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. This home offers spectacular first floor living with plenty of room for guests on the upper and lower levels. The sprawling front lawn, terraced perennial gardens and custom masonry stone walls provide the perfect estate setting for a large inground pool and tennis court off the walkout lower level, or just the space to run around, chase fireflies and have a fun game of flashlight tag. With land all around this home the possibilities are endless, fruit trees, vegetable gardens, or a greenhouse. Two paved driveways and separate entrances complement the many lifestyle options and provide ample parking for you and your guests. The southwest driveway leads to the two car garage under with a surprise brick fireplace & large windows. Off the cul d sac, the northeast driveway welcomes you down a walkway to a covered porch and into a sun streamed foyer where one of the home's two great rooms with cathedral ceilings, beams, hardwood floors and soaring brick fireplace impress. Large windows & french doors bring the outside in as a wrap-around porch reaches around the home for enjoyment of the predominantly south westerly breezes and views of your future swimming pool. The great room flows seamlessly into the open kitchen and dining rooms. The kitchen's large island with rich granite countertops and desk area are the perfect spot to organize your day and enjoy breakfast while gazing out the bank of windows to a majestic red copper beech tree beyond. The adjacent dining room's french doors lead to a private fenced backyard, perfect for a kitchen garden, sunning, or letting the dog out while you prepare an evening meal. Beyond the kitchen, a separate great room beacons you. French doors, large windows, cathedral ceilings, warm wooden beams & another stunning brick fireplace with gas insert are the perfect gathering space. Sun streams in from the expansive wrap around deck for your outdoor enjoyment and steps lead down to the side yard where your guests may arrive. When day is done a first floor primary suite with double closets, tiled bath and stackable laundry is conveniently located in the quiet rear of the house. While your guests retire to a second floor primary bedroom with fireplace, sitting area and two walk-in closets, a third bedroom and a full bath with shower and jetted tub. The walkout lower level offers a spacious fourth bedroom, full bath with shower, second laundry area, additional space with potential for finishing a family /entertainment room, and the garage with its own fireplace. The walk-out patio with custom stone bench and firepit invites you to imagine entertaining with a future pool, hot tub and indoor bar area. It's mere minutes from this peaceful retreat to the excitement of Chatham village, beautiful ocean beaches, boating and the bike path, at 55 Winterset Drive the world is your oyster and possibilities abound! Schedule a Private Showing

Listing courtesy of CCI / Tara J Schiffmann / Bayview Real Estate

Last checked: Checking… • Last updated May 14, 2025 • Source: CCI

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