Homes for Sale Winchester MA

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. 

Discover Winchester Real Estate

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67 Dunster Lane Winchester MA 01890

Price$610,000

Est. Mortgage: $/month

MLS Number 72540447

  • Single Family
  • Garage 1
  • Parking Spaces 2
  • Year Built 1920
  • Full Bath 1

COZY LITTLE HOUSE LOCATED IN WINCHESTER'S DESIRABLE WEST SIDE! Within the Vinson Owen school district & a short walk to Wright Locke Farm for strawberry picking or farm to table outdoor dinners. Very sweet home in a quiet neighborhood with an exceptional back yard. Kitchen is a good size, original to the house and in need of updating. Hardwoods throughout. Nice sun filled dining & family rooms. 2 bedrooms & a full bath on the 2nd floor. Basement is unfinished with a fieldstone foundation. Priced to sell & a great condo alternative. A short drive to Winchester center where you'll find a plethora of coffee shops, salons, restaurants & boutiques. A 15 minute train ride to North Station on the Commuter Rail. Easy access to major highways and 7 miles North of Boston.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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14 Watson Place Winchester MA 01890

Price$779,000

Est. Mortgage: $/month

Open House

MLS Number 72539691

  • Single Family
  • Next Open House: Sun 25th 12:30 pm - 2:00 pm
  • Garage 2
  • Parking Spaces 4
  • Year Built 1896

This beautiful turn of the century Victorian is conveniently located near all that Winchester has to offer: shops, commuter rail, library, Farmer's Market, Middlesex Fells Reservation, and award-winning schools. The inviting wrap around front porch immediately welcomes you into the home. The spacious remodeled kitchen is a chef's dream, with granite counters and stainless appliances, including a 6-burner Jenn-Air stove. The kitchen flows into the dining room, which features a charming original fireplace and built-in hutch. The first floor continues into the sunny living room. The second floor offers three generous bedrooms, remodeled bath with double vanity, and walk-in closet with built-in storage. Finished attic would be a great office, playroom, or guest room. Additional features include gleaming hardwood floors, generous storage throughout, central air, two car garage, fenced in side yard, and location at the end of a dead end street. Move right in and start enjoying Winchester!

Listed by Theuer, Pirani & Wile of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 White Street Winchester MA 01890

Price$899,900

Est. Mortgage: $/month

MLS Number 72539605

  • Single Family
  • Parking Spaces 6
  • Year Built 1952
  • Full Bath 3
  • Bathroom 4

Contemporary Multi-Level home - nearly 2,800 sq ft - for an outstanding value in Winchester! Open concept floor plan with cathedral ceilings, skylights, 2 master suites, and so much more. 4+ Bedrooms and 3.5 Baths. Unique floor plan offers unlimited possibilities for this truly one-of-a-kind home. Corner lot in a quiet residential neighborhood, yet just steps to Main St and a short ride to everything downtown offers. Large bar area in lower level as well as a second kitchen (no stove) and a huge laundry room, plus an office and possible 5th bedroom. Opportunity is there for an in-law/utility apartment for an extended family situation. FHA/Gas heat with central A/C, plus a ductless mini split system in the 2nd floor addition. First time available for sale in 40+ years, your custom touches will make this home a true masterpiece.

Listed by Cassidy Real Estate Partners and Christopher Cassidy of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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42 Mayflower Road Winchester MA 01890

Price$1,599,000

Est. Mortgage: $/month

MLS Number 72537821

  • Single Family
  • Garage 6
  • Parking Spaces 4
  • Year Built 1975
  • Full Bath 3

What's on the top of your "must have" list? Perhaps it's a great community? A nice yard? A garage? Or one level living? What if we told you that you could have an AMAZING community, HUGE and LEVEL yard, 6+ CAR GARAGE (yes, you read it right) and a SPRAWLING ranch style home with additional living space in the lower level? You'd probably say "sign me up!" Let us introduce to you 42 Mayflower Road. A property AS HOT AS THE WEATHER! From the moment you enter into the oversized foyer and step down into the sunken fireplaced living room, you'll see why this home is so special. With 2,700+ SF just on the main level, the grand characteristics will never get old. In addition to being a car enthusiast are you a wine enthusiast? The cedar wine closet of your dreams is just off the kitchen. Let's not forget to mention the backyard, a true oasis with covered patio and expansive lawn. You'll feel like you're on vacation everyday! Located just footsteps to Wright-Locke Farm and Mullen Field.

Listed by Philip J. Vita of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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379 Main Street Winchester MA 01890

Price$1,800,000

Est. Mortgage: $/month

Open House

MLS Number 72536636

  • Single Family
  • Next Open House: Sun 25th 1:00 pm - 3:00 pm
  • Garage 2
  • Parking Spaces 6
  • Year Built 1846

Have you been looking and looking for a large updated classic Winchester home with an open floor plan and close to town? Finally it's come on the market! This handsome updated home with an open sunny floor plan is only a 5-10 min walk to town center, train, and schools. The 21 x 15 kitchen flows into the 21 x 21 fireplaced skylit family room. Off the family room is a sky-lit cathedral ceiling sunroom featuring a hot tub and French doors out to the garden. The fully equipped kitchen has everything you could want: separate gas cooktop, 2 wall ovens, plus built-in microwave, 2 warming drawers and an abundance of cabinets. On the second floor there are 3 bedrooms and a laundry. The fireplaced master suite has a walk-in closet and custom bathroom with heated towel bar. With 2 more bedrooms and a full bath on the 3rd floor you have options for more family bedrooms, an office, or a nanny suite. This quintessential Winchester home awaits you.

Listed by Judith Ober of Berkshire Hathaway HomeServices N.E. Prime Properties

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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22 Gershon Way Winchester MA 01890

Price$1,299,000

Est. Mortgage: $/month

MLS Number 72535655

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

WINCHESTER'S 1ST 55+ LUXURY COMMUNITY!!! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 10' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package, including Bosch & Sub Zero. Cozy up to the gas fireplace or enjoy entertaining in the dining room featuring coffered ceilings & a slider to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, 2 full baths and an open loft area. A short drive to downtown Winchester and only 7 miles from Boston.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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666 Main Winchester MA 01890

Price$618,000

Est. Mortgage: $/month

MLS Number 72533470

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,170
  • Complex Wedgewood

**CLICK THE "V" ON TOP RIGHT FOR 3D TOUR! Welcome to Wedgewood Place, on Wedge Pond in the heart of Winchester Center! Talk about LOCATION...In 2017, Boston Magazine chose Winchester as one of the "Best Places to Live North of Boston!" This Condo has much to offer with it's bright, skylit open floor plan and upgrades consisting of new granite counters throughout the kitchen, breakfast bar and 2 baths, modern clean flooring in kitchen, living/dining room and hallways in addition to newer carpeting in both bedrooms. The living room/dining room has a working wood fireplace and walk out balcony overlooking the beautifully landscaped in-ground pool/common area. The private master bedroom suite offers a large walk in closet and a Roman-tub master bath. Enjoy central air, washer/dryer in unit, covered parking, bicycle storage, additional storage locker. Charming Winchester Center is engaging and ribboned with restaurants, shops, markets, parks and ponds,T /Commuter Rail & more. Move in READY!

Listed by Laurie Holman of American STAR Realty Group

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 Woodside Road Winchester MA 01890

Price$1,079,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72532169

  • Single Family
  • Garage 2
  • Parking Spaces 3
  • Year Built 1928
  • Full Bath 2

Rare opportunity! Classic English colonial nestled within Winchester's Flats neighborhood with beautiful views of Winter Pond and an expansive, private back yard. This lovely home evokes a Tudor styling with so much original character- gumwood beamed ceilings, French doors, custom built-ins, and a fireplaced living room overlooking the scenic pond. In addition to its oversized living & dining rooms, the 1st floor boasts an inviting cherry kitchen with adjacent mudroom, half bath, and a separate office/den. Enjoy indoor/outdoor living from the breezy three-season porch which opens to a patio, detached 2-car garage, and large leafy backyard. Upstairs, you'll find two bedrooms each with water views, full bath, and a master suite with walk-in closet & private bath. The lower level offers pure potential with a large family room, laundry, half bath & addl storage. You're sure to love this convenient location, close to schools, Winchester Ctr, and commuter rail to Boston. Welcome home!

Listed by Louise Coakley of Better Homes and Gardens Real Estate - The Shanahan Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 Cross Street Winchester MA 01890

Price$575,000

Est. Mortgage: $/month

Open House

MLS Number 72531019

  • Single Family
  • Next Open House: Sun 25th 12:00 pm - 2:00 pm
  • Parking Spaces 2
  • Year Built 1916
  • Full Bath 1

Move in before the school year! Here is your chance to live in one of the area's most desirable locations! Whether it be for commuting ease to anywhere, excellent school choice or just the sheer pleasure to live in a wonderful community, you have found it! This sun filled, well updated and maintained 3bedroom Colonial boasts hardwood floors throughout the first floor. The kitchen/dining room area serves as a perfect space to entertain and have those special dinners. Kitchen counter tops are granite and stainless steel appliances surround you! The familyroom and bonus room could serve as an office, bedroom or playroom finish off the floor! Access to the fenced in back yard and patio is a plus! Up the stairs are two more bedrooms, a full bathroom and laundry! All windows (except the two kitchen) have been updated with in the last 10 years! Super close to Muraco Elementary, WHS, Winchester Center and Hospital. Quick closing possible!

Listed by Knox Haschig Real Estate Group and Deborah Austermann of William Raveis R.E. & Home Services

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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29 McCall Road Winchester MA 01890

Price$2,600,000

Est. Mortgage: $/month

MLS Number 72526503

  • Single Family
  • Garage 3
  • Parking Spaces 3
  • Village Myopia Hill
  • Year Built 1994

Custom built Myopia Hill Colonial was part of the Schrafft Estate peacock garden. From the moment you traverse the driveway nestled in greenery, this exceptional setting will capture your heart. The magical lot with beautiful mature plantings offers privacy with front porch, patios & lawn space. The spacious kitchen provides ample room for cooking & gathering with dining area & center island which flows into the 2 story, beamed ceiling family room with fireplace, interior balcony & oversized windows on three sides to enjoy all seasons. The elegant foyer opens to fireplace living room & vaulted ceiling dining room - both with access to serene patios for gracious entertaining. Enjoy a treetop view from the 2nd floor which includes a private master suite bedroom, guest room with ensuite bath, 2 additional bedrooms with shared bath & game room. Direct entry from the 3-car garage with access to both the basement & large mudroom, half bath & laundry, offers ease of living. Truly a retreat!

Listed by Anne Spry and Stephanie Mcgowan of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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195 Cambridge Street Winchester MA 01890

Price$859,000

Est. Mortgage: $/month

MLS Number 72523776

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1820
  • Full Bath 3

Are you looking for a new home that is out of the ordinary? Step into this home and you have stepped into the extraordinary - a five bedroom home that is steeped in history and full of charm and character.This is the homestead of the fabled "White Horseman" Hezekiah Wyman, who at 55 years with long locks of white hair, rode off on his white mare to fight the retreating British after their battle in Lexington and Concord in 1775. This home retains much of its character with fine craftsmanship and comfortable living spaces. And, if you are looking for that perfect escape from the city or hustle and bustle of every day life, this home has a back yard that will take you away from it all. Escape to the gardens, the play areas, the perfect sitting areas under the broad reach of beautiful trees that you will find in this glorious and very private back yard. So, here, not only will you own a spacious and charming home but you will also own a piece of Winchester's and our National history

Listed by Stephen DeConto of Coldwell Banker Residential Brokerage - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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146 Ridge Street Winchester MA 01890

Price$1,250,000

Est. Mortgage: $/month

MLS Number 72522156

  • Single Family
  • Garage 1
  • Parking Spaces 3
  • Year Built 1951
  • Full Bath 5

Move right in to this thoughtfully designed West Side colonial, a short walk to award winning Vinson Owen school. The open-plan living/dining is bright & sunny and leads to private office with brick backdrop from the living room fireplace. Kitchen features granite counters, stainless appliances, & sunny breakfast nook. Formal sitting room, a bedroom & full bath complete the 1st floor. Elegant staircase leads to gorgeous master suite with custom walk-in closet, 3 additional spacious corner bedrooms, and 2 full baths. Finished, walk-out lower level ideal as family/game room or separate space for the aupair. Newly built deck overlooks sprawling tree-lined, flat yard - perfect for summer fun! Hardwood floors throughout, 2 laundry rooms (lower level & 2nd floor!), excellent storage, attached garage & dry-walled/carpeted attic ready for completion. Easy access to major highways & only 7 miles to Boston. A great home with space for everyone!

Listed by The Gillach Group and Noha Soliman of William Raveis R. E. & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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