Pound Ridge, NY Homes for Sale | Luxurious Woodland Retreats

Set on a peaceful country road in bucolic Pound Ridge, this move in ready 4 bedroom Colonial is impeccable and filled with natural light. The formal living room and dining room (with bay window) offer classic scale, while the updated kitchen features white cabinetry, quartz counters, and stainless steel appliances. The family room, anchored by a fireplace, opens through French doors to the rear deck — perfect for indoor-outdoor living. Lovely hardwood floors and fresh Farrow & Ball paint run throughout. Outside, nearly three bucolic acres unfold in level lawns, old stone walls, and wooded privacy. This home is just minutes to the New Canaan train station for direct service to NYC as well as to the charming towns of Scotts Corners and Bedford. Recent updates include a brand new Bosch 2 zone heat pump, a new mini-split heat pump in the basement, a new hot water heater, and attic insulation. New roof and well pump 10/23. A charming, fully updated home offering the best of country living!

78 Hack Green Road, Pound Ridge

$2,350,000

1029454 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

$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

$2,409,990

4 Beds ⋅ 6 Baths ⋅ 1019164 MLS

Antique lovers... A near impossible to find rare gem set on a small quiet back road of only a handful of homes - step into the timeless charm of the landmarked Sarles-Bode house, a quintessential c.1750 home in Pound Ridge, NY. This is a rare offering where timeless character and everyday livability come together in the main house, guest house, gunite pool and extensive outdoor entertainment areas. Layered with history, the original 18th-century main residence, later expanded in both the 19th and 20th centuries, retain its original charm throughout a complete and careful top to bottom renovation (2023-2026) This remarkable property showcases beautifully preserved wide plank flooring and hand hewn beams throughout the interior. The exterior is complemented by extensive dry stone walls, exceptional stonework patios, and amazing rock outcroppings. All rooms offer their own charm, highlighted by built ins, bookcases and distinctive wooden doors- each with its own character and paired with original materials that create a true sense of history. The living room features a wood-burning fireplace and built-ins, while the dining room offers a second fireplace. The primary bedroom sits privately at the back of the main residence featuring his and her baths, a huge lounge area and amazing sunset views. The large 2 story guest cottage is private from the main house yet easily accessible to the pool and property featuring 2 full baths, a great room downstairs and oversized guest bedroom upstairs. Set on over 2 beautiful, private professionally landscaped acres, this one of a kind cherished residence seamlessly blends historic character with the modern-day comforts of today. Seller Financing Available. Property is available fully furnished (with the exception of a few family heirlooms/antiques) including most furniture, wall art, lighting and televisions.

35 Old Snake Hill Road, Pound Ridge

$525,000

1015458 MLS

RARE BUILDING LOT. Ready to go! Private two-acre building lot with BOH approval for five-bedroom home. Abutting Pound Ridge Conservancy lands, fabulous location across from the Pound Ridge Golf Course. Easy access to Scotts Corners, town park, Stamford shopping and Merritt Parkway.

15A High Ridge Road, Pound Ridge

$1,595,000

3 Beds ⋅ 4 Baths ⋅ 1008473 MLS

Nestled on one of South Salem's most picturesque country lanes, 78 Old Church Lane offers a beautiful blend of privacy, comfort, and timeless style. Set on 4.6 magical, level acres surrounded by classic architecture and rolling countryside, this beautifully maintained residence is move-in-ready and designed for effortless living. Completely renovated in 2004, the home features sun-filled interiors, rich wood floors, a fabulous fireplace, and an excellent floor plan for everyday living and entertaining. At the heart of the home is a classic Poggenpohl kitchen, as functional and elegant today as when it was first installed, opening seamlessly to inviting gathering spaces filled with natural light. Offering three bedrooms and three-and-a-half baths, the home lives comfortably with generous entertaining areas, excellent indoor flow, and peaceful views of the spacious deck and surrounding property. The expansive grounds provide exceptional privacy and ample room for a pool, creating the opportunity to further enhance this special setting. A rare offering in a coveted South Salem location, 78 Old Church Lane is ready to be enjoyed from day one.

78 Old Church Lane, Pound Ridge

$2,650,000

5 Beds ⋅ 6 Baths ⋅ 1001204 MLS

Fabulous Country Retreat. Absolute serenity! Long drive through scenic woodlands to peaceful privacy. Fabulous high site with glorious sunset views. Beautifully landscaped grounds with an array of fine and flowering plantings, fenced for deer. Free-form Swimming Pool with spa and two waterfalls. Perfectly positioned Tennis Court. Architect-designed Country House with contemporary and traditional elements. Stunning interior spaces with beautifully scaled rooms, vaulted ceilings and walls of windows. Exceptional craftsmanship with substantial millwork, wide board oak floors and high-end finishes. Nearly 5700 square feet of finely appointed living space. Fabulous open floorplan with impressive main rooms for entertaining. Chef’s Kitchen with center island, custom cabinetry, marble counters and high-end appliances. Five Bedrooms include a spectacular Primary Suite with Dressing Room, Office, Gym and Two Baths. Lower level Recreation Room. The ultimate estate for the most discerning buyer.

17 Eastwoods Road, 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

$960,000

4 Beds ⋅ 3 Baths ⋅ 1007052 MLS

Private updated retreat within minutes to Scott's Corners, and across the street from Pound Ridge Town Park. Enjoy the wood burning fireplace in the living room, updated kitchen with new appliances, updated baths, and hardwood floors throughout. Easy flow with rooms bathed in natural light and deck off kitchen makes entertaining, or basking in the sun, a breeze. This home sits on 2.81 private acres, with a long driveway and mature trees. For the car and storage fanatics, this home boasts a two car garage on the main house and another three car detached garage on property with the option of 24' ceilings. Perfect for car enthusiasts who want lifts, or mutliple car storage, or to lease out as extra garage space. Recent updates include: New roof 2016, new septic fields 2021, new windows, new driveway, new bib in garage, newly done retaining wall, and freshly painted! Don't miss this hilltop charmer.

186 High Ridge Road, Pound Ridge

$1,195,000

5 Beds ⋅ 4 Baths ⋅ 1007911 MLS

Nestled in sought-after Pound Ridge, this exceptional 5BR/3.5BTH residence offers an extraordinary blend of sophisticated living and natural tranquility. Spanning over 3,600 sq ft, this home presents an ideal sanctuary for discerning buyers seeking both luxury and comfort in one of Westchester's most coveted locations. Upon entering, you are immediately struck by the dramatic architectural elements that define the home's character. Soaring sky-high ceilings create a sense of space and grandeur, while exposed wood beams add warmth and rustic elegance throughout the interior. The thoughtfully designed floor plan maximizes both functionality and flow, accommodating the needs of modern life while maintaining distinct spaces for relaxation and entertainment. Five generously sized bedrooms provide ample accommodation offering comfortable sleeping quarters and tons of natural light. The primary bedroom serves as a true retreat, featuring the tastefully renovated ensuite bathroom (2025) that showcases high-end materials and modern amenities. Three and a half bathrooms throughout the home ensure convenience and privacy for all occupants, with each space thoughtfully appointed. The additional half bathroom provides practical functionality for entertaining and daily use, conveniently located off of the mudroom. The heart of the home encompasses inviting living spaces that seamlessly blend comfort with style. Whether hosting intimate gatherings or large celebrations, the open and airy layout accommodates various entertainment needs while maintaining a sense of warmth and intimacy. The exposed beam details and soaring ceilings create architectural character that distinguishes this property from typical suburban offerings. Boasting nearly 2.25 acres, the outdoor space extends the home's living area seamlessly into the natural environment which provide the canvas for year-round outdoor living experiences. While tucked away on a quite cul-de-sac, the location still offers an enviable combination of small-town charm and NYC accessibility. Just one mile from the charming Pound Ridge Village, residents can explore local shops, restaurants, and tons of community events. Nature enthusiasts will appreciate the proximity to De La Torre Preserve, offering hiking trails, wildlife observation and peaceful spaces for outdoor recreation. New Canaan Metro North located just a short 12 minute drive makes your NYC commute easy, with just a 68 minute express train to Grand Central Station. First time on the market in over 25 years, this truly stunning home is just waiting for its new owners!

22 Peters Lane, Pound Ridge

$2,750,000

4 Beds ⋅ 5 Baths ⋅ 993992 MLS

Cozy-chic country Colonial thoughtfully reimagined from top to bottom by an award-winning international designer. Many details reflect quality materials and a highly curated aesthetic. The heart of the home is a bespoke chef's kitchen anchored by striking Viola Fantastico marble, a deVOL English sink, professional-grade ILVE range, Waterworks fixtures, Apparatus lighting, custom Vermont oak cabinetry, and radiant-heated Belgium bluestone floors. French doors lead to a large deck overlooking level lawns and stone walls. Designed for both entertaining and comfortable daily living, the main level offers exceptional flow through the living room with marble fireplace, formal dining room, expansive great room with stone fireplace, and a sun-filled conservatory. Retreat to the primary suite with a lounge, dedicated office, window seat nooks, and a spa-inspired bath with Waterworks fixtures and a Penhaglion soaking tub. Three more bedrooms, one that can be used as a second primary, round out the second level. The finished walkout lower level adds an additional 1,737 square feet of flexible recreation, fitness, or work space. The property abuts more than 70 acres of protected watershed land, offering an exceptional sense of privacy and tranquility. Set on a quiet country lane, yet just moments from the shops, restaurants, hiking trails and amenities in Scotts Corners and New Canaan -- including the New Canaan train. One hour to Manhattan.

240 Eastwoods 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

$2,995,000

4 Beds ⋅ 5 Baths ⋅ 995187 MLS

Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridge’s most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence. The grounds are thoughtfully designed to enhance both beauty and livability. The three ponds are supported by aerator systems that maintain water quality, circulation, and ecological balance, allowing them to remain vibrant and visually striking year-round. A wireless deer fence system, along with perimeter fencing, helps preserve the integrity of the landscape and plantings, ensuring the setting remains peaceful, natural, and undisturbed. The result is an environment that feels both curated and effortless, offering a true sense of calm and connection to nature. Outdoor living is elevated with an infinity-edge saltwater pool and spa positioned to overlook the property, a full tennis court, and multiple outdoor spaces designed for both entertaining and quiet relaxation. The residence, a meticulously maintained stone and shingle Country House, offers over 5,500 square feet of light-filled living space. A two-story entrance hall introduces the home, leading into a series of elegant yet comfortable interiors defined by high ceilings, custom millwork, and walls of windows that bring the outdoors in. At the center of the home, a dramatic great room with a soaring ceiling and fireplace anchors the main living level, flowing seamlessly into a chef’s kitchen with a large center island and adjoining breakfast area. Formal living and dining rooms provide a more classic setting, while the overall layout remains open and adaptable for modern living. The home offers four bedrooms, including a first-floor primary suite designed as a true private retreat. The suite features a double-sided fireplace, a spa-like en-suite bath, and custom walk-in closets, along with direct access to the grounds, creating a seamless connection between indoor comfort and the surrounding landscape. Additional spaces include a large playroom, multiple offices, and flexible bonus rooms suited for today’s lifestyle. A screened porch and expansive rear terrace extend the living spaces outdoors, creating a natural flow for entertaining or quiet evenings overlooking the property. Complete with a three-car garage and surrounded by preserved land and natural beauty, this is a home that offers both substance and ease. Just minutes to Katonah, Bedford Village, Ridgefield CT and Metro-North, yet entirely removed, this is Pound Ridge at its best: understated, private, and enduring.

127 Boutonville Road, Pound Ridge

$2,795,000

5 Beds ⋅ 5 Baths ⋅ 991143 MLS

This one-of-a-kind 5 bedroom, 5 full bathroom rustic California inspired residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned by Ted Sorenson, JFK's speechwriter, the unique estate is ideal as a year-round home, weekend retreat or secluded hideaway with Belgian block and chestnut floors, stone columns (the stone of which was excavated from the site), tongue-in-groove cedar walls, soaring beamed ceilings, 22 skylights and custom windows. Custom stair railings designed by renowned rustic artist, Daniel Mack. Enjoy lavish entertaining in impressive living spaces with floor-to-ceiling fireplace and windows. The rustic dining room seats 16, the masterful kitchen with original copper bar counter, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite, home gym, media room, sauna and office with custom desk made of one solid piece of hundreds of years old Baobab tree. The lower level en suite bunk room provides ample accommodations, with private entrance. Resort-like grounds and a bucolic location make this an exceptional country estate. Custom, high level properties like this don't come up very often.

217 Trinity Pass, 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

$1,895,000

5 Beds ⋅ 4 Baths ⋅ 983422 MLS

Perfectly sited at the end of a quiet cul-de-sac, this Pound Ridge residence combines timeless charm with modern comfort on two beautifully landscaped acres. Surrounded by specimen plantings, gardens, and mature trees, the property offers exceptional privacy, a large level yard, a stone-lined koi pond, and a stunning slate patio with a fire pit - an ideal setting for entertaining or simply enjoying the outdoors. Inside, the home is rich with detail, featuring wide-board floors, custom moldings, and built-ins throughout. The heart of the home is the gorgeous kitchen, designed with marble countertops, a beadboard ceiling, brass pendant lighting, and a large center island that invites gathering. A commercial-grade range, separate full-size Sub-Zero refrigerator and freezer, and farmhouse sink make the space both beautiful and functional. The kitchen opens seamlessly to the family room, where exposed beams and a stone fireplace create a warm and inviting atmosphere. Additional features include new composite siding, a new roof, many new windows, central air, and a whole-house generator. The finished lower level (not included in the listed square footage) adds flexible living space, while the circular drive enhances curb appeal. With a potential pool site and peaceful setting just minutes from town, this property offers the best of country living-only about an hour from New York City.

33 Peters Lane, Pound Ridge

$1,499,000

3 Beds ⋅ 4 Baths ⋅ 975865 MLS

A Modern Colonial Retreat, 83 Upper Shad Road, is situated on 2.25 private, level acres in the heart of Pound Ridge. Mature trees and professionally designed landscaping create a serene, park-like environment, with an in-ground pool and manicured green expanses that surround the home. (Did I forget to mention the babbling brook at the corner of the property?) The home features a primary bedroom suite plus 2 additional, generously sized bedrooms, 3.5 bathrooms, living room, den, formal dining room and kitchen with center island. The finished lower level adds an open-plan living area with a large office, library, entertainment center, and full bath. The heart of the home is a breathtaking living room featuring double-height, vaulted ceilings and classic wood-burning fireplace. French doors open to the patio dining area and offer clear views of the private backyard and sparkling heated pool. Adjacent to the living room, a separate den and large dining room open onto each other, making the space perfect when hosting large gatherings. The Chef’s kitchen features a large central island and abundant cabinets with room for a cozy breakfast nook. The formal dining room adjoins the kitchen, while the kitchen backdoor flows directly onto a private deck--an ideal BBQ space overlooking the pool and gardens. Just beyond the deck is a large stone patio perfect for seasonal dinners. The gated sparkling gunite pool and expansive deck area are flanked by lush flowering landscaping including magnificent rhododendron, Japanese maples, hydrangeas, and an array of colorful flowering plantings. A cedar shed, an attached 2-car garage and Invisible fencing help keep your cars and tools snow-free and your pets secure. The total square footage of the home includes the large finished lower level. The location offers exceptional convenience, just minutes from shopping and dining in Pound Ridge, Bedford, New Canaan, Stamford and Ridgefield. Commuters will appreciate the easy access to the Merritt Parkway and I-684, as well as the nearby Metro-North stations.

83 Upper Shad Road, Pound Ridge

$3,250,000

4 Beds ⋅ 5 Baths ⋅ 979591 MLS

The Cross Pond Residence, designed by acclaimed architect Frank Lupo, FAIA, is a rare architect-designed estate set on 3.48 private acres overlooking a large pond in Pound Ridge. Conceived as a series of interconnected structures thoughtfully positioned within the landscape, the property offers a level of design, craftsmanship, and flexibility seldom found in residential architecture. The main residence is organized around dramatic living spaces that embrace the surrounding landscape through expansive walls of glass, soaring ceilings, and carefully framed views of the water and grounds. The primary living area flows seamlessly to dining and kitchen spaces, creating an environment equally suited for everyday living and entertaining. The upper level serves as a private retreat with a spacious primary suite, while the lower level provides additional recreation and gathering space. Complementing the main residence is a fully self-contained secondary living quarters featuring its own living room, dining area, kitchen, bedroom, elevator, and private primary suite. Ideal for extended family, guests, live-in staff, or multigenerational living, it offers complete independence while remaining architecturally integrated with the overall composition. Additional structures include a substantial heated studio building with exceptional flexibility for creative work, hobbies, fitness, collector use, or additional vehicle storage, as well as a detached six-car garage with front and rear access, providing ample space for automobiles, equipment, and storage. Constructed with a level of detail and material quality rarely seen today, the residence incorporates steel framing, glulam beams, commercial-grade window systems, lead-coated copper roofing, standing-seam metal roofing, cedar siding, radiant heating, humidity control, and a hydraulic elevator. The result is a home designed not only for visual impact, but for longevity and performance. The grounds are equally compelling, with expansive lawns, mature trees, exposed rock outcroppings, gardens, and a large pond that serves as the focal point of the property. The landscape was conceived as an extension of the architecture, creating a seamless relationship between built form and nature. For buyers seeking additional outdoor amenities, the property offers attractive opportunities for a future pool installation. Conceptual plans have been prepared illustrating both a garage-side pool pavilion overlooking the pond and a more secluded pool retreat adjacent to the studio building, allowing future owners to tailor the outdoor experience to their lifestyle and entertaining preferences. Published in The New American House 2: Innovations in Residential Design and Construction, The Cross Pond Residence represents a rare opportunity to own an architecturally significant estate where design, landscape, and function exist in complete harmony.

54 Cross Pond Road, Pound Ridge

$2,599,000

5 Beds ⋅ 7 Baths ⋅ 976870 MLS

Step into a slice of Mediterranean paradise at 105 Cross Pond Road, where timeless elegance meets modern luxury. This breathtaking villa, inspired by classic European architecture, boasts over 6,000 square feet of refined living space on 5.+ meticulously landscaped acres. From the iconic red clay roof to the graceful stucco and stately arches, this property exudes sophistication at every turn. Key Features That Will Steal Your Heart: Mediterranean Charm: The distinctive architectural elements create an enchanting, old-world aesthetic. Expansive Interiors: Multiple fireplaces, private terraces, and oversized balconies invite seamless indoor-outdoor living. Private Waterfront Oasis: Your very own lagoon offers tranquil views, waterside relaxation, and kayaking adventures just steps away. Luxurious Finishes Throughout: Marble and natural stone details bring warmth and elegance to every room. Nature’s Playground: Over 5+ acres of pristine grounds, complete with a private island, provide endless opportunities for outdoor entertaining and peaceful solitude. Inside the Villa: From the moment you enter, the grand scale and thoughtful design captivate. Open-concept spaces flow effortlessly, perfect for everything from quiet evenings to hosting grand gatherings. Marble and stone finishes elevate the interiors, while fireplaces add cozy charm. Step outside onto expansive terraces and balconies to savor al fresco dining or watch the sunset over your serene property. The home also offers flexible spaces ideal for a chef’s kitchen, wine room, home gym, or a luxurious primary suite. Unbeatable Location for a Coveted Lifestyle: Nestled on prestigious Cross Pond Road in Pound Ridge, this estate combines privacy with accessibility. It’s part of the highly regarded Bedford Central School District and offers convenient access to I-684, Saw Mill Parkway, and Metro-North stations for an effortless commute to Manhattan. Nature lovers will adore the proximity to Ward Pound Ridge Reservation for hiking, camping, and fishing, while the charming nearby towns of Katonah, Bedford, and Stamford, CT, provide boutique shopping, fine dining, and cultural experiences. For wine enthusiasts, local vineyards and specialty shops await to help you curate the perfect collection. A Once-in-a-Lifetime Opportunity: 105 Cross Pond Road isn’t just a home—it’s an experience. Whether you’re savoring lakeside mornings, hosting elegant, or simply enjoying the serene beauty of your surroundings, this estate offers a lifestyle of unparalleled luxury and tranquility. Don’t miss your chance to make this extraordinary retreat your own.

105 Cross Pond Road, Pound Ridge

$915,000

4 Beds ⋅ 3 Baths ⋅ 961485 MLS

This private and spacious home sits on 2.5 acres of beautiful land in Pound Ridge, and is the ideal Westchester retreat. It has that perfect mix of "peace and quiet" without being completely off the grid. With 4 bedrooms and 3 full bathrooms, you’ll have plenty of room for everyone. The versatile floor plan offers endless possibilities to make the space your own. Enjoy a bright eat-in kitchen with skylights that fill the room with natural light—perfect for morning coffee. The large quartz-topped island is perfect for meal prep and entertaining, and features a gas cooktop. A wood-burning stove in the den is cozy and warm on cold nights. Large windows throughout the home create a light and airy atmosphere. This home features an elegant formal dining room—perfect for hosting holiday feasts and candlelit dinner parties. The living room centers around a classic fireplace, offering a warm, relaxing retreat for evenings at home. An unfinished space just off the living room offers exciting potential. Create a sunroom, screened-in porch, home office, or additional living area tailored to your vision. The newly built two-car garage (2022) provides ample storage. New roof in 2025. Whirlpool dishwasher 2021, Stove top on Island 2023, Oven and in-wall microwave 2020/2021. GE Refrigerator 2023. Taxes will have substantial reduction.

17 Highview Road, Pound Ridge

$795,000

937855 MLS

Just Listed: Experience a rare chance to build in one of Pound Ridge’s most desirable settings at Joshua Hobby Farm. Lot 5 is a newly listed flat lot at the end of the cul-de-sac, lightly wooded and offers over three acres of natural beauty, framed by rock outcroppings, mature trees, and long views across protected open space. Peaceful and private, yet moments to Pound Ridge, Bedford, and the Merritt Parkway, the location blends seclusion with everyday convenience. The property is part of an exclusive collection of ten estate lots, each thoughtfully positioned to maximize light, landscape, and privacy. Backing directly to the Westchester Wilderness Walk, it enjoys enduring protection and a rich habitat of birds and wildlife. With Board of Health approval for a five-bedroom residence, the lot provides an exceptional foundation for a custom build—whether a modern escape, classic country home, or architectural statement. A unique opportunity to create your own retreat in one of Pound Ridge’s most captivating natural environments.

32 Joshua Hobby Lane, Pound Ridge

$2,500,000

6 Beds ⋅ 8 Baths ⋅ 928343 MLS

Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of elegance and ease. Enter through the impressive oversized foyer and immediately sense the grandeur. Sunlight pours through large windows, highlighting the home’s impeccable finishes and thoughtful design. The gourmet kitchen, appointed with granite countertops, opens seamlessly to the expansive living room which is ideal for both intimate gatherings and large celebrations. Additional main level spaces include a formal dining room, front and rear staircases, and a private home office with its own entrance. Upstairs, six spacious bedrooms offer exceptional comfort, each with oversized walk-in closets. Four bedrooms feature en-suite baths, while two share a classic Jack-and-Jill perfect for guests, or multi-generational living. Beautiful stone walls, natural rock outcroppings, lush lawns and wooded landscape frame the outdoor spaces. Relax on the expansive stone patio, unwind in the hot tub, or enjoy quiet evenings in the screened porch. There's even ample space for a pool. A semi-circular drive, 3-car garage, large recreation or game room, home gym, five fireplaces and whole-house generator complete this exceptional offering. Located minutes from Pound Ridge’s charming Scotts Corners and convenient to New Canaan, this home combines country serenity with everyday accessibility to shops and restaurants. A true retreat only 50 miles from Manhattan. Also available for rent at $20,000/month.

11 Lost Nations Road, Pound Ridge

$550,000

932661 MLS

Build your dream home! This lot offers a quiet retreat in one of the most sought after areas in Pound Ridge. Backs onto the Ward of Pound Ridge, and can connect into that trail system, as well as the BRLA. Own driveway can be created from the road already in place. This property is BEHIND the dead end roadway. The sign is just a visual cue.

17 Spring House Road, Pound Ridge

$679,000

863526 MLS

Meandering long drive past dramatic rock outcroppings and open lightly wooded spaces leads to a totally private and dramatic home site and pool site. Rarely found, a 5 acre parcel in an established area bordering Pound Ridge and Bedford. Previous BOH approval expired, perc tests recently done successfully with two different options for septic location. Architectural plans available.

Brook Farm Road, Pound Ridge

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