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. 

28 Surrey Road Winchester MA 01890

Winchester, MA28 Surrey Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 72807662

  • Single Family Detached
  • Bathroom 6
  • Rooms 14
  • Bedrooms 5
  • Acreage 0.73

Fabulous new construction opportunity awaits you in Winchester. Spectacular floorplan with 14 magnificent rooms, 5 bedrooms, 5 1/2 baths. Winchester luxury living encompassing choice materials and tasteful design by well known Master Builder from Winchester. Casual elegance with features such as beautifully appointed culinary grade kitchen, large finished family room and office with full bath in basement, primary bedroom with den, tasteful mudroom, heated 2 car garage, and more! Exceptional 31,800 square foot lot capable of an optional pool and pool house with striking optics overlooking the Ledges of Winchester. Quiet, popular neighborhood. Unmistakable benefits of New construction in a classic New England town with TOP rated schools. Built with perfection as a goal, and excellence as a result for a fortunate family to enjoy for many years to come.

Listed by Anthony Marino of Marino Real Estate Group

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$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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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22 Mccall Road Winchester MA 01890

Winchester, MA22 Mccall Road

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72804848

  • Single Family Detached
  • Bathroom 6
  • Rooms 11
  • Bedrooms 5
  • Acreage 0.75

Newer construction, custom built shingle style home in top Myopia/ Winchester Country Club location! Designed for ease of living with direct entry garage into mudroom, 1/2 bath leading into sun-drenched kitchen/ family room spanning the rear of the home, oversized windows overlooking conservation & providing an abundance of privacy and tranquility. Top of the line finishes both inside and out with natural cedar shake roof, natural stone accents, copper gutters & high end Andersen aluminum clad windows. First floor w/ high ceilings, family room w/ sliders to oversized deck, gas FP, formal dining room and living room with cathedral ceilings can also serve as second master suite w/ full bath! 2nd level features 4 beds, 2 ensuite; gorgeous master with high ceil, spa- like bath, 2nd fl. laundry. Full walk out lower level w/ private entry featuring full summer kitchen, bedroom, living room and full bath complete with full size windows leading to stone patio. Elevator shaft in place B-2nd Fl

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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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21 Laurel Hill Lane Winchester MA 01890

Winchester, MA21 Laurel Hill Lane

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72802704

  • Single Family Detached
  • Village Sunset
  • Bathroom 5
  • Rooms 10
  • Bedrooms 5

NEW CONSTRUCTION~Must see this stunning 4/5 bedroom home with luxurious design & high end finishes. This custom home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen will feature an 8' island with seating/ quartz countertops, high-end Thermador/ SUB-ZERO appliances, wine bar w/fridge, breakfast/ morning /dining area, spacious family room with gas FP off the kitchen w/ direct exterior access w/ sliders leading out to deck & large private rear yard; first floor also has formal dining room & 5th bed OR home office w/ 3/4 bath. The 2nd level master suite is a dream, offering a spacious master bedroom, with separate sitting room, dual walk-in closets, lavish bath with tiled shower/glass encl. double vanities & soaking tub! Three add'l beds incl. junior suite w/ bath, full hall bath and laundry room finish this level. Lower level full walk out w/ oversized media/game w/ kitchenette & full bath! 2 car garage/ mudroom~

Listed by Kim Covino of Compass

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$
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$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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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3 Indian Hill Road Winchester MA 01890

Winchester, MA3 Indian Hill Road

Price$2,300,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72806760

  • Single Family Detached
  • Bathroom 5
  • Rooms 9
  • Bedrooms 4
  • Acreage 0.36

Stunning New Construction by a local builder known for his functional design and impeccable craftsmanship that creates a statement of casual elegance and comfortable luxury. A Colonial with modern farmhouse accents has a unique U-shaped staircase with handcrafted iron balusters within a dramatic 2-story foyer; a fireplaced living room/study to the left; to the right is a dining room defined by coffered ceilings, open to the kitchen with multiple prep and gathering areas including the impressive fireplaced family room. The gourmet kitchen dazzles with quartz counters, a huge island, Thermador appliances, and white cabinetry with blue accents. More sizzle: Dine al fresco on the deck in the covered outdoor heated kitchen for the shoulder seasons. The 2nd floor includes an owner's suite w/ a luxurious spa bath; Bonus room & wine room on the lower level; 2-car garage. Sited on a large L-shaped lot w/green space for outdoor activities, potential for a built-in pool. Ambrose School district.

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

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$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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 Sunset Road Winchester MA 01890

Winchester, MA73 Sunset Road

Price$2,300,000

Est. Mortgage: $/month

MLS Number 72808584

  • Single Family Detached
  • Bathroom 5
  • Rooms 11
  • Bedrooms 5
  • Acreage 0.59

Better than new! Thoughtfully designed and updated cul-de-sac home with all the details you wish for. Covered front entry leads to gracious, welcoming foyer w/ double closets. To your left, a formal LR or office. To your right, an open, large dining room and powder room. High ceilings expand this sunlit home where the family room, chef's kitchen, sunroom all seem to flow into the gardens. Another large front corner room can be a BR, office or playroom. Upstairs, 5 spacious BRs open to the circular hallway with laundry. Owner's suite has exceptional closets, walk-in shower and jacuzzi tub. Two more baths serve other BRs. Over-sized 2+ car garage leads you to large mudroom, full bath, expansive media/rec room plus a workroom, ample wine cellar and great storage. Home's clever details not found anywhere else. And the real gem: Expansive, very private, must-see garden oasis with bluestone patio, natural stream, koi pond and hot tub. Very convenient to 93, 128, the Fells and more.

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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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21 Ridgefield Road Winchester MA 01890

Winchester, MA21 Ridgefield Road

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72808764

  • Single Family Detached
  • Village Town Forest
  • Bathroom 4
  • Rooms 13
  • Bedrooms 6

Location is everything! This stunning Revival home abutting Town forest land and near downtown offers unparalleled privacy & spectacular views! This spacious home stuns with impeccable old world craftsmanship mixed with sophisticated updates. You'll be wowed by the high ceilings, architectural mastery & stylish design. Grand foyer leads into an expansive living room with fireplace and gorgeous hardwood floors, flowing into a dining room with custom built-ins. Don't miss the cozy family room with dazzling views & additional fireplace! Modern kitchen with granite countertops, stainless steel appliances and two dishwashers. Fully screened-in porch with skylights is an entertainer's dream. Huge master suite complete with en-suite bath, sitting area, fireplace & full bonus room! Another two bedrooms & full bath complete the 2nd floor. Upper level features two more bedrooms, full bath & office. Manicured yard with stone patio and 2 car garage. Simply an exceptional home in a prime location!

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: 3.13% last updated on Apr 8, 2021
* 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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61 Yale Street Winchester MA 01890

MLS Number 72807165

  • Single Family Detached
  • Village Flats /Wedgemere
  • Bathroom 4
  • Rooms 8
  • Bedrooms 4

Enjoy living in the Flats! This expanded 4 bedroom 3.5 New England cape style home will meet your every need! A perfect blend of space, location, layout and updates. An inviting front porch welcomes you into this charming home with spacious formal living room w/ gas fireplace & custom built ins, formal dining with original natural woodwork & china hutch, updated eat in kitchen with gas cooking, adjacent family room addition in rear offers a sun-drenched room to enjoy throughout the year w/gas fireplace, built-ins and walls of windows overlooking the beautiful rear yard w/ deck and patio. The second floor offers an expanded master suite with new tile bath and walk in closet with custom shelving. Two additional bedrooms on second and full bath. The third floor offers a large bedroom and full bath. Lower level with additional space for family/game room. Two car garage direct to mudroom. Many upgrades including *new windows, *central A/C, *two story addition on rear, *new hot water heater.

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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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27 Gershon Way Winchester MA 01890

Winchester, MA27 Gershon Way, Unit 27

Price$2,050,000

Est. Mortgage: $/month

Open House

MLS Number 72757101

  • Condo or Co-op
  • Next Open House: Mon 04/12 11:00 am. to 4:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

ONLY 3 HOMES REMAIN out of 29! Designed by national, award-winning architect Gary Snider. Live surrounded by luxurious finishes, soaring ceilings, hardwood throughout & plenty of natural sunlight. This open concept plan boasts a 1st floor master suite with tray ceiling, a super-sized walk-in closet and luxurious en suite bath. The eat in kitchen is adorned with ceiling height cabinets, quartz countertops and top of the line stainless steel appliance package featuring Sub*Zero, Bosch, Wolf... The dining room has a stately coffered ceiling, bay window and sliders to a private, covered deck. The flex room can be a home office or studio for your beloved hobbies. 1st floor also features a powder room, mudroom and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath, a library and a large open loft for movie watching or game night. The icing on the cake: attached 2 Car garage with electric car charging station AND a 1,500 SF Walkout basement! MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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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75 Thornberry Road Winchester MA 01890

Winchester, MA75 Thornberry Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72807083

  • Single Family Detached
  • Village West side
  • Bathroom 4
  • Rooms 9
  • Bedrooms 5

Spectacular home w/ gorgeous yard & pool! This stunning west side property on a 20k lot offers a country club setting in your own back yard! Custom chefs kitchen w/ Sub-Zero fridge and gas cooking, adjacent breakfast room with walls of glass overlooking backyard oasis flowing into sun-drenched family room with soaring ceilings, living room w/ fplc & formal dining room, a perfect blend of formal and casual spaces to enjoy. First floor also offers private office with built-in desk/shelving and an elegant foyer. Master suite with walk in closet & updated bathroom plus 3 additional spacious bedrooms & a full bathroom on second level. Lower level offers 5th bedroom/family room w/fireplace, game room & bonus room w/ full bath; great for au-pair! Enjoy family time and entertaining with the meticulously maintained rear yard featuring a custom heated Gunite pool w/ LED color changing lights, tiger wood deck, w/plumbing for jacuzzi and fire-pit. Smart house technology for lighting..don't miss!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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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12 Mount Pleasant Street Winchester MA 01890

Winchester, MA12 Mount Pleasant Street

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72812251

  • Single Family Attached
  • Bathroom 4
  • Rooms 11
  • Bedrooms 6
  • Acreage 0.21

RARE FIND! Must see this spectacular turn of the century home completely renovated & restored inside and out! This spacious home offers a prime downtown location with 4 floors of space featuring 5+bedrooms, 3.5 baths complete with private ELEVATOR! This recently renovated custom designed town home lives like a single family and offers all the luxuries todays buyers desire, close to town, shops, schools, train to Boston. Stunning kitchen with cherry cabinets, stainless appliances, dining area flooded with sunlight, and family room with walls of windows overlooking beautifully manicured grounds. Formal LR with gas fireplace and detailed moldings. Spacious Master suite with w/fplc, walk in closet & marble bath w/ soaking tub. Third floor w/ 4 addl. beds and full bath. EXCLUSIVE to this unit is also a 3 CAR GARAGE/ CARRIAGE HOUSE w/ full in-law apartment above. The carriage house is handicapped accessible equipped with chair lift, full bath, laundry, kitchenette, living and bedroom areas.

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.13% last updated on Apr 8, 2021
* 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.