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. 

34 Everett Avenue Winchester MA 01890

Winchester, MA34 Everett Avenue

Price$2,699,000

Est. Mortgage: $/month

MLS Number 72727846

  • Single Family Detached
  • Village Lake
  • Bathroom 4
  • Rooms 11
  • Bedrooms 6

Old world beauty and detailing are perfectly preserved throughout this home that sits majestically above the upper Mystic Lake on desirable Everett Avenue. Enjoy watching the sunrise every morning over the water from your private deck or sunroom, take in the wildlife that is abundant and enjoy a swim or kayak ride at your leisure. 6 bedrooms provide ample room for all and offer options of home offices and remote learning areas as well. Each room in this home is grand in scale, with hard wood floors, gorgeous mahogany detailing and doors and a fabulous butler's pantry. There's a huge lower level playroom that opens directly to the back yard, upper deck for dining and a one-car garage. Walk to the train, schools, town center and parks easily. This home is priced well below neighborhood value and awaits your special touch!

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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65 Myopia Road Winchester MA 01890

Winchester, MA65 Myopia Road

Price$2,650,000

Est. Mortgage: $/month

MLS Number 72652226

  • Single Family Detached
  • Bathroom 5
  • Rooms 14
  • Bedrooms 4
  • Square Feet 7,206

A stately Colonial set atop Myopia Hill in one of Boston's most desired suburbs, 65 Myopia Road is a tranquil & immaculate estate well adapted to modern family living. Beyond the grand entry foyer are graciously scaled living & entertaining rooms with oversized windows highlighting beautiful views of the private outdoors. These include the double height living/family room with impressive stone fireplace, chef's kitchen with vaulted breakfast nook, & formal dining room with elegant fireplace. The home's 4 generous bedrooms are all located on the 2nd level. The Master suite is breathtaking with spacious walk-in closet and luxurious bath. Additional features of this residence include the 2nd floor mezzanine game room, home gym, expansive outdoor mahogany deck, & heated outdoor pool. This home is only 9 miles north of Boston, accessible to the commuter rail to North Station, within ½ mile +/- of Ambrose School, & within close proximity to all the shops & restaurants of downtown Winchester.

Listed by Mark Doherty of Campion & Company Fine Homes Real Estate

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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

Winchester, MA310 Main Street

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72730144

  • Single Family Detached
  • Bathroom 6
  • Rooms 14
  • Bedrooms 5
  • Square Feet 5,204

Stunning recreation of a true Winchester home! This modern day classic with great curb appeal, has been impeccably designed and beautifully constructed by top design/build team. Located on prominent Main St. just outside the center, with quick easy access to schools, the train to Boston, shops, restaurants, ponds, trails. This glorious home offers high end designer finishes and style that cannot compare. First floor w/ gorgeous kitchen, 48' Wolf Stove, Sub Zero fridge,oversized island and adjacent family room w/fireplace, direct entry to garage. 1st floor office, living room w/fplc, stylish dining rm w/ soapstone wet bar/server great for entertaining! step outside the french doors to bluestone patio with wrap around seating. Second floor offers 4 beds 3 baths with a master that is straight out of a magazine! 20' Cathedral ceilings, cozy fireplace, spa-like bath w/ soaking tub and oversized shower. Third floor offers 2 add'l rooms & full bath. Finished LL media/playroom/Gym w/ full bath

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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11 Niles Lane Winchester MA 01890

Winchester, MA11 Niles Lane

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72727847

  • Single Family Detached
  • Bathroom 4
  • Rooms 12
  • Bedrooms 6
  • Square Feet 6,354

Imagine coming home to a quiet home flooded with natural light, nestled in privacy & across the street from the Mystic Lake. This sprawling contemporary Colonial offers just that, on one of the most prized street in town, where homes rarely convey. And it comes with deeded land directly on the lake, so you have full access whenever you want. 6 bedrooms, including a first floor en-suite set up, perfect for nannies or guests. The large open floorpan offers a gigantic kitchen and family room, and a design that just begs you to entertain. French doors flank the rear of the house, leading to a sprawling patio and BBQ area. The master suite offers a huge bed chamber, large dressing room w/multiple closets and a private bath. Custom finishes highlight this home at every turn, including the hand-made iron stair rails, builtins, columns, trim and elaborate entry chandelier. A large playroom is located in the basement, and there is ample room to add a wine cellar or work room. Plus, 2 car garage

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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19 Wedgemere Avenue Winchester MA 01890

Winchester, MA19 Wedgemere Avenue

Price$2,349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72675475

  • Single Family Detached
  • Bathroom 6
  • Rooms 12
  • Bedrooms 5
  • Square Feet 7,472

Wedgemere Avenues very first home! Situated on one of the largest lots on the street & in desirable Ambrose elementary district, this magnificent property offers a front porch like no other! Grand oversized rooms, gorgeous millwork, 4 fireplaces & many updates including new heating and cooling systems! Stunning entry foyer with grand staircase welcomes you into the home, flanked by a front to back living room and formal dining room both flooded w/ sunlight and extraordinary details. Expanded Kitchen w/ original butlers pantry and adjacent family room/den w fireplace overlook sprawling fenced rear yard w/in-ground gunite pool and plenty of lawn space. Second features Grand Master suite complete with fireplace, coffered ceiling, sitting room, walk in closet and private bath. Three additional rooms and 2 baths on 2nd . Full third floor with 2 bedrooms, recreation room and full bath. Lower level walk out with wine cellar, full laundry room, family/game room & utility rm w/updated systems.

Listed by Kim Covino of Leading Edge Real Estate

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%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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 GROVE Street Winchester MA 01890

MLS Number 72658095

  • Single Family Detached
  • Bathroom 4
  • Rooms 12
  • Bedrooms 5
  • Square Feet 5,400

Old world charm and satisfaction perfectly blended with all the comforts and luxuries of today's new construction. Manicured grounds invite you up onto the quintessential New England front porch. Open the front door and instantly take in the grand foyer, beautiful moldings and detailed wood work. On the first floor, you will find a classic front parlor to one side and a front to back living room both swimming in natural light. Dining room with fireplace and built-in china cabinet perfectly located off the large, brand new eat-in kitchen makes entertaining a breeze. The beautiful bright kitchen boasts an over-sized quartz island with seating, stainless steel appliances, large pantry, kitchen table for 6+ and access to the exterior patio, back entry or 2-car garage. The expansive second floor features 5 large bedrooms, plus a home office/guest room, 2 laundry rooms and master suite. Lower level offers great flex space for a home gym, teen get-away etc. Winchester at its finest.!

Listed by Bill Caci and Catherine Albiani of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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432 South Border Road Winchester MA 01890

Winchester, MA432 South Border Road

Price$2,249,000

Est. Mortgage: $/month

MLS Number 72665236

  • Single Family Detached
  • Bathroom 7
  • Rooms 11
  • Bedrooms 5
  • Square Feet 6,095

NEW CONSTRUCTION Step right into this beautifully designed custom home and make it yours. This spectacular home offers 5 bedrooms and 6.5 baths, and is situated on a large lot across from the Middlesex Fells, just minutes from downtown Boston. This beautiful home offers today's amenities with two car garage, direct entry into mudroom, high-end chef's kitchen, great room with fireplace, and office, all with luxury finishes such as coffered ceilings and hardwood floors. First floor offers guest bedroom with full bath. Second floor includes master suite with walk-in closet and master bath with soaking tub, laundry room and three additional bedrooms. Expansive finished basement with full bath, perfect for exercise space or media. Large, flat backyard offers ideal space for outdoor dining and entertaining. Enjoy all that Winchester offers, including award-winning schools, quaint Winchester Center with restaurants, shopping, Farmer's Market, and library, and two commuter rail stations.

Listed by Pirani & Wile Group and Peter Pirani of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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 Sheffield Road Winchester MA 01890

Winchester, MA4 Sheffield Road

Price$2,229,000

Est. Mortgage: $/month

MLS Number 72729287

  • Single Family Detached
  • Bathroom 4
  • Rooms 12
  • Bedrooms 6
  • Square Feet 4,159

Storybook colonial with all the updates you desire & an address that can not be beat! Located on one of Winchesters most desired streets, this home is with filled with character & detail, perfectly blended with modern amenities and high end finishes. Direct access from the 2 car garage to side porch, mudroom with built in bench and storage lockers, half bath & laundry. The kitchen; the heart of this home is stunning and feat. viking appliances, granite counters, double ovens, center island and cozy breakfast nook with built in seating overlooking rear patio and beautifully manicured yard. The dining room can seat many and offers original coffered ceilings & wood fireplace. Formal living room with fireplace & beamed ceilings, large family room on first floor & great screen porch complete this floor. Second floor offers 4 large bedrooms, master with full bath, third floor offers two additional rooms great for home office. Lower level w/media/game/gym rooms w/ full bath & 2nd laundry rm.

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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 TourAsk A QuestionMore Details

19 Windemere Road Winchester MA 01890

Winchester, MA19 Windemere Road

Price$2,125,000

Est. Mortgage: $/month

MLS Number 72681452

  • Single Family Detached
  • Village Westside
  • Bathroom 5
  • Rooms 12
  • Bedrooms 5

Stunning Colonial with contemporary flair! As you enter the spacious foyer,you will appreciate many custom features. Bathed in natural light, with high ceilings,each room flows into the next. Open concept eat-in gourmet kitchen with island is perfect for entertaining, with easy access to backyard and patio. Enjoy family gatherings in spacious formal dining room. As the unique layout continues with formal living room and generous size family room each boasting its own fireplace. The second floor stairwell with Brazilian Cherry flooring leads to four bedrooms and separate laundry. Private master suite on third level will wow you in every way! High ceilings, fireplace, walk-in closet and designer bath with double vanity, separate shower and soaking tub makes this space feel like a Spa get-away. Adjacent room with balcony is great for home office etc.Large finished basement with cedar storage, bar area and more,,This beautiful home is is ideal for extended family, au pair or in laws.

Listed by Cathy Paolillo of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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39 Myopia Road Winchester MA 01890

Winchester, MA39 Myopia Road

Price$2,099,000

Est. Mortgage: $/month

MLS Number 72651112

  • Single Family Detached
  • Village Myopia
  • Bathroom 5
  • Rooms 14
  • Bedrooms 5

If you are searching for privacy in a sought after enclave of Winchester this is the home for you. Large sunfilled 1st floor with a flexible floor plan. Enter into a gracious foyer with a dramatic curved staircase. The kitchen is open to family room with wide-planked hardwood floors. Huge 4 season sunroom w/ fireplace, Palladian windows and a series of glass french doors overlooking your private oasis & pool area. Formal living rm w/ marble fireplace. A sophisticated study w/ bay window & fireplace overlooking the back yard. Beautiful dining room perfect for entertaining large gatherings or intimate family meals. 2nd floor offers a private master bedroom suite w/ 4 additional bedrooms. Finished walk-out lower level w/ a large tiled bonus room, additional space for guest or au pair. Attached 2 car-garage. Close to Country Club, Boat Club & only 8 miles from Boston. Bring your design ideas and make this your forever home. House cannot be seen from street.

Listed by Leigh Ventura and David Hayes of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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 TourAsk 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.