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.
For sale
Price cut: $50K (8/1)
$2,445,000
55 Winterset Drive, Chatham, MA 02633
4beds
4,072sqft
Est.:
Single Family Residence
Built in 1970
1.94 Acres Lot
$2,318,200 Zestimate®
$600/sqft
$-- HOA
What's special
Tennis courtStunning stone wallsWrap-around decksGuest room and bathCathedral great roomsDaylight lower levelSprawling lawn
- 89 days
- on Zillow |
- 1,056 |
- 43 |
Zillow last checked: 7 hours ago
Listing updated: August 01, 2025 at 05:31pm
Listed by:
Tara J Schiffmann 774-810-6381,
Bayview Real Estate
Source: CCIMLS,MLS#: 22502257

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 2
Primary bedroom
- Description: Flooring: Carpet
- Features: Recessed Lighting
- Level: First
Bedroom 2
- Description: Fireplace(s): Wood Burning,Flooring: Carpet
- Features: Bedroom 2, Shared Full Bath, Walk-In Closet(s), Recessed Lighting
- Level: Second
Bedroom 3
- Description: Flooring: Carpet
- Features: Bedroom 3, Closet
- Level: Second
Bedroom 4
- Description: Flooring: Carpet
- Features: Bedroom 4
- Level: Basement
Primary bathroom
- Features: Private Full Bath
Dining room
- Description: Flooring: Wood,Door(s): French
- Features: Dining Room
- Level: First
Kitchen
- Description: Flooring: Wood,Stove(s): Gas
- Features: Pantry, Upgraded Cabinets, Kitchen Island
Living room
- Description: Fireplace(s): Wood Burning,Flooring: Wood
- Features: Cathedral Ceiling(s), Living Room, Beamed Ceilings
Heating
- Hot Water, Other
Cooling
- Has cooling: Yes
Appliances
- Included: Dishwasher, Washer, Refrigerator, Microwave, Gas Water Heater
- Laundry: Laundry Room, In Basement
Features
- Recessed Lighting, Pantry, Mud Room, Linen Closet, HU Cable TV
- Flooring: Hardwood, Carpet, Tile, Other
- Doors: French Doors
- Windows: Bay/Bow Windows
- Basement: Bulkhead Access,Interior Entry,Full,Finished
- Number of fireplaces: 4
- Fireplace features: Wood Burning
Interior area
- Total structure area: 4,072
- Total interior livable area: 4,072 sqft
Property
Parking
- Total spaces: 6
- Parking features: Basement
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Stories: 2
- Entry location: First Floor
- Exterior features: Garden
- Fencing: Fenced
Lot
- Size: 1.94 Acres
- Features: Bike Path, Near Golf Course, Marina, Conservation Area, Cleared, East of Route 6, North of Route 28
Details
- Parcel number: 11G74H108
- Zoning: R60
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Foundation: Block, Slab
- Roof: Asphalt, Pitched, Flat
Condition
- Updated/Remodeled, Actual
- New construction: No
- Year built: 1970
- Major remodel year: 1999
Utilities & green energy
- Sewer: Private Sewer
Community & HOA
Community
- Features: Deeded Beach Rights
- Subdivision: Great Hills Estates
HOA
- Has HOA: Yes
Location
- Region: Chatham
Financial & listing details
- Price per square foot: $600/sqft
- Tax assessed value: $2,122,900
- Annual tax amount: $5,179
- Date on market: 5/14/2025
- Road surface type: Paved
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