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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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20 Mayflower Road Winchester MA 01890

Winchester, MA20 Mayflower Road

Price$1,495,000

Est. Mortgage: $/month

Contingent

MLS Number 73014698

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,744
  • High School Winchester High

Magnificent Multi Level in sought after West Side neighborhood. Beautifully appointed throughout, this home combines classic details w/modern upgrades & a desirable open floor plan. Gourmet granite kitchen w/center island, wine fridge, double oven, SS appliances, & plenty of cabinetry is truly a cook & entertainer’s dream! The kitchen opens to a family room & also features an impressive vaulted, beamed ceiling & large oversized windows allowing an abundance of natural light & views of the beautifully landscaped yard w/a double tiered deck. Spacious living room w/fireplace & formal dining room w/french doors complete this level. Just a few steps down, you'll find a convenient half bath, laundry room, flex home office space & a mudroom leading out to an oversized 2 car garage. 2nd level consists of a primary bedroom suite w/double custom closets & 3 additional bedrooms. Finished lower level w/fireplace'd great room & game room offers endless possibilities! An ideal property to call home!

Listed by McGlynn Splaine & Nigro Team, Michele McGlynn and Antonella Nigro of Berkshire Hathaway HomeServices Commonwealth 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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28 Pierrepont Road Winchester MA 01890

Winchester, MA28 Pierrepont Road

Price$1,275,000

Est. Mortgage: $/month

Open House

MLS Number 73012272

  • Residential
  • Next Open House: Sun 08/7 3:15 pm. to 4:30 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,623

Gorgeous colonial that offers lots of privacy in a picturesque neighborhood. Cozy up next to the wood fireplace (w/ pipes for gas!) in the living room before you make your way into the family room. Then, take a seat at the eating area where you can watch the birds or enjoy the view of the backyard through the expansive corner of windows. From there, you can either go into the kitchen or walk out onto the deck and enjoy the serenity of the private backyard. The dining room exudes elegance with its beautiful built-in corner cabinet, bay window and dentil molding. If you like to work from home, then you’ll love the private office with separate entry and an adjacent full bathroom. Up on the second floor, you’ll find the master suite with full bath and spacious walk-in closet- along with 2 more bedrooms, a family bath, and built-in cabinets in the hallway. Lastly, the finished lower level makes for a perfect playroom or exercise room.

Listed by Anne Spry of Barrett Sotheby's International Realty

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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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101 Harvard Street Winchester MA 01890

Winchester, MA101 Harvard Street

Price$839,000

Est. Mortgage: $/month

MLS Number 73013205

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,236
  • High School Winchester High

Wonderful renovated Colonial in Winchester's desirable Muraco School District is waiting for you to just move in and unpack! Walking distance to parks, town center, and the Commuter Rail to Boston. Fully equipped with efficient systems and Central Air. Crisp Hardwood floors throughout. Sunlit and semi-open First Floor with handsome architectural details, a lovely kitchen with gas cooking, granite counters, stainless steel appliances and conveniently located laundry. Three bedrooms upstairs with a terrific family bathroom and an office complete the Second Floor. Additional finished Lower Level not included in the square footage makes for an excellent playroom or bonus space. Fenced in backyard is perfect for hosting family and friends on a nice day. Located on a dead end street where you can enjoy your mornings on your beautiful fieldstone porch. Don't delay on this charming Winchester home!

Listed by Charles Elia and Casey L. Elia of RE/MAX Renaissance Inc.

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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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9 Blossom Hill Road Winchester MA 01890

Winchester, MA9 Blossom Hill Road

Price$1,050,000

Est. Mortgage: $/month

MLS Number 73012722

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,376
  • High School Winchester Hs

Expanded and inviting 8 room 3 bedroom ranch in one of Winchester's finest neighborhoods with easy access to shopping,highway! Enter into this lovely home with some handicap features including an entry ramp, stair chair and easy handle grips and step into the oversized entry hall. Hardwood floors throughout this home offering a large living room with bay window and fireplace. The dining room is old charm with built in china cabinet, chandelier and French door to the heated sunroom with stone floor and lots of light. Kitchen is bright and sunny with a large bay window & is fully set up with eating area waiting for your touches! Primary bedroom is kingsized with closet and a 3/4 tiled bath. Two additional bedrooms and full tiled bath. Lower level is finished with a huge family room with fireplace and closet for great entertaining! Lots of storage, laundry with large work sink. New roof (2021) and newer Buderus heating system. Two car garage.This home is ready for you to make it your own!

Listed by Beverlee Vidoli of RE/MAX Realty Experts

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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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12 Albamont Road Winchester MA 01890

Winchester, MA12 Albamont Road

Price$1,079,000

Est. Mortgage: $/month

MLS Number 73012569

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,413
  • High School Winchester High

Super West Side Location! Spacious one owner ranch in Ambrose School District. Lovingly cared for and well maintained property only minutes to Boston.The first floor consist of an eat-in kitchen, formal dining room great for the holidays. A sun filled enclosed porch is great for the summer months and overlooks a lovely landscaped yard. An oversized fireplaced living room will keep you warm in the winter or enjoy a movie night in the cozy den, 3 spacious bedrooms with hardwood floors have been covered. The finished lower level features a familyroom with fireplace, additionally a large open second space consisting of a laundry room, work space and1/2 bath. Large 2 car garage and driveway give you plenty of parking space. Short distance to Winchester Hospital, major routes and train depot. Many fine restaurants and shops in charming town center. Great school system and prestigious suburban community north of Boston.

Listed by Michael Austin of Austin Realty Group

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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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133 Johnson Road Winchester MA 01890

Winchester, MA133 Johnson Road

Price$1,699,000

Est. Mortgage: $/month

MLS Number 73012065

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,000
  • High School Whs

Beautifully renovated home within the Vinson Owen district!! This newly completed, lovingly designed 5 bedroom, 4.5 bathroom home is ideal for raising a family & enjoying everything Winchester has to offer, including a bustling downtown & 2 commuter rails to Boston. The spacious floor plan is comfortable for entertaining with an oversized kitchen boasting white cabinetry, SS appliances & Quarts counters. The family room offers a wood burning fireplace. Hardwood floors & plenty of natural light throughout. Two convenient primary en-suite bedrooms located on the 1st & 2nd floors, both featuring double vanities & glass enclosed walk-in-showers. Designated & quiet home office with distant tree views. The finished lower level features an outstanding recreation room with wet bar & space for a 2nd refrigerator, the perfect place for watching sports. Spacious backyard with large deck for outdoor entertaining. Easy access to major highways & 7 miles North of Boston.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

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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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99 Ridge Street Winchester MA 01890

Winchester, MA99 Ridge Street

Price$1,990,000

Est. Mortgage: $/month

MLS Number 73011808

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 5,203
  • High School Winchester High

Set back off Ridge St on the west side of Winchester, this 2004 custom colonial has an efficient layout that provides generous spaces to entertain, work from home, play and live comfortably. The 1st level offers a south facing great room w/ large windows and high ceilings. It connects seamlessly with the chef's kitchen and formal dining room. Off the center entrance is the bright family room and a private office next to the kitchen. On the 2nd level, you will find the primary bedroom with en-suite bath, walk-in closet, three additional bedrooms, a 2nd full bath, and laundry. Use your imagination in the lower level to create an in-law, au pair or rec room complete w/ full bath and the 5th br. A level private yard awaits out back. It curves around the side of the house leading to exceptional stonework and multiple patios all situated on a half-acre of land. Recent improvements include ext painting and new AC. A short walk to Vinson Owen and Wright Locke Farm. Come experience Winchester!

Listed by Doug Hills 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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1 Aricia Lane Winchester MA 01890

Winchester, MA1 Aricia Lane

Price$2,499,000

Est. Mortgage: $/month

MLS Number 73010137

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 6,165
  • High School Winchester High

Quite possibly the most gorgeous home to hit the market in Winchester in 2022. Welcome to 1 Aricia Lane, a property so mouth watering we don't even know where to begin! Situated prominently upon its corner lot, this property boasts a fully fenced in rear yard with oversized patio and plentiful green space. Enter in and be greeted by a lovely staircase that takes you up to the 2nd level where all 4 bedrooms are found including the master with (2) walk-in closets, dressing area, and oversized bath PLUS an additional en-suite bedroom. The 1st level of this home is what truly shines. The library is straight out of a magazine with palatial fireplace and floor to ceiling rich wood walls and built-ins. The family room with soaring, coffered, ceilings and floor to ceiling fireplace is where you'll want to host every family gathering. The eat-in kitchen with top of the line appliances and butlers pantry make entertaining effortless. Finished lower level w/ wine room, craft room, and rec room!

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

$
$
%
$/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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45 Hemingway Street Winchester MA 01890

Winchester, MA45 Hemingway Street

Price$999,000

Est. Mortgage: $/month

MLS Number 73008897

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,268
  • High School Whs

Aggressive price change & must see value!! Picture perfect 4 bed home w/ fabulous fenced in yard and lots of curb appeal! This home boasts a brand new stunning kitchen with quartz counters, gas range, island seating and access out to the deck, a perfect spot for morning coffee overlooking the sunny rear yard. The kitchen flows nicely into the spacious dining room & oversized living room with wood burning fireplace and beautiful custom built-ins. The main floor also offers 2 bedrooms & new full bath, or use one room as an office w/ the flexible floor plan. The second floor has two additional generously sized bedrooms, another new bath & lots of closet/storage space. The lower level has a gym, office space, storage & laundry with super high ceilings throughout plus attached 2 car tandem garage. This home is situated on a beautiful lot w/ a great yard & includes a handmade wooden playhouse, a child's dream come true! Don't miss the opportunity to call this special home yours!

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

$
$
%
$/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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32 Nathaniel Road Winchester MA 01890

Winchester, MA32 Nathaniel Road

Price$1,089,900

Est. Mortgage: $/month

MLS Number 73008764

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,681
  • High School Winchester High

Welcome home to easy living in this stately, well maintained colonial in the highly sought after Muraco School neighborhood. Traditional in appearance & located on a beautiful tree lined street, this house & this top location will never go out of style or demand. You get that “right at home” feeling upon entering this bright sunlit home. A generous sized frplcd livrm leads to dining w/built in corner cabinet & opens to a large updtd kit w/bkfst rm addition. The 1st flr also features a nice sized famrm w/built in desk, perfect for working at home. This home flows like it was made for entertaining, both inside & out, & if this isn’t enough, sliders lead to a private patio overlooking a gardeners paradise, all while taking in views of a lge level yard! 2nd flr feat 3 generous szd bedrms, all w/hw flrs & an updated bath. The lower level offers a playrm w/exercise area for additional space. Located mins to parks, schools, close to center & commuter rail make this home the total package!

Listed by Eileen Doherty of Lamacchia Realty,Inc.

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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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987 Main Street Winchester MA 01890

Winchester, MA987 Main Street

Price$1,295,000

Est. Mortgage: $/month

MLS Number 73008548

  • Land
  • Acreage 0.11
  • Zoning res

2618 sq ft multi family house currently on the property. Seller has written permission by historical commission to take down the house. Seller has architectural drawings for condo conversion. Contractors & builders take notice of this rarely available multi in a superb location 1 mile from Winchester Town Center! Land is a TREMENDOUS OPPORTUNITY FOR CONDO CONVERSION OR REHAB/NEW CONSTRUCTION! 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!

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

$
$
%
$/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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49 Edward Drive Winchester MA 01890

MLS Number 73008287

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,183
  • High School Winchester Hs

Enjoy this beautiful home with freshly painted three bedrooms plus a guest room/office (perfect for working from home), newly installed appliances (microwave/stove/dishwasher, and washer/dryer) in the kitchen and laundry room, and hardwood floors (installed 2021/2022). It has two fireplaces, 2.5 baths, central A/C and heating, and picture windows facing conservation land with a large lot in the backyard. It has a garage and three additional off-street parking spaces. Professionally managed HOA will take care of the landscaping and trash/snow removal. Closely located near the Blue Ribbon Vinson Owen Elementary School, Wright-Locke Farm, Mullen Field, McClennen Park, and Whipple Hill Reserve with ponds and trails. Easy access to Winchester Town Center, Arlington Heights, and Lexington Town Center!

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

$
$
%
$/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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