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Homes for Sale Winchester MA

Browse current homes for sale in Winchester MA. Contact Barrett Sotheby's International Realty 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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53 Hutchinson Road Winchester MA 01890

Winchester, MA53 Hutchinson Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 73000316

  • Residential
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4,805
  • High School Winchester

Meticulously cared for Colonial with picture perfect golf course views! This stunning "Smart" home has been designed with incredible craftsmanship and to suit today's modern lifestyle. Generous formal entry with dramatic high ceilings and gorgeous hardwood floors throughout. Chef's kitchen features stainless steel appliances, granite countertops & custom cabinetry. Open concept to the kitchen is the living room with a coffered ceiling & custom built-ins for additional storage. First floor includes a formal dining room, home office along w/ a bedroom & full bathroom. Main bedroom is a retreat! Featuring two walk-in closets & a spa like en-suite bathroom! Additional 4 spacious bedrooms and 3 bathroom complete this level. Finished lower level w/ a generous bonus room! Conveniently located near Vinson Owen & a short distance from downtown Winchester, restaurants, boutiques, and not to mention the commuter rail to Boston! Exceptional opportunity to become a part of this Winchester community

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

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%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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17 Clark Street Winchester MA 01890

MLS Number 72999357

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,500
  • High School Whs

OPEN HOUSE SUNDAY 8/7, 11-1 Beautifully RENOVATED townhome that lives and feels like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 mile to the high school, Wedge Pond, Elliot Park, Borggaard Beach & Splash Park & the Tri-Community bike path,1/2 mile to commuter rail and town center shops and restaurants and 7 miles to Boston! The main floor of this open concept, fresh & clean unit boasts lofty ceiling heights, oak flooring throughout, living room with electric fireplace open to the dining area and a beautiful white kitchen with bar seating, quartz counters, tiled backsplash, high end stainless appliances & brass hardware. 3 bedrooms, more lofty ceilings, beautifully restored pine flooring, a dedicated laundry room, super spacious full bath and storage everywhere! All new systems including central air, Anderson windows throughout and a full basement for storage.Enjoy your private, backyard sanctuary & off street parking!NO FEES just INS

Listed by Chrisanne Connolly of Wilson Wolfe Real Estate

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%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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17 Clark Street Winchester MA 01890

MLS Number 72998841

  • Condo
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,500
  • High School Whs

OPEN HOUSE SUNDAY 8/7, 11-1Beautifully RENOVATED townhome that lives and feels like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 mile to the high school, Wedge Pond, Elliot Park, Borggaard Beach & Splash Park & the Tri-Community bike path,1/2 mile to commuter rail and town center shops and restaurants and 7 miles to Boston! The main floor of this open concept, fresh & clean unit boasts lofty ceiling heights, oak flooring throughout, living room with electric fireplace open to the dining area and a beautiful white kitchen with bar seating, quartz counters, tiled backsplash, high end stainless appliances & brass hardware. 3 bedrooms, more lofty ceilings, beautifully restored pine flooring, a dedicated laundry room, super spacious full bath and storage everywhere! All new systems including central air, Anderson windows throughout and a full basement for storage.Enjoy your private, backyard sanctuary & off street parking!NO FEES other than INS

Listed by Chrisanne Connolly of Wilson Wolfe Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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28 Henry Street Winchester MA 01890

Winchester, MA28 Henry Street

Price$749,000

Est. Mortgage: $/month

MLS Number 72998264

  • Residential
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,279

Classic ranch style home with room to grow and expand. Freshly painted inside and out. Family friendly neighborhood in the esteemed Vinson Owen School district. Readily within walking distance of Locke Farm. Finished basement with additional wood burning fireplace and access to car garage. Extra large deck and newly fenced in yard perfect for entertaining. Easy access to Arlington, Cambridge and Boston via car or bus route.

Listed by Dave White of OwnerEntry.com

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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73 Sheridan Circle Winchester MA 01890

Winchester, MA73 Sheridan Circle

Price$1,799,000

Est. Mortgage: $/month

MLS Number 72989773

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,090
  • High School Whs

Stunning 4 bedroom 3.5 bath Colonial home from premier builder resides in a desirable neighborhood is a must see! Only a few minutes walk to Horn Pond. This beautiful home features High ceilings, large sunny rooms, beautiful details, and custom woodwork. 1st level offers sunlit formal living room and dining room. Chef's kitchen with custom built cabinetries, granite counter tops, kitchen island and stainless steel appliance opening to the spacious rear deck through a French door.Upper level houses a generous master suite with spa bath, 3 additional bright oversized bedrooms and custom full bathrooms. The walk-up attic can be finished for extra living spaces. Finished basement with windows and a full bath can be used for additional bedrooms/entertaining. This home is everything you've been searching for!

Listed by Alina Wang and Lin Zhu of Coldwell Banker Realty - Lexington

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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3 Alice Lane Winchester MA 01890

Winchester, MA3 Alice Lane

Price$2,699,000

Est. Mortgage: $/month

MLS Number 72986324

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 6,000
  • High School Winchester Hs

NEW CONSTRUCTION!! Must see this gorgeous 4/5 bedroom home with thoughtful design & high end finishes! This luxurious home is spacious and inviting, offering a grand open floor plan ideal for entertaining & modern day family living. The kitchen features an oversized island with seating/ double thick quartz countertops, high-end appliances, wine bar w/ fridge, breakfast nook/dining area. Off the kitchen is a spacious family room w/gas fireplace & direct exterior access w/ sliders leading to large deck or patio & private rear yard. The first floor also has a formal dining room and 5th bed OR home office with adj. bath. The second level master suite is a DREAM, offering a 2 room suite; bedroom with separate sitting room, dual walk-in closets, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds incl. junior suite w/ bath, full hall bath & laundry room finish this level. Finished lower level media/ rec room w/ full bath, 2 car garage direct to great mudroom!

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

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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54 Johnson Road Winchester MA 01890

Winchester, MA54 Johnson Road

Price$4,175,000

Est. Mortgage: $/month

MLS Number 72984802

  • Residential
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 7,982
  • High School Winchester

Presenting a new construction masterpiece that's a refreshing break from the ordinary, it's extraordinary! This exceptional home was designed to be beautiful yet casual, where everyday living is fabulous! From the moment you step through the 8’ arched handcrafted wrought-iron front doors you are struck by the impressive 20' soaring foyer, 10' ceilings, custom rift-sawn beams and massive floor-to-ceiling windows. Unparalleled construction, quality and craftsmanship from a master builder w/ 25 yrs experience are apparent. The striking architecture continues on all 4 finished levels leaving one wanting for nothing. Features include incredible kitchen w/ 2 islands, vaulted ceilings throughout, a 3 bay (6 car) garage, breathtaking breakfast nook, butlers & dry pantries, 1st fl study/inlaw, open finished attic, huge finished basement w/ natural light that feels like a 1st floor with game, exercise and media rooms. With excellent location & schools, this unequaled home is a must-see!

Listed by Team Suzanne and Company and Suzanne Koller of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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380 Highland Avenue Winchester MA 01890

Winchester, MA380 Highland Avenue

Price$1,289,000

Est. Mortgage: $/month

MLS Number 72982187

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,633
  • High School Winchester

Your second chance at moving into this exceptional Cape on the corner of a private cul-de-sac in East Hill! Just minutes from Winchester Center, the Fells, restaurants & the commuter rail. Captivating Cape has been updated w/ modern conveniences while still maintaining the integrity & charm of the original home. Beautiful craftsmanship throughout featuring gorgeous hardwood floors, custom built-ins, oversized wood burning fireplace, along w/ a sunny Florida room with access to the outdoor patio. Formal dining room is located near the updated chef's kitchen. Kitchen features custom cabinetry, SS appliances, beamed ceiling, ample storage & space to eat-in. A cozy family room completes this level. Spacious main bedroom with custom California closets and ensuite bathroom. Three additional bedrooms & a full bathroom complete the second floor living. Outdoor patio surrounded by flower gardens, storage shed & a newly paved driveway.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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10 Sheffield Road Winchester MA 01890

Winchester, MA10 Sheffield Road

Price$3,550,000

Est. Mortgage: $/month

MLS Number 72978329

  • Residential
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 5,877
  • High School Winchester High

Refined, elegant and turnkey, this Colonial Revival is on one of Winchester’s premier streets. Steps to train, town, and the desirable Ambrose school. Designed for entertaining, working from home and multi-generational, family life, the 1st floor features a beautifully functional, customized chef’s kitchen, spacious living room, family room, dining room, a half bath, & mud room. The 2nd floor boasts a luxurious master suite w/ walk-in closets & large master bath/jacuzzi, plus 2 additional bedrooms & updated bathroom. The 3rd floor includes 3 large bedrooms, walk-ins & other large closets, plus 2 full bathrooms, currently configured w/ large studio/office & spacious study with lovely views of the Sheffield/Everett neighborhood. Fully finished basement with wet bar & wine cellar. New two-car garage, storage shed, patio/deck & sizeable lot. Renovations include kitchen extension, deck, wrap around porch, HVAC, windows, top grade electric & IT wiring, beautiful wood flooring, and more!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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7 Brantwood Road Winchester MA 01890

Winchester, MA7 Brantwood Road

Price$949,900

Est. Mortgage: $/month

MLS Number 72947675

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,630
  • High School Whs

Major Price Adjustment, now is your time to get in before the school year starts! Charming Colonial is within walking distance to Horn Pond. Exceptionally well cared for home with LANDSCAPED YARD. The 1st floor has a four-season enclosed porch that overlooks the SPACIOUS BACK YARD, Hardwood Floors, Pella Windows, FP Living Room, Dining Room, Kitchen, and a half bath. The lower level has a workspace and a finished room that is great for families or future home gym. There are 3 good-sized bedrooms on the top floor and a spacious family bathroom. The two-car garage has a LOFT AREA that may be used for a future Yoga Room. ENJOY THJE EASE OF HAVING THE LYNCH ELEMENTARY SCHOOL STEPS FROM YOUR HOME, SEASONAL ICE SKATING, AND FISHING ON BIG & LITTLE WINTER PONDS, or JOGGING OR WATCHING THE SUNSETS on HORN POND. WHOLEFOODS SHOPPING PLAZA IS ALSO CLOSE BY!.7 Brantwood is a DEAD END STREET. The home was fully insulated by Mass Save.

Listed by Boston RE Group, Anthony Menounos and Heather Olin of Coldwell Banker Realty - Back Bay

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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