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.

r=11-20
205 Mystic Valley Parkway Winchester MA 01890

MLS Number 72847738

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.1

Lovely 4 bedroom, 2.5 bath, Colonial Revival home, with loads of period detail and charm, within a short walk of Winchester Town Center. This 4 level home offers lots of great living space, including a bonus playroom in the basement. Beautiful crown molding and hardwood floors are throughout this home. All baths have Italian marble and imported tile. The third floor has a large walk-in cedar closet, which offers lots of storage options. The Living Room, Dining Room, and Kitchen have a speaker system in the ceiling. Private outdoor deck and multiple patio areas are perfect for family gatherings and cookouts. Exquisite gardens surround the house, full of mature perennial plantings. Walk to the Center, Train Station, Library, Schools, Restaurants, Playgrounds, Fells Reservation... and so much more. A charming home in a fabulous location!

Listed by John and Maria Reilly and Maria Reilly of JMR Real Estate Group LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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

40 Elmwood Avenue Winchester MA 01890

MLS Number 72846475

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,130
  • Complex Allegro

al·le·gro | at a brisk tempo. Much like how we live our busy lives. Living Allegro means having convenience outside your door in the heart of Winchester center. 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 brick building boasts units with private outdoor space, 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! Whether you are looking to downsize or just starting out don't miss your opportunity to own! Move into this brand new luxury condominium building. Come see for yourself what it 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: 2.96% last updated on Jun 10, 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

40 Elmwood Avenue Winchester MA 01890

MLS Number 72846476

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,573
  • Complex Allegro

al·le·gro | at a brisk tempo. Much like how we live our busy lives. Living Allegro means having convenience outside your door in the heart of Winchester center. 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 brick building boasts units with private outdoor space, 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! Whether you are looking to downsize or just starting out don't miss your opportunity to own! Move into this brand new luxury condominium building. Come see for yourself what it 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: 2.96% last updated on Jun 10, 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

43 Oak Street Winchester MA 01890

Winchester, MA43 Oak Street

Price$719,000

Est. Mortgage: $/month

MLS Number 72846766

  • Single Family Detached
  • Bathroom 2
  • Rooms 6
  • Bedrooms 3
  • Acreage 0.17

This sunny Cape offers a flexible floor plan with two full bathrooms, 3 bedrooms, and an office/den. An adorable mud room leads to an open kitchen with brand-new cabinets, quartz countertops and recent stainless appliances. Current owners have replaced the roof, installed new 200amp electrical, MassSaves insulation, switched to an efficient gas boiler, certified de-leading and it has been freshly painted. In a sought-after location, there is convenient access to bike paths, commuter transportation, and top-rated schools - and it is around the corner from a neighborhood diner and the hottest bakery in town. Two driveways means easy parking and the exceptionally large yard is irrigated. The basement is partially finished and W/D is on the second floor. There is a virtual tour. Any offers will be held until noon on Wednesday, June 16th.

Listed by Timothy Haynes of Keller Williams Realty Signature Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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 Grayson Road Winchester MA 01890

Winchester, MA35 Grayson Road

Price$869,000

Est. Mortgage: $/month

MLS Number 72846807

  • Single Family Detached
  • Bathroom 2
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.18

Enjoy all of Winchester with this lovely 4bedroom, 1.5bath Colonial style home close to everything. Leonard Field is directly at the end of the street, Fells reservation with over 100 miles of mixed-use trails is one block away and the town center is just one mile away allowing you take part in shops, dining, public transportation, etc. The first floor features a classic dining room with large built-in china cabinet directly off the kitchen and half bath. Oversized Livingroom connected by French doors to a wonderful family room with cathedral ceiling. The second floor has a traditional layout with four bright bedrooms all with hardwood floors and a full bath. The front yard is beautifully landscaped with mature plantings. The flat, rear yard has a wonderful patio directly connected to the family room for easy entertaining, and generously sized lawn for yard games, soccer practice or just to sit privately and listen to nature. This is a home you cant afford to miss.

Listed by Catherine Albiani of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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

33 Mccall Road Winchester MA 01890

Winchester, MA33 Mccall Road

Price$1,795,000

Est. Mortgage: $/month

MLS Number 72846769

  • Single Family Detached
  • Village Myopia Hill
  • Bathroom 2
  • Rooms 8
  • Bedrooms 4

A rare offering in a beautiful setting- welcome to 33 McCall Road! This extraordinary mid century modern property is a perfect combination of updates, smart home technology and location. Situated in the heart of Myopia Hill, this home features a renovated kitchen with high end Miele appliances, Subzero fridge and marble and quartz counters in an open concept main level, open to to dining area and living room. Large windows throughout, the living room has a stone fireplace and overlooks the recirculating waterfall in the backyard. A main level family room with beamed ceiling is bright during the day and transforms to a media room in the evening. Lovely and updated master suite on the ground level has walk in closet and opens to a conservatory, perfect for home gym. Spacious office/guest space and laundry room on the lower level. Three additional bedrooms and full bath on the upper level complete this unique property. Truly a must-see property!

Listed by Kara Spelman and Karen S. Garrett of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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

4 Palmer Street Winchester MA 01890

Winchester, MA4 Palmer Street

Price$849,000

Est. Mortgage: $/month

MLS Number 72846724

  • Single Family Attached
  • Bathroom 3
  • Rooms 9
  • Bedrooms 3
  • Acreage 0.24

Welcome to this lovely 3 bedroom townhouse near Winchester Center and The Flats. This spacious home lives and feels like a single with private fenced-in landscaped garden area, private entrance and plenty of parking. This home features a sparkling newly updated kitchen with quartz counters and all new SS appliances open to the dining room, living room with wood burning fireplace and a convenient home office. On the 2nd floor, the primary bedroom features a newly updated bath and customized walk-in closet. There is another generously sized bedroom on the 2nd floor as well as one on the 3rd level. The lower level has a game room, family room and a home gym. There is storage in the attic as well as lower level. Enjoy the convenient location close to the Town Center, tennis courts and Borggaard Beach.

Listed by Naomi DeLairre of Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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

4 Palmer Street Winchester MA 01890

Winchester, MA4 Palmer Street

Price$849,000

Est. Mortgage: $/month

MLS Number 72846668

  • Condo or Co-op Condex
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,591

Welcome to this lovely 3 bedroom townhouse near Winchester Center and The Flats. This spacious home lives and feels like a single with private fenced-in landscaped garden area, private entrance and plenty of parking. This home features a sparkling newly updated kitchen with quartz counters and all new SS appliances open to the dining room, living room with wood burning fireplace and a convenient home office. On the 2nd floor, the primary bedroom features a newly updated bath and customized walk-in closet. There is another generously sized bedroom on the 2nd floor as well as one on the 3rd level. The lower level has a game room, family room and a home gym. There is storage in the attic as well as lower level. Enjoy the convenient location close to the Town Center, tennis courts and Borggaard Beach.

Listed by Naomi DeLairre of Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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

8 Blossom Hill Road Winchester MA 01890

Winchester, MA8 Blossom Hill Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 72845971

  • Single Family Detached
  • Bathroom 4
  • Rooms 9
  • Bedrooms 4
  • Acreage 0.23

Home sweet home in one of Winchester's best locations! 3500 sq ft, 4 beds, 4 baths, 4 fireplaces with a well landscaped yard and a waterfall! Desirable open living concept features a spacious kitchen filled with custom cabinets and SS appliances, leading to a family room with a gas fireplace, cathedral ceilings and a wet bar. Master bedroom suite on a separate level with gas fireplace, cathedral ceiling, custom walk-in closet, and exterior porch. Master bath has a whirlpool, steam shower and a heated floor. Lower level includes a laundry area with a slop sink, full bath, private office and a game room with full wet bar, and a wood-burning fireplace. Other amenities include beautiful oak flooring throughout, an alarm system, central vac, central A/C, new Weil-McClain Gold HW boiler and new oil tank. Newer roof, newer vinyl shake siding, patio, pergola, irrigation system, exterior gas connection for a grill, 2 car under garage with 2 new garage doors, and SDL windows.

Listed by Shane Marrion and Caroline Holland of Benoit Real Estate Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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

7 Mayflower Road Winchester MA 01890

Winchester, MA7 Mayflower Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 72844657

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.52

Top Westside location ! This home has been loved and cared for the last 50 years by its present owner. Mayflower Road is a dead end street so traffic belongs to residents. Sitting on a lovely half acre lot, the property boasts Nine Rooms, Four Bedrooms (4TH on lower level, perfect for Nannie), and Three Full Baths. Extra Rooms include a Screen Porch, Laundry Room and Shed. Custom Pained Windows invite in plenty of natural light. Entering the house through the spacious garage is very desirable in Winter. This home can't wait for you to update it and make it your own. Vinson Owen School. Sold "As Is." Offers reviewed on Tuesday, June 15 at Noon. Please allow time for reply.(48 hours)

Listed by Carolyn Vernaglia of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Jun 10, 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.