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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3 Gershon Way Winchester MA 01890

Price$1,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72459269

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! 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. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders 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, a full bath and an open loft area. 2 Car garage. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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2 Gershon Way Winchester MA 01890

Price$1,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72462916

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! 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. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders 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, a full bath and an open loft area. 2 Car garage. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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5 Gershon Way Winchester MA 01890

Price$1,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72462917

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! 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. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders 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, a full bath and an open loft area. 2 Car garage. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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183 Mystic Valley Parkway Winchester MA 01890

MLS Number 72477446

  • Single Family
  • Parking Spaces 1
  • Half Bath 1
  • Year Built 1905
  • Full Bath 2

In the heart of downtown Winchester where shops schools and the trains are there for your convenience, this beautiful 1905 colonial has it all. Inviting front porch welcomes you into this vintage home that includes a den, living room and fireplace dining room on first floor along with a modern updated kitchen with half bath. Enjoy the private rear patio off the kitchen and dining room. Upstairs has four bedrooms and modern bath. On the third level there is a master suite with bath and large walk in closet. Additionally there is a finished room in basement perfect for work out room or play area. So convenient so charming and ready to move in!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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
Open House

MLS Number 72473798

  • Condo or Co-op
  • Next Open House: Sun 28th 2:00 pm - 3:00 pm
  • Half Bath 1
  • Bathroom 3
  • Year Built 2017

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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7 Wainwright Road Winchester MA 01890

MLS Number 72471472

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 1994

This is the Ledges unit you have been waiting for! Sitting at the top of the hill this light filled unit has sweeping sunset views to the west from a deck that spans the entire width of the condo. Step inside and see how the owner has meticulously maintained and decorated this home.There are many custom additions unique to this condo and this includes discreet handicap accessibility such as extra wide doors; a closet storage unit over the garage, custom lighting system; custom kitchen pantry; built in shelves and cabinets in both dining room and family room. Large basement enables easy conversion to living space, with walk out slider, large windows and plumbing set up for a bathroom.Master bedroom suite is on the first level with plentiful storage and closet space and access to the rear deck.Modern kitchen overlooks fireplace family room. The second floor has two large bedrooms and full bath in addition to storage closet and hall study. Hardwood floors throughout. Move right in!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

24 York Road Winchester MA 01890

Price$1,150,000

Est. Mortgage: $/month

MLS Number 72474227

  • Single Family
  • Garage 2
  • Parking Spaces 2
  • Year Built 1980
  • Full Bath 3

ORIGINAL OWNER OFFERS METICULOUSLY MAINTAINED home with 4+ bedrooms and 3 Baths; with 12 closets. Highly efficient structure with High level of insulation -10" walls and quadruple glazed windows. Hard wood floors on upper level and potential au pair suite on lower. Walk in cedar closet and cold storage room, study, office or small guestroom. Brick exterior offers low maintenance. Stroll to the Town Forest Conservation land. Home is built with Steel center supporting beams and 2 X 6 exterior wall framing resulting in very low heating and maintenance costs. Neither of the two fireplaces have ever been used. Convenient commuter access to Boston via 93 and Commuter Rail station less than a mile away.

Listed by Bill Caci and Rosanne Coric of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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$1,109,000

Est. Mortgage: $/month

Open House

MLS Number 72465456

  • Single Family
  • Next Open House: Sat 27th 11:00 am - 1:00 pm
  • Garage 2
  • Parking Spaces 6
  • Year Built 1820

Welcome to the Wyman House! This beautiful historic 5 bedroom, 3 bedroom Colonial home offers a spacious and welcoming atmosphere both inside and out. Generations have enjoyed get togethers in the large sun-filled family room featuring a working fireplace and beehive oven. The eat-in kitchen is fully applianced and overlooks the large and private fenced-in back yard. Original wood flooring in the formal dining room, living room and family room. A stunning circular staircase is located at the front of the house with a second set of stairs off the kitchen area. First floor laundry. Two of the five bedrooms have fireplaces and all have wood flooring. Walk-up third floor attic offers extra storage. Detached two car garage and plenty of off street parking. Back yard has mature plantings, ornamental trees, garden area and a shed. Conveniently located near the schools, shopping and commuting. Make this your next home!

Listed by Cory Gracie of Dimacale & Gracie Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

27 Mayflower Road Winchester MA 01890

Price$1,100,000

Est. Mortgage: $/month

MLS Number 72483878

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Half Bath 1
  • Village West Side

Welcome to this beautifully renovated multi-level home on a dead end street, convenient location in the desirable Vinson Owen district. Updates include high-end appliances kitchen, bathroom with SPA shower system, and hardwood floors. First floor features open floor plan, living room with picture window and dining room with direct access to back deck and level lot. Gorgeous eat-in kitchen w/ SS appliances. Option of office / family room and lower level family room with direct access to backyard and wood burning fireplace create mutiple living areas. Master bedroom with gracious closets and en suite plus three other large bedrooms complete the sleeping area. This home offers an easy flow for entertaining. Spacious two car garage plus easy access to major commuting routes make this a must see home.

Listed by Ides Figueiredo and Anne Spry of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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$1,099,000

Est. Mortgage: $/month

MLS Number 72480169

  • Single Family
  • Parking Spaces 5
  • Year Built 1890
  • Full Bath 2
  • Bathroom 2

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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.

Save 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.