North Boston 55+ Communities

Explore all 55+ community homes for sale in the Winchester area North of Boston, MA. Active adult communities offer a retirement friendly and low maintenance lifestyle. Many of these homes and condos provide easy access to shops, restaurants, and other attractions. Current listings are shown below. If you don’t see what you’re looking for, you may want to try a custom search or reach out to an agent. We know the local area and can help you find just the right home.

Search Homes in Adult Communities Winchester MA Area

Questions? Contact Better Homes and Gardens Real Estate The Shanahan Group at 781-729-9030 or online!

190 High Street Medford MA 02155

MLS Number 72747348

  • Condo or Co-op
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 501

Great price for Boston for living! Well Maintained Condo at The Regency! Easy access to parks, healthcare facilities, highway, local shops and more! New flooring in living room and bedroom. Open concept with updated appliances. Enjoy access from the slider in the living room and bedroom to outdoor covered patio. The Regency offers secure entry with 2 elevators, a clubhouse with full kitchen, exercise room, common laundry and an in-ground pool. Deeded parking space for one. In Downtown Medford Square which has many amenities such as quaint shops, restaurants and theatre within a short walk. Close to Tufts University, MBTA, Mystic Lake. Easy access to Dowtown Boston and 93.

Listed by Cheryl Waitt of Homes of New Hampshire, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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24 Gershon Way Winchester MA 01890

Winchester, MA24 Gershon Way, Unit 24

Price$1,625,000

Est. Mortgage: $/month

Open House

MLS Number 72740227

  • Condo or Co-op
  • Next Open House: Fri 10/30 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

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: 2.81% last updated on Oct 29, 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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36 Abigail Way Reading MA 01867
Open House

MLS Number 72738288

  • Condo or Co-op
  • Next Open House: Sun 11/1 11:00 am. to 1:00 pm.
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 1,030

Immaculate one bedroom "Active Adult Building", 55+ at Reading Woods. Copley Floor Plan with many upgrades. Hardwood Flooring, beautiful tiles ,back splash with granite counters in kitchen, upgraded cabinets with under mounted lights, crown molding, Open floor plan for easy entertaining w/balcony. Enjoy custom walk-in closet in bedroom. French Doors entering den, could be used as an office or dining area. In unit washer/dryer with additional storage. The Clubhouse features exercise room available to residents, also available for social events. Property comes with Heated Garage Space, #21. The community of Reading Woods also offers walking trails. Convenient to Shopping, Hospital and Highways. Open House 11/1-11:00-1:00

Listed by Maria Doherty of The Russell Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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21 Gershon Way Winchester MA 01890

Winchester, MA21 Gershon Way, Unit 21

Price$1,590,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72730250

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

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: 2.81% last updated on Oct 29, 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

23 Gershon Way Winchester MA 01890

Winchester, MA23 Gershon Way, Unit 23

Price$1,575,000

Est. Mortgage: $/month

Open House

MLS Number 72725119

  • Condo or Co-op
  • Next Open House: Sat 10/31 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,549

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: 2.81% last updated on Oct 29, 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

25 Gershon Way Winchester MA 01890

Winchester, MA25 Gershon Way, Unit 25

Price$1,475,000

Est. Mortgage: $/month

Open House

MLS Number 72725070

  • Condo or Co-op
  • Next Open House: Fri 10/30 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

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 or Quartz (your choice) 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 to accommodate your working demands, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious en suite bedrooms 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: 2.81% last updated on Oct 29, 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

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