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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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5 Fox Hunt Lane Winchester MA 01890

Price$2,275,000

Est. Mortgage: $/month

MLS Number 72506669

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

Understated and unique luxury. This traditional brick colonial opens into an interior of simple, contemporary beauty. Situated on 1.2 acres that border the 13th fairway of the Winchester Country Club, the home's 300-foot elevation affords sweeping views across the Mystic Lake and into East Boston, with brilliant sunrises that change hourly with the light and weather. A large deck and patio invite outside entertaining. Inside, the home mixes traditional and contemporary elements: an expansive living room with custom Butternut woodwork and vaulted ceiling; a kitchen/family room with a gas fireplace; a TV and billiards room; a master bedroom suite with a fireplace and attached office/dressing room. The second floor features two ensuite bedrooms, plus options for additional bedrooms. The walk-out lower level includes an indoor pool, greenhouse, and a fourth bedroom with a separate entrance, bathroom, and sauna.

Listed by Cynthia Houle 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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326 Highland Avenue Winchester MA 01890

Price$2,199,000

Est. Mortgage: $/month

Open House

MLS Number 72551945

  • Single Family
  • Next Open House: Sun 25th 1:30 pm - 2:30 pm
  • Garage 2
  • Parking Spaces 8
  • Year Built 1903

Majestic Winchester home with detail and craftsmanship unlike any other~ Situated proudly on a private, oversized lot with lovely level rear yard, patio and 2 car garage, offering some of the most gorgeous custom hand milled woodwork you've ever seen~ breathtaking bridal staircase with 30' ceilings, spectacular stained glass windows, from one room to the next, this home will impress. Formal Mahogany dining room with beamed ceilings and oversized fireplace, living and family rooms each w/ fireplaces~ 5/6 bedrooms, Master with french doors to sunroom/enclosed balcony, updated electrical, newer heating system, central a/c, Perfect opportunity to expand /renovate the kitchen with adjacent mudroom offering plenty of space to create todays dream kitchen, add french doors to patio and the space is beautifully blended. This home was valued at over 4Million dollars to recreate & can now be yours ~this is a very special home & a once in a lifetime opportunity! Please call for a private showing

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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38 Prospect Street Winchester MA 01890

Price$1,949,000

Est. Mortgage: $/month

MLS Number 72490271

  • Single Family
  • Garage 2
  • Parking Spaces 8
  • Year Built 1910
  • Full Bath 3

Fabulous price for this home! Nestled amidst the most beautiful landscape & serene settings you will find, this very special home is like no other! This gorgeous 4/5 bed 3.5 bath home was expanded & renovated inside and out by the current owners. From the moment you enter into the stunning foyer, you will feel the welcoming warmth and see the quality that surrounds with the wide plank Hickory floors, open concept living room/dining room with high coffered ceilings, oversized wood-burning fireplace, custom built-ins, and sun-filled sitting room off to the side with exterior access to private fieldstone patio. Chef's kitchen featuring inset cabinets, breakfast nook w/ bench, built-in desk, butler's pantry w/ wet-bar, coffee bar, wine storage & add'l pantry/mudroom. Cozy family room just off kitchen with custom built in media wall. 2nd level features master suite w/ walk-in closet & spa-like master bath; three additional room unique w/ gorgeous views . LL mudroom direct access to garage

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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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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$
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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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24 Calumet Road Winchester MA 01890

Price$1,780,000

Est. Mortgage: $/month

Open House

MLS Number 72545296

  • Single Family
  • Next Open House: Sat 24th 12:00 pm - 2:00 pm
  • Garage 1
  • Parking Spaces 4
  • Village The Flats

This well-designed Dutch Colonial Revival in the Winchester Flats, marked by modern amenities, radiates original warmth & character. Formal & informal rooms on the 1st floor are connected by a pleasing circular flow that feels open & natural. Elegant details include high ceilings, crown moldings, wainscoting, hardwood floors, built-ins & a split formal staircase. Entertaining is a pleasure w/both formal dining & living rooms leading to a large kitchen w/island, breakfast bar, & dining area w/sliders to a secluded deck & fenced backyard. A stunning living room w/fireplace is flanked on both sides by two pairs of uniquely crafted French doors leading to a lovely sun room/family room. A 1st floor home office is a perfect workspace. The 2nd floor master suite w/walk-in closet has a spa-like bath w/steam shower, soaking tub, & radiant floors - a true oasis. Custom mudroom off kitchen & garage. Gorgeous landscaping/perennial gardens. Close to Town Center, Commuter Rail & Ambrose Elementary.

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

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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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272 High Street Winchester MA 01890

Price$1,725,000

Est. Mortgage: $/month

Open House

MLS Number 72509896

  • Single Family
  • Next Open House: Sun 25th 12:00 pm - 1:30 pm
  • Garage 2
  • Parking Spaces 4
  • Year Built 1995

Looking for some peace and quiet? You will find it at 272 High Street! This meticulously maintained colonial was custom built for its current owners, in a magnificent setting abutting the Whipple Hill conservation area. Lots of beautiful windows allow tons of natural light and a spectacular view. Large open kitchen, with island and eating area, open to a bright family room. First floor also includes formal dining room, living room and office. Second floor offers four large bedrooms, one with en suite bathroom and including a large master suite with gorgeous built in dressers, two walk in closets and bright bathroom. Game room in finished basement with walk out to the backyard. Need even more space? The basement has additional space to finish and is framed for an additional bathroom, as well as an entire third floor level, ready to make your own. Follow the trails to Wright Locke Farm, take a hike at Whipple Hill and close proximity to VO School and Winchester Swim and Tennis Club.

Listed by Karen S. Garrett 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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46 Lorena Road Winchester MA 01890

Price$1,699,000

Est. Mortgage: $/month

Open House

MLS Number 72509519

  • Single Family
  • Next Open House: Sun 25th 11:00 am - 12:30 pm
  • Garage 2
  • Parking Spaces 8
  • Year Built 1957

MUST SEE INSIDE this beautiful East Side contemporary home, set on a large private lot surrounded by homes 2M+ in very desirable area near center. This 5 bedroom, 3.5 bath home is completely renovated~ Close to Winchester Center schools, shops & train to Boston! Plenty of living space on the first floor, boasting a gorgeous high end kitchen w/Sub Zero fridge, double wall oven, walk-in pantry with wine fridge, playroom/ mudroom off the kitchen, dining room w/walls of windows, living room with fplc, and a bonus great room with floor to ceiling stone fireplace that is a focal point in this remarkable home! The master suite is private & includes a gorgeous spa like bath w/ walk in shower, double vanity & soaking tub; four additional bedrooms are generously sized w great windows & deep closets. 2 add'l baths and 2nd floor laundry complete this floor.The exterior includes a screen porch, beautiful patio, 2 car garage, mature perennials and large private yard to enjoy! Lincoln Elementary

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/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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5 W Chardon Road Winchester MA 01890

Price$1,699,000

Est. Mortgage: $/month

Open House

MLS Number 72520138

  • Single Family
  • Next Open House: Sat 24th 11:00 am - 12:30 pm
  • Garage 2
  • Parking Spaces 6
  • Year Built 1950

Well maintained custom colonial in desirable neighborhood. Corner lot w/mature plantings & great curb appeal. This sun-filled home boasts six bedrooms & three fireplaces, completely renovated approx. 2008. First floor offers two generous sized bedrooms w/versatility; office, au pair or in-law w/full bathroom & shower. Large eat in kitchen flows into family room w/gorgeous stone fireplace. French doors lead to dining room with double sided fireplace shared with living room. Second floor offers a grand oversized master bedroom suite w/high ceilings, large walk in closet, spacious master bathroom w/tub, separate shower & double vanity sinks. Add'l three bedrooms one en-suite, plus a jack & jill bathroom shared by other bedrooms . Walk up attic with plenty of storage or choose to finish space. Oversized two car garage with direct entry to mudroom. High velocity A/C. New boiler/manifold/pump 2018. Radiant flooring throughout entire home. 75 gal hot water tank. Close to train and town.

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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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: 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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48 Cabot Street Winchester MA 01890

Price$1,600,000

Est. Mortgage: $/month

Open House

MLS Number 72488975

  • Single Family
  • Next Open House: Sun 25th 12:30 pm - 2:45 pm
  • Garage 2
  • Parking Spaces 4
  • Village Flats

Stunning 5 bedroom Colonial in Winchester's desirable Flats neighborhood, First floor features hardwood floors, high ceilings, formal dining room with chair rail, inviting living room with fireplace, adjacent sun-room with built-in cabinets & study/home office with french doors & custom book shelves. Gourmet kitchen with high-end stainless steel appliances, large island & french doors leading to a lovely deck, patio, fenced yard & 2-car garage. Large master suite with full bath, double vanity, soaking tub & tiled shower. Three additional bedrooms with ample closet space, full bath & laundry room on 2nd floor. Bonus third floor bedroom suite with full bath, cathedral ceiling & skylights. Huge lower level playroom,exercise room & half bath. Improvements include high efficiency split system heating and cooling with 9 zones, new driveway,new carpet in lowest level. Beautiful fenced in back yard. 2008 home updated.with all new tilt windows.This is a Cool home during the Hot summer months

Listed by Richard Brenner of Brenner Real Estate

$
$
%
$/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.