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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. 

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73 Thornberry Road Winchester MA 01890

Winchester, MA73 Thornberry Road

Price$1,475,000

Est. Mortgage: $/month

Open House

MLS Number 73089498

  • Residential
  • Next Open House: Sun 03/26 12:00 pm. to 1:30 pm.
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,046

From the moment you step inside this 4 bedroom & 2.5 bath home, you’ll be struck by the timeless elegance & warm ambiance of this classic Colonial. Situated on a sprawling half-acre lot, this stunning home boasts ample living space w/ gleaming newly refinished hardwood floors throughout. The main level offers a sun-filled formal living room w/ fireplace. Opposite is an elegant dining room. The eat-in kitchen opens up to a great room w/ a soaring ceiling and custom built-ins which leads to a bright sun room w/ access to a private deck. A half bath, laundry, & access to an oversized two-car garage complete this floor. Upstairs you’ll find a primary suite w/ two walk-in closets & an ensuite bath plus 3 generous-sized bedrooms, an additional full bath, & pull-down access to the attic. Lower level includes a finished room w/ fireplace & 2 additional rooms ideal for storage. New roof, boiler, decking & electrical. Located near Vinson Owen school & Whipple Hill trails. Welcome Home!

Listed by Paula R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group

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$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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 Stowell Road Winchester MA 01890

Winchester, MA17 Stowell Road

Price$1,465,000

Est. Mortgage: $/month

Open House

MLS Number 73090241

  • Residential
  • Next Open House: Sun 03/26 12:00 pm. to 3:30 pm.
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,705

This bright & airy classic home is completely renovated w/ great attention to detail & hardwood floors throughout. 1st flr has great circular flow between the living rm, dining rm, family rm & kitchen. Fireplace family rm & eating area blend together to create an open & inviting atmosphere. Kitchen features marble countertops, windowed cabinets, downdraft stove, two sinks, deck access, & a passthrough into the family rm- perfect for entertaining guests! On the 2nd flr, the high-ceilinged primary bdrm features two walk-in closets w/ pocket doors & en suite bath. Down the hallway are two bright & cheerful bdrms & family bath w/ backlit mirror. The 3rd flr provides privacy w/ its romantic fourth bdrm w/ custom paneled walls. Spacious heated basement has laundry rm, two flexible rooms perfect for a gym & playroom, & a beautiful reclaimed wood barn door leading into a storage rm. Out front is a wraparound porch, & in the backyard you'll be able to enjoy the private pond from the back deck.

Listed by Anne Spry of Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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40 Elmwood Avenue Winchester MA 01890

Winchester, MA40 Elmwood Avenue, Unit 10

Price$1,349,999

Est. Mortgage: $/month

MLS Number 73073522

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,662
  • High School Winchester High

The CROWN JEWEL of the building! This truly special unit is flooded with light and boasts (2) private decks, (2) master suite options, and (2) garage parking spaces. Allegro is conveniently located in DOWNTOWN WINCHESTER. Picture yourself strolling down for your morning cup of joe, then over for a quick visit to the farmers market to pick up some fresh items for dinner. Don't feel like cooking? We don't blame you! Out the door you go, AGAIN, to enjoy any one of the fabulous restaurants our town center has to offer. This is how you live when you live Allegro. This elegant Penthouse unit boasts in-unit laundry and easy one level living. Don’t forget about the elevator and heated garage for your car. Condo fee includes trash service, landscaping, snow removal, property maintenance, PLUS HEAT & WATER!

Listed by Vita Realty Group, Robert Cipro and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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 Alden Lane Winchester MA 01890

Winchester, MA15 Alden Lane

Price$1,235,000

Est. Mortgage: $/month

Open House

MLS Number 73090254

  • Residential
  • Next Open House: Sun 03/26 11:30 am. to 1:00 pm.
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,814

Welcome to 15 Alden Ln! From the bright, cathedral ceilinged family room, you can go out to the back deck and enjoy the exceptionally spacious backyard or stay inside and look out the windows on three sides letting you enjoy nature inside and out! Open kitchen and dining area features stainless steel appliances and a bay window overlooking the deck and backyard. Make your way to the fireplace living room, across from the dining room with built in cabinets. The first floor has a flexible bedroom/office space with adjacent full bath. The second floor offers three unique and spacious bedrooms. With its abundance of space and privacy, plus a full bath, the lower level offers great flexibility for a workout room, hobby room, or lounge space for out-of-town guests. Also on the level is the laundry with fold out ironing board and ample storage space. Attached garage with entry from mudroom.

Listed by Anne Spry of Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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30 Symmes Road Winchester MA 01890

Winchester, MA30 Symmes Road

Price$1,170,000

Est. Mortgage: $/month

MLS Number 73082440

  • Residential
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,341

Have the feel of a single-family home with EXCLUSIVE entrance on Symmes Rd and driveway with 2-car garage plus outdoor space with rear yard and patio. Outstanding location and home in wonderful neighborhood near Town Center, Lincoln Elementary School, Ginn Field and playground, the Tri-Community bike path and Wedgemere Train Station. Enchanting details - high ceilings, built-in hutch, hardwood floors, quality replacement windows with beautiful sunny exposure, wood burning fireplace and more. You'll find 3 bedrooms plus an office nook and full bath on the 2nd floor. The 3rd floor provides 2 more bedrooms, a landing perfect for study space, a full bath and plenty of storage space. Wanting more? Finishing part of the basement is a good opportunity. Easy access to 93, 3, 2 and 128/95 or take advantage of the short distance to the commuter rail to Boston. Get involved at Wright-Locke Farm, experience the Middlesex Fells or appreciate the quick ride to enjoy Boston just 8 miles away.

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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30 Symmes Road Winchester MA 01890

Winchester, MA30 Symmes Road, Unit 30

Price$1,170,000

Est. Mortgage: $/month

MLS Number 73082439

  • Condo
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,341

Have the feel of a single-family home with EXCLUSIVE entrance on Symmes Rd and driveway with 2-car garage plus outdoor space with rear yard and patio. Outstanding location and home in wonderful neighborhood near Town Center, Lincoln Elementary School, Ginn Field and playground, the Tri-Community bike path and Wedgemere Train Station. Enchanting details - high ceilings, built-in hutch, hardwood floors, quality replacement windows with beautiful sunny exposure, wood burning fireplace and more. You'll find 3 bedrooms plus an office nook and full bath on the 2nd floor. The 3rd floor provides 2 more bedrooms, a landing perfect for study space, a full bath and plenty of storage space. Wanting more? Finishing part of the basement is a good opportunity. Easy access to 93, 3, 2 and 128/95 or take advantage of the short distance to the commuter rail to Boston. Get involved at Wright-Locke Farm, experience the Middlesex Fells or appreciate the quick ride to enjoy Boston just 8 miles away.

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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4 Valleywood Circle Winchester MA 01890

Winchester, MA4 Valleywood Circle

Price$1,125,000

Est. Mortgage: $/month

Open House

MLS Number 73089610

  • Residential
  • Next Open House: Sun 03/26 1:30 pm. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,936

Don't miss out on this charming 3 bedroom, 3 bath home in Winchester, situated on over half an acre at the end of a quiet cul-de-sac. The spacious main floor features beautiful hardwood floors throughout, an inviting living room, formal dining room, and a generously sized kitchen. You'll love the 3 bedrooms, including a main suite with its own full bath. Downstairs, The lower level offers a large family room with fireplace, an additional recreation room perfect for games or playtime, and a separate room that can be used as home office. An additional bathroom and garage access complete this space. Relax in the three-season porch overlooking the tranquil backyard or host a cookout on the patio with friends and family. With a 2-car garage and ample off-street parking, this home has it all! Minutes from Vinson-Owen Elementary School, Whipple Hill, and Tennis and Swim Club. Don't wait to make it yours!

Listed by Alina Wang and Sophia Gao of Coldwell Banker Realty - Lexington

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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40 Elmwood Avenue Winchester MA 01890

Winchester, MA40 Elmwood Avenue, Unit 4

Price$974,900

Est. Mortgage: $/month

MLS Number 73068446

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,296
  • High School Winchester High

The new year is all about starting fresh; pursuing things you may not have achieved during the year before. Perhaps you missed out on an opportunity to live in Winchester’s newest development right in our town center. You’re in luck, HERE’S ANOTHER CHANCE! Welcome to unit #4 at Allegro. This is the first time this front facing unit is available for sale! Boasting in-unit laundry and easy one level living. Don’t forget about the elevator and heated garage for your car. Condo fee includes trash service, landscaping, snow removal, property maintenance, PLUS HEAT & WATER! This location is truly not to be missed. Everything is just outside your door including shops, restaurants, banks, grocery store, hardware store, and the commuter rail station. Book your visit today and see what is means to live Allegro!

Listed by Vita Realty Group, Michael Askjaer and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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132 Cambridge Street Winchester MA 01890

Winchester, MA132 Cambridge Street

Price$950,000

Est. Mortgage: $/month

MLS Number 73066517

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,636

Welcome to this move in ready Craftsman Colonial Style Home. Walk into an open Living room and Dining room with gleaming hardwood floors. The Kitchen is open and has plenty of cabinet space with access to the fenced in large shaded back yard in the warmer months with beautiful patio to enjoy. There are three bedrooms and three bathrooms plenty of storage in the Attic as well. and a partially finished basement downstairs. Don’t miss this opportunity on a beautiful majestic home close to highway, train station and shopping centers and town center.

Listed by Anas Mtet of Premier Property Solutions,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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118 Wendell Street Winchester MA 01890

Winchester, MA118 Wendell Street

Price$899,000

Est. Mortgage: $/month

MLS Number 73085295

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,760
  • High School Whs

Hurry! This charming cape located in desirable Winchester is just waiting to be transformed into the luxurious home of your dreams! Don’t miss out on this meticulously maintained home on a quiet street. The exterior of the home is low maintenance vinyl siding. The interior is carpeted with beautiful hardwood underneath. Take advantage of two full bathrooms and TWO gorgeous wood burning fireplaces. The home has a newly installed natural gas furnace. The unfinished walk-out basement has unlimited potential. Located just a short walk to McDonald field which hosts a playground, baseball fields and tennis court for great family activities. Take advantage of all that Winchester has to offer including award-winning schools, Middlesex Fells Reservation, bike path, and easy access to Boston.

Listed by Stephanie Johnson of Premium Realty Group LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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. MLSPIN 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.