New Listing - 05/06/2025

$2,495,000 ($612.72 per sqft)

Est. Mortgage $0/mo *

Call Text Schedule Tour Request More Information

Open House Schedule

Fabulous 4 bedroom, 3.5 bath home on almost two acres with deeded rights to Lover's Lake, bike path and village. Spectacular first floor living with room for guests and almost 2 acres to enjoy and make your own - how about a pool, guest house, garage work shop or ADU? You'll love the two great rooms and potential to finish off a grand family room in the lower level. Not to be missed.

05/17/2025
2:00 PM to 4:00 PM
Google calendar
Other calendars

05/18/2025
2:00 PM to 4:00 PM
Google calendar
Other calendars

55 Winterset Drive, Chatham, MA, 02633

View larger map Directions

8 rooms

4 beds

3 Full / 1 Half baths

1970

4,072 sqft

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & 2 walk-in closets, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. May be sold furnished.

Status:

Active

Type:

Single-family residential

Laundry Remarks:

Laundry Room, In Basement

Zoning:

R60

Subdivision:

Great Hills Estates

Garage:

2-car Basement

Heating:

Hot Water, Other

Basement:

Bulkhead Access, Interior Entry, Full, Finished

Levels:

Parking:

6-car

Acreage:

1.94

Est. Taxes:

$5,179

Assessment

$2,122,900

Construction

Shingle Siding

Lot Description:

Bike Path, Near Golf Course, Marina, Conservation Area, Cleared, East of Route 6, North of Route 28

Amenities:

Deeded Beach Rights

School District:

Monomoy

Days on Market:

Appliances:

Dishwasher, Washer, Refrigerator, Microwave, Gas Water Heater

MLS #:

22502257

Community Info

School Info

Walk Score

Mass Transit

Yelp

Similar Properties

$2,500,000

4 beds

3.5 baths

3,865 sqft

25 Menekish Lane, Chatham, MA, 02633

Price Reduced!

$2,445,000

3 beds

3.5 baths

3,304 sqft

$2,375,000

3 beds

4.5 baths

3,310 sqft

98 Horizon Drive, Chatham, MA, 02633

Price Reduced!

$2,699,999

4 beds

3 baths

3,843 sqft

193 Quanset Road, Orleans, MA, 02653

Price Reduced!

$2,445,000

3 beds

3.5 baths

3,304 sqft

88 Eel River Rd, Falmouth, MA, 02536

$2,580,000

5 beds

5.5 baths

3,944 sqft

20 Stanley Place, Barnstable, (Hyannis), MA, 02601

Price Reduced!

$2,295,000

3 beds

3.5 baths

1,863 sqft

16 Little Beach Road, Chatham, MA, 02633

$2,539,000

3 beds

2 baths

1,224 sqft

42 Bayberry Avenue, Provincetown, MA, 02657

$2,395,000

4 beds

3.5 baths

3,263 sqft

11 Moss Road, Yarmouth, (West Yarmouth), MA, 02673

$2,695,000

5 beds

4 beds

3.5 baths

4,695 sqft

49 Longfellow Road, Wellesley, MA, 02481

New Listing!

$2,450,000

3 beds

3.5 baths

1,923 sqft

211 1/2 Bradford Street, Provincetown, MA, 02657

$2,450,000

4 beds

3.5 baths

2,988 sqft

19 Weston Taylors Lane, Orleans, MA, 02653

New Listing!

$2,650,000

4 beds

2.5 baths

3,747 sqft

38 Charles Street, Yarmouth, (South Yarmouth), MA, 02664

New Listing!

$2,550,000

3 beds

2.5 baths

3,056 sqft

$2,495,000 ($612.72 per sqft)

Open House Schedule

55 Winterset Drive, Chatham, MA, 02633

Community Info

School Info

Walk Score

Mass Transit

Yelp

Similar Properties

$2,500,000

25 Menekish Lane, Chatham, MA, 02633

$2,445,000

88 Eel River Road, Falmouth, (East Falmouth), MA, 02536

$2,250,000

277 Bradford Street, Provincetown, MA, 02657

$2,499,999

92 Absegami Run, Chatham, MA, 02633

$2,250,000

409 Main Street, Chatham, MA, 02633

$2,485,000

18 Old County Road, Truro, MA, 02666

$2,699,999

193 Quanset Rd, Orleans, (South Orleans), MA, 02653

$2,365,000

5 Bentley Road, Harwich, MA, 02645

$2,375,000

98 Horizon Drive, Chatham, MA, 02633

$2,699,999

193 Quanset Road, Orleans, MA, 02653

$2,445,000

88 Eel River Rd, Falmouth, MA, 02536

$2,580,000

20 Stanley Place, Barnstable, (Hyannis), MA, 02601

$2,295,000

16 Little Beach Road, Chatham, MA, 02633

$2,539,000

42 Bayberry Avenue, Provincetown, MA, 02657

$2,395,000

11 Moss Road, Yarmouth, (West Yarmouth), MA, 02673

$2,695,000

5 Rockhill Road, Sandwich, MA, 02563

New or Coming Soon Properties

$2,249,000

130 Rogers Way, Duxbury, MA, 02332

$2,675,000

2 Buttercup Lane, Yarmouth, MA, 02664

$2,650,000

38 Charles St, Yarmouth, MA, 02664

$2,549,000

213 Main Street, Chatham, MA, 02633

$2,299,999

2 Little Cove Lane, Orleans, MA, 02653

$2,300,000

292 Stage Harbor Road, Chatham, MA, 02633

$2,550,000

7 Colonial Drive, Chatham, MA, 02633

$2,299,000

534 Commercial Street, Provincetown, MA, 02657

$2,500,000

12 Sheldon Road, Cohasset, MA, 02025

$2,300,000

56 Rip Van Winkle Way, Bourne, (Buzzards Bay), MA, 02532

$2,350,000

10 Lake Farm Lane, Orleans, MA, 02653

$2,450,000

49 Longfellow Road, Wellesley, MA, 02481

$2,450,000

211 1/2 Bradford Street, Provincetown, MA, 02657

$2,450,000

19 Weston Taylors Lane, Orleans, MA, 02653

$2,650,000

38 Charles Street, Yarmouth, (South Yarmouth), MA, 02664

$2,550,000

7 Colonial Dr, Chatham, MA, 02633

55 Winterset Drive, Chatham, MA, 02633

Your Raveis Experience

Your best can only get better...