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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23 Yale Street Winchester MA 01890

Price$2,249,000

Est. Mortgage: $/month

MLS Number 72485458

  • Single Family
  • Garage 2
  • Parking Spaces 3
  • Village The Flats
  • Year Built 1901

This stunning colonial in the Flats takes “dream home” to the next level! Kitchen features granite counters, large island, Thermador gas range, Wolf microwave/ovens, Sub-zero fridge & radiant floor heat. Family room adjacent to kitchen w/ exterior access, formal dining room & sitting room, living room with dramatic brick fireplace & ½ bath complete 1st floor. Soak up modern luxury in the master suite: bedroom boasts a gorgeous brick fireplace, rounded bay & celeb-style closet with California Closet built-ins, & the ensuite bath features mosaic tiles contrasted w/ striking granite. 4 additional bedrooms, 1 full bath & laundry hookups complete 2nd floor. The 3rd floor has 2 bedrooms, 1 full bath & large playroom/office. Head to the finished lower level to relax in the media room, break a sweat in the personal gym, throw in another load of laundry or store off-season items. Enjoy the warm weather in the spacious backyard. 2 car garage, close to schools, Winchester Center & commuter rail.

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

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$/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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6 Thornton Road Winchester MA 01890

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72425766

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2013
  • Full Bath 3

Prepare to be impressed by this well-crafted 5 year old 14 room colonial with 5 bedrooms & 3 1/2 baths, just under 7000 sqft. The first floor features an oversized gourmet kitchen w/breakfast area, 2-tiered island, & stainless steel appliances. The adjoining family room has a gas fireplace, cathedral ceiling and a glass sliding door to a large deck overlooking a spacious flat back yard. The open living room with gas fireplace & built-in bookcases, dining room w/ bay window, and a private office complete the first floor. The 2nd floor consists of 4 bedrooms including a spacious master bedroom w/ walk-in closet & premium en-suite, laundry room & sitting area. On the 3rd floor you will find a 5th bedroom with en-suite, plus an airy playroom w/ reading nooks. The finished lower level with high ceilings consists of two sizable rooms and walk-out access to the rear yard. Convenient location in the desirable VO school district close to parks, shopping, & public transportation.

Listed by Errico Team of Waterfield Sotheby's International Realty

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$/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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15 Yale Street Winchester MA 01890

Price$2,100,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72476863

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Year Built 1906
  • Full Bath 3

Renovated 11 room home in the desirable flats area with inviting front porch offering the charm and character of historic Winchester, with amenities and layout desired today. Magazine worthy kitchen/dining/ family room renovation just completed with a new design that will wow every buyer! Open concept first floor with 3 rooms directly overlooking gorgeous and private rear yard w/ deck, patio, mature landscape and an abundance of privacy. Oversized 2 car new construction garage is a huge bonus and rarely found in this part of town! Prior renovation includes new front porch, roof, windows, heat, a/c, baths, plumbing, electrical, large brick patio great for outdoor entertaining. Second floor w/4 beds, 2 full baths & laundry room. 3rd level offers 3 sun drenched BR's & full bath. Master bed suite w/ spa like bath; oversized steam shower w/body sprays/bench/surround sound, radiant flooring & towel warmer. This home is move in ready, close to the center & train to Boston. Ambrose School !

Listed by Kim Covino of Leading Edge Real Estate

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$/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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29 Dunster Lane Winchester MA 01890

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72484222

  • Single Family
  • Parking Spaces 7
  • Village Westside
  • Year Built 1945
  • Full Bath 5

MUST BE SEEN. Spacious and elegant don't begin to describe this spectacular 7700+sf. home. Masterful design and modern luxury are uniquely blended into the construction of this exceptional property. It is truly an entertainers dream. The incredible gourmet kitchen will please even the most demanding culinary artist. The newly renovated kitchen flows into the dining area and unsurpassed Great Room, which is the heart of this home. The Great Room features a full wet bar, Brazilian cherry floors, fireplace and coffered ceilings. 5 bedrooms, 5 baths and an abundance of comfortable spots to gather provides everyone their place to "live". Enormous Master Bedroom boasts of a fireplace, walk-in, sitting area, bathroom w/soaking tub, heated floors and sauna. Relax and consider star gazing from the Hot Tub on the 3rd floor roof deck. There's also a steam/shower on this level along with a kitchenette. The lower level home office and play room with wet bar complete this incredible home.

Listed by Steve O Brien of Century 21 Adams KC

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$/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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66 Arlington Street Winchester MA 01890

Price$1,995,000

Est. Mortgage: $/month

MLS Number 72470156

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1971
  • Full Bath 2

Stunning contemporary home abutting the Winchester Country Club with breathtaking views and private setting is one of a kind! This uniquely styled French Mansard on Myopia Hill is an entertainer's dream and features the expansive living level upstairs, capitalizing on the gorgeous golf course views from floor to ceiling windows, and a fabulous deck for al fresco dining in warm weather. Back inside,the dining area has pickled fir wood ceilings and is open to the kitchen with peninsula for casual seating. Tucked away is the den with sliding doors and built in shelving, and off the living room is a back “corner” office behind French doors. The first floor has an additional family room, master with ensuite and luxurious separate dressing room, and three additional bedrooms, two with their own attached sitting rooms. Situated within close proximity to the Elementary School, Wright Farm, with easy access to Rts 93, 95, 2 & 3, two trains and bustling Downtown Winchester, this home is a dream!

Listed by Elizabeth Crowley and Eric Rollo of William Raveis R.E. & Home Services

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$/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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4 Town Way Winchester MA 01890

Price$1,949,000

Est. Mortgage: $/month

MLS Number 72424070

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 2018
  • Full Bath 4

Recently completed NEW CONSTRUCTION - this exquisite 5 beds 4.5 bth colonial features open floor concept for today's family living! Thoughtfully designed with a high-end finishes & details, this homes offers an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island & Wolf/Subzero appliances, FR with FP & direct exterior access , formal LR & DR with crown moldings & wainscoting. Second floor features include master suite w/ walk-in closets, luxurious master bath, laundry room with custom cabinetry and sink, 4 oversized corner bedrooms flooded with light & ample closet space. Third floor with bonus room, add'l bedroom & full bath. Great rear yard w/deck & sliders from kitchen. The lower level bonus space features spacious family room w/fireplace, kitchenette/ full bath &-plenty of space for gym. This home is located in sought after East side of town, convenient to the center, Lincoln school district, and is truly a great neighborhood!

Listed by Kim Covino of Leading Edge Real Estate

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$/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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112 Highland Avenue Winchester MA 01890

Price$1,900,000

Est. Mortgage: $/month

MLS Number 72455664

  • Single Family
  • Garage 1
  • Parking Spaces 5
  • Year Built 1890
  • Full Bath 3

This home exudes opulence. The attached Porte Chochere (portico) conveniently located in middle of semi-circle drive, provides overhead coverage, car to door, very nice during inclement weather. Feel the elegance as you enter this exceptionally maintained home, which retains its historic character from the late 19th century. Built in 1890, with 12 rooms covering 4858 sq. ft. of living area, including 6 bedrooms and 3.5 baths, there's plenty of space for your antique furnishings and collections. New roof and outside paint were completed in 2017. Tasteful interior updates include Victorian period wallpaper, adding to its special appeal. Nothing more to do but enjoy! Showings begin on 2/28, M-F, 9:00 to 5:00 - Weekend showings by special appointment, for second viewings only. Basement and garage available for inspection 3/31. (Interior photos coming by 3/1)

Listed by Metrowest Homes Team and Ray Paulk of Keller Williams Realty

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$
%
$/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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6 FAIRFIELD Place Winchester MA 01890

Price$1,850,000

Est. Mortgage: $/month

MLS Number 72465453

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2016
  • Full Bath 4

New construction home with details complete such as mature landscaping & fencing; custom window treatments; bathroom fixtures & so much more. It is tucked away in a quiet neighborhood yet steps to town center, The Flats, schools, pond, tennis courts & train. A residence offering over 4,500 sq ft of luxurious living on 4 levels; has 5 large sunny bedrooms & 4 full baths. An inviting floor plan for all family members to enjoy with a blend of formal & informal spaces such as dining & living rooms; large 3rd fl playroom with full bath; exquisite oversized kitchen/family room that has direct access to paver patio & fenced in rear yard~ perfect for kids & pets; grand master suite & a finished lower level ideal for out or town guests or au pair suite. Amenities include hardwood floors; multi zone gas heating & cooking; attached garage; generous storage & so much more. Truly an urban oasis 7 miles from Boston.

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

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$
%
$/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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508 South Border Road Winchester MA 01890

Price$1,649,900

Est. Mortgage: $/month

MLS Number 72483056

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2019
  • Full Bath 4

This beautiful new construction, three level Colonial home is a must see, with a 60 day delivery! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home will feature gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room! Property will have underground lawn irrigation, to help maintain the exterior of this gorgeous property!

Listed by Gary J. Litchfield and Brittany Gray of Mass. Real Estate Solutions, LLC

$
$
%
$/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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16 Gershon Way Winchester MA 01890

Price$1,600,000

Est. Mortgage: $/month

MLS Number 72478906

  • 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. 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.

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.