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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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5 Clearwater Road Winchester MA 01890

Winchester, MA5 Clearwater Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 73154946

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,713
  • High School Winchester

Opportunity abounds at this East Hill Colonial in a highly sought-after neighborhood where new construction goes for well over $2 million. Available for the first time in 50 years, this cherished home offers a wide-spanning floor plan and perfect canvas for creating a modern living space. The sunny living room with wood burning fireplace, adjacent dining room, and eat-in kitchen with quartz countertops and white cabinetry ensures comfortable daily living while you dream up the ideal design. A front-to-back family room, home office, and 1.5 baths complete the main level. Upstairs offers four bedrooms, a full bath, and unfinished bonus space that is bursting with potential for an expanded primary suite. An unfinished basement and walk-up third floor attic also offer room to further improve this property. With proximity to the Middlesex Fells and Winchester Center, this is your chance to create a dream home in an unbeatable location that seamlessly blends convenience and tranquility.

Listed by Erica Carson and Renee Ryan 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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228 Ridge Street Winchester MA 01890

Winchester, MA228 Ridge Street

Price$2,725,000

Est. Mortgage: $/month

MLS Number 73152537

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 6,265

This stunning new construction colonial showcases a sprawling 6,265 sf of luxurious living space, offering ample room for entertaining & comfortable everyday living. With 5 beds, 5.5 baths & a 2-car garage, this home is designed to accommodate your family's every need. The grand foyer welcomes you with its soaring ceilings & exquisite detailing, setting the tone for the rest of the home. The kitchen features top-of-the-line appliances & a generous island that serves as the centerpiece for gatherings & casual dining. Adjacent to the kitchen, an inviting family room with fireplace. Retreat to the master suite, boasting a spa-like bath & walk-in closet. Five additional bedrooms including a 1st floor guest suite offers room for everyone in the family. Lower level bonus room, can be used as a home office, playroom, or gym, conveniently connects to the yard, allowing easy access. Outside, a professionally landscaped yard surrounds the property, providing a serene oasis for outdoor enjoyment.

Listed by Pirani & Wile Group, Peter Pirani and Julie Wile Fish 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 Kirk Street Winchester MA 01890

Winchester, MA18 Kirk Street

Price$1,150,000

Est. Mortgage: $/month

MLS Number 73151112

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,653
  • High School Winchester High

One of the best deals on price per square foot for Winchester, AND18 Kirk St has everything you could ask for! Located on a dead-end street, in walking distance to McDonald field with its baseball field, tennis and basketball courts. Less than a mile walk to downtown shops and restaurants and the outstanding Winchester high school, easy access to routes 93 and 95. Even just a 3 minute drive to Horn Pond in Woburn. The first level has a recently remodeled kitchen, living room, dining room, family room with vaulted ceiling, bedroom and full bath. Level two features two additional bedrooms and second full bath. The lower level boasts a large playroom with bar and fireplace, laundry and storage, with in-law potential having the exterior walkout along with water lines ready to be tied into for a sink behind the bar. With a completely new interior paint job, 3 year old heating system, recently installed central AC this home leaves nothing left to do other the hand over the keys!

Listed by Jared Venezia of Cameron Prestige,LLC

$
$
%
$/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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50 Emerson Road Winchester MA 01890

Winchester, MA50 Emerson Road

Price$2,599,000

Est. Mortgage: $/month

Open House

MLS Number 73150154

  • Residential
  • Next Open House: Sun 09/24 12:00 pm. to 2:00 pm.
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,051

Don’t miss this stately young Colonial beautifully sited atop a hillside in this sought-after West Side neighborhood. The home is brilliantly designed with open floor plan that integrates indoor and outdoor living space including a covered patio and in-ground pool. Other design features include en-suite bedrooms, two story foyer with chandelier lift, private first floor office/library with custom built-in shelving, bar with 2 refrigerators, 3 fireplaces, heated garage and chef's center island kitchen with Wolf Range, Sub Zero, Miele coffee maker, 2 dishwashers, 2 sinks and warming drawer. Need more space? There is plenty of room for expansion both on the second floor (687 SF) and basement (1,917 SF). Recent updates include all new HVAC equipment. This home is ideal for those seeking a village lifestyle with privacy and modern living just steps from the A+ rated Ambrose Elementary school, library, Winchester Center, restaurants, farmer’s market, commuter rail and major commuting routes.

Listed by Steve Leavey of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/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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8 Glenwood Avenue Winchester MA 01890

MLS Number 73148193

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,225
  • High School Winchester

Newly constructed 3-bedroom townhouse. First floor has great open floor plan with hardwood floors throughout. Kitchen features all stainless steel appliances, granite countertops, center island, and dining area. Living room has gas fireplace. Sliding door grants access to deck and back yard. Second floor has 3 nicely sized bedrooms with a full bath. Primary bedroom with walk-in closet and beautiful en-suite. Finished front-to-back third level provides great extra space as family room or home office. Maintenance free exterior, Hardy Plank Siding and Treks for the front porch and back deck. Large driveway provides plenty of off street parking. Basement has high ceilings and walk out to the back yard.

Listed by Michael Rauseo 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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8 Glenwood Avenue Winchester MA 01890

MLS Number 73148188

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,225
  • High School Winchester

Newly constructed 3-bedroom townhouse. First floor has great open floor plan with hardwood floors throughout. Kitchen features all stainless steel appliances, granite countertops, center island, and dining area. Living room has gas fireplace. Sliding door grants access to deck and back yard. Second floor has 3 nicely sized bedrooms with a full bath. Primary bedroom with walk-in closet and beautiful en-suite. Finished front-to-back third level provides great extra space as family room or home office. Maintenance free exterior, Hardy Plank Siding and Treks for the front porch and back deck. Large driveway provides plenty of off street parking. Basement has high ceilings and walk out to the back yard.

Listed by Michael Rauseo 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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18 Middlesex Street Winchester MA 01890

Winchester, MA18 Middlesex Street

Price$2,650,000

Est. Mortgage: $/month

MLS Number 73147332

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,233
  • High School Winchester

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: 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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7 Grant Road Winchester MA 01890

Winchester, MA7 Grant Road

Price$999,000

Est. Mortgage: $/month

Open House

MLS Number 73140496

  • Residential
  • Next Open House: Sat 09/23 11:00 am. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,034

A Wonderful home to make your own! Or Contractors, envision the future! Enter into the Living Room with a beautiful bow window overlooking the front. The Dining Room is open to the Living Room making a spacious entertaining area. The kitchen is centrally located to all rooms and has access to the solarium, back yard, and the downstairs. The main level has Hardwood floors and tile in the kitchen. Downstairs you will find a Family Room with wood stove, & a bar area, (plumbing is available to add a sink). A full bath, separate laundry area & a large storage area with direct access to the garage complete this level. Upstairs are 3 generous bedrooms, hardwood floors, & a full bath with tile floor. The backyard is fenced with raised garden beds perfect to add your favorite veggies or flowers! The Sun Room has a hot tub and overlooks the fenced backyard along with an adjacent deck. Great Location, easy access to 93. Sold as is, quick close possible.

Listed by Karen Brown of RE/MAX Innovative Properties - Hollis

$
$
%
$/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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15&lot227 Vinson Circle Winchester MA 01890

Winchester, MA15&lot227 Vinson Circle

Price$6,500,000

Est. Mortgage: $/month

MLS Number 73134071

  • Residential
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 8,805
  • High School Winchester

Visionary New Construction has begun! Quality and 1st class design define this rare legacy residence.Spectacular interpretation of a modern colonial designed by acclaimed architect & built by Master Builder.Impeccably positioned on one of the highest points in Winchester & commanding seasonal skyline vistas.Start your tour with the Grand 23' Entrance Hall.Sail under fabulous 10' ceilings throughout the main floor as they carry you past the library,dining room,into the living room, stunning kitchen & breakfast room.2nd floor provides 3 generous en suite BR's,Gallery,and the Grand Primary Suite with sensational dressing room & bathroom.Lower living/play space enhanced with magnificent family room,kitchenette,glass enclosed gym,game room,wine lounge,connecting wine cellar,and au pair suite with adjacent full bath.Close to an acre on 2 lots,home will be majestically oriented boasting a deep 85' setback from the street while providing rear entertaining grounds of magazine quality. No equal.

Listed by Anthony Marino of The Marino Group Collection

$
$
%
$/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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34 Edward Drive Winchester MA 01890

MLS Number 73132032

  • Condo
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,754
  • High School Winchester

Don't miss this light-filled, spacious townhome at Pepper Hill Estates! Enjoy the best of open concept living in a 3 bedroom, 3.5 bath that directly abuts Wright Locke Farm conservation land and offers gorgeous, tree-lined views and abundant natural light. The first floor offers both a front sitting room with fireplace and an oversized living room that leads to a screened in private deck overlooking the Whipple Hill conservation area. Entertain in the lovely chef's kitchen and spacious dining area. Walk directly from the 1st floor to your private attached garage. Upstairs you'll find two generous bedrooms, including a master with ensuite bath. A fully finished basement includes a large office/game room with direct backyard access as well as laundry, 3rd bedroom, storage area and a full bath! Conveniently located in Winchester, but close to Arlington Heights, Whipple Hill Reserve and Mullen Field. This truly special home awaits you!

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

$
$
%
$/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 Winchester Place Winchester MA 01890

MLS Number 73122982

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,256
  • High School Winchester

New white kitchen! Move right in & live in the heart of Winchester! This stunning high end penthouse condo is the premiere unit in the building with 2 beds/2 baths plus a giant private deck with spectacular views of the center! Enjoy easy living w/ 2 car garage parking & having local coffee shops, restaurants, public transportation & more right outside your door! With its rich finishes & elegant design, this stunning unit is a great place to call home. Enjoy high ceilings throughout, beautiful hardwood floors & a gorgeous oversized private roof deck plus a balcony. The kitchen boasts custom cabinetry, gas range & stainless steel appliances. The light filled, open concept family room has a stunning fireplace & a large wall of glass overlooking the center. Spacious walk in closet attached to the large primary bedroom. This elevator building provides easy access w/ 2 deeded parking spots in the heated garage, 228 sqft private storage space on the lower level & gorgeous common lobby entry.

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

5 Swan Road Winchester MA 01890

Winchester, MA5 Swan Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 73122720

  • Residential
  • Bedrooms 7
  • Bathroom 3
  • Square Feet 4,090
  • High School Winchester

Must see this one of a kind home nestled into Myopia hill, a top Winchester neighborhood! Customize this rare gem offering grand yet intimate shared family spaces, plus a 3 room in law or au-pair suite w/ separate entry. Stunning formal dining, living room with fireplace & beautiful molding detail, adjacent office & sunny oversized family room w/ walls of windows. You will love the quaint yet updated kitchen, butlers pantry & breakfast nook off playroom/ den (or 1st floor bed) & full bath. 5 bedrooms on the 2nd floor with a second living room, sitting room plus 2 full bathrooms. Two additional bedrooms and an oversized storage room on the 3rd floor. Enjoy relaxing on the glorious wrap around porch, overlooking the gorgeous, lush yard w/meandering walkways, flowering perennial plantings & 2 car garage/carriage house w/ ample parking. 5 Swan Road offers incredible privacy & undeniable curb appeal located just minutes from downtown Winchester, the Mystic lakes and just 7 miles from Boston

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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