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: 2.93% last updated on Jun 17, 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

MLS Number 72757101

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

2021 Winner for BEST NEW 55+ COMMUNITY IN THE COUNTRY. ONLY 2 HOMES REMAIN out of 29! 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: 2.93% last updated on Jun 17, 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$1,799,000

Est. Mortgage: $/month

Price Changed

MLS Number 72812251

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

AMAZING VALUE! Must see this spectacular home with EXCLUSIVE carriage house 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 great for au/ pair, in law/office/ gym/ with full bath, laundry, kitchenette, living and bedrm.

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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
Price Changed

MLS Number 72852748

  • Condo or Co-op
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,782

AMAZING VALUE! Must see this spectacular home with carriage house 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 great for au/ pair, in law/office/ gym/ with full bath, laundry, kitchenette, living and bedroom

Listed by Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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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33 Mccall Road Winchester MA 01890

Winchester, MA33 Mccall Road

Price$1,795,000

Est. Mortgage: $/month

MLS Number 72846769

  • Single Family Detached
  • Village Myopia Hill
  • Bathroom 2
  • Rooms 8
  • Bedrooms 4

A rare offering in a beautiful setting- welcome to 33 McCall Road! This extraordinary mid century modern property is a perfect combination of updates, smart home technology and location. Situated in the heart of Myopia Hill, this home features a renovated kitchen with high end Miele appliances, Subzero fridge and marble and quartz counters in an open concept main level, open to to dining area and living room. Large windows throughout, the living room has a stone fireplace and overlooks the recirculating waterfall in the backyard. A main level family room with beamed ceiling is bright during the day and transforms to a media room in the evening. Lovely and updated master suite on the ground level has walk in closet and opens to a conservatory, perfect for home gym. Spacious office/guest space and laundry room on the lower level. Three additional bedrooms and full bath on the upper level complete this unique property. Truly a must-see property!

Listed by Kara Spelman and Karen S. Garrett of Better Homes and Gardens Real Estate - The Shanahan Group

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$
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$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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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13 Gershon Way Winchester MA 01890

Winchester, MA13 Gershon Way, Unit 13

Price$1,787,500

Est. Mortgage: $/month

MLS Number 72809921

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,550

PRICE IMPROVEMENT for this PRISTINE 3 bed, 2.5 bath end unit townhome at Winchester's Winning Farm, a gold medal award winner from NAHB for best 55+ community in the US. The layout offers great flexibility for today's lifestyle with superior quality and charm. The first floor open concept features living room with gas fireplace and large windows to let in loads of natural light and great views. The dining room has coffered ceiling and door to outside deck. The office/den is accessed through double French doors. The custom chef's kitchen has high-end appliances, quartz countertops, and large island. The 1st fl master suite has walk-in closet with custom shelving, door to outside patio, and bathroom with double vanity, walk-in shower with bench, and separate soaking tub. The second floor has two large bedrooms, full bath with walk-in shower and loft/open space. There is a two-car attached garage and approx 1300 sq ft in basement with high ceilings that offers many options for future use

Listed by Tom Doherty of Gibson Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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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44 Glen Road Winchester MA 01890

Winchester, MA44 Glen Road

Price$1,675,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72832591

  • Single Family Detached
  • Bathroom 3
  • Rooms 11
  • Bedrooms 5
  • Acreage 0.34

Welcome to 44 Glen Road - where old meets new with stunning results! Updated eleven room Antique Colonial fashioned for today's comfortable living. Beautifully renovated chef's kitchen with large, granite center island. A bonus breakfast area with fireplace and large dining room make the 'heart of the home' ideal for family gatherings and holiday get-togethers. Enjoy outdoor living with direct access from the kitchen to a magnificent mahogany deck overlooking a beautifully landscaped yard and stone patio! Large living room with fireplace. Open floor plan with family room adjacent to the kitchen and a sweet sitting area complete the first floor. Master suite with a deck plus 4 additional bedrooms and a common play area on the 2nd floor. Located in one of Winchester's finest neighborhoods, close to the town center, schools and all the amenities Winchester has to offer. Imagine being part of the history of this special property! Perfectly suited for working/learning from home.

Listed by Nancy Fleming and Ann Basmaji of Barrett Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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 Ox PASTURE Winchester MA 01890

Winchester, MA3 Ox PASTURE

Price$1,675,000

Est. Mortgage: $/month

MLS Number 72850452

  • Single Family Detached
  • Bathroom 4
  • Rooms 10
  • Bedrooms 4
  • Acreage 0.25

TOP location, Ambrose school! Put your own personal touch on this spacious 3,900 sf 4 bedroom 3.5 bath colonial offering a flowing floor plan that many of todays buyers desire! First floor features a cathedral ceiling family room adjacent to the kitchen with direct access to an oversized deck and great rear yard with many mature perennial plantings. Front to back double living room w/ slider to deck, formal dining room, spacious eat in kitchen with high end stainless appliances & gas cooking, sunny family room w/ fireplace, mudroom/laundry/ direct entry to 2 car garage. Second floor offers a spacious master suite with walk in closet & private bath plus 3 additional bedrooms & hall bath. Full finished lower level with TV/ game room/ Media w/ built in cabinetry, separate private office with built in desk, and adjacent full bath ~New heating system, newer roof, must see this home!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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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6-8 Richardson Street Winchester MA 01890

Winchester, MA6-8 Richardson Street

Price$1,600,000

Est. Mortgage: $/month

Open House

MLS Number 72782963

  • Multi-Family 2 Family
  • Next Open House: Sun 06/27 11:00 am. to 12:00 pm.
  • Total Parking Spaces 2
  • Year Built 2020
  • Bathroom 4

The search for a perfect investment opportunity is over with this meticulously remodeled multi family home located in desirable Winchester. A short distance to the commuter train and a bustling downtown with quaint coffee shops, restaurants and shopping. Boasting 3,615 sq. ft of living area, 4 bedrooms and 4 full bathrooms, modern open concept main living areas and hardwood floors throughout. High ceiling dining rooms designed with architectural details. Fireplaces in each living room, perfect for chilly evenings! Both units have in-units laundry. Deeded parking spaces and charming private manicured garden areas and rooftop terrace with exceptional views of Winchester! Property has been virtually staged.

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: 2.93% last updated on Jun 17, 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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90 Thornberry Road Winchester MA 01890

Winchester, MA90 Thornberry Road

Price$1,549,000

Est. Mortgage: $/month

MLS Number 72852189

  • Single Family Detached
  • Bathroom 3
  • Rooms 10
  • Bedrooms 5
  • Acreage 0.46

Must see this fabulous new renovation/ expansion nestled on a premiere 20k West side lot with large level yard, gorgeous views & offering an abundance of privacy!This spacious 5 bedroom 2.5 bath home will meet your every need, custom designed with gorgeous high end designer kitchen featuring an 8' island, gas cooking, quartz countertops and backsplash.The fresh new open concept beautifully blends the kitchen with the casual dining room showcasing a wall of windows overlooking the rear yard w/ access to a large enclosed porch great for 3 season enjoyment! This meticulously renovated home also features an optional two-room master suite with custom walk in closet w/ shelving system, dressing area & featuring a stunning spa like bath. 4 Spacious bedrooms on the upper level with 2 baths & a full lower level offering an additional bedroom/office, Large sunny family rm w/ fireplace, bath, mudroom, lndry & storage w/direct access to oversized 2 car garage. Don't miss this picture perfect home

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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.