$2,495,000
4 Bed
3 Bath
4,072 Sqft Building
84,506 Sqft Lot

55 Winterset Drive, Chatham, Massachusetts 02633

  • Residential Property Type
  • 612.72 Price/Sqft
  • 6 Cars Garage
  • 1970 Year Built

Property Description

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 & walk-in closet, 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.

Basic Details

CCIMLS
$2,495,000
$5,179
2025
Residential
For Sale
4
3
1
3.5
8
1970
4,072 Sqft
84,506 Sqft
Active
Single Family Residence
22502257
Bayview Real Estate
Tara J Schiffmann

Features

: Other, Hot Water
: Finished, Full, Interior Entry, Bulkhead Access
: Fenced
: 6
: Gas Water Heater, Dishwasher, Microwave, Refrigerator, Washer
: Deeded Beach Rights
: French
: Garden
: Wood Burning
4
: Tile, Carpet, Hardwood, Other
2
: Hu Cable Tv, Pantry, Recessed Lighting, Linen Closet, Mud Room
: Laundry Room, In Basement
: Bike Path, Conservation Area, Near Golf Course, Marina, Cleared, North Of Route 28, East Of Route 6
: Basement
: Flat, Asphalt, Pitched
: Dining Room
: Living Room, Cathedral Ceiling(s), Beamed Ceilings
: Private Full Bath
: Private Sewer
No
1 To 2

Additional Information

Annually
: Shingle Siding
: Block, Slab
: Actual, Updated/remodeled
: Public
R60
No
56
07/01/2025

Address Map

55 Winterset Drive
MA
Barnstable
Chatham
Chatham
02633
0
W70° 1' 20.7''
N41° 41' 38.7''
Rte. 28 to Old Queen Anne Rd. to Winterset Drive, to upper driveway on left off Cul d Sac.
Great Hills Estates
Property