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. You may also be interested in viewing all condos.

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!

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: Tue 04/20 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

2021 Winner for BEST NEW 55+ COMMUNITY IN THE COUNTRY. ONLY 2 HOMES REMAIN out of 29! Live surrounded by luxurious finishes, soaring ceilings, hardwood throughout & plenty of natural sunlight. This open concept plan boasts a 1st floor master suite with tray ceiling, a super-sized walk-in closet and luxurious en suite bath. The eat in kitchen is adorned with ceiling height cabinets, quartz countertops and top of the line stainless steel appliance package featuring Sub*Zero, Bosch, Wolf... The dining room has a stately coffered ceiling, bay window and sliders to a private, covered deck. The flex room can be a home office or studio for your beloved hobbies. 1st floor also features a powder room, mudroom and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath, a library and a large open loft for movie watching or game night. The icing on the cake: attached 2 Car garage with electric car charging station AND a 1,500 SF Walkout basement! MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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.

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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: Tue 04/20 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

2021 Winner for BEST NEW 55+ COMMUNITY IN THE UNITED STATES. ONLY 2 HOMES REMAIN out of 29! Imagine luxurious finishes throughout: 10'+ ceilings, hardwood floors and plenty of natural light. This open concept plan has a 1st floor master suite with oversized walk-in closets and a great bathroom. The kitchen is adorned with ceiling height cabinets, Quartz countertops & island, a spacious pantry + top of the line SS appliance package. The dining room features a beautiful coffered ceiling. Just beyond, the room opens up to a 22' ceiling in the dramatic living room featuring a floor to ceiling fireplace. Abutting the covered porch, a wall of windows pours sunlight into this home. The 1st floor flex room can be a home office, a library or studio for your beloved hobbies. 1st floor also features a powder rm and laundry. Upstairs you'll find 2 additional spacious EN SUITE bedrooms and a bright open loft. 2 Car garage with electric car charging station.*MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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

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