Massachusetts
Chatham
55 Winterset Drive

$2,495,000

55 Winterset Drive, Chatham, MA 02633

4 beds |
4 baths |
4,072 sqft

Single-Family Home
Built in 1970
1.94acre lot
2 car garage
$613/sqft
Listed 1 month ago

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.

Listing Status:: Active
Date Added:: May 14, 2025 at 05:00AM
Listing Office:: Bayview Real Estate : 508-362-8543
Listing Agent:: Tara J Schiffmann : 774-810-6381
MLS ID:: 22502257

General: Walk-In Closet(s)Central VacuumMud RoomHU Cable TVLinen ClosetPantryRecessed LightingKitchen IslandNo
Appliances: Water HeaterWasher/Dryer StackedGas RangeDishwasherMicrowaveRefrigeratorWasher
Laundry: Washer HookupElectric Dryer HookupElectric DryerLaundry Room
Basement: Walk-Out AccessBulkhead AccessGarage AccessInterior AccessFinishedFull
Flooring: HardwoodOtherTileCarpet
A/C: Wall Unit(s)
Heating: OtherNatural Gas
Fireplace: FireplaceFireplaces: 4

This listing courtesy of Tara J Schiffmann, Bayview Real Estate

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
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Location

Schools Nearby

Monomoy Regional Middle School

425 Crowell Rd, Chatham, MA, 02633

Grades 5-7

0.30 miles away

Monomoy Regional Middle School

425 Crowell Rd, Chatham, MA, 02633

Grades 5-7

0.30 miles away

Monomoy Regional High School

75 Oak St, Harwich, MA, 02645

Grades 8-12

4.65 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.