Winchester MA Real Estate

View the latest real estate listings in Winchester MA below.

Winchester Homes for Sale

Contact The Home Advantage Team at 781-645-0505 or online for more information or to schedule a private tour.

3 Pilgrim Drive Winchester MA 01890

Winchester, MA3 Pilgrim Drive

Price$2,399,000

Est. Mortgage: $/month

MLS Number 72761553

  • Single Family Detached
  • 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 Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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 HOLLYWOOD Road Winchester MA 01890

Winchester, MA17 HOLLYWOOD Road

Price$1,399,900

Est. Mortgage: $/month

MLS Number 72760799

  • Single Family Detached
  • Rooms 8
  • Bedrooms 5

You'll fall in love with this beautiful Custom Built Colonial in this coveted East Hill neighborhood. This attractive home is over 4500 SF & features 9 rooms, 5 bedrooms including dual Master Bedrooms, 5 Baths, open concept Kitchen & Family room, 1st Floor Master addition is spacious with a sizable walk in closet, built in office area and a premium bath en suite. Beautiful front to back Living Room with fireplace too! 2nd Floor offers 4 bedrooms, 2 baths & plenty of closet space. Lower Level includes another finished family room with fireplace & a walk out to a patio. 2 car garage. This home is perfect for modern family living & perfect for entertaining too. Easy access to major highways & only 8 miles to Boston. Enjoy the Middlesex Fells Reservation too! Close to the T & to downtown Winchester resplendent with Restaurants, Coffee bistros & unique shops. Don't miss this opportunity to live in one of Winchester's favorite neighborhoods. View floorplans & Matterport online.

Listed by Jan Triglione Team and Jan Triglione of Premier Realty Group, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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 Windsong Lane Winchester MA 01890

Winchester, MA1 Windsong Lane

Price$1,575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72758770

  • Single Family Detached
  • Rooms 10
  • Bedrooms 5

This gorgeous ranch home was thoughtfully designed as an entertainer's dream, inside & out! Huge lower level is custom-built for sports lovers, featuring an exercise room w/ sauna, 3/4 bathroom, mini kitchen, gorgeous built-in bar, walk-in cedar closet & even a built-in ping pong table! Main level boasts a recently renovated chef's kitchen offering custom cabinets, silestone counters & Bosch appliances, including double dishwashers! Oversized kitchen includes both eat-in & bar seating as well as separate desk & mudroom spaces. In addition to 4 sizable bedrooms, enjoy a private master suite w/ ensuite bath. Spacious family room is highlighted by a marble fireplace & slider leading out to your new backyard oasis! Enjoy a heated pool w/ diving board, surrounded by bluestone patio w/ built-in fireplace. 2 car garage w/ circle driveway, located on quiet cul de sac in new VO district. Entertain all year long!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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5 Grant Road Winchester MA 01890

Winchester, MA5 Grant Road

Price$999,000

Est. Mortgage: $/month

MLS Number 72758868

  • Single Family Detached
  • Rooms 7
  • Bedrooms 3

This one-owner, three bedroom Ranch style home has been beautifully maintained and is close to major commuting routes. Located in the Muraco School District, you will enjoy its bright, open concept living room, which is perfect for entertaining. There is also a wood-burning fireplace and a large bow window which overlooks the front yard. The dining room leads to a large den which is adjacent to the spacious back-yard. Upon entering the two-car garage you have access to the finished lower level with a second fireplace. Don't miss this great opportunity!!

Listed by Nancy O'Herron and Sal Dipinto of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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666 Main Street Winchester MA 01890

MLS Number 72757979

  • Condo or Co-op
  • Rooms 5
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1982

Location, Location. Wedgewood Place is located on Main Street, Winchester. Close to restaurants, shopping, banks, hardware store, coffee shops and more. Also close to highways and commuter rail station. Well managed building by professional management company. One level living on the second floor with elevator. Open floor plan with kitchen (few years old), dining room and living room with wood burning fireplace and crown molding. A small screen porch is off the living room overlooking the pool. Two bedrooms and two baths complete the space. Good closet space with a storage area off the garage where your parking place is located. Don't miss out having this special condo full of natural light for yourself !

Listed by Carolyn Vernaglia of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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 Thornberry Road Winchester MA 01890

Winchester, MA49 Thornberry Road

Price$1,399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72757514

  • Single Family Detached
  • Rooms 8
  • Bedrooms 4

COMPLETELY RENOVATED SINGLE FAMILY! A short drive to downtown where you'll find plentiful boutiques, restaurants, coffee shops and the Commuter Rail to North Station. Within the 4-year old Vinson Owen School district. The first floor features an open floor plan for today's modern lifestyle, with a fireplace living room, dining room, and kitchen boasting a top of the line SS appliance package and Quartz counters, a perfect place to host your family for the holidays. Hardwood floors throughout and plenty of natural light. Experience the great outdoors featuring 2 large composite decks and a spacious back yard for your children to play catch with Rover. 3 bedrooms and 2 bathrooms are located on the second floor, including the master with gorgeous en-suite bathroom. The lower level features another bedroom, a full bath, access to the exterior and family room with fireplace #2. Easy access to major highways and 7 miles from Boston.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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

666 Main Street Winchester MA 01890

MLS Number 72757615

  • Condo or Co-op
  • Rooms 6
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1982

Don't miss this great opportunity to own this spacious, sunny 2 bedroom 2 bath home at desirable Wedge Pond Condominiums...being offered at a very competitive price! Situated on Wedge Pond & in a TOP downtown location with all Winchester center has to offer right outside your door! Enjoy the ease of one level living with this great floor plan; elevator access, garage parking and association pool to enjoy during summer months! This freshly updated home features newly installed wide plank wood flooring, all new appliances, fresh paint throughout, large living room w/ fireplace, porch, and adjacent dining area. Two spacious sunny bedrooms, Master with walk in closet & private bath. Move right in and enjoy! *Home is virtually staged and is currently empty*

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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23 Arthur Street Winchester MA 01890

MLS Number 72757138

  • Condo or Co-op
  • Rooms 5
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1890

This antique townhouse was renovated in 2016 and provides 3 levels of living spaces and large master suite on 3rd floor. The 1st floor features two large rooms with white cabinets, stainless steel appliances and granite countertops. The 2nd level features two large sized bedrooms and a tiled bathroom. The top level spacious master suite with plenty of closet spaces and a tiled bathroom. There are many great restaurants nearby, close to the Town Center, Commuter Rail Station.

Listed by Hongmei Wang of HMW Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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 11/30 11:30 am. to 2:30 pm.
  • Rooms 8
  • Bedrooms 3
  • Bathroom 3

ONLY 5 HOME OPPORTUNITIES REMAIN!!! Designed by national, award-winning, architect Gary Snider. Imagine luxury finishes throughout, including 10' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. The dining room has a beautiful coffered ceiling and sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage.***MODEL HOME OPEN DAILY 11 - 4PM***

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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

29 Vine Street Winchester MA 01890

MLS Number 72756346

  • Condo or Co-op
  • Rooms 5
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1980

Gorgeous condo across from Wedge pond in the Heart of Downtown Winchester at the Winchester Lakeside. Walk into a breathtaking sunny living room with lush red hardwood floors, fireplace and working Pellet stove, and look out your sliding door onto a private deck and view of downtown Winchester. A Modern kitchen w breakfast bar, boasts granite counter tops, lots of cabinet space, and an over-sized detached pantry for plenty of storage. Walk down your spiral staircase to your pristine full bath, master and guest bedrooms, that features lots of closet space, and their own sliding door access to another deck balcony views of the city. With access to train less than .3 mi away, public library/elementary/middle/high schools .4 miles, and a vibrant restaurant and shopping scene downtown all within walking distance, this is quintisential downtown Winchester living, and this opportunity wont last long. Come see it before its gone.

Listed by Joseph Barnes of Keller Williams Realty Boston-Metro | Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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 Mayflower Road Winchester MA 01890

Winchester, MA22 Mayflower Road

Price$1,275,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72754941

  • Single Family Detached
  • Rooms 8
  • Bedrooms 4

**Multiple offers, highest/best due on Friday November 20th at Noon** An exceptional opportunity abutting the Winchester Country Club. Renovate, expand or design your dream home. The options are endless for this never before offered home. Enjoy spectacular sunrises and long views from the 4 bedroom 2 -1/2 bath home. Absolutely gorgeous golf course lot with winter views of Boston. Come take a look at this Diamond in the rough!!

Listed by Ronald Buck of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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18 Hancock Street Winchester MA 01890

MLS Number 72754135

  • Condo or Co-op
  • Rooms 6
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1880

Move right into this thoughtfully remodeled town home located on a quaint tree lined street within a short distance to the shops, restaurants, Winchester Center commuter rail & nearby walking trails in the Fells. Featuring a custom designed kitchen with modern stainless steel appliances, cherry cabinets & granite countertops. The front to back open floor plan is great for everyday living and entertaining. In addition, the first floor has a laundry area, half bath and mudroom. Oak floors flow throughout the home. Period details include beautiful Victorian bay windows and an elegant stained-glass accent window. The outside offers a full-length porch, professionally landscaped yard and 2 car off-street parking. Other highlights upstairs include a generous master suite with a walk-in closet and two additional bedrooms. The third-floor attic provides ample additional storage and potential for future expansion. A perfect home to call your own! Showings by private appointment only.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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