New Listing - 05/20/2026

$995,000 ($300.24 per sqft)

Est. Mortgage $0/mo *

Quick Pre-Approval

Brochure

Call Text Schedule Tour Request More Information

Open House Schedule

05/30/2026
11:00 AM to 2:00 PM
Google calendar
Other calendars

05/31/2026
11:00 AM to 2:00 PM
Google calendar
Other calendars

24 Winding Way, Plymouth, MA, 02360

View larger map Directions

11 rooms

4 beds

3 Full baths

1987

Colonial

3,314 sqft

Located in Plymouth's highly desirable Chiltonville Village, on a quiet peaceful road, sits this large magnificent 3-story colonial home, offering a private setting yet is only a short distance to downtown, Plymouth Beach, Bramhall's Country Store, Plimoth Patuxet & highway access. Enter through the foyer w/cathedral ceiling & grand staircase. 1st floor kitchen has cherry cabinets, granite countertops & stainless-steel appliances, breakfast bar, and is open to the family rm w/slider to outside deck. Deck also connects to the 4-season vaulted ceiling sunroom, making for easy entertaining. 1st floor continues with large living rm, dining rm, bedrm & full bathrm. 2nd floor spacious master suite has cathedral ceilings, sitting rm w/double closets, walk-in closet, two vanities, jacuzzi tub, shower, and fireplace. Two other bedrms and the laundry room complete the 2nd floor. 3rd floor bonus suite has bedrm or office, & storage. Relax & enjoy nature in the treehouse feeling of the back deck.

Status:

Active

Type:

Single-family residential

Laundry Remarks:

Laundry Room, Sink, Built-Ins, Second Floor

Zoning:

R25

Subdivision:

Chiltonville

Garage:

2-car Basement

Heating:

Hot Water

Cooling:

Central Air, Other

Basement:

Interior Entry, Full

Levels:

Parking:

6-car

Acreage:

0.86

Est. Taxes:

$11,200

Assessment

$892,500

Construction

Clapboard

Lot Description:

Bike Path, School, Medical Facility, Major Highway, Near Golf Course, Shopping, Conservation Area, Wooded

School District:

Plymouth

Days on Market:

Special Listing Condition:

Standard

Appliances:

Cooktop, Wall/Oven Cook Top, Refrigerator, Electric Range, Microwave, Dishwasher, Electric Water Heater

MLS #:

22602327

Community Info

School Info

Walk Score

Mass Transit

Yelp

Similar Properties

Price Reduced!

$949,000

2 beds

2 baths

2,244 sqft

35 Snapping Bow, Plymouth, (Pinehills), MA, 02360

$919,000

3 beds

2.5 baths

2,018 sqft

7 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$904,900

3 beds

2.5 baths

2,120 sqft

5 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$989,000

2 beds

3 baths

1,913 sqft

12 Owls Nest, #5, Plymouth, (Pinehills), MA, 02360

$1,075,000

3 beds

4 baths

3,078 sqft

92 Lookout Point Rd, Plymouth, (Ellisville), MA, 02360

Price Reduced!

$959,000

2 beds

2 baths

1,913 sqft

59 Kestrel Heights, #57, Plymouth, (Pinehills), MA, 02360

$1,089,000

3 beds

3 baths

2,442 sqft

81 Kestrel Heights, #46, Plymouth, (Pinehills), MA, 02360

$999,000

3 beds

0.5 baths

709 sqft

0 Off Canoe Landing, Plymouth, (Pinehills), MA, 02360

Price Reduced!

$999,900

4 beds

3.5 baths

4,000 sqft

54 Overlook Cir, Plymouth, MA, 02360

$899,900

3 beds

2.5 baths

2,605 sqft

4 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$1,084,000

3 beds

4 baths

2,442 sqft

18 Owls Nest, #8, Plymouth, (Pinehills), MA, 02360

Price Reduced!

$1,050,000

2 beds

2 baths

1,271 sqft

4 Osprey Ln, Plymouth, (Manomet), MA, 02360

$919,900

3 beds

2.5 baths

2,018 sqft

12 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$999,000

3 beds

0.5 baths

709 sqft

0 Off Canoe Landing, Plymouth, (Pinehills), MA, 02360

Price Reduced!

$1,079,000

2 beds

3 baths

1,913 sqft

45 Kestrel Heights, #67, Plymouth, (Pinehills), MA, 02360

Price Reduced!

$1,019,000

2 beds

4 beds

3 baths

2,000 sqft

$995,000 ($300.24 per sqft)

Open House Schedule

24 Winding Way, Plymouth, MA, 02360

Community Info

School Info

Walk Score

Mass Transit

Yelp

Similar Properties

$949,000

35 Snapping Bow, Plymouth, (Pinehills), MA, 02360

$919,000

7 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$904,900

5 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$989,000

12 Owls Nest, #5, Plymouth, (Pinehills), MA, 02360

$1,075,000

92 Lookout Point Rd, Plymouth, (Ellisville), MA, 02360

$959,000

59 Kestrel Heights, #57, Plymouth, (Pinehills), MA, 02360

$1,089,000

81 Kestrel Heights, #46, Plymouth, (Pinehills), MA, 02360

$999,000

0 Off Canoe Landing, Plymouth, (Pinehills), MA, 02360

$999,900

54 Overlook Cir, Plymouth, MA, 02360

$899,900

4 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$1,084,000

18 Owls Nest, #8, Plymouth, (Pinehills), MA, 02360

$1,050,000

4 Osprey Ln, Plymouth, (Manomet), MA, 02360

$919,900

12 Preservation Way, Plymouth, (South Plymouth), MA, 02360

$999,000

0 Off Canoe Landing, Plymouth, (Pinehills), MA, 02360

$1,079,000

45 Kestrel Heights, #67, Plymouth, (Pinehills), MA, 02360

$1,019,000

12 Loons Call, #104, Plymouth, (Pinehills), MA, 02360

New or Coming Soon Properties

$985,000

30 Stone Gate Dr, Plymouth, MA, 02360

$995,000

30 Barnswallow, Plymouth, (Pinehills), MA, 02360

$979,000

63 Oakdale Ave, Marion, MA, 02738

$949,000

9 Saddleback, Plymouth, (Pinehills), MA, 02360

$995,000

56 Canterbury St, Hingham, (Weir River), MA, 02043

$949,000

84 Newport Rd, Hull, MA, 02045

$959,900

7 Yellow Birch Dr, Plymouth, MA, 02360

$899,000

12 Trouants Is, #12, Marshfield, MA, 02050

$999,999

10 Cranberry Farm Rd, Plymouth, MA, 02360

$965,000

4 Pocohontas Way, Mattapoisett, MA, 02739

$925,000

83 Winding Way, Plymouth, MA, 02360

$950,000

85 Crescent St, West Bridgewater, MA, 02379

$1,089,000

87 Kestrel Heights, #43, Plymouth, (Pinehills), MA, 02360

$999,777

59 Briarcliff Rd, Brockton, MA, 02301

$939,000

86 Shallow Pond Lane, Plymouth, MA, 02360

$899,000

17 Forbes Road, Rochester, MA, 02770

24 Winding Way, Plymouth, MA, 02360

Your Raveis Experience

Your best can only get better...