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$2,799,999

Est. Mortgage: $/month

Open House

MLS Number 72650982

  • Single Family
  • Next Open House: Sun 07/12 1:30 pm. to 3:00 pm.
  • Garage 2
  • Parking Spaces 5
  • Total Parking Spaces 7

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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11 Lorena Road Winchester MA 01890

Winchester, MA11 Lorena Road

Price$2,550,000

Est. Mortgage: $/month

MLS Number 72680206

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

Steeped in history, 11 Lorena Road features 7,549 square feet of living space & is a quintessential New England home in both setting & style. Originally designed by renowned architect Miles Standish, a 1960s addition by Richard Wills of the elite Royal Barry Wills architecture firm-featured in Life Magazine in both 1938 & 1946 for his classic Cape Cod & Colonial home designs-added an early American pub w/ beautiful pine-paneled walls, full bar, fireplace & abundant seating as well as a country living room. In 1999 Richard's son, also of RBW, added an updated kitchen, family room & second floor bedrooms. All of this is set on 1.5+ acres of terraced land w/ patio spaces, embedded mill stones & spectacular gardens with a number of rare & unusual plantings including a certified Dawn Redwood that is one of the oldest in the US & believed to be from the original batch of seeds brought to the US from China by the Arnold Arboretum. Additional details abound in this unique, special home!

Listed by Anne Spry and Lesley Smith of Waterfield Sotheby's International Realty

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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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$
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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

MLS Number 72676963

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

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

$
$
%
$/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.

Virtual TourSave 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.