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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111 Highland Avenue Winchester MA 01890

Price$999,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72442290

  • Single Family
  • Parking Spaces 4
  • Year Built 1940
  • Full Bath 3
  • Bathroom 3

Step into the welcoming foyer of this stately 1940's Colonial to find beautiful character and a versatile layout with extra space on each floor. Fireplaced living room with beamed ceilings and oversized windows are flanked by the bright sunroom. Updated kitchen with granite countertops and cozy breakfast nook with access to side yard. Office and full bath complete this floor. The second floor spacious master bedroom has a walk in closet and an en-suite bath with an additional room that could be used as a nursery, office, or even a guest room. There are two more abundant bedrooms, full family bath, and a generous landing with closet space. Lower level includes an unheated family room with unique decorative fireplace, laundry and access to 2 car garage. Beautiful, spacious fenced backyard. Proximity to The Fells, make this home one to cherish!

Listed by Mariette Scheele of Waterfield Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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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38 Amberwood Drive Winchester MA 01890

Price$995,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72447683

  • Single Family
  • Parking Spaces 6
  • Year Built 1981
  • Full Bath 2
  • Bathroom 3

Outstanding Center Entrance Colonial in one of Winchester's top neighborhoods! The unique, serene and idyllic setting affords unparalleled privacy at this price point. The moment you step inside the front door, the lovely formal living room and dining room delight you with their charm and views. The fireplaced first-floor family room, with its adjoining half-bath, provides a fabulous place to entertain and relax. Just steps away is the oversized twenty-foot kitchen with its woodland views, custom painted pastoral mural, and central island. The kitchen's expanse offers a warm, inviting gathering space for the entire family! From the rear kitchen door, step onto the enormous deck abutting the dining room and kitchen to experience the peaceful tranquility in the private wooded world that surrounds you, yet with all the joys of home at your fingertips. Plenty of room beyond the driveway to clear and level for a grassy play area. Don't wait! See it today!!

Listed by Don Coughlin of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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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24 Brookside Avenue Winchester MA 01890

Price$979,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72442646

  • Single Family
  • Parking Spaces 3
  • Year Built 1905
  • Full Bath 2
  • Bathroom 3

Newly gut renovated breathtaking single family home in Winchester! Enter into this exquisite modern design containing an inviting living room, formal dining room featuring a stunning modern light fixture and box window, allowing ample natural light to stream through. The gorgeous kitchen contains elegant granite countertops, stainless steel appliances, a breakfast bar overlooking the sun-drenched family room and mudroom with access to the deck, patio and backyard. Enjoy the master suite, with his and her closets and a spa-like master bath featuring a floating double vanity and oversized shower. Two additional bedrooms and another full bath complete the second floor. The lower level is completely finished and offers an open floor layout with a media room, workout room or game room and a large laundry room. With these meticulous details, recessed lighting, stunning granite countertops and hardwood floors throughout; this newly renovated home is everything you've dreamed of!

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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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44 Edward Drive Winchester MA 01890

Price$749,000

Est. Mortgage: $/month

MLS Number 72387298

  • Single Family
  • Parking Spaces 3
  • Year Built 1987
  • Full Bath 3
  • Bathroom 4

BEST PRICE by far PER SQ' in WINCHESTER. Absolutely Gorgeous - "Spacious Townhouse" - Desirable Pepper Hill Estates - 3 Floors of Finished Living Space - 9 Rooms - 1st Floor - Open Floor Plan - Kitchen - Living Room w/Marble Fireplace and Sliders to a large Balcony overlooking Conservation - Dining Room w/views of Whipple Hill - Office/4th BD. 2nd Flr has 2 BD's - lg Master Suite w/BA, Jacuzzi Tub, Shower, Custom Walk-in Closet, a 2nd BD w/Slider Closet, Washer/Dryer and Bathroom. Lower Level has a spacious Recreation Rm w/Sliders to Patio, 3rd Bedrm/Exercise Rm, BA and lg Storage Rm. Exterior has lovely Garden Area - Garage and 3 Off-Street Parking Spaces. Recent UPDATES include - New Heating System - New Roof - New Skylight - Ceramic Tile Lower Level Flr - Corian Countertops and Sinks in Kitchen & BA's. Enjoy all Winchester Amenities - Winchester Center - one of the Top School Systems in Massachusetts. Just 12 Miles to Boston.

Listed by Lucille Murray of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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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44 Edward Drive Winchester MA 01890

MLS Number 72386482

  • Condo or Co-op
  • Half Bath 1
  • Bathroom 4
  • Year Built 1987
  • Full Bath 3

BEST VALUE PRICE PER SQ' in WINCHESTER. Absolutely Gorgeous - "Spacious End-Unit Townhouse" - Desirable Pepper Hill Estates - 3 Floors of Finished Living Space - 9 Rooms - 1st Floor - Open Floor Plan - Kitchen - Living Room w/Marble Fireplace and Sliders to a large Balcony overlooking Conservation - Dining Room w/views of Whipple Hill - Office /4th BD. 2nd Flr has 2 BD's - lg Master Suite w/BA, Jacuzzi Tub, Shower, Custom Walk-in Closet, a 2nd BD w/Slider Closet, Washer/Dryer and Bathroom. Lower Level has a spacious Recreation Rm w/Sliders to Patio, 3rd Bedrm/Exercise Rm, BA and lg Storage Rm. Exterior has lovely Garden Area - Garage and 3 Off-Street Parking Spaces. Recent UPDATES include - New Heating System - New Roof - New Skylight - Ceramic Tile Lower Level Flr - Corian Countertops and Sinks in Kitchen & BA's. Enjoy all Winchester Amenities - Winchester Center - one of the Top School Systems in Massachusetts. Just 12 Miles to Boston.

Listed by Lucille Murray of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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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22 Grove Place Winchester MA 01890
Active With Contract

MLS Number 72440854

  • Condo or Co-op
  • Half Bath 1
  • Bathroom 2
  • Year Built 1986
  • Full Bath 1

The meticulously remodeled townhouse you have been waiting for at White Horse Commons has finally come available. Excellent location just steps from the Wedgemere MBTA Commuter Rail Station. This magnificent end unit boasts two generous bedrooms, one and a half baths, a sun filled living room, dining room, family room, and chef's kitchen. The kitchen comes complete with new stainless steel appliances, tasteful white cabinets, gorgeous granite countertops, breakfast bar, and recessed lighting throughout. New high efficiency heating system with stainless steel hot water tank. Enjoy all the amazing features and recent updates! Don't let this home pass you by.

Listed by and of Boston Hub Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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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62 Swanton Street Winchester MA 01890
Active With Contract

MLS Number 72445922

  • Condo or Co-op
  • Bathroom 2
  • Year Built 2018
  • Full Bath 2
  • Bedrooms 3

NEW CONSTRUCTION- MOTIVATED SELLER-- Three bedroom two bathroom condo with open concept kitchen, family room, and dining for easy entertaining. Kitchen boasts beautiful white cabinets with granite counters, stainless steel appliances including 5 burner gas range, large island with built in beverage fridge. Master bedroom has walk in closet and spacious master bathroom with subway tile shower. Two additional bedrooms with spacious double closets. Bonus room in upper level that could be used for recreation/exercise/play room. Spacious central bathroom with laundry. Home features gleaming hardwood floors throughout, central air, 6 panel shaker style doors, private driveway, patio, and lots of storage. Close to charming Winchester Center with great restaurants, coffee shops, boutiques, and commuter rail station for easy commute into the city. Nearby to brand new Tri-town bike path and highly sought after schools. Don't miss this opportunity.

Listed by Kristine Welch of Greater Metropolitan R. E.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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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62 Swanton Street Winchester MA 01890
Open House

MLS Number 72426564

  • Condo or Co-op
  • Next Open House: Sun 17th 1:00 pm - 2:00 pm
  • Bathroom 2
  • Year Built 2018
  • Full Bath 2

NEW PRICE-MOTIVATED SELLER-- Brand new construction! Three bedroom two bathroom condo with open concept kitchen and family room for easy entertaining. Kitchen boasts beautiful white cabinets with granite counters, stainless steel appliances including 5 burner gas range with exhaust hood fan. Master bedroom has walk in closet and spacious master bathroom with subway tile shower. Two additional bedrooms with spacious double closets. Bonus additional recreation room in lower level and full laundry room. Home features gleaming hardwood floors throughout, central air, 6 panel shaker style doors, private driveway, patio, and farmers porch. Close to charming Winchester Center with great restaurants, coffee shops, boutiques, and commuter rail station for easy commute into the city. Nearby to brand new tri-town bike path and highly sought after schools. Routes 93 and 95 close by! Truly a commuters dream!

Listed by Kristine Welch of Greater Metropolitan R. E.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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

41 Canal Street Winchester MA 01890
Open House

MLS Number 72451860

  • Condo or Co-op
  • Next Open House: Sun 17th 1:00 pm - 2:00 pm
  • Half Bath 1
  • Bathroom 2
  • Year Built 1880

Original craftsmanship details are enhanced with fresh modern touches. The 1st floor features beautiful hardwood floors throughout, a light-filled living room, half bath & an updated kitchen with stainless steel appliances, island, recessed lighting, gas stove & granite countertops. The open-concept kitchen has a clear view of an elegant dining room, complete with a chandelier. The 2nd floor contains 3 spacious bedrooms & a full bath. Just steps up to the 3rd floor you'll find a fourth bedroom with a walk-in closet, which could also be used as an office or playroom. Head through the kitchen & out the door to relax on the private deck, which was redone in 2017, perfect for summer barbecues! Store extra items in the basement, or fix it up & create another hangout space. Off-street parking for 4 cars. Don't miss out on this opportunity to live in a well maintained home, with a new heating & central AC system installed in 2018. Located minutes from downtown Winchester & the commuter rail!

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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

18 Border Street Winchester MA 01890

Price$599,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72404962

  • Single Family
  • Parking Spaces 2
  • Year Built 1890
  • Full Bath 1
  • Bathroom 2

NEW PRICE!! Amazing opportunity to own a single family in Winchester! This charming DELEADED turn-key home is in pristine condition and is full of character and personality. Everything has been beautifully and tastefully updated, including new kitchen appliances, beautiful quartz countertops, and many cosmetic upgrades. Enjoy breakfast in the sun-filled dining area with skylight and sliders out to the deck, which overlooks a STUNNING fenced in back yard that features mature fruit trees, gorgeous landscaping, storage shed, and a SPRINKLER SYSTEM. Enjoy cozy evenings in front of the beautiful gas fireplace. Hardwood floors, high ceilings, ample closet and storage space (including potential expansion in the partially finished basement), and second floor laundry top off the list to make this home perfect. All in Winchester for under $600K!

Listed by Jennifer Hardin of True North Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 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.

Save 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.