaxing. A large, comfortable family room with fireplace is on the lower level along with an office which can also be used as a bedroom. Enjoy outdoor living and gardening in the gorgeous, manicured back yard or from the front, seasonal views of the Boston skyline. This is a very attractive, well planned split level home in an amazing, tranquil setting!

Listed by Nancy O'Herron of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

21 Englewood Road, Winchester, MA

Price$949,000

Est. Mortgage: $/month

MLS Number 72215413

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Parking Spaces 1
  • Lot Description Paved Drive

Move right into this expanded cape that has been completely updated and renovated.Sunny open floor plan with granite kitchen and island and room for dining and entertaining. Relax in pretty fireplace living room or play in the other family room which is perfect for a pool table or ping pong. Attractive master suite with cathedral ceiling and two large bedrooms on second floor. Additional rec room in basement. This home is located close to Muraco School and also to Winchester Hospital and highways to the north and south. Also right down the street from The Fells Reservation. Relax on the patio in a location you will love!

Listed by Nannette Shanahan and Stephanie Walsh of Better Homes and Gardens Real Estate - The Shanahan Group

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1 Woodside Road, Winchester, MA

Price$1,599,900

Est. Mortgage: $/month

MLS Number 72212050

  • Single Family
  • Bedrooms 6
  • Bathroom 4
  • Parking Spaces 2
  • Property Style Colonial

Welcome to the Flats and this Beautiful 1895 Colonial. Inviting front porch enters into grand foyer with a classic staircase. Bright, sun drenched double parlor with lovely built-in details. Formal dining room, newer kitchen with granite counters/island, gas stove, stainless steal appliances and half bath complete the 1st floor. The second floor offers a master bedroom with walk-in closet, beautifully updated master bath, three additional bedrooms and large family bath. Third floor is wonderful space with full bath, 2 bedrooms and ample storage. The partially finished lower level is great flex space with even more storage options. Last but certainly not least is the private back yard. Located directly off the kitchen with blue stone patio, sprinklers and brand new 2-car garage with a 22x14 2nd floor just waiting for your imagination to finish. Great home in a wonderful location...close to all Winchester has to offer. Open House Sat 8/12 & Sun 8/13, 12-2pm

Listed by Catherine Albiani and Carrie Simpson of Century 21 Commonwealth

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

171 Swanton, Winchester, MA 01890

Price$539,900

Est. Mortgage: $/month

MLS Number 72211015

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2

Downsizing or starting out? This may be your opportunity for a move. Enjoy the private setting of this unit overlooking the Aberjona River as you relax on the patio. Stroll over to the community pool for a swim or grab your racket for a round of tennis on the community court. First level features a tiled kitchen with stainless appliances, separate dining room, and large living room with crown molding and wood burning fireplace. On the second level find the spacious master bedroom featuring a walk-in closet, second bedroom with over sized closet, tile bath, laundry room, and additional space for office/ storage. Large storage room is adjacent to carport parking. The "Village" is close to the shops and restaurants of downtown Winchester, the commuter rail and jogging /bike trails.

Listed by Deborah Heffernan of Avenue 3 Real Estate, LLC

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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