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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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27 Mount Pleasant Street Winchester MA 01890

Winchester, MA27 Mount Pleasant Street

Price$3,199,000

Est. Mortgage: $/month

MLS Number 73060152

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,284

This redefined custom built home is just a couple minutes walk to downtown! While the floor plan has been finalized, there is still opportunity to customize the home of your dreams. The finished home will include 5 beds and 4.5 baths. 1st floor will be state of the art kitchen inclusive of Thermador appliances with 54" fridge/freezer combo and double wall oven anchored by a generous island. The fireplaced family room, formal dining room, casual eating/craft area, pantry, mudroom, fireplaced living room, and guest suite all on 1st floor with custom built ins and detailed moldings throughout. 2nd floor will consist of 4 bedrooms, laundry room, reading nook/study, and 3 bathrooms. Basement includes bonus areas, storage and lower mudroom. 2 car attached garage. Outdoor patio area and professionally landscaped lawn space complemented by extensive stonework throughout the property.

Listed by Mark Donnellan of Better Homes and Gardens Real Estate - The Shanahan Group

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%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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20 Westland Avenue Winchester MA 01890

Winchester, MA20 Westland Avenue

Price$2,299,000

Est. Mortgage: $/month

MLS Number 73059770

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,400
  • High School Whs

Extraordinary ALL NEW renovation/expansion! 4 bedroom 3.5 bath colonial with 2 story rear addition in top west side neighborhood; the most recent project by premier design/build team “Renew” w/ high end finishes from Ralph Lauren, Restoration Hardware, Duravit, Emtek & more! The must see kitchen is the focus of main level boasting an oversized Carrera marble island, custom cabinetry & gorgeous overhead designer light fixture. Desirable open concept kitchen & family room w/fireplace, walls of windows & French doors leading to oversized patio & newly landscaped yard. Living room w/wood burning fireplace & french doors plus a great home office flooded w/ sunlight, mudroom side entry w/built-ins & spacious half bath complete the first level. Second level has a fabulous primary suite with high cathedral ceilings, sitting area & marble spa-like bath plus 3 additional bedrooms & 2 full gorgeous baths. Lower level offers a large family room w/fireplace & office/rec/workout room. Just perfect!!

Listed by Kim Covino & Co. Team of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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48 Oak Street Winchester MA 01890

Winchester, MA48 Oak Street

Price$2,099,000

Est. Mortgage: $/month

MLS Number 73059441

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,534

New Construction just a short walk to downtown! Development is underway and slated for completion in late spring! 1st floor has an inviting open concept layout with kitchen, family room and dining room. Workstation with built in desk and walk in pantry adjacent to kitchen area as well! The balance of the 1st floor offers a living room/office and bedroom with bath or could also be used as a study or extra play area! 2nd floor has spacious primary suite with generous closet and dream bathroom with dual vanities and plenty of storage. 2nd bedroom upstairs also has en-suite bath. 2 additional bedrooms on 2nd floor. Laundry room on 2nd floor completes the level. Bonus room in lower level will truly be a great bonus! Exterior offers patio with built in entertainment center! The design board pictures are attached also with pictures from a recently completed project in Winchester...

Listed by Mark Donnellan of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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241 Cross Street Winchester MA 01890

Winchester, MA241 Cross Street

Price$729,900

Est. Mortgage: $/month

MLS Number 73056235

  • Residential
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 828

Here is your opportunity to own in Winchester! Close to Winchester Hospital, Horn Pond, and public transportation. Just minutes from I93 for a quick drive into Boston. This 2 Bedroom ranch is situated on a beautiful corner lot with a fenced yard and a detached garage. Endless opportunities and potential!

Listed by Shawn McEntee of Classified Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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44 Clark Street Winchester MA 01890

Winchester, MA44 Clark Street

Price$1,449,000

Est. Mortgage: $/month

Price Changed

MLS Number 73055391

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,498

Absolute dream of a home that was redeveloped by maximizing the interior and exterior space. Perfect for today's living with home office/1st floor bedroom flex space. Kitchen, dining, living space blended wonderfully together. Separate pantry and mudroom areas on 1st floor. Spacious lower level family room with vaulted ceilings. 3 bedrooms upstairs with primary bath offering dual sink vanity as well as common bath also with dual sink vanity. The finishing touches of every area of the home exude luxury and warmth! Exterior space includes a sprawling patio with fire pit! Short 5 minute walk to downtown!!

Listed by Mark Donnellan of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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12 George Winchester MA 01890

Winchester, MA12 George, Unit 12

Price$495,000

Est. Mortgage: $/month

MLS Number 73055486

  • Condo
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 968
  • High School Winchester High

Wonderful opportunity to live in Winchester or investment for rental income! Welcoming, light-filled, move-in ready condo. Inviting living room beckons to relax & flows into the dining room & adjacent kitchen which overlook the fenced backyard. 2nd floor offers a spacious primary bedroom, secondary bedroom (or home office) & full bath. Hardwood floors in living room, dining room & bedrooms. Lower level has washer & dryer, ample room for storage or infuse your own personal style to finish it. October 2022: Upgraded bathroom & several rooms freshly painted. Parking for 2 cars in driveway. Winchester is a delightful town with shops, restaurants, excellent schools – Winchester High ranked #2 in the state, approximately 8 miles from Boston & 2 commuter rail stations.

Listed by V. Charlotte Richardson of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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200 Swanton Street Winchester MA 01890

MLS Number 73054579

  • Condo
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 613
  • High School Winchester High

Don't miss this special one-bedroom with remodeled kitchen, a spacious peninsula, and a ceiling fan. The large living room boasts of lots of wall space for wall hangings and a dining area. You will enjoy the organized bedroom walk-in closet. Easy access right off the West Entrance elevator. Relax by the fenced-in pool and barbecue garden area at the rear of the complex. One unassigned parking is guaranteed by deed, but a second may be available for $600 per year plus $65 for the extra parking pass. The low monthly condo fee of $332 includes heat, air conditioning, electricity, and hot water. A ceiling-to-floor storage unit is for your use in the lower level of the complex. A rather unusual amenity is the large guest parking lot with a separate entrance. Enjoy beautiful Winchester and all it has to offer. Great for commuters - close proximity to Boston, Cambridge, and the North Shore.

Listed by Mary Lou Bigelow of Gibson Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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 Socrates Way Winchester MA 01890

Winchester, MA1 Socrates Way

Price$1,995,000

Est. Mortgage: $/month

MLS Number 73054183

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 5,122
  • High School Whs

SPACE GALORE! Welcome to this fantastic 5 BR, 3.5 bath colonial on a little over an acre lot. The comfortable floor plan maximizes space with plenty of room for entertaining and spreading out. The light and airy living and dining room lead to a good size open concept kitchen which sits right in the center of the home. You'll feel as though you are perched up on a bird's nest looking out from the family room to the deck. On the 2nd FL, the primary suite is equipped with a fireplace, walk-in closet & full bath with a soaking tub. Laundry and 2 additional bedrooms complete this floor. The third level offers 2 additional bedrooms w/ full bath and office/media room. You'll love the convenience of simply taking a few stairs to your own home gym and hair/make up studio in the basement level, offering perfect for access for trainers and stylists. Outside this home is surrounded by mature trees and a direct path to Nutile Field make for a picturesque suburban setting.

Listed by Johan Lopez of Home Shop Properties,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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70 Canal Street Winchester MA 01890

Winchester, MA70 Canal Street

Price$799,900

Est. Mortgage: $/month

MLS Number 73053612

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,765
  • High School Whs

70 Canal Street is a 4 bedroom cape with character! This home, situated on a corner lot, is awaiting its new owners and their ideas! The first floor living room includes a wood burning fireplace, hardwood floors and the doorway to the spacious three season sunroom. Next you will find the dining room-which is nestled between the living room and the kitchen. The door off the kitchen allows access to the nice backyard space for easy entertaining outside in the warmer weather. There are two bedrooms (or work from home space) and a full bathroom that complete this floor. Upstairs you will find the other two generous sized bedrooms and second full bathroom. Laundry is in the spacious lower level along with plenty of storage space and a bonus finished room. This quaint New England town has everything you need including easy access to 93 and less than 10 miles to downtown Boston. Plenty of coffee shops, restaurants, salons, boutiques, bookstores & more.

Listed by Melanie Lentini of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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422 Highland Avenue Winchester MA 01890

Winchester, MA422 Highland Avenue

Price$1,495,000

Est. Mortgage: $/month

MLS Number 73053016

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,808
  • High School Whs

Welcome home to an updated, charming Colonial near the heart of Winchester Town Center! Meticulously cared for with endless updates and enhancements throughout the entire home. Gorgeous craftsmanship and hardwood floors throughout. Enter into an open foyer w/ impressive staircase & including custom built-in organizational shelving. Formal dining room features wainscoting, crown molding, along with a built-in cabinet for extra storage. Chef's gourmet kitchen w/ updated stainless steel appliances & ample storage. Newly renovated half bathroom! First floor bedroom including custom built-ins. Spacious living room with wood burning fireplace. Sun room is perfect for a play area or home office. Second living level features a completely renovated primary bedroom with a spa-like en-suite. Two additional bedrooms with a full bathroom complete this level. Expansive lower level has great potential and ample storage. Two car garage with a phenomenal backyard for entertaining!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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987 Main Street Winchester MA 01890

Winchester, MA987 Main Street

Price$1,245,000

Est. Mortgage: $/month

MLS Number 73048427

  • MultiFamily
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,618
  • Parking Spaces 6

A solid built 2 family house, circa 1910, offering a flat 4,600 sq ft lot. This residence is a TREMENDOUS OPPORTUNITY FOR CONDO CONVERSION OR REHAB! 1st floor unit has 2 beds & currently used as an office. The 2nd floor has 3 bedrooms & large eat in kitchen. Amenities include detached 2 car garage; a private rear yard; welcoming front porch & basement laundry hook ups. Dynamite commuter location! Sold as is.

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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 Middlesex Street Winchester MA 01890

Winchester, MA18 Middlesex Street

Price$2,595,000

Est. Mortgage: $/month

MLS Number 73047571

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,500

This extraordinary property is privately situated, yet, just minutes from Boston. European inspired and masterfully crafted, showcases sophisticated design and top-of-the-line systems. A well appointed floor plan awaits with grand scale rooms and elegant charm. Enter through the magnificent foyer, featuring a beautiful curved staircase that leads into the formal living room and separate family room. Bespoke chef's kitchen comes outfitted with professional grade appliances, fireplace and adjoining mudroom. In addition to 3 en-suite secondary bedrooms, the primary suite rivals the finest hotels offering a spa like bath, complete with bidet and w/I closet. Seamless indoor/outdoor flow through 8 sets of French doors to marble columned loggia, lush landscaping, sparkling salt water heated pool and sound system thru-out. An unparalleled entertainment oasis. Other features incl 350 gallon Reef Tank, full wet bar, ideal LL au-pair suite, heated driveway. All a stones throw from town center.

Listed by Candice Macoul of Luxury Living Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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

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