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. 

65 Myopia Road Winchester MA 01890

Winchester, MA65 Myopia Road

Price$2,599,999

Est. Mortgage: $/month

MLS Number 72775321

  • Single Family Detached
  • Bathroom 5
  • Rooms 14
  • Bedrooms 4
  • Square Feet 7,206

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: 2.79% last updated on Jan 14, 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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49 Allen Road Winchester MA 01890

Winchester, MA49 Allen Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 72742401

  • Single Family Detached
  • Village East Hill
  • Bathroom 6
  • Rooms 10
  • Bedrooms 5

Desirable East Side location! Luxurious 5-beds 6 full bath colonial currently under construction and ready for occupancy by end of the year!! Spacious and inviting - this custom designed home offers a grand open floor plan ideal for entertaining and modern day family living.The kitchen features 8' island with seating/ quartz countertops, high-end WOLF/SUB-ZERO appliances, butler's pantry w/ wine fridge, breakfast area. Formal dining room w/ coffered ceiling, family room with gas FP off the kitchen has direct exterior access w/ sliders leading out to deck & rear yard. The 2nd level master suite is the the definition of luxury & relaxation - offering a spacious master bedroom, dual walk-in closets, bath with tiled shower/glass encl. double vanity & soaking tub! Three add'l beds incl. junior suite w/ bath, full hall bath and laundry room finish this level. Finished 3rd level is ideal for 5th bed/ in-law suite/bonus space, LL feat. walk-out, oversized media room, full bath and storage!

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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 Pilgrim Drive Winchester MA 01890

Winchester, MA3 Pilgrim Drive

Price$2,249,000

Est. Mortgage: $/month

MLS Number 72761553

  • Single Family Detached
  • Village West Side
  • Bathroom 5
  • Rooms 15
  • Bedrooms 5

Spectacular one of a kind home situated on a premiere lot offering almost an ACRE of level land! If you are looking to build a pool or tennis court or even both, this could be your chance! This home has been beautifully expanded and renovated by a top builder offering over the top quality and designer finishes creating this 6,000 sf masterpiece! This chic, custom designed home has an expansive floor plan w/space for the entire family to enjoy! First floor direct entry 2-car garage leads into great mudroom, gorgeous kitchen with induction stove, high end appliances, & quartz counters .. adjacent breakfast room plus family room w/ gas fplc, dining room, formal living w/ add'l fplc, First floor master suite w/ office / sitting room and lavish spa-like bath! Stunning second family room with walls of windows will for sure be your favorite room, overlooking gorgeous, expansive rear yard! Second floor offers 2nd master en-suite option lower level full walk out / use as gym/ media/ game room.

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

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: 2.79% last updated on Jan 14, 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 Lakeview Road Winchester MA 01890

Winchester, MA3 Lakeview Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72768286

  • Single Family Detached
  • Bathroom 4
  • Rooms 10
  • Bedrooms 6
  • Square Feet 3,958

Don't miss this once in a lifetime opportunity to turn this elegant, quintessential Winchester property into your DREAM home! First time available in over 50 years, this beautifully cared for home is awaiting its new owners. Offering 6 large bedrooms, 3.5 baths across three spacious levels with inviting farmers porch, gorgeous entry foyer, 30' front to back double living room w/ beamed ceilings & wood-burning FP, custom eat-in kitchen w/french doors / direct access to deck overlooking private rear yard, & mudroom with laundry. Cozy wood paneled office/study with exterior access to the lower deck & formal DR w/ FP complete the main level. Located in one of Winchester's most sought after neighborhoods, proudly situated on over 14,600 sf in desirable Ambrose School district. Close to Wedgemere train station, Ginn Field, scenic Mystic Lakes offering walking trails, fields, parks, & sandy beach. Detached garage, new windows, new boiler & HW floors throughout. This home will not last!

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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1 Stonefield Circle Winchester MA 01890

Winchester, MA1 Stonefield Circle

Price$1,899,000

Est. Mortgage: $/month

MLS Number 72725701

  • Single Family Detached
  • Bathroom 5
  • Rooms 14
  • Bedrooms 5
  • Square Feet 5,116

Must see this modern colonial farmhouse w/ oversized 2 car attached garage and wrap around farmers porch! Completely renovated and expanded by top local builder, this home is located across from the flats area in desirable Stonefield Estates cul-de-sac. This beautiful sprawling home boasts a grand yet very livable first floor with high end chefs kitchen, first floor office/ family room, beautiful dining room and front to back living room with floor to ceiling windows, access to deck / side yard and fireplace. Second floor offers 4 large bedrooms w/ 3 baths .. second floor laundry and study room. The master is beautiful with cathedral ceilings, walk in closet & custom designer bath. Finished third floor offers great space for guests/ additional office or nanny quarters! Lower level game room/ family room / gym with add'l bath. Curb appeal doesn't get much better than this! Enjoy all of the modern amenities along with the old world charm this special home offers! Ambrose elementary.

Listed by Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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248 Forest Street Winchester MA 01890

MLS Number 72770374

  • Single Family Detached
  • Bathroom 5
  • Rooms 11
  • Bedrooms 5
  • Square Feet 5,200

~NEW CONSTRUCTION IN WINCHESTER~ Here you will enjoy a tremendous location with convenient access to the Middlesex Fells, Rt 93 while also being located in the popular Muraco School District. All this and a unique scenic setting with wooded views. This 11 room 5 bed, 4.5 bath Colonial built by a prominent local builder has it all! Four fully finished floors provide plenty of space for the whole family plus comfortable space for guests, in-laws and areas for working from home. A gorgeous kitchen opens to a fireplaced family room with sliders to a large deck overlooking a landscaped yard with pleasant views. The finished basement is complete with a full bath and separate storage area. The 3rd floor has a large recreation room a 5th bedroom and a full bath. Covid-19 safe showing guidelines to be adhered to

Listed by The Synergy Group and Paul Cirignano of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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2 Hastings Road Winchester MA 01890

Winchester, MA2 Hastings Road

Price$1,875,000

Est. Mortgage: $/month

MLS Number 72752353

  • Single Family Detached
  • Bathroom 4
  • Rooms 8
  • Bedrooms 5
  • Square Feet 4,036

This Pristine Colonial Home is located on a lovely cul de sac in a very desirable Winchester neighborhood close to the town forest. Upon entering this home, you will be captivated by all the attention to detail, wonderful scale with tall ceilings and the excellent flow that leads you to the magnificent custom designed chef's kitchen which is the heart of this home. No expense was spared in this dream kitchen with very high end appliances featuring Wolf, Thermador, Subzero and Fisher & Paykel, hand stained custom cabinetry and the 11 ft. center island which offers perfect function and ease for everyday living and entertaining. The second floor offers a wonderful master bedroom suite with a beautiful master bath that includes a BainUltra tub, a steam shower and a custom designed walk in closet plus three additional bedrooms. The media room, exercise area and and private guest suite is found in the nicely finished lower level. Professionally landscaped lot. Truly Special, Don't Miss It!

Listed by Ida M. Bianco of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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508 South Border Road Winchester MA 01890

Winchester, MA508 South Border Road

Price$1,649,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72483056

  • Single Family Detached
  • Bathroom 5
  • Rooms 12
  • Bedrooms 5
  • Square Feet 4,450

Winchesters finest new home value!!This beautiful new construction (originally the model home), three level Colonial home is a must see and is move in ready! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home features gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room! Property has underground lawn irrigation, to help maintain the exterior of this gorgeous property!

Listed by Gary J. Litchfield and Brittany Gray of Mass. Real Estate Solutions, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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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25 Gershon Way Winchester MA 01890

Winchester, MA25 Gershon Way, Unit 25

Price$1,475,000

Est. Mortgage: $/month

MLS Number 72725070

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

This fabulous townhome bordering the woods was designed by national, award-winning, architect Gary Snider. Imagine luxurious finishes throughout: 10'+ ceilings, hardwood floors and plenty of natural light. This open concept plan has a 1st floor master suite with oversized walk-in closets and a great bathroom. The kitchen is adorned with ceiling height cabinets, Quartz countertops & island, a spacious pantry + top of the line SS appliance package. The dining room features a beautiful coffered ceiling. Just beyond, the room opens up to a 22' ceiling in the dramatic living room featuring a floor to ceiling fireplace. Abutting the covered porch, a wall of windows pours sunlight into this home. The 1st floor flex room can be a home office, a library or studio for your beloved hobbies. 1st floor also features a powder rm and laundry. Upstairs you'll find 2 additional spacious EN SUITE bedrooms and a bright open loft. 2 Car garage with electric car charging station.*MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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.