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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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: 3.55% 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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15 Tanglewood Lane Winchester MA 01890

Price$1,597,000

Est. Mortgage: $/month

MLS Number 72520252

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1982
  • Full Bath 5

Sprawling custom contemporary home on the West Side with a beautiful 30,536 sq ft lot. This one owner home circa 1982, offers luscious gardens and spacious privacy on a cul de sac in the VO school district. This home provides great space inside and out for busy lives, entertaining, celebrating and relaxing. There are 5 bedrooms including a spacious Master, en suite baths, a full finished Lower Level and open and flexible first floor plan with direct access to the back yard. The first floor also features beautiful and thoughtfully designed architectural details, 2 fireplaces, a family room overlooking the gardens and a spa bath for some very special down time.

Listed by Naomi DeLairre of Waterfield Sotheby's International Realty

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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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174 Forest Street Winchester MA 01890

Price$1,499,000

Est. Mortgage: $/month

Open House

MLS Number 72514312

  • Single Family
  • Next Open House: Sun 25th 2:00 pm - 3:30 pm
  • Garage 2
  • Parking Spaces 3
  • Year Built 2001

METICULOUSLY MAINTAINED SINGLE FAMILY SEEKING A NEW OWNER! This majestic Colonial featuring an open concept floor plan for today's modern lifestyle recently went through a significant transformation & is now ready to show. The welcoming 2-story foyer with formal dining & living rooms on either side are just the beginning of the journey. The Chef's style kitchen features granite counters, subway tile backsplash, SS appliances & breakfast nook, the perfect space for entertaining a large crowd. The fireplaced family room abuts the kitchen allowing for the whole family to be together. The 2nd floor is home to 4 generous bedrooms, including the master suite with oversized bathroom & WIC, another full bath & laundry. The walk up attic or finished lower level are perfect for teens to play games & swap stories. Newly finished HD floors in 2018. New backsplash, interior & exterior paint & many light fixtures 2019. Muraco School district & easy access to major highways. 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: 3.55% 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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70 Wedgemere Avenue Winchester MA 01890

Price$1,490,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72509182

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1976
  • Full Bath 2

Exceptional and amazing attention to detailed renovations and upgrades in this Classic Brickfront CE Colonial in one of Winchester's Premier Locations!! Large Spacioius rooms, gleaming hardwood floors, 2 Family rooms, 2 fireplaces, 2 car heated garage. Beautlifully redone kitchen/family room with skylight and half bath. Kitchen has large pantry closet. Large formal dining room. Master BR suite with full bath and abundant closet space. See Attached feature/upgrade sheet for more details on 5star heating and cooling systems plus much more. Seller requests accompanied showings at times TBD. All tv's remain as well as All appliances.

Listed by Martha Nappi of Berkshire Hathaway HomeServices Commonwealth 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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4 Summit Avenue Winchester MA 01890

Price$1,450,000

Est. Mortgage: $/month

MLS Number 72512386

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1897
  • Full Bath 1

This may be your "Forever" home! Ideally located on a quiet cul de sac above the Town Center, this Painted Lady is just a few short blocks to Winchester's shops, bistros, Farmers' Market, schools and Boston commuter train. From the inviting front porch and huge welcoming Foyer, the two fireplaced parlors w/oak pocket doors and Dining Room w/2 leaded-glass china cabinets will be perfect for gathering family and friends. The large Kitchen offers a breakfast bar, the original 'Baking Room', first floor Laundry, half-bath and convenient back stairs. An impressive turning staircase leads up to 4 Bedrooms, upstairs sitting alcove, and an office/craft room. The large fireplaced Master Bedroom has adjacent space for adding your Master Bath and Walk-in Closet. Two more interesting bedrooms with built-ins on 3rd floor, plus a great walk-in attic. All new siding and house-wrap insulation in 2017. Impressive room sizes, wonderful original details preserved, just steps to downtown - perfect!

Listed by Loraine Murtagh of Coldwell Banker Residential Brokerage - Winchester

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$
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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 Gershon Way Winchester MA 01890

Price$1,450,000

Est. Mortgage: $/month

MLS Number 72550729

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

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: 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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8 Gershon Way Winchester MA 01890

Price$1,400,000

Est. Mortgage: $/month

Open House

MLS Number 72464290

  • Condo or Co-op
  • Next Open House: Sat 14th 1:00 pm - 4:00 pm
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,549

HARD HAT OPEN HOUSE 9/14 & 9/15 1-4PM. 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.

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

$
$
%
$/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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2 Alben Street Winchester MA 01890

Price$1,349,000

Est. Mortgage: $/month

MLS Number 72499325

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1988
  • Full Bath 2

SELLER MOTIVATED - BRING OFFERS. This gorgeous, over-sized, custom built colonial has been meticulously cared for by the original owners and is perfect for today's young family. Front to back family room with fireplace and French doors to very large deck has cathedral ceiling and wraps around to an enormous breakfast area and then on to the kitchen with loads of cabinets, pantry closets and a planning desk! Formal living room, huge dining room, laundry room and half bath complete the 1st floor; 3 large bedrooms plus sunny sitting area on 2nd floor and if you still need more space, the walk out basement with sliders to a covered patio is fully finished and includes a kitchenette and full bath which is perfect for entertaining or for an extended family. A 2 car garage, beautiful landscaping, a new roof and the close proximity to the Fells Reservation for walking trails make this the perfect setting. Come see all that Winchester has to offer besides its fabulous schools

Listed by Diane Plunkett of Plunkett Properties

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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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22 Gershon Way Winchester MA 01890

Price$1,299,000

Est. Mortgage: $/month

Open House

MLS Number 72535655

  • Condo or Co-op
  • Next Open House: Sat 14th 1:00 pm - 4:00 pm
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

HARD HAT OPEN HOUSE 9/14 & 9/15 1-4PM. 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.

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

$
$
%
$/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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8-10 Winter Street Winchester MA 01890

Price$1,250,000

Est. Mortgage: $/month

MLS Number 72453632

  • Multi-Family Duplex
  • Year Built 1881
  • Bedrooms 6

OUTSTANDING DUPLEX IN WINCHESTER!!! Two-Family DUPLEX Style Home on EXTRA LARGE LOT with TWO driveways.THIS HOME HAS BEEN COMPLETELY RENOVATED , EVERYTHING IS BRAND NEW ! Close to Winchester's FINEST Restaurants and Shops, Commuter Rail, MBTA & Newly Renovated Winchester High School. EASY access to 93, 95 & Route 3. Each unit has three bedrooms with 2 1/2 baths. New cabinets with granite countertops, all newer windows, flooring, roof, heating & electric ! Each side has private patio in the back. HUGE driveway with parking for at least 10 CARS. QUIET STREET & NEIGHBORHOOD. Close to brand new Tri-town bike path and highly sought after schools. Perfect investment for owner occupant or investor! Easy conversion to condo. Lots of privacy.

Listed by Mark Sullivan of T.A. Sullivan Agency Inc.

$
$
%
$/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.

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.