Winchester Homes for Sale

Winchester, Massachusetts is a quiet, bedroom community conveniently located just 8 miles north of Boston. Winchester is home to several lakes and parks. Winchester is a family-friendly community that is home to several well-maintained parks, several lakes, and lots of trails.

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Browse all homes for sale in Winchester, Massachusetts below. Contact us to schedule a showing or if you have any questions. Create an account to save your favorite Winchester listings and to receive email notifications when similar properties become available. 

34 Everett Avenue Winchester MA 01890

Winchester, MA34 Everett Avenue

Price$2,799,999

Est. Mortgage: $/month

MLS Number 72650982

  • Single Family
  • Garage 2
  • Parking Spaces 5
  • Total Parking Spaces 7
  • MLS Status Active

It's been almost 45 years since this iconic lakefront property has been available to own. For Winchester aficionados, you know the home in which we're referring to. From the moment you turn onto the highly acclaimed Everett Avenue this stately 6 bedroom, mediterranean style mansion, captures your eye and doesn't let it go until you approach. Once proudly featured as “THE” home on Everett Ave in the Boston Globe Magazine, “Top Spots to Live” addition, here is your chance to make it “YOUR” home. From the moment you enter into the foyer the water views will captivate you. 4 levels of living, including a walk-out basement with access to level green space overlooking the Mystic Lake. Boating, fishing, and fun right in your backyard! Stunning period detail can be found throughout including mahogany woodwork, coffered ceilings, and multiple fireplaces. Fall in love with this idyllic location. Walk to the Winchester Boat Club, Winchester Country Club, Winchester Center, AND the commuter rail.

Listed by Vita Realty Group and Philip J. Vita of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

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: 3.07% last updated on Jul 2, 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$2,499,000

Est. Mortgage: $/month

MLS Number 72675475

  • Single Family
  • Parking Spaces 6
  • Total Parking Spaces 6
  • MLS Status Active
  • Year Built 1899

Wedgemere Avenues very first home! Built in 1899, this magnificent and historically significant property offers timeless grandeur blended with many updates desired for todays living and is truly one of a kind! Stunning entry foyer with grand staircase welcomes you into the home, flanked by a front to back living room and formal dining room each with fireplaces and gorgeous handcrafted millwork. 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 and a utility room with all updated systems including central A/C.** With additional updates this is a 3M+ home!!**

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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$2,475,000

Est. Mortgage: $/month

MLS Number 72665236

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Total Parking Spaces 12
  • MLS Status Active

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: 3.07% last updated on Jul 2, 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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28 Fells Road Winchester MA 01890

Winchester, MA28 Fells Road

Price$2,400,000

Est. Mortgage: $/month

Price Changed

MLS Number 72676963

  • Single Family
  • Garage 4
  • Parking Spaces 2
  • Total Parking Spaces 6
  • MLS Status Price Changed

Welcome Home to 28 Fells Road, a magnificant 3 year young colonial with 4 finished levels, scenic veiws, and everything you could need! This 6 bedroom, 6.5 bath home features spectacular grounds perfect for entertaining with an outdoor dining area, firepit, waterfall, and level fenced in grass area. Main floor centers around the kitchen, which is every cooks dream, a fireplaced family room with built in shelves, formal living room, stunning dining room, office, and en-suite bedroom. Master bedroom is made to impress with a fireplace, walk in closet, and master bath complete with vanity and soaking tub. Finished basement with large media room, exercise/game room, and full bath. Walk up attic not only features plenty of storage, but also a family room, bathroom, and additional office area. 4 car garage enters into a mudroom. Just steps away from the Middlesex Fells where you can enjoy hiking/biking/walking on over 100 miles of trails! Enjoy all Winchester has to offer!

Listed by Team Blue and Linda Ducharme of ERA Key Realty Services

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%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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$2,349,000

Est. Mortgage: $/month

MLS Number 72651112

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Total Parking Spaces 12
  • MLS Status Active

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 Residential Brokerage - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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73 Yale Street Winchester MA 01890

Winchester, MA73 Yale Street

Price$2,329,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72672785

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Contingent

Welcome to the highly desirable Winchester neighborhood of "The Flats." This exceptional property is not to be missed. Traditional elegance with relaxed comfort for family living. Upon entering the spacious hall, on your right is the Living Room with gas fireplace. The oversized windows allow natural light to flow throughout the house. There is an oversized opening to the Dining Room which offers continued flow. The Gourmet Eat In Kitchen with oversized island beckons you in with Sliding Doors to the Deck and Patio. The fireplaced Family Room continues the flow. Don't miss the screened porch through the French Doors. There is a mud room with entrance from the garage as well as from outside. A lavatory (plumbed for a shower) and wonderful office completes the first floor. Upstairs, there are four good sized bedrooms, Family Bath, Master Bath, Laundry Room and a Great Room over the garage. The Lower Level welcomes entertainment with Billiard Table and TV Area and tons of storage.

Listed by Carolyn Vernaglia of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

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: 3.07% last updated on Jul 2, 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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18 Brooks Street Winchester MA 01890

Winchester, MA18 Brooks Street

Price$2,249,000

Est. Mortgage: $/month

MLS Number 72654732

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

Imagine a Back Bay mansion set in bucolic Winchester...this home personifies the look and feel.This is one of those homes that just stop you in your tracks, in an A++ location. It's all about the soaring ceilings, incredible moldings and trim. The original leaded glass windows that beckon from all over the house, a spectacular foyer that embraces with beauty, numerous windows seats, pocket doors and huge fireplaces. Spectacularly oversized custom French doors highlight the front of the house and open onto a stone porch that wraps around the house and creates an amazing entertaining flow. The living room is bathed in light and across the extra large entry hall is a matching parlor, currently being used as a study. The dining room can hold 30 for dinner! The kitchen is enormous with a big walk in pantry, and leads to a large family room.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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 Windemere Road Winchester MA 01890

Winchester, MA19 Windemere Road

Price$2,225,000

Est. Mortgage: $/month

MLS Number 72681452

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

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 Residential Brokerage - Winchester

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$
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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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43 Grove Street Winchester MA 01890

Winchester, MA43 Grove Street

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72629238

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

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 & high end 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, full bath &-plenty of space for gym. Looking to build an in-ground pool? This home has the perfect setting and yard to accommodate all your backyard needs. Don't miss this opportunity to customize some interior finishes!

Listed by Kim Covino of Leading Edge Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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7 St Thomasmore Drive Winchester MA 01890

Winchester, MA7 St Thomasmore Drive

Price$2,100,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72674299

  • Single Family
  • Garage 3
  • Parking Spaces 6
  • Total Parking Spaces 9
  • MLS Status Contingent

Stylish & meticulously maintained Colonial in Winchester's desirable West Side! Located on a quiet street, this inviting home has everything today's savvy buyer seeks. This lovingly designed 4 bedroom, 3.5 bathroom house is ideal for raising a family. Enjoy the expansive deck for Summer BBQ's with family, a large fenced yard for playing catch with Rover & a life-size dollhouse, ready for curious tots to play in or backyard storage. Desirable open floor plan with dining, sun & family rooms (soaring ceilings & massive fireplace) centered around the oversized kitchen w/ 9' island. The office w/ gas fireplace provides ample space to accommodate your working demands. The walk-out lower level is perfect for your beloved hobbies or spacious playroom & plumbed for an additional bathroom. Within the highly acclaimed Vinson Owen school district & a short drive to Whipple Hill or Horn Pond for the hiking enthusiast. Explore bustling Winchester boasting 2 train stations, coffee shops & more.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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