Nestled in the timeless charm of Nantucket, four extraordinary estates await those seeking unparalleled beauty and serenity. From the reimagined elegance of 20 North Pasture Lane in tranquil Polpis to the rolling landscapes of Gerald’s Farm, and the architectural brilliance of High Point, these homes—priced between $7,995,000 and $10,995,000—offer a rare blend of classic design and natural splendor. Located across coveted addresses like Quidnet Road and Main Street, each property captures the island’s unique allure, promising a lifestyle defined by sophistication and the quiet luxury of coastal living.
Reimagined Polpis Estate | $10,995,000


Gary Winn & Morgan Winn

Gary Winn & Morgan Winn
Set against the tranquil backdrop of Nantucket’s Polpis area, 20 North Pasture Lane emerges as a reimagined rural estate on 2.75 acres of pristine land bordering conservation territory. With captivating views of Polpis Harbor, this fully renovated home, completed in 2024, marries classic island charm with modern sophistication. Sunlight pours through new Anderson thermopane windows, illuminating thoughtfully redesigned interiors, including stylish bathrooms and a custom “his and her” bunk room with a shared lounge for eight. Outdoors, a new in-ground pool, hot tub, expansive Ipe wood deck, and stainless steel grill create an entertainer’s paradise, framed by stunning sunsets over the water. Enhanced with a new roof, siding, and five-bedroom septic system, the property ensures enduring quality. Ideal for year-round living or seasonal escapes, this estate offers a seamless blend of indoor comfort and outdoor serenity in one of Nantucket’s most peaceful enclaves.
- Price:
- $10,995,000
- Size:
- 3,344 sq ft
- Contact:
- Gary Winn & Morgan Winn, Maury People Sotheby’s International Realty, 508.330.3069 , 508.332.9088
1-20 Geralds Farm Dr | $10,000,000


Jim Derentis

Jim Derentis
Nestled within the serene embrace of a tree-lined valley, Gerald’s Farm emerges as a distinguished country estate, where rolling landscapes and manicured lawns create a picturesque retreat. The centerpiece, a grand estate house, welcomes with a soaring foyer adorned by a marble pool and French doors that frame verdant garden views. Expansive living spaces seamlessly blend indoor and outdoor realms through striking windows, while the chef’s kitchen boasts custom cabinetry, marble countertops, and premium appliances. A first-floor primary suite with a spa-inspired bath ensures comfort across generations. Upstairs, three spacious bedrooms, two elegant marble baths, and a home gym await. Beyond, a two-story carriage house with a vaulted hall offers a perfect venue for gatherings, complemented by a full in-law apartment. An Amish-built barn, complete with a terrace and fire pit, enhances the idyllic grounds. Positioned at the junction of Exeter, North Kingstown, and East Greenwich, this estate offers unparalleled privacy alongside effortless access to Southern Rhode Island’s natural splendor.
- Price:
- $10,000,000
- Size:
- 6,122 sq ft
- Contact:
- Jim Derentis, Residential Properties Ltd., 401.529.2188
Private Nantucket Sanctuary | $9,995,000


Gary Winn & Morgan Winn

Gary Winn & Morgan Winn
Set against the serene waterfront of one of Nantucket’s most coveted areas, this 3.78-acre estate at High Point offers an unparalleled blend of classic architecture and modern sophistication. Two meticulously designed homes invite you into sunlit spaces, where designer chef’s kitchens with premium appliances, spa-inspired bathrooms adorned in Carrera marble, and versatile living areas create a haven for both relaxation and entertaining. Cozy up by the fireplace, stay active in the private gym, or enjoy cinematic evenings in the media room. Second-floor and rooftop terraces unveil breathtaking ocean views, transforming daily life with natural beauty. Outside, resort-like amenities await—lounge by the expansive pool, take in panoramic island vistas from the elegant roof walk, or gather in the curated outdoor space featuring a firepit, dining area, and refreshing alfresco showers, all designed for seamless coastal living.
- Price:
- $9,995,000
- Size:
- 6,072 sq ft
- Contact:
- Gary Winn & Morgan Winn, Maury People Sotheby’s International Realty, 508.330.3069 , 508.332.9088
29 Main Street | $7,995,000


Chandra Miller

Chandra Miller
Situated in the heart of Sconset, 29 Main Street presents a charming historic home that seamlessly blends classic elegance with modern upgrades. This striking white clapboard residence, thoughtfully renovated in 2023, offers 5 bedrooms and 4 bathrooms, creating an ideal setting for family living and entertaining. Step into a gracious front foyer that flows into a cozy family room and a living room warmed by a wood-burning fireplace. The eat-in kitchen impresses with a gas range, dual Bosch refrigerators, and a spacious island sink designed for effortless meal prep. French doors open to a private deck and a new gunite heated swimming pool, perfect for summer gatherings. A first-floor primary suite ensures convenience and tranquility, while central air conditioning provides year-round comfort. With a sun porch for quiet retreats and a large yard for outdoor activities, this home embodies the essence of village living.
Size: –
- Price:
- $7,995,000
- Contact:
- Chandra Miller, Maury People Sotheby’s International Realty, 508.360.7777













