Winchester MA Real Estate

Winchester, Massachusetts is located 8 miles north of Boston If you are relocating to the Boston area and looking to buy a home let Sweeney & O’Connell Real Estate’s team of professionals help you with all your Real estate needs. Our team of top notch brokers maintains up-to date knowledge about properties, market values, and market trends in order to better serve you and get you the information you are looking for. View current listings below. You may also be interested in browsing listings in other Arlington area towns.

Winchester Condos | Winchester Single Family Homes | Winchester Multi Family HomesWinchester Open Houses

Find Winchester MA Homes for Sale

Contact Sweeney & O'Connell Real Estate online or call 781.643.7478 with any questions or to schedule a private tour.

Save time! Sign up to get email notifications when similar properties matching your search criteria become available.

113 Cambridge Street Winchester MA 01890

Winchester, MA113 Cambridge Street

Price$849,000

Est. Mortgage: $/month

Open House

MLS Number 72870768

  • Single Family Detached
  • Next Open House: Sun 07/25 12:30 pm. to 2:00 pm.
  • Bathroom 2
  • Rooms 8
  • Bedrooms 4

Don't miss this opportunity. This four bedroom home offers many updates including central air, central Vac., newer windows and roof. Enjoy the private, spacious fenced yard, public transportation and close access to major highways.

Listed by Peggy Otis of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

7 Wainwright Road Winchester MA 01890
Open House

MLS Number 72869905

  • Condo or Co-op
  • Next Open House: Sun 07/25 12:00 pm. to 1:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,276

Beautiful townhome in the Ledges community in Winchester. Nice open floor plan with vaulted ceilings in the great room, a fireplace, and slider leading to the large deck with an awning. First-floor primary bedroom with two large walk-in closets and bath. The second floor includes a loft, perfect for an office and two additional bedrooms, and a bath. The basement is partially finished with a sitting area, room for woodworking, and office space. Attached two-car garage!! Clubhouse, Tennis court, walking/jog trails, and swimming pool!!

Listed by Kathryn Malisheski of Redfin Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

27 Cabot Street Winchester MA 01890

Winchester, MA27 Cabot Street

Price$1,875,000

Est. Mortgage: $/month

Open House

MLS Number 72869967

  • Single Family Detached
  • Next Open House: Sun 07/25 1:00 pm. to 2:30 pm.
  • Village Flats neighborhood
  • Bathroom 4
  • Rooms 10

Once upon a time... this storybook-like french country tudor is an opportunity you won't want to miss! This special home is situated on one of the most beautiful lots in the desirable flats area of Winchester and has been lovingly cared for through the years. The sprawling first floor features a charming entry foyer, mudroom, beautiful oversized living room with fireplace leading to a charming brick screen porch; formal dining room w/ custom mill work and built ins, butlers pantry china cabinets, eat in kitchen & attached garage complete the main level. The second floor offers a large master suite with sitting area, full bath & walls of windows overlooking the private gardens; plus two additional spacious bedrooms and full bath. The third floor suite includes a bedroom and full bath. The lower level features a grand family room/ media room with fireplace and high ceilings, a summer kitchen, laundry and utility rooms. This home is a rare find and one you will want to make your own!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

35 Nathaniel Road Winchester MA 01890

Winchester, MA35 Nathaniel Road

Price$1,029,000

Est. Mortgage: $/month

Open House

MLS Number 72869738

  • Single Family Detached
  • Next Open House: Sun 07/25 11:30 am. to 1:00 pm.
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4

Must see this wonderful updated 4 bedroom 2.5 bath home situated in a great elementary school neighborhood close to Muraco school fields, tennis courts, playgrounds, and the bike path! This recently renovated and expanded home offers a great layout with sunny rooms, hardwood floors, and a location that can't be beat! The first floor features a lovely living room with fireplace & bay window, dining room, updated kitchen, family room/sunroom & half bath. Sliders to large deck offer easy access to amazing back yard connecting to Muraco fields, bike path, playgrounds & school. The second floor offers a master suite with tiled bath, bay window, three additional bedrooms and full bath. The lower level is finished with a game room/playroom & utility area with laundry. New furnace, hot water tank, ductless A/C units, newer windows,updated kitchen and baths. Must see this great home close to Winchester center, train to Boston, and all Winchester has to offer!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

52 Graystone Circle Winchester MA 01890
Open House

MLS Number 72869009

  • Condo or Co-op
  • Next Open House: Sun 07/25 12:00 pm. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,924

Looking for a move-in ready and spacious condo located in desirable Graystone? This is the unit you have been searching for. Freshly painted with the lower level finished, this expansive unit has so much potential to make your own. Featuring hardwood floors, high ceilings with an open and airy layout. This chef's kitchen has a gas countertop range, stainless steel appliances, custom cabinetry and a cozy breakfast nook. Master bedroom is located on the first level with hardwood floors, walk-in closet and full en-suite bathroom. Second level features and open loft/family room with two additional bedrooms and full bathroom. The lower level has been partially finished and heated making it perfect for a gym/media/playroom. Private outdoor patio is a wonderful location for entertaining guests. Now is the perfect opportunity to purchase in this Winchester community!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

114 Main Street Winchester MA 01890

Winchester, MA114 Main Street

Price$899,900

Est. Mortgage: $/month

MLS Number 72868918

  • Single Family Detached
  • Bathroom 2
  • Rooms 7
  • Bedrooms 3
  • Acreage 0.26

Lovely 3 bedroom, 1.5 bath raised ranch home with gas fireplaces on each level. Perfect for getting to town center, the library and schools. On public transportation route. This home has been well maintained. Family room was added on with rubber roof. The lower level offers a large finished playroom with gas fireplace that leads to the garage or to the unfinished laundry room with exterior access. Patio in back with stairs that lead up to a large sprinklered backyard with storage shed. Front yard is sprinklered as well. Amenities include central air, insulated windows and doors. 1/2 mile to Wedgemere Commuter Rail and 1 mile to center, McCall and Lincoln School. Perfect location to enjoy all that Winchester has to offer. Refrigerator, Washer, Dryer are gifts from the Seller. Offers kindly requested by Monday 7/26 at 5pm for seller review. Seller reserves the right to accept an offer prior to the deadline.

Listed by Kristen Mulkerin of J. Mulkerin Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

210 Pond Street Winchester MA 01890

Winchester, MA210 Pond Street

Price$1,109,900

Est. Mortgage: $/month

Open House

MLS Number 72868798

  • Single Family Attached
  • Next Open House: Sun 07/25 12:00 pm. to 2:00 pm.
  • Bathroom 4
  • Rooms 10
  • Bedrooms 4

Don't miss this sleek and stylish, tastefully updated 4 bedroom, 3.5 bath colonial with a park like beautiful backyard. You will certainly appreciate the open floor plan with a gourmet kitchen, dining and a fireplaced living room which lead to the vaulted family room perfect for living and entertaining. The private master bedroom suite is found on the second floor and features a vaulted ceiling with skylights, custom walk in closet and a luxurious master bath. This home also offers a great second ensuite bedroom and bath on the first floor separate from the main living area ideal for guests, extended family or au-pairs. The finished basement can be used for a home office, exercise area or a large recreation room. You will surely love the spacious patio area and very large professionally landscaped back yard complete with irrigation. Conveniently located within a very short walk to Lynch Elementary School, Horn Pond and Winter Pond with easy access to shopping and the highway. A GEM!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

9 Trinity Road Winchester MA 01890

Winchester, MA9 Trinity Road

Price$1,099,000

Est. Mortgage: $/month

Open House

MLS Number 72868665

  • Single Family Detached
  • Next Open House: Sun 07/25 12:00 pm. to 1:00 pm.
  • Bathroom 3
  • Rooms 8
  • Bedrooms 3

Welcome to Winchester! This mid-century Ranch single family home is ready to move-in. Gleaming hardwood floors throughout. A modern eat-in kitchen featuring stainless steel appliances & commercial hood. The dining room is perfect for entertaining & opens to the sunken living room w/ fireplace. A separate office/family room has new carpeting w/ plenty of natural sunlight. Master bedroom is spacious & has an en-suite bathroom. Two additional large bedrooms & full bathroom complete the main living area. A partially finished newly carpeted basement has a wonderful media room w/ fireplace, laundry room, half bath & plenty of storages! Exterior features includes an oversized enclosed heated patio with skylights and sliders for outdoor access. Nice sized lot with a storage shed and a one car garage. This home has much potential for expansion. Located on a quiet cul-de-sac, Vinson Own school district, and near Winchester Golf Club, Mystic Lakes. Wright-Locke Farm, Whipple Hill & so much more!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

282 High Street Winchester MA 01890

Winchester, MA282 High Street

Price$3,600,000

Est. Mortgage: $/month

MLS Number 72867636

  • Single Family Detached
  • Bathroom 5
  • Rooms 16
  • Bedrooms 6
  • Acreage 0.56

Stunning family compound setting built with pride & quality offered for first time.Once in a generation opportunity.Uniquely generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and 66" of refrigeration.Grand formal dining room,serving pantry,dinette,and fabulous living room make up the first floor common areas.Add a main level bedroom,seperate full and half baths,and large office complete the primary level.Upstairs,open primary suite complete with stone fireplace,ensuite bath,and dressing room.Three additional bedrooms,big full bath,and laundry on second level.Full,finished walkout basement with kitchen,living area,brick oven,fireplace,dinette,and additional 6th bedroom and bathroom ideally suited for in-law,au pair,or multigenerational suite.Rare,attached 4 bay garage.

Listed by Anthony Marino of Marino Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

49 Florence Street Winchester MA 01890

Winchester, MA49 Florence Street

Price$1,499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72868153

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.23

This thoughtfully designed home is a lovely, warm and truly inviting space. It is nicely situated on a corner lot in a great location and short walk to the downtown area. The floor plan was designed to allow for an abundance of natural light throughout. The house was renovated and expanded within the last year and has all new hvac, electrical, plumbing, insulation, windows, flooring, painting, etc. There is an absolutely perfect balance of interior and exterior living space. The first floor includes-living room, dining room, kitchen, half bath, mudroom and fireplaced living room. The second floor-3 bedrooms, 2 baths, a reading nook, and laundry. The third floor has an open area and 4th bedroom.

Listed by Mark Donnellan of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.