Winchester MA Real Estate

View the latest real estate listings in Winchester MA below.

Winchester Homes for Sale

Contact The Home Advantage Team at 781-645-0505 or online for more information or to schedule a private tour.

79 Wendell Street Winchester MA 01890

Winchester, MA79 Wendell Street

Price$1,199,999

Est. Mortgage: $/month

MLS Number 72690804

  • Single Family
  • Rooms 10
  • Bedrooms 4
  • Year Built 1938

Dreaming of a park-like setting for your family? Perhaps a home that has beautiful updates, in a town you've always dreamed of living? This 4 bedroom, 3.5 bath, beauty will check all the boxes! Located across the street from McDonald Field, in our quintessential New England town, is 79 Wendell. Immediately upon entering you will swoon over the large dining room with access to the first of TWO home office spaces! But the real WOW factor will come when you enter into the kitchen and family room area. This open concept space has been renovated to please even the most discerning buyer. With stone accents and warm tones, this is the ideal place to quarantine! The 2nd level is home to 4 bedrooms, including the master. With vaulted ceilings, skylight, walk-in closet, and master bath, there is little left to desire! Let's not forget about the child's bed with spiral staircase and loft. Ideal for the Prince or Princess in your life. Boasting TWO driveways and a fully finished basement!

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

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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25 Lakeview Road Winchester MA 01890

Winchester, MA25 Lakeview Road

Price$1,550,000

Est. Mortgage: $/month

Open House

MLS Number 72690445

  • Single Family
  • Next Open House: Sat 07/18 12:00 pm. to 2:00 pm.
  • Rooms 9
  • Bedrooms 5
  • Year Built 1917

Beautiful colonial in wonderful neighborhood near Wedgemere train station offers 5 bedrooms and 3.5 baths. Built in 1917, you'll appreciate the quality and proportions of the home. Notice the details of wainscoting, hardwood floors, plate rail, french doors and corner hutch. Expanded over the years to create a large family room and a large en-suite bedroom with walk-in shower, dressing area and cedar closet. The second floor offers 4 bedrooms (one is currently used as an office) and the 3rd floor with bedroom and bath are a perfect spot for an au-pair or guests. Enjoy the partially fenced yard, private bluestone patio, corner lot, glimpses of Upper Mystic Lake. Exceptional location near Ginn Field, Tri-Community Bikeway and Shannon Beach. Convenient to 93, 2,3,128. Less then 10 miles to Boston, this is a rare opportunity to own a well maintained and updated home. Shown by appointment and open house. Website and 3D Tour: https://bostonrep.MLSPropertyWebsite.com/1643006?idx=1.

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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28 Fells Road Winchester MA 01890

Winchester, MA28 Fells Road

Price$2,400,000

Est. Mortgage: $/month

MLS Number 72690275

  • Single Family
  • Rooms 15
  • Bedrooms 6
  • Year Built 2017

Welcome Home to 28 Fells Road, a magnificant 3 year young colonial with 4 finished levels, scenic veiws, and everything you could need! This 6 bedroom, 6.5 bath home features spectacular grounds perfect for entertaining with an outdoor dining area, firepit, waterfall, and level fenced in grass area. Main floor centers around the kitchen, which is every cooks dream, a fireplaced family room with built in shelves, formal living room, stunning dining room, office, and en-suite bedroom. Master bedroom is made to impress with a fireplace, walk in closet, and master bath complete with vanity and soaking tub. Finished basement with large media room, exercise/game room, and full bath. Walk up attic not only features plenty of storage, but also a family room, bathroom, and additional office area. 4 car garage enters into a mudroom. Just steps away from the Middlesex Fells where you can enjoy hiking/biking/walking on over 100 miles of trails! Enjoy all Winchester has to offer!

Listed by Team Blue and Linda Ducharme of ERA Key Realty Services

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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76 North Border Road Winchester MA 01890

Winchester, MA76 North Border Road

Price$1,375,000

Est. Mortgage: $/month

MLS Number 72689694

  • Single Family
  • Rooms 9
  • Bedrooms 4
  • Year Built 1950

Has there ever been a better time to live in the suburbs? And yet downtown Boston is just 10 miles away! Enjoy both worlds in this charming craft home located directly across from The Fells!!! So much space, inside and out! A versatile floor plan with a first floor bedroom and bath (in law/nanny potential) plus three bedrooms and full bath on the second floor. Large living room with beamed ceiling and working fireplace. The dining room with beamed ceiling looks out onto a private patio. Recently renovated eat in kitchen opens into an enormous family room with stone fireplace - overlooking the half acre lot and a 'bonus' shed. Need a home office? This home has one!! Attached two car garage completes this perfect picture!

Listed by Nancy Fleming of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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 Sunset Road Winchester MA 01890

Winchester, MA3 Sunset Road

Price$1,249,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72688978

  • Single Family
  • Rooms 8
  • Bedrooms 4
  • Year Built 1980

You won't want to miss this great home in top neighborhood! With the perfect blend of location, space, price and renovation; this home is a gem! Situated on over a half acre lot with expansive private back yard, beautiful oversized kitchen with dining area & french doors leading to deck and fire pit area overlooking yard. Dining room or add'l living room w/ wood burning fplc, spacious and sunny cathedral ceiling family room, first floor optional master suite with newly renovated bath, adj. sunroom/ office or gym area, second floor features 3 bedrooms w/additional master & full bath. Lower level will not disappoint and offers beautifully finished playroom/ family room area with custom built in shelving/ wainscoting, laundry room and storage area. House is in beautiful condition with new roof recently installed. Enjoy beautiful weather in your private backyard oasis, room for a play structure, skating rink or whatever you desire!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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94 Thornberry Road Winchester MA 01890

Winchester, MA94 Thornberry Road

Price$1,225,000

Est. Mortgage: $/month

MLS Number 72688816

  • Single Family
  • Rooms 8
  • Bedrooms 4
  • Year Built 1970

Welcome home! Opportunity knocks on the very desirable Thornberry Road. This property is set on 20,000 sqft. with over 3000sqft of living space. 4-bed, 3-bath split entry home in the West side of Winchester, Beautiful open concept on main level; sun-filled kitchen offers bar seating that opens to the large family room complete with a gas stove and skylights, perfect for entertaining friends and family. The dining room opens to your very own private deck and after dinner you can relax in the fireplaced living room. The 3 bedrooms on the main level have hardwood floors and ample closet space, and the master comes with an en-suite bathroom. The Garden level/lower level boasts fireplaced family playroom/game room, bedroom, full bathroom, full laundry room and your own home office, Spacious garage & storage. Easy access to Winchester and Lexington town centers, Whipple Hill Nature Preserve, Wright-Locke Farm, Winchester Swim & Tennis Club, and major routes and commuter rail Stations.

Listed by Peter Rooney of William Raveis R.E. & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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1 Lantern Lane Winchester MA 01890

Winchester, MA1 Lantern Lane

Price$1,100,000

Est. Mortgage: $/month

MLS Number 72685634

  • Single Family
  • Rooms 8
  • Bedrooms 3
  • Year Built 1932

NEW kitchen and baths! Close to town, tennis courts and Winchester amenities. This sunny cape offers a new kitchen with island and bay window, first floor family room with gas fireplace, dining room with built in hutches and a large front-to-back living room with fireplace. Upstairs there are 3 bedrooms, a new master bath and a new shared bath - each with tiled tub and shower. On the basement level, find plenty of storage and a play room. Enjoy living "on the lane". This is NOT an association. Each single family home has a distinctly separate lot and is situated in an oval. Incredible yard with beautiful plantings. Less than a mile to Winchester Center train, shops, restaurants. Enjoy all Winchester has to offer including Packer-Ellis Tennis Courts, Middlesex Fells, Wright-Locke Farm and so much more. This is the perfect spot for the buyer looking for community. PLEASE park on Palmer Street when visiting. Follow COVID19 protocol - wear masks and gloves.

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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 Lorena Road Winchester MA 01890

Winchester, MA11 Lorena Road

Price$2,550,000

Est. Mortgage: $/month

MLS Number 72680206

  • Single Family
  • Rooms 16
  • Bedrooms 7
  • Year Built 1930

Steeped in history, 11 Lorena Road features 7,549 square feet of living space & is a quintessential New England home in both setting & style. Originally designed by renowned architect Miles Standish, a 1960s addition by Richard Wills of the elite Royal Barry Wills architecture firm-featured in Life Magazine in both 1938 & 1946 for his classic Cape Cod & Colonial home designs-added an early American pub w/ beautiful pine-paneled walls, full bar, fireplace & abundant seating as well as a country living room. In 1999 Richard's son, also of RBW, added an updated kitchen, family room & second floor bedrooms. All of this is set on 1.5+ acres of terraced land w/ patio spaces, embedded mill stones & spectacular gardens with a number of rare & unusual plantings including a certified Dawn Redwood that is one of the oldest in the US & believed to be from the original batch of seeds brought to the US from China by the Arnold Arboretum. Additional details abound in this unique, special home!

Listed by Anne Spry and Lesley Smith of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

17 Cranston Road Winchester MA 01890

Winchester, MA17 Cranston Road

Price$1,349,000

Est. Mortgage: $/month

MLS Number 72684905

  • Single Family
  • Rooms 8
  • Bedrooms 4
  • Year Built 1950

Welcome to this stylish and very versatile East Hill Custom/Expanded Cape home. Whether you choose to enjoy sunrise from the expansive front porch or fires in the back yard hearth and patio or exercise in the nearby Middlesex Fells, this home will beckon you inside. The spacious living room with a beautiful stone hearth as the focal point and french doors flows into the recently renovated kitchen with gathering island, quartz counter tops and a large dining area. The first floor offers and addition 2 bedrooms which can used as 1st floor family room and office for flex space. The second floor features one large possible master bedroom with 2 additional bedrooms, 2nd full bath and laundry area. The garage with direct entry to the finished recreation room, half bath and plentiful storage makes this a forever home. showings start Tuesday, 7/7. Click on ShowingTime link, not a phone service subscriber.

Listed by Anne Spry of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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18 Bonad Road Winchester MA 01890

Winchester, MA18 Bonad Road

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72681312

  • Single Family
  • Rooms 7
  • Bedrooms 3
  • Year Built 1942

Inviting Cape/Colonial style home in picturesque setting on a serene street. Enjoy morning coffee relaxing on the screen porch or sunset views from the master bedroom. This home has a great flexible floor plan. The front to back fireplace living offers great light and flows into both the kitchen and dining room with built in china cabinets. A half bath and screen porch complete the first floor. The second floor includes a master bedroom with 3 closets, 2 additional rooms, and a full bath. The central air, hardwood floors, quartz counters and irrigation system make this a home for today's living.

Listed by Anne Spry of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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19 Windemere Road Winchester MA 01890

Winchester, MA19 Windemere Road

Price$2,225,000

Est. Mortgage: $/month

MLS Number 72681452

  • Single Family
  • Rooms 12
  • Bedrooms 5
  • Year Built 1969

Stunning Colonial with contemporary flair! As you enter the spacious foyer,you will appreciate many custom features. Bathed in natural light, with high ceilings,each room flows into the next. Open concept eat-in gourmet kitchen with island is perfect for entertaining, with easy access to backyard and patio. Enjoy family gatherings in spacious formal dining room. As the unique layout continues with formal living room and generous size family room each boasting its own fireplace. The second floor stairwell with Brazilian Cherry flooring leads to four bedrooms and separate laundry. Private master suite on third level will wow you in every way! High ceilings, fireplace, walk-in closet and designer bath with double vanity, separate shower and soaking tub makes this space feel like a Spa get-away. Adjacent room with balcony is great for home office etc.Large finished basement with cedar storage, bar area and more,,This beautiful home is is ideal for extended family, au pair or in laws.

Listed by Cathy Paolillo of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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36 Hemingway Street Winchester MA 01890

Winchester, MA36 Hemingway Street

Price$1,579,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72681663

  • Single Family
  • Rooms 10
  • Bedrooms 4
  • Year Built 2020

This beautiful home is located in a wonderful neighborhood near Lynch Elementary and minutes from the town center, schools, shops and restaurants etc...Offering over 4,000 SF of living space on three finished levels, this could be your dream home! Open floor plan kitchen with quartz countertops/ large island with seating, high end appliances, breakfast area, Family room off the kitchen w/ gas FP and door leading to rear patio with nice level yard .. home is stunning with high ceilings, large sunny rooms, beautiful high quality details & designer finishes..4 generously sized bedrooms, laundry on 2nd floor, spacious master suite w/ double walk in closets, oversized bath, custom shower and soaking tub. 2-car garage w/direct access to house/ mudroom , Lower level with high ceilings, family room / media room & full bath .. don't miss out ~hard to find new construction at this price! Call for a private showing!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details