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. 

6 Harrison Street Winchester MA 01890

Winchester, MA6 Harrison Street

Price$2,995,000

Est. Mortgage: $/month

MLS Number 72466644

  • Single Family
  • Garage 3
  • Parking Spaces 4
  • Village The Flats
  • Year Built 2019

New construction colonial will take your breath away! Entryway opens up to an open concept layout: Family room w/ gas fireplace, dining room, living room, grand kitchen, office, mudroom w/ built-ins & 1.5 baths. The kitchen features an oversized island w/ White Rhino counters, Wolf double oven w/ grill, griddle, custom hood & pot filler, 54" sub zero fridge/freezer, 2 sinks, 2 dishwashers & pantry. Sliders open up to a patio & expansive lawn. 2nd floor features the grand master suite plus 3 additional bedrooms, all w/ ensuite bathrooms & walk-in closets. Master includes dramatic vaulted ceilings, cupola, attached sitting room, oversized celebrity style closet & master bathroom w/ soaking tub, rain shower & marble floors. The 3rd floor has 2 bedrooms & 1 full bathroom. Finished lower level w/ sunken media room, cable/internet setup, central vac & sitting room w/ full bathroom. Additional features: oversized laundry room; heated floors in full bathrooms; heated oversized 3-car garage.

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: 3.75% last updated on Nov 14, 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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65 Myopia Road Winchester MA 01890

Winchester, MA65 Myopia Road

Price$2,699,000

Est. Mortgage: $/month

MLS Number 72506620

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 1952
  • Full Bath 4

IMMACULATE ESTATE WITH STUNNING GROUNDS & HEATED POOL!!! This prestigious Myopia Hill address is an incredible Colonial set on an acre of land, affording privacy & tranquility. The home features a grand foyer, elegant dining room with fireplace, a chef's kitchen, and a vaulted breakfast nook; perfect for all your entertaining needs. The adjoining living & family room boasts soaring ceilings, natural light streaming through oversized windows & an impressive stone fireplace. The 2nd level features 4 spacious bedrooms, including the grand master suite with elegant master bath & dream walk-in closet. 2nd floor mezzanine game room, 3rd floor open office loft, home gym area,

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

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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 Wagon Wheel Road Winchester MA 01890

Winchester, MA5 Wagon Wheel Road

Price$2,680,000

Est. Mortgage: $/month

MLS Number 72542662

  • Single Family
  • Garage 3
  • Parking Spaces 12
  • Year Built 2015
  • Full Bath 6

This massive home sits on an acre of land of one of Winchester neighborhoods. Recently built (2015) and meticulously maintained, it is turn-key at a very high standard. It includes 7,097 square feet of living space, a huge heated pool, year-round 10 person spa, and professionally landscaping. Extreme privacy like no other. Fourteen rooms, 5 bedrooms, 6 full baths, finished basement, and a 3-car heated garage are the core of this estate. The patio has an extensive yard and room for a tennis court. A wrought-iron elegant entrance door will welcome you featuring a family room with a fireplace, formal living room, dining room, office, and the gorgeous kitchen in the first floor. The private master bedroom area dominates the second floor with a fireplace, heated tile bathroom, a large walk-in closet, and a reading room. Three large bedrooms complete the second floor including walk-in closets for each of them. The third floor offers a great living area for visitors and an addl master suite

Listed by Lisa Berry of Simply Sell Realty LLC

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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39 Myopia Road Winchester MA 01890

Winchester, MA39 Myopia Road

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72574074

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Village Myopia
  • Year Built 1966

Stately Brick 5 bedroom classic Colonial tucked away on Myopia Hill. 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 hom

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: 3.75% last updated on Nov 14, 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 Fenwick Road Winchester MA 01890

Winchester, MA16 Fenwick Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 72583824

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2019
  • Full Bath 5

Spectacular New Construction home with great curb appeal! This gambrel colonial home features 5 bedrooms, & 5 baths & is currently under construction by top local builder; to be complete Dec/Jan. This beautiful home with ideal layout features an oversized 2 car garage, direct entry into mudroom a gorgeous kitchen with high end appliances, 9' center island, sliders to rear yard, adjacent family room, formal living and dining w/ butlers pantry. 1st floor guest bedroom suite w/adjacent full bath, or first floor office. Grand master with 2 rooms, huge walk in closet, and lavish bath~ finished third level offers 5th/6th bedroom and full bath. Designer finishes throughout and a top location close to Wedgemere train station and the town center! Ambrose school don't miss out! Call list agent for a private accompanied showing.

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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18 Brooks Street Winchester MA 01890

MLS Number 72573913

  • Single Family
  • Garage 2
  • Parking Spaces 5
  • Year Built 1898
  • Full Bath 4

Welcome to the Alex Blaisdell House! This custom built Colonial Revival home features numerous, classical, architectural features which are waiting to be discovered by its new owners. The pediment entrance is supported by Ionic columns and sets the tone for the feeling of elegance throughout. The first floor is perfect for entertaining with its large, center hall which is open to the adjacent formal living room, dining-room and and office---all with high ceilings, gorgeous woodwork and and stunning windows. For the serious cook, the large open kitchen is perfect and is adjacent to the nicely appointed family room. Discover the spacious bedrooms on the second floor---especially the master suite with a walk-in closet, fireplace and large bathroom. It is located on a side street near the commuter rail to North Station and a short distance to downtown shopping and restaurants plus it is also close to major routes to Boston. Enjoy this great find which is one of a kind!

Listed by Nancy O'Herron of Coldwell Banker Residential Brokerage - Winchester

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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 Fox Hunt Lane Winchester MA 01890

Winchester, MA5 Fox Hunt Lane

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: 3.75% last updated on Nov 14, 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 Dean Road Winchester MA 01890

Winchester, MA5 Dean Road

Price$2,235,000

Est. Mortgage: $/month

MLS Number 72582583

  • Single Family
  • Garage 3
  • Parking Spaces 6
  • Year Built 2019
  • Full Bath 5

BEAUTIFUL NEW CONSTRUCTION in Winchester's Muraco school district, recognized by the state for its outstanding 2019 MCAS achievement! This STUNNING 6-bedroom, 5-bath home with approx. 6125 sq. ft. of living space offers extraordinary comfort for the entire family, and the details throughout are absolutely exquisite. The sun-filled main level boasts a grand two-story foyer, living & dining rooms, gorgeous high-end kitchen w/ elegant cabinetry, large family rm. w/ fireplace, sitting rm., office area, + a guest bdrm & full bath. Second level has 4 spacious bdrms., including a fabulous master en-suite w/ soaking tub, striking tile, his/her sinks, + jetted shower; there are 2 more full baths, and laundry. Lower level offers GREAT spaces; exercise rm., playroom, media room, mudroom, + bedroom & full bath. The top floor is +900 sq. ft. of unfinished storage space. There's a 3 car garage, + terrific level back yard. Welcome home!

Listed by Anne Spry and Jane Byrne of Waterfield Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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17 Squanto Road Winchester MA 01890

Winchester, MA17 Squanto Road

Price$2,099,000

Est. Mortgage: $/month

MLS Number 72585667

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

Thanksgiving dinner would be so lovely here at 17 Squanto Road. Host your friends and family in a magnificent new construction property with a first floor layout that was MADE for entertaining. Enter in to a soaring two story foyer drenched with sunlight. Your guests will be immediately impressed. To your left is the family room with coffered ceiling, fireplace, and custom built in's. This space is open directly to the oversized kitchen, with eat-in, where you'll prepare this scrumptious meal. How better to do it then with 17 Squanto's top of the line appliances including Wolf cooking and SubZero refrigeration. The formal dining room is where you'll have your main event. After dinner, drinks and dessert in the formal living room. Need a place for the kids to run around? The finished lower level with full bath is ideal! 5 bedrooms and 4.5 bathrooms in total. Enough space for your family AND those visiting from out of town! If you hurry, you may be able to make this dream a reality ...

Listed by Philip J. Vita of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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45 Bacon Street Winchester MA 01890

Winchester, MA45 Bacon Street

Price$2,099,000

Est. Mortgage: $/month

MLS Number 72567397

  • Single Family
  • Garage 3
  • Parking Spaces 5
  • Year Built 2011
  • Full Bath 6

PREMIER LOCAL BUILDER's PERSONAL RESIDENCE! Incredible location in Winchester's desirable "Flats" neighborhood, walk to the commuter rail to Boston. The welcoming double story foyer is flanked by a spacious dining room & sunny living room. Host a cooking class in the incredible Chef's style kitchen, boasting a top of the line SS appliance package & enormous granite island. Sit by the fireplace to unwind or enjoy the impending cooler days on the deck & spark up the firepit. Puppies love frolicking in the fenced in backyard! The master suite boasts a large WIC, radiant heated floors & a steam shower. 4 other bedrooms with en-suite baths & an "au pair" living quarter with separate entrance from the garage. The basement features a fabulous bar & bonus room, a great space for parties! Downtown Winchester, bustling with coffee shops, salons & restaurants is a short walk. Ginn Field & playground is around the corner. Within the Ambrose school district and easy access to major highways.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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.