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 Medford MA single family homes or Lexington MA single family homes.

Tour Single Family Homes in Winchester MA

Contact Sweeney & O'Connell Real Estate online or call 781.643.7478 with any questions or to schedule a private tour.

Save time! Sign up to get email notifications when similar properties matching your search criteria become available.

22 Hillside Avenue Winchester MA 01890

Price$1,385,000

Est. Mortgage: $/month

MLS Number 72524363

  • Single Family
  • Garage 2
  • Parking Spaces 5
  • Year Built 1950
  • Full Bath 4

Truly special original Winchester Estate known as "The Field Stone Lodge" Flanked by two stone pillars as you enter, this one of a kind rambling stone and shingle style bungalow is nestled into the Hillside and is truly a nature lovers dream come true! Offering 1/2 acre+ of rolling fields, gorgeous perennials, secret gardens w/ unparalleled views & an abundance of privacy! Large spacious rooms, living room and family room each with oversized fireplaces & beamed ceilings, Master with cathedral ceilings, second floor laundry/office, decks and multiple patios perfectly placed add to the gorgeous setting and create a European/Italian villa feel! Gorgeous views from almost every room toward the West, offering wonderful sunlight and spectacular sunsets. Lower level in law/au-pair with private entry! Home does need a bit of repair but make the investment & put your personal touch on this home and it will be breathtaking! TOP location near Winchester center! Call for PRIVATE SHOWINGS today~

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

10 Lawrence Street Winchester MA 01890

Price$1,220,000

Est. Mortgage: $/month

MLS Number 72523673

  • Single Family
  • Garage 1
  • Parking Spaces 4
  • Year Built 1923
  • Full Bath 2

A fantastic opportunity to renovate, expand, or design your "dream home" within Winchester's desirable Flats area! This four bedroom two and a half bathroom Colonial with a one -car detached garage was custom built in 1923. There are many built-ins throughout, hardwood floors, fireplaces in the living room and office/sunroom opening to rear patio/yard. The first floor has a large eat-in kitchen, dining room, front to back living room and nice entry area with graceful staircase. Large master bedroom with sunroom, Sitting area and attached master bath. Three other bedrooms and bath on second floor. The basement has high ceilings, direct access from driveway, and dual furnaces. Current owner entity is tax exempt at this time. More pictures coming soon...

Listed by William J. Murphy of Colony Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

195 Cambridge Street Winchester MA 01890

Price$859,000

Est. Mortgage: $/month

MLS Number 72523776

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1820
  • Full Bath 3

Are you looking for a new home that is out of the ordinary? Step into this home and you have stepped into the extraordinary - a five bedroom home that is steeped in history and full of charm and character.This is the homestead of the fabled "White Horseman" Hezekiah Wyman, who at 55 years with long locks of white hair, rode off on his white mare to fight the retreating British after their battle in Lexington and Concord in 1775. This home retains much of its character with fine craftsmanship and comfortable living spaces. And, if you are looking for that perfect escape from the city or hustle and bustle of every day life, this home has a back yard that will take you away from it all. Escape to the gardens, the play areas, the perfect sitting areas under the broad reach of beautiful trees that you will find in this glorious and very private back yard. So, here, not only will you own a spacious and charming home but you will also own a piece of Winchester's and our National history

Listed by Stephen DeConto of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

18 Euclid Avenue Winchester MA 01890

Price$779,000

Est. Mortgage: $/month

MLS Number 72523331

  • Single Family
  • Parking Spaces 2
  • Year Built 1961
  • Full Bath 1
  • Bathroom 2

Have you been searching for a home in a natural and very private wooded setting, surrounded by nothing but tall trees, a blend of carefully cultivated plantings, natural foliage, gentle breezes and birds? Here is a three bedroom home, perched upon a gentle knoll in that exact glade-like setting, located within a very desirable area of Winchester that may be the home you have been looking for. BUYERS and BUILDERS, bring your dreams and vision to 18 Euclid Ave. Here you will find a home on almost 18,000 sq.ft. of pristine wooded land in a neighborhood of homes easily worth in the millions! Your backyard is the magical Middlesex Fells, nearby is the top rated Muracco School and best of all, you have a very special, one-of-a-kind home in Winchester, so close to everything and yet so far away from it all.

Listed by Stephen DeConto of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

2 Bates Road Winchester MA 01890

Price$1,190,000

Est. Mortgage: $/month

MLS Number 72523438

  • Single Family
  • Garage 1
  • Parking Spaces 5
  • Year Built 2009
  • Full Bath 3

You'll be impressed with the quality and upgrades in this STUNNING 5 bedroom, 3 bath Townhouse with FOUR FINISHED LEVELS. The first floor boasts a GORGEOUS Chef's kitchen with SS appliances, granite counters, island with seating, living room with gas fireplace and a door leading to the deck, formal dining room, bedroom and full bath. The second floor has a master suite with walk in closet and private bath with tiled shower. 3 additional bedrooms and a full bath complete this level. Upstairs there is a huge bonus room with cathedral ceilings and custom built ins. Walk out lower lever with family/game room, laundry, mud room, and access to the 1 car garage. Other features include closet organization units, new heating system, tankless hot water, central AC, 200 amp electrical, security and irrigation systems, and a partially fenced yard. Great location - walking distance to the sought after Muraco School, Winchester Center, and train. Easy access to Rte. 93 and Boston. Pet friendly!

Listed by Julie Darcangelo of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

5 Fairlane Terrace Winchester MA 01890

Price$899,900

Est. Mortgage: $/month

MLS Number 72522351

  • Single Family
  • Garage 1
  • Parking Spaces 4
  • Year Built 1958
  • Full Bath 1

Welcome Home! This lovingly maintained and spacious Colonial is nestled on a picturesque cul-de-sac bordered by over 80 acres of conservation land. Enjoy all this land has to offer and feel like you're in the woods of Maine but only minutes to Winchester Center, historic Lexington and Burlington's chic "Third Ave". Entertaining and casual family living are a breeze with this classic layout including a screened-in porch, deck and stone paved patio! Large bedrooms, oak hardwoods though out, plenty of closets, huge finished walk-out basement with lots of windows and one car garage make this home an A+. Bonus room could be used as a 5th bedroom, den, office or playroom. New furnace in 2016, newer oil tank, Windows in 2004, Professional landscaping and irrigation system are some of the features.

Listed by Rose Manni and Christine Beaudry of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

181 Mystic Valley Parkway Winchester MA 01890

MLS Number 72522730

  • Single Family
  • Parking Spaces 2
  • Year Built 1906
  • Full Bath 2
  • Bathroom 4

This truly classic Colonial on the tree-lined Mystic Valley Parkway welcomes you home. The unique double-width driveway leads to a private Beacon Hill patio accessed from Winthrop St. Feel the heartbeat of the town from the timeless, wide front porch with matchstick ceiling & recessed lights. The symmetrical Victorian facade with bay windows is framed by mature plantings. Step through the elegant wooden door with oval glass into the bright & airy foyer. The adjoining formal living room leads to a dining room with lead glass cabinet & fireplace. The convenient layout of the kitchen with breakfast bar opens to the family room with windows on three sides. Upstairs, the unique front-to-back master suite includes a dressing room, wet bar, & spacious en-suite bath. The 2nd flr is complemented by two additional bedrooms & an updated full bath. 3rd flr getaway space includes a bedroom, office & cedar closet. Take this rare opportunity to own a home close to the Fells, train, schools & Center!

Listed by Anne Spry and Nancy Fleming of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

30 Clark Street Winchester MA 01890

Price$535,000

Est. Mortgage: $/month

MLS Number 72522510

  • Single Family
  • Parking Spaces 2
  • Year Built 1890
  • Full Bath 1
  • Bathroom 1

Looking for the perfect investment opportunity? Here it is! Located on a dead end street right off Main Street, walking distance to the commuter rail, local schools and less than one mile to the downtown. Excellent opportunity to rebuild/rehab this charming 2 bedroom, 1 bath New Englander with enclosed front porch. Newer appliances, tile in kitchen, hardwood in living room and on stairs and carpeting in bedrooms. Laundry in basement, which also has a partially finished space. Looking for someone who doesn't mind a little work. Sold AS IS. Showings begin Saturday, June 22nd 10 am at the open house.

Listed by Kimberley Tufts of Jill & Co. Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

3 Olde Lyme Road Winchester MA 01890

Price$959,900

Est. Mortgage: $/month

MLS Number 72522929

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1960
  • Full Bath 3

This surprisingly spacious home nestled on a wooded, private lot with access to the conservation land of Sucker Brook Trails is truly a gem. Entertaining is made easy by the extended kitchen with breakfast bar and dining area flowing perfectly to the family room, dining room and fireplace living room. The master suite located on the 4th level with skylight, 3 closets and master bath offers privacy from the 3 additional, spacious bedrooms located on the 3rd level. Second bedroom with its en-suite bath offers great versatility for extended family or guests. Easy access from the 2 car garage into the laundry/mudroom and office level add to this home. The fireplace game room adds further flexibility to this home. French drain system, a/c and newer Buderus heating system reflect the pride of ownership. Sought after Vinson Owen school district and its proximity to Lexington and Arlington make this home a winner.

Listed by Anne Spry and I-Ching Scott of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

146 Ridge Street Winchester MA 01890

Price$1,250,000

Est. Mortgage: $/month

MLS Number 72522156

  • Single Family
  • Garage 1
  • Parking Spaces 3
  • Year Built 1951
  • Full Bath 5

Move right in to this thoughtfully designed West Side colonial, a short walk to award winning Vinson Owen school. The open-plan living/dining is bright & sunny and leads to private office with brick backdrop from the living room fireplace. Kitchen features granite counters, stainless appliances, & sunny breakfast nook. Formal sitting room, a bedroom & full bath complete the 1st floor. Elegant staircase leads to gorgeous master suite with custom walk-in closet, 3 additional spacious corner bedrooms, and 2 full baths. Finished, walk-out lower level ideal as family/game room or separate space for the aupair. Newly built deck overlooks sprawling tree-lined, flat yard - perfect for summer fun! Hardwood floors throughout, 2 laundry rooms (lower level & 2nd floor!), excellent storage, attached garage & dry-walled/carpeted attic ready for completion. Easy access to major highways & only 7 miles to Boston. A great home with space for everyone!

Listed by The Gillach Group and Noha Soliman of William Raveis R. E. & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.