Winchester Real Estate

Just 15 minutes northwest of Boston is the beautiful town of Winchester, MA. When your kids are on summer vacation from Winchester's top-ranked public school system, have them spend time sailing at the Winchester Boat Club, keeping fit at the Winchester Swim and Tennis Club, or golfing at the Country Club. A quick trip on the Communter Rail's Purple Line will drop you right at the Fleet Center in central Boston, perfect for easy commuting to work or for an evening out. Don't miss out on D'Agostino's Deli, a famous local spot for subs, sandwiches, party trays, and more delicious deli wonders.

And Winchester real estate doesn't disappoint: find many new construction single-family homes, historic estates, luxurious condos, and more.

View currently listed real estate in Winchester below and contact Century 21 Advance Realty with any questions or to schedule a tour. You can also register with our site to save your favorite properties and receive notifications via email when a new listing matches your preferred criteria. 

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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

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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51 Amberwood Drive Winchester MA 01890

Price$1,249,000

Est. Mortgage: $/month

Open House

MLS Number 72551672

  • Single Family
  • Next Open House: Sat 24th 12:00 pm - 1:30 pm
  • Garage 2
  • Parking Spaces 4
  • Year Built 1985

Live with your head in the clouds! 51 Amberwood Drive is situated ever so perfectly on its oversized lot. With treetop views from every window you'll feel tranquil energy from each room in the home! From the moment you enter you'll appreciate this beautiful traditional layout with a fireplaced living room and sunny dining room on either side of you. You'll be lead with ease from there to the oversized kitchen with granite counters and stainless appliances. Don't forget the fireplaced family room with slider to the rear patio. Perhaps you have an extended family, or visitors from out of state? The 1st floor bedroom with full bath just outside its door is an IDEAL in-law space. It even boasts a separate entry for ADDED privacy! The second level features 4 additional bedrooms, including the expansive master suite with walk-in closet. Need more space? The lower level recreation room is the ideal gym, game room, or play room. FOOTSTEPS to Vinson-Owen and just 1 mile to Wright Locke-Farm!

Listed by Philip J. Vita of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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55 Johnson Road Winchester MA 01890

Price$1,099,000

Est. Mortgage: $/month

Open House

MLS Number 72457850

  • Single Family
  • Next Open House: Sat 24th 1:00 pm - 2:30 pm
  • Garage 2
  • Parking Spaces 4
  • Year Built 1957

Location, location, location! This well maintained center entranced colonial is a short walk to Vinson Owen Elementary School. Beautifully situated on a corner lot with loads of sunlight beaming through! Pride of ownership! This home is known around town for its pristine landscaping! Enjoy the backyard patio while listening to the peaceful sounds from the waterfall. Screened in porch for those warm summer nights. Charming custom built ins and fireplace living room add loads of character. Four good sized sun filled bedrooms with hardwood floors. Step down master suite with walk in closets. Large lower level family room with fireplace. Two car garage with breezeway access into the house. Updates include roof, heating system, windows, oil tank, refrigerator, granite countertops. A/C unit with Allergen Filtration system. Easy access to major highways, town train and 8 miles to Boston! You don't want to miss this one! Call for your private showing today!

Listed by Sharyn Pasquale of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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: 3.55% last updated on Aug 22, 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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23 Elmwood Avenue Winchester MA 01890

MLS Number 72473798

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,094
  • Complex THE ELMWOOD

GORGEOUS, NEW CONSTRUCTION CONDO WITHIN WALKING DISTANCE TO DOWNTOWN & THE COMMUTER RAIL! LOCATION, LOCATION!!! Welcome home to The Elmwood. Boasting over 2000 SQ FT of living all on one level. Beautiful, open & spacious floor plan with the kitchen, dining and living areas integrated to please today's savvy buyer. Top of the line finishes with Quartz counters and a SS appliance package. High Ceiling and stunning hardwood floors throughout except in bedrooms which are carpeted. Separate home office just waiting for you to "work from home"!!! Two oversized bedrooms both with en-suite bathrooms. Beautiful details throughout including crown molding and trendy light fixtures. Walk to downtown Winchester where you'll be greeted with multiple coffee shops, restaurants, boutiques and the commuter rail to North Station. Don't miss out on this opportunity. ONLY ONE LEFT IN THE BUILDING. Easy access to major highways and only 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: 3.55% last updated on Aug 22, 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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812-814 Main Street Winchester MA 01890

MLS Number 72551202

  • Commercial
  • Year Built 1890

EASY TO SHOW!! ~Fantastic opportunity to own this meticulous and lovingly maintainted property owned and occupied by same family for over 75 years. This duplex style 2-family home is also zoned as "general business" offering a multitude of possibilities for interested buyers.Each side features 8 rooms, 3 bedrooms and 1 full bath and a 3rd floor with 2 partially finished rooms on each side. One unit has converted to natural gas and the other has the rough gas line installed. More recent updates include: replacement vinyl clad windows throught the entire property, roof stripped and shingled in 2008 and electrical system on circuit breakers.The immaculate, level and usable yard has irrigation, mature planting and an irrigation system. 2 car off street parking and a wonderful location within a mile to commuter rail, the Tri-Community Greenway, thriving Winchester center and area schools.This home is absolutely spotless!See floor plans attached and on paperclips

Listed by Chrisanne Connolly of Wilson Wolfe Real Estate

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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812-814 Main Street Winchester MA 01890

Price$999,900

Est. Mortgage: $/month

MLS Number 72551194

  • Multi-Family 2 Family - 2 Units Side by Side
  • Year Built 1890
  • Bedrooms 6

EASY TO SHOW !!~Fantastic opportunity to own this meticulous and lovingly maintainted property owned and occupied by same family for over 75 years. This duplex style 2-family home is also zoned as "general business" offering a multitude of possibilities for interested buyers.Each side features 8 rooms, 3 bedrooms and 1 full bath PLUS a 3rd level of living space with 2 partially finished rooms on each side. One unit has converted to natural gas and the other has the rough gas line installed. Additional recent updates include: vinyl replacement windows throught the entire property, roof stripped and shingled in 2008 and entire electrical system on circuit breakers.The immaculate, level and usable yard features mature plantings, large patio and an irrigation system. 2 car off street parking and a wonderful location within a mile to commuter rail,the Tri-Community Greenway,dowtown & is a quick walk to the high school.Unit 814 is a mirror image of 812 and can be accessed for 2nd showings.

Listed by Chrisanne Connolly of Wilson Wolfe Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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310 Main Street Winchester MA 01890

Price$999,000

Est. Mortgage: $/month

Open House

MLS Number 72480169

  • Single Family
  • Next Open House: Sun 25th 1:00 pm - 2:30 pm
  • Parking Spaces 5
  • Year Built 1890
  • Full Bath 2

**GREAT PRICE **Here's the perfect opportunity to design, renovate and create your dream home! This grand colonial with incredible curb appeal is located just outside the town center and near desirable Lincoln Elementary & McCall Middle School! This home is situated on a 10,000+ sq. ft. level lot and features 13 rooms, 5/6 spacious bedrooms & 2 full baths. If you have vision and the willingness to renovate & build substantial equity for future resale, this home is a great opportunity for you! Contractor references available to help through the process & funding available from local banks... please reach out and take a look at this "Diamond in the rough" This home is surrounded by homes in the $1.8M -$3 Million dollar range~ neighborhood can support substantial renovation! Accompanied showings available any time!

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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 Sussex Road Winchester MA 01890

Price$969,000

Est. Mortgage: $/month

Open House

MLS Number 72520218

  • Single Family
  • Next Open House: Sun 25th 12:30 pm - 2:00 pm
  • Garage 2
  • Parking Spaces 6
  • Year Built 1954

10 Sussex Road, Winchester, MA 01890 Desirable location, this lovely ranch has been renovated from top to bottom and meticulously maintained - it's sunny and spacious. Open floor plan with updated kitchen and baths, roof updated, tilt-in windows, central air, 30 x 12 deck off the kitchen, irrigation system, insultation, updated heat and electric and shed. A beautiful home at a great price - 2 car under garage with door openers and direct access. Situated on a spectacular corner lot with mature plantings and a great neighborhood. 1 mile to downtown, walk to commuter rail to Boston, Town Forest at end of street.

Listed by Jason Saphire of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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33 Lockeland Road Winchester MA 01890

Price$949,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72494416

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1966
  • Full Bath 3

Beautiful Cape home in the heart of Winchester designed for grand entertaining as well as intimate family living. Bright, open living room with floor-to-ceiling bay windows, spacious eat-in kitchen with ample cabinet & storage space, formal dining room, & window-lined sunroom overlooking backyard for ultimate relaxation. Three bedrooms (one with ensuite bath) & full bath complete the first floor. Upstairs, find a luxurious master bedroom with attached oversized, celeb-style walk-in closet, featuring skylight windows & shelving for maximum storage. Enjoy ultimate serenity in attached ensuite bathroom with spa-like tub, standing shower & stacked laundry. Office space right down the hall. Partially-finished lower level contains a large family room with fireplace, office (could also be a media room, playroom or bedroom). Laundry & storage areas plus half bath complete lower level. Additional property features include large front & back yard, driveway, 2-car garage & off-street parking.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.