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$2,350,000
3 Beds ⋅ 3 Baths ⋅ 1019874 MLS
Originally built in 1860 as the Samuel Parker House, this extraordinary property has been thoughtfully transformed into a one-of-a-kind luxury live/work compound featuring a main residence, a street-level showroom, and a heated, air-conditioned barn with a private studio above. Set in the heart of Pound Ridge's charming hamlet, directly across from The Inn at Pound Ridge by Jean-Georges, it offers a rare blend of historic character, modern functionality, and exceptional lifestyle appeal. Following a complete, no-compromise 2019 renovation under acclaimed New York interior designer Jenny Wolf of The Huntress, every element, infrastructure, mechanical systems, and all interiors alike - was reimagined to honor the homes history while delivering modern luxury. The result adapts effortlessly to almost any life: full time residence, weekend retreat, designer showroom, creative studio, gallery, or true live/work estate, creating a home that is as functional as it is beautiful. The beautifully finished street-level space offers remarkable flexibility and may continue as an inspiring showroom or seamlessly become part of the residence, creating expansive living and entertaining areas. The private upper-level home is filled with warmth and character, where soaring vaulted beamed ceilings, abundant natural light, and timeless architectural details create an atmosphere of understated elegance. A spacious great room anchors the residence, complemented by a beautifully appointed kitchen with soapstone countertops, a serene primary suite with a walk-in closet, two additional bedrooms, and thoughtfully designed baths that reflect the home's refined aesthetic. Adding to the property's exceptional appeal is a heated and air-conditioned barn offering endless possibilities. With an expansive first level ideal for a showroom, studio, workshop, entertaining, business use, or storage, and a spacious second-level studio or office, it is a rare complement to an already extraordinary offering. Life here extends far beyond the property itself. Spend mornings walking the picturesque hamlet, enjoy world-class dining just steps away at The Inn at Pound Ridge by Jean-Georges, explore nearby hiking trails, nature preserves, and equestrian estates, or simply embrace the quiet beauty and timeless charm that define Pound Ridge. Located within the highly regarded Katonah-Lewisboro School District and just over an hour from Manhattan, this is a rare opportunity to experience a lifestyle where history, design, creativity, and modern luxury exist in perfect harmony. Properties of this caliber rarely come to market. Rich in history, impeccably renovated, and genuinely unlike anything else available today, this is a singular opportunity to own one of Pound Ridge's most distinctive homes.

259 Westchester Avenue, Pound Ridge
$15,000,000
5 Beds ⋅ 6 Baths ⋅ 1007263 MLS
EASTLAKE. Nearly 39 serene acres offering the ultimate in privacy. Long, gated drive over rushing stream and through manicured grounds. Remarkable estate compound owned for years by renowned fashion designer as a family residence. Impressive architect-designed Stone and Country House positioned to overlook a private eight-acre lake. Striking and sophisticated Contemporary with elements of a Mid-Century Modern. Impressive rooms with natural finishes of fine woods and hand-cut stone. 5500 square feet of airy, loft-like living space positioned to capture views of the water. Beautifully scaled main rooms with vaulted ceilings, finished in warm woods, stone and hardwood floors and walls of glass. Striking Living Room with stone fireplace and vaulted ceiling lit by a modern cupola. Doors to wrap-around porch for fantastic indoor-outdoor living. Open-concept Dining Area also with water view, perfectly scaled for entertaining. Sleek Kitchen designed for the consummate chef. Private Office with conference area and wet bar. Lower Level Family Room for more casual everyday living. Spacious first floor Primary Suite with ample closets and private Bath. Four additional Bedrooms, most with en-suite Baths. Breathtaking grounds amid dramatic rock outcroppings with stone walls and terraces, an incredible array of flowering plantings, rare and specimen trees and rolling lawns down to the water. Fenced garden for flowers and seasonal produce. Lakefront dock, heated Swimming Pool with Pool House and privately sited Tennis Court make for an incredible sporting lifestyle. Separate building complex with a Three-Bedroom, fully equipped Guest House, Garages for six-plus cars and equipment storage. The perfect, peaceful refuge.

164 Eastwoods Road, Pound Ridge
$1,198,000
3 Beds ⋅ 3 Baths ⋅ 1007115 MLS
Nestled on two private acres, The Owl’s Nest is a striking 3-bedroom, 2-bath mid-century modern chalet that blends architectural character, privacy, and modern convenience. Surrounded by nature, the home feels like a secluded retreat while remaining easily accessible to nearby towns and commuting routes. The heart of the home is a dramatic living room with soaring 18-foot ceilings and wall-to-wall windows that flood the space with natural light and bring the outdoors in. Warm wood tones, clean lines, and custom doors reflect the timeless appeal of mid-century design, while wraparound, treehouse-like decks create a seamless indoor-outdoor living experience. Outside, the property features a pool, landscape lighting, and a traditional wood-fired sauna, creating a private oasis perfect for entertaining or quiet evenings under the stars. The home also includes upgraded systems throughout, including a modern boiler, water pump, smart home controls, and a full-house Kohler generator for year-round peace of mind. Conveniently located with easy access to the Merritt Parkway and Interstate 684, The Owl’s Nest is just 15 minutes from the train station in Stamford, with additional nearby access in Mount Kisco and Bedford Hills for convenient travel to New York City and beyond. More than a home, The Owl’s Nest is a private sanctuary with timeless design, modern comforts, and an extraordinary connection to nature.

380 Long Ridge Road, Pound Ridge
$1,499,000
5 Beds ⋅ 4 Baths ⋅ 1000762 MLS
First time on the market from the original owner, 80 Hack Green Road is a rare opportunity to own a timeless and rare in Pound Ridge Tudor-style house, where exceptional craftsmanship, architectural character, and beautifully landscaped grounds come together. Privately set behind a classic stone wall on a rare 2.6 acres of impeccably landscaped, flat level land between Scotts Corners and New Canaan, this distinctive custom brick-and-stucco Tudor is immediately recognizable by its striking rooflines and timeless curb appeal. Built by a professional contractor well beyond standard specifications, this 4,015 sq.f. home offers five bedrooms, three three and half bathroom bathrooms, and timeless character throughout. A sweeping semicircular driveway provides a gracious arrival and generous parking for entertaining. Inside, 13 unique custom stained-glass windows serve as stunning architectural focal points throughout the home. The spacious eat-in kitchen flows seamlessly into the dramatic great room with a soaring 16-foot ceiling, skylights, French doors to the outside, and a custom wet bar. A richly appointed wood-paneled office overlooks the gardens, while the recreation room with a high-efficiency cast-iron wood-burning fireplace offers a warm and inviting gathering space. A whole-house central audio system enhances everyday living and entertaining. The second floor features a spacious primary suite with an updated en-suite bathroom, four additional bedrooms, and an updated hall bathroom. One of the bedrooms, with vaulted ceilings, is currently configured as a spacious den/playroom and can easily be converted back into a bedroom. The finished walk-out lower level with a full bathroom provides flexible recreation and media space, ideal for a home gym, game room, or movie nights. The extraordinary grounds have been cultivated over decades and feature an exceptional collection of mature specimen trees, including Japanese maples, Atlas cedar, Japanese umbrella pine, and weeping evergreens. The expansive, level lawn, with lights and uplighted trees, is a true rarity in Pound Ridge - offering endless opportunities for recreation, sports, relaxation, and outdoor enjoyment, as well as for entertainment. The outdoor patio features rare pink granite cobblestone, handcrafted by Italian masons, overlooking a tranquil koi pond with twin waterfalls. A charming playhouse, professional-grade swing set, half basketball court, and exceptional privacy complete this remarkable property. New above-oil tank, full house generator, updated bathrooms, new GE Cafe refrigerator, new GE Profile induction cooktop, and many more updates throughout. Ideally located just minutes from New Canaan, Grace Farms, Scotts Corners, Pound Ridge amenities, area preserves and parks, St. Luke's School, and the New Canaan train station, this exceptional home offers the perfect balance of peaceful country living and everyday convenience within the Bedford Central School District. Timeless. Refined. Exceptional.

80 Hack Green Road, Pound Ridge
$3,995,000
5 Beds ⋅ 6 Baths ⋅ 823299 MLS
Behind private gates, nearly six acres of bucolic countryside unfold around a spring-fed lake — a setting that feels worlds away, yet sits just one hour from Manhattan. Gut-renovated to the studs and reimagined from the ground up, this Pound Ridge estate blends Mid-Century Modern design with original stone construction and hand-hewn beams — a rare marriage of architectural integrity and contemporary refinement. The result is a home that feels both timeless and entirely of the moment. The main residence offers four bedrooms and has sweeping water views that define the property. A detached guest studio with two-car garage provides flexible accommodation for visitors or staff, while the heated gunite pool and pool house — complete with full bath, wet bar, and huge fireplace — create an effortless setting for both quiet evenings and elevated entertaining. An additional detached two car garage rounds out the offering. Outside, the grounds have been as thoughtfully curated as the interiors: new landscaping, artisan stonework, full irrigation system, patios, and mature tree work frame the lake and connect seamlessly to the Pound Ridge Land Conservancy — a permanent buffer that ensures the privacy and natural beauty of this property endure. Truly turnkey. Completely one-of-a-kind.

39 Old Snake Hill Road, Pound Ridge

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.