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Homes for Sale Winchester MA

Browse current homes for sale in Winchester MA. Contact Barrett Sotheby's International Realty or call our Winchester office directly at 781-729-7900 with any questions or to schedule a viewing. Register on the site to save your favorite listings and to receive email notifications when similar listings come to market.

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. 

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8 Olde Lyme Road Winchester MA 01890

Winchester, MA8 Olde Lyme Road

Price$1,799,000

Est. Mortgage: $/month

Open House

MLS Number 73159333

  • Residential
  • Next Open House: Sun 09/24 1:00 pm. to 2:30 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,603

Get ready to live your dream life! This house isn't just a home; it's a lifestyle upgrade with everything you could ever want. Step inside and prepare to be amazed by the huge family room, perfect for hosting Netflix marathons and epic game nights. The open kitchen and dining room are ready for your gourmet creations or takeout feasts – no judgment here. The real star of the show? A huge 3-season porch; highly coveted but rarely seen. Host dinner parties, enjoy a rain storm, make an outdoor living room. When it gets chillier, take out the screens and put in the glass inserts. There's also a large living room with a fireplace and a first-floor home office. 5 bedrooms upstairs plus a laundry room, and the lower level is home to a huge playroom and home gym, wine cellar and workshop. Oh, and the yard? Swoon worthy. Private, manicured, with gorgeous landscaping. Plus a 2-car garage. All in a super-quiet, much loved VO neighborhood.

Listed by The Pallotta Group, Christine Hintlian and Nancy S. Pallotta of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Ledgewood Road Winchester MA 01890

Winchester, MA25 Ledgewood Road

Price$5,800,000

Est. Mortgage: $/month

MLS Number 73159196

  • Residential
  • Bedrooms 7
  • Bathroom 5
  • Square Feet 4,231
  • High School Winchester

Opportunity abounds on a picturesque estate on a private road 7 miles from Boston and half mile from Winchester’s center. Custom built home on 3 heavily wooded acres and meticulously maintained by one family. This unique offering is an opportunity to create a private family compound or develop the approved 3 separate lots. A winding driveway leads to a mid-century modern masterpiece hidden from the road, offering unparalleled privacy. Floor plan is perfectly suited for entertaining as the large kitchen provides direct views into the family room with built-in bar. Generous dining room and formal living room offer views of the pastoral setting. High ceilings, a main floor study with access to one of 2 patios and en-suite bedroom on the main level. Upstairs 6 bedrooms each with dramatic views of the wooded grounds including owner’s suite with dressing room. Main house sits on over 1.6 acres with two additional lots measuring 0.5 acres each. A special property, looking for its next owner.

Listed by Karen S. Garrett, Robert Ellington and Kara Spelman of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Priscilla Lane Winchester MA 01890

Winchester, MA11 Priscilla Lane, Symmes Corner

Price$2,598,000

Est. Mortgage: $/month

Open House

MLS Number 73159121

  • Residential
  • Next Open House: Fri 09/22 5:30 pm. to 7:00 pm.
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 6,323

Stunning 6 bed, 5.5 bath NEW CONSTRUCTION Colonial. on quiet side st, minutes to Rte 3, I-93, Winchester Center & The Middlesex Fells. Thoughtfully designed with first floor suite style bedroom off main living area plus expansive second floor primary suite. Gorgeous transomed windows welcome sun throughout formal dining room and living room with custom shelving & gas fireplace. Impressive kitchen w/center island, extensive quartz counter space & high-end appliances plus a large walk-in pantry, bev center, home office & 1/2 bth complete this level. 4 Bedrooms on 2nd flr including an expansive primary bedroom suite w/cathedral ceilings, large walk in closet & luxurious bath w/shower, soaking tub & double vanity. Tiled laundry room on this level w/sink & shelving. 6th BDRM on 3rd floor, w/full bth & private sitting room perfect for in-laws or teen suite. Finished lower level w/family room, exercise room, media room & mudroom lead to attached 2 car garage. OH Fri 5:30-7pm, Sat/Sun 1130-1pm

Listed by The Synergy Group and Paul Cirignano of The Synergy Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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9 Upland Road Winchester MA 01890

Winchester, MA9 Upland Road

Price$998,000

Est. Mortgage: $/month

Open House

MLS Number 73158950

  • Residential
  • Next Open House: Sat 09/23 12:00 pm. to 2:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,468

Welcome to 9 Upland Rd, a beautiful and newly renovated colonial. As you enter the home, you’ll be greeted by the dining room, which flows effortlessly into the renovated white kitchen- featuring stainless steel appliances and an island that separates the two rooms. On your way to the spacious fireplaced living room, you’ll find a half bath with laundry, featuring a new washer and dryer. From the living room, enter the attached study/office space. On the second floor, you’ll find the primary bedroom with a beautifully redone ensuite bath, along with two more large bedrooms and a second renovated bath. The finished lower level has a versatile recreation space, and the level backyard provides the perfect space for outdoor activities.

Listed by Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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10 North Gateway Winchester MA 01890

Winchester, MA10 North Gateway, Symmes Corner

Price$2,899,000

Est. Mortgage: $/month

Open House

MLS Number 73158946

  • Residential
  • Next Open House: Sun 09/24 11:30 am. to 1:00 pm.
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 6,067

Welcome to the market 10 North Gateway, a stunning new construction property in a neighborhood that everyone in Winchester LOVES! Enter in and immediately be greeted by a gorgeous 2 story foyer with access to your formal living room. The kitchen features an oversized island and is open to the fireplaced family room. A formal dining room with slider to the patio, first floor bed/office with private full bath, pantry, and mudroom with 1/2 bath are also found on this main level. The second floor is home to 4 bedrooms including the expansive primary suite. The finished basement offers a recreation room, gym, a potential 6th bedroom, and full bath! For the outdoor enthusiast, this is where you want to live! Take advantage of the Town Forest being just outside your door for hiking, biking, bird watching, or just a simple after dinner stroll. This property is located less than 1 mile from our beautiful Town Center. Take advantage of an opportunity for a home AND location as special as this!

Listed by Vita Realty Group and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Brooks Street Winchester MA 01890

Winchester, MA11 Brooks Street

Price$3,099,000

Est. Mortgage: $/month

MLS Number 73158209

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,208
  • High School Winchester

Embrace elegance, relish a private setting & enjoy one of Winchester's finest neighborhoods! Main level open floor plan showcases a kitchen replete w/luxury ~ Quartz counters, Laurier Max cabinetry, walk-in pantry & the culinary technology of Gagganeau appliances. An expansive LR w/gas fpl & custom built-ins flows into a sunrm surrounded by a canopy of trees & outdoor patio ~ sure to make entertaining exciting! Coffered ceiling & wainscoting details accent the DR plus large windows bring in natural light and the beauty of the outdoors. FIVE spacious bedrms w/built-in closets, incl. 1st FL suite & sumptuous 2nd FL Primary Suite w/vaulted ceilings & rear-facing deck! Family Rm in LL for movie & game nights w/half bath & walkout to outdoor space plus front yard to play hoops or catch. Crafted w/attention to modern desires, nestled in a slice of serenity w/easy access to Town Forest Trails, Commuter Rail, Bus and Winchester's beloved Town Center. Private financing may be available!

Listed by Michaela Pixie Mahtani of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Forest Street Winchester MA 01890

Winchester, MA18 Forest Street

Price$1,399,000

Est. Mortgage: $/month

Open House

MLS Number 73158206

  • Residential
  • Next Open House: Sat 09/23 11:00 am. to 12:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,365

Welcome to this custom built home w/ a fabulous yard abutting town field/conservation! Stunning open floor plan, ideal for hosting gatherings, seamlessly connecting all of your spaces for modern living! The kitchen is a chefs dream which boasts custom cabinetry, high-end GE appliances, quartz countertops & a generously sized island, perfect for culinary enthusiasts. On the first floor you will also love the private deck off the kitchen, a built in bench / mudroom, the office and half bath. As you ascend up the stunning staircase to the second floor, you'll discover a primary bedroom with beautiful designer bath that features an oversized shower & double vanity w/ a large walk in closet. 2 additional bedrooms, a full bath and 2nd floor laundry complete this level which is all illuminated by a hallway skylight. The versatile lower level with a wet bar is the perfect spot to enjoy a movie, or workout, or both! Located close to town, bike path, popular parks & the train into Boston!

Listed by Kim Covino & Co. Team of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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27 Brooks Street Winchester MA 01890

Winchester, MA27 Brooks Street

Price$2,599,000

Est. Mortgage: $/month

Open House

MLS Number 73158073

  • Residential
  • Next Open House: Sat 09/23 12:30 pm. to 2:00 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,650

This gorgeous custom home in coveted Brooks neighborhood features a fabulous floor plan with stunning finishes! Thoughtfully designed w/ a dramatic living room featuring vaulted ceilings & floor to ceiling windows w/ fplc, formal dining, open concept sun-drenched kitchen w/ custom cabinetry, chefs applc’s & large island w/seating leading to family room & direct access to glorious fenced yard/patio. A convenient home office space, plus 1/2 bath & direct access to garage w/ lift complete this floor. The striking primary suite boasts vaulted ceilings, a reading nook, large walk in closet and en-suite bath. The 2nd floor includes 3 additional spacious bedrooms, a full hall bath & laundry room. Enjoy working out, movie nights & more in this homes fabulous finished basement incl. a home office w/ built in desks & a half bath. Fenced back yard w/ beautiful bluestone patio, lush landscape & turf area perfect for a play-set or pets! Across from town forest trails & close to town center / train.

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Socrates Way Winchester MA 01890

Winchester, MA19 Socrates Way

Price$3,299,000

Est. Mortgage: $/month

Open House

MLS Number 73156754

  • Residential
  • Next Open House: Fri 09/22 11:00 am. to 12:00 pm.
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5,678

ULTIMATE DESIRABLE LOCATION - CUSTOM BUILT HOME - PRISTINE CONDITION - 7 MILES to BOSTON - HALF ACRE LOT - PERFECT FLAT LOT - RARE FIND in WINCHESTER - SPACE for YOUR EVERY DESIRE . Having 14 Rooms - 5+ Bedrooms, 4 Full Bathrooms and 2 Half Bathrooms - 3 floors of finished living space with a magnificent Grand Two-Story Foyer large enough to host your holidays and family celebrations. Lower Level has four spacious rooms - including a large Family/Recreation Room - perfect for a Nanny/In-Law Suite. Professionally landscaped yard and an oversized three-car Garage. Located a short distance to Schools - Winchester Center - Library - Restaurants -Coffee Shops, Town Taverns - Boutiques - Salons and two Commuter Rail stations to Boston. Do not miss this rare opportunity to own a true dream home and become part of the Winchester Community and all it has to offer.

Listed by Lucille Murray of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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148 Highland Avenue Winchester MA 01890

Winchester, MA148 Highland Avenue, Winchester Highlands

Price$2,450,000

Est. Mortgage: $/month

Open House

MLS Number 73156261

  • Residential
  • Next Open House: Fri 09/22 5:00 pm. to 6:30 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,583

Extraordinary 5 bed, 3.5 bath Arts & Crafts Colonial, steps to The Fells. Total kitchen renovation in 2019 created chefs kitchen with 48” dual fuel Wolf range, double ovens, high velocity hood, Sub-Zero fridge, marble counters/backslash & 2 bev coolers and new 1/2 bath. Cherry hardwood on 1st & 2nd flrs, third floor finished 2019. Living room w/transom windows, coffered ceiling, custom shelving & gas fireplace. 1st floor office w/custom shelving. Primary bedroom w/cathedral ceilings, walk-in closet & sitting area w/gas fireplace & built-ins. Primary bath renovated 2015 includes steam shower & double vanity. Four additional bedrooms, 2 full baths & laundry room w/sink complete this level. Lower level finished 2019 has home gym & family room w/12’ projector & surround sound, bev center & 2nd garage access, in-law potential. Front walk, rear blue stone patio w/fire pit in 2014. 6 car driveway plus 2 car garage w/12’ ceilings. Smart Home system throughout. OHs Fri 5-6:30pm & Sun 2-3:30pm

Listed by The Synergy Group and Paul Cirignano of The Synergy Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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 Elmwood Avenue Winchester MA 01890

Winchester, MA36 Elmwood Avenue, Unit 11

Price$1,274,000

Est. Mortgage: $/month

MLS Number 73155578

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,573

SELLER FINANCING AVAILABLE!!!!! Best in class! Loads of upgrades! Introducing an exquisite new condominium that sets the bar for modern luxury living right in Winchester Center. This exceptional penthouse at Allegro boasts a plethora of upgrades, ensuring an unparalleled level of comfort, style, and sophistication. The open-concept layout seamlessly blends functionality and elegance. A gorgeous living room wall has custom wood detailing; designer lighting has been added and custom closet systems installed. Big bonus: custom made plantation shutters on the windows, offering an elegant and expensive upgrade. The kitchen is a chef's dream, with plenty of counter space and sleek appliances. This home offers the very best layout at Allegro, plus it comes with two parking spaces, washer and dryer and extra garage storage. A secure building has an intercom and camera, heated garage and an elevator. Walk to the brand new train, shops, restaurants and come back home to easy living and beauty.

Listed by The Pallotta Group and Nancy S. Pallotta of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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

34 Eaton Street Winchester MA 01890

Winchester, MA34 Eaton Street

Price$1,500,000

Est. Mortgage: $/month

Open House

MLS Number 73154965

  • Residential
  • Next Open House: Sat 09/23 12:00 pm. to 2:00 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,577

Classic details and space to fall in love with! Close to TOWN, TRAIN, SCHOOLS, LIBRARY and MIDDLESEX FELLS. WalkScore of "Very walkable" for you to enjoy all that Winchester has to offer. Move right in. Spacious 5 bedroom home offers 4 beautiful floors for all your needs. Gracious front porch, high ceilings, bullseye molding, gorgeous wood floors and lovely details to please the discerning buyer looking to be close to everything. Well maintained and thoughtfully improved: repainted exterior (2023), added ductless mini-splits (multiple years), new hot water heater, insulated third floor, smart thermostats and switches, new basement carpet and stair runner, replaced ceiling fans. Lots of storage space. Back door from kitchen leads to secluded patio with climbing hydrangeas. Less than 9 miles to Boston. Convenient to 93, 128, 2 and 3, or take advantage of the Commuter Rail.

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* 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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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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. MLSPIN 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.