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$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
$2,320,000
4 Beds ⋅ 4 Baths ⋅ 1023671 MLS
Perfectly situated on one of Bedford's quintessential country roads, this exceptional renovated 4-bedroom three-and-a-half bath home offers the ideal combination of privacy, timeless charm, and modern updates. Set on a beautifully landscaped property surrounded by mature trees, you'll enjoy complete tranquility while relaxing by the in-ground pool or entertaining on the expansive wraparound deck. Recently reconstructed retaining walls, seasonal gardens, and a brand-new perimeter fence further enrich the picturesque setting. A dramatic two-story entry welcomes you with a floating staircase and striking fieldstone chimney, creating an unforgettable first impression. Inside, soaring ceilings, abundant natural light and hardwood floors, create a bright and inviting atmosphere further enhanced by the addition of remote-controlled window shades throughout the home . The thoughtfully designed open floor plan is ideal for both everyday living and entertaining. At the heart of the home is the tastefully updated kitchen with door to fabulous wrap around deck. The Kitchen is open to the formal dining room on one side and family room, warmed by a pellet stove, adding comfort and character during the cooler months, on the other side. The flexible floor plan includes a desirable main-level primary suite complete with a spa-inspired bath and walk-in closet—an ideal retreat for guests or multigenerational living. Upstairs, the luxurious primary suite features a spacious bedroom, spa bath, private sitting room or office, and door to finished attic space perfect for a home gym or additional storage. Two additional bedrooms, a full bath, and an open balcony overlooking the foyer complete the upper level. Additional highlights include a detached three-car garage with potential for future expansion above, a whole-house propane generator, app controlled Google Nest smart detectors and a security system for added peace of mind. Offering exceptional privacy in a spectacular Bedford setting, this is country living at its finest. Professional photos of interior & exterior will be added by 7/15.

230 E Middle Patent Road, Bedford
$600,000
4 Beds ⋅ 2 Baths ⋅ 957556 MLS
Charming 1965 Cape Cod offering timeless character and endless potential. This three level home features a traditional layout with well proportional rooms, hardwood floors, and classic architectural details reflective of its era. The main level includes sun filled living room, dining area, kitchen, and comfortable bedrooms or flexible office space. The upper level offer additional bedrooms with sloped ceilings and good closet space. The lower level provides versatile space for storage, utilities or future finishing. Recent improvements include a newly replaced roof and gutters, providing peace of mind and added value. Enhancing its appeal, a scenic pathway runs parallel to the Saw Mill River at the rear of the property ideal for long strolls, fishing, walking your dog, or a peaceful evening surrounded by nature. Being sold as is, this property, presents a prime opportunity for investor, builders, or end users looking to renovate and build equity. Excellent opportunity to maximize ARV in desirable setting.

76 Beverly Road, Mount Kisco
$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
$5,880,000
8 Beds ⋅ 10 Baths ⋅ 1012962 MLS
Welcome to “Apple Blossom Farm”, an extraordinary opportunity to own a remarkable private estate designed for grand-scale living, entertaining, and multi-generational enjoyment. Set on beautifully landscaped grounds in desirable Bedford Corners, this impressive 12,000-square-foot residence offers 8 bedrooms and an exceptional collection of indoor and outdoor amenities. Designed as the ultimate compound, the property comfortably accommodates both intimate gatherings and large groups, making it ideal as a private retreat, wellness destination, luxury vacation residence, or year-round estate. Expansive living and entertaining spaces create the perfect balance of grandeur, comfort, and privacy. A stunning glass-enclosed sunroom adjacent to the music room fills the home with natural light and showcases beautiful views of the surrounding property, creating a serene space for relaxation and entertaining. The lower-level fitness center offers ample space for a professional-caliber gym, easily accommodating strength-training equipment, cardio machines, and dedicated yoga or Pilates areas. Resort-style amenities abound, including a tennis court, sparkling swimming pool, and extensive outdoor spaces designed for recreation, relaxation, and unforgettable gatherings. Whether enjoying summer weekends by the pool, holiday celebrations with friends, or extended stays in a peaceful country setting, the estate delivers an unparalleled lifestyle experience. Beyond its exceptional residential appeal, Apple Blossom Farm has a proven history as a successful investment property, generating impressive returns while offering substantial income-producing potential for investors and owners alike. A truly rare offering that seamlessly combines luxury, versatility, and investment opportunity in one exceptional Bedford Corners estate. “Apple Blossom Farm” presents a unique chance to own a destination property where recreation, wellness, and hospitality come together in spectacular fashion.

196 McLain Street, Bedford Corners
$49,500,000
8 Beds ⋅ 10 Baths ⋅ 000006 MLS
ONE OF NEW YORK'S MOST COVETED ESTATES. Enter a world where timeless elegance meets state-of-the-art luxury. Originally built in 1901 for renowned financier J. Borden Harriman, this legendary estate - historically known as Devonshire, and earlier as Uplands - stands as a rare example of Gilded Age grandeur, reimagined for modern living. Over its long history, the estate has been owned by some of the nation’s most distinguished families, including relatives of the Vanderbilt dynasty and other notable private owners. When it last sold in 2012, it set a record as the highest residential sale in Westchester County history - an extraordinary testament to its significance and stature. Set on more than 100 acres of pristine landscape, the property offers exceptional scale, privacy, and breathtaking natural beauty, all within easy reach of Manhattan. Rolling meadows, sweeping vistas, and picturesque terrain create an unparalleled setting suited for equestrian pursuits, recreation, and refined country living. A substantial expansion is already underway, offering the next steward a rare opportunity to complete the vision, by selecting finishes, materials, and design elements tailored to their unique lifestyle. Architectural highlights include the iconic grand staircase crowned by its attributed original Tiffany stained-glass ceiling, a defining centerpiece of the home. Several accessory buildings include a carriage house, caretaker's cottage, barn with apartment, elegant gated entry and cloister with apartment, and a spectacular 33,000 sq. ft. collector car gallery designed to accommodate more than 66 automobiles. Estates of this magnitude, provenance, and proximity seldom become available. More than a grand residence, this is a legacy property and enduring asset ready to be shaped for generations to come. 2-Acre Zoning. Square Footage is for main house only and does not include outbuildings.

Bedford Corners
$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
$849,500
3 Beds ⋅ 4 Baths ⋅ 999831 MLS
Over $100,000+ less than recent sales in Lake Marie! Great downsizer! Largest Condo In Lakeside, Lake Views from 3 floors. Best location on Lake Marie Lane - No pedestrian traffic to the park & ball fields. Higher elevation - never flooded. Adjacent to Town Pool & Tennis & Day Camps. End Unit w/Private Entrance. Large Kitchen & Pantry with charming Breakfast Nook. Spacious 2 car garage with door to Kitchen. Large Open Dining Room & Living Room. Windows Galore on 3 Sides. Gleaming Wood Floors. Marble Corner woodburning Fireplace in Living Room. Sliding glass door out to Trex deck with Lake views. Many large Closets + Storage on each floor. Huge Primary Suite with soaring ceilings, Built-in Wall of Storage, Loft and door out to Trex balcony deck. Luxurious Primary Bath w/Double Vanity, Stall Shower & Whirlpool Bath. Two additional bedrooms on the second floor with Hall Bath. Lower Level is fully finished with slider out with powder room, laundry storage & utilities. 2 Full Baths, 2 Half Baths total. Close To Town & Train Station, Saw Mill River Pkwy, 684.

74 Lake Marie Lane Unit #74, Bedford Hills
$2,425,000
5 Beds ⋅ 6 Baths ⋅ 969675 MLS
Some properties simply cannot be recreated. They are collected over centuries. Layer by layer. Story by story. Stone by stone. Set behind towering trees and abutting hundreds of protected acres of the Mianus River Gorge Preserve, this exceptional Bedford estate offers a rare opportunity to own a thoughtfully restored historic property surrounded by natural beauty and privacy. Dating back to 1825, the historic main residence was once part of a larger Long Ridge Road estate and formerly operated as the Wilkenloh Hotel in the early 19th century. Today, the home has been tastefully renovated and refreshed, blending timeless architectural character with modern comfort and functionality. As you enter through two dramatic stone entry boulders, a winding gravel driveway leads to the main residence, separate cottage and expansive grounds featuring rolling lawns, mature trees and historic stone walls. Set on over 5.5 acres, the property offers a peaceful setting with scenic landscape views in every season. Inside the main residence, original wide plank floors, a natural stone fireplace and gracious living spaces showcase craftsmanship rarely found today. Walls of windows and glass doors fill the home with natural light while framing picturesque views of the surrounding property. The open-concept kitchen, dining and family room create an ideal layout for everyday living and entertaining. A covered rocking-chair porch supported by stately pillars overlooks the property and provides a tranquil setting to enjoy the changing seasons of Bedford. Outdoor amenities include a restored 22x44 heated gunite pool with updated mechanicals and an expansive 1,400+ square foot pool house featuring wraparound decking, outdoor fireplace, screened-in entertaining area with fireplace, wet bar, ice machine, full bath, kitchenette and flexible guest or recreation space. The separate cottage offers its own private driveway entrance and features cathedral ceilings, a palladium window, kitchen, full bath, garage, additional flexible-use rooms and extensive storage space, ideal for guests, home office use, or extended living arrangements. Additional highlights include bluestone patios, restored landscape features and a private three-acre trail system suitable for walking, jogging, mountain biking and outdoor recreation. Conveniently located near Bedford, major roadways, shopping, dining and Metro North train access, this unique Westchester County property offers a rare combination of historic character, updated amenities, flexible living space and exceptional natural surroundings. square footage consitst of: 4017sqft of total living space includes 5 bedrooms, 3.5 baths, cottage (independent assessor 834sqft attached documents) includes kitchen, bath, 2 rooms with garage below and separate driveway entrance. Pool house, 2 car garage below, heat pump air, playroom, bath, kitchenette, 3/4 wrap-around deck overlooking pool, screened in stone patio with fireplace (1469 sqft

233 Long Ridge Road, Bedford
$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
$4,125,000
5 Beds ⋅ 5 Baths ⋅ 987844 MLS
Refined and timeless, this gracious residence has been meticulously preserved and maintained for over a century. Approached by a gated, tree-lined gravel drive, the house is a distinguished example of early 20th-century Georgian architecture, offering exceptional privacy and a profound sense of tranquility. Set on over five acres in the heart of Bedford Hills, surrounded by majestic specimen trees and beautifully curated perennial gardens, the property embodies the essence of a classic country estate. Amenities include a heated pool, an enchanting guest cottage, a greenhouse, a caretaker’s residence, a detached two-car garage, and dedicated maintenance buildings. Inside, the house reflects the signature elegance and proportion associated with Delano & Aldrich; high ceilings, expansive openings between principal rooms, and refined architectural detailing create a seamless flow for both formal entertaining and relaxed living. Fireplaces anchor the generously scaled living and dining rooms, while framed-glass French doors open to a grand sunroom. This light-filled space extends to a stone terrace overlooking the gardens—ideal for summer gatherings or sunlit winter afternoons. The kitchen, complemented by an adjoining sitting room, offers an inviting setting for intimate meals and everyday living. Upstairs, the primary suite provides a serene retreat, complete with its own fireplace and a luxurious ensuite bath designed for quiet indulgence. A former sleeping porch has been thoughtfully reimagined as a charming playroom with adjoining guest quarters, accompanied by an additional spacious bedroom and hall bath. Each bedroom features its own distinctive fireplace and enjoys picturesque garden views through large casement windows. The third floor offers two substantial bedrooms, a classic bath, and a skylit artist’s studio filled with natural light, along with an adjoining atelier and generous storage. More land available.

328 McLain Street, Bedford Hills
$2,999,000
6 Beds ⋅ 6 Baths ⋅ 979303 MLS
This Prime Bedford Estate, solidly built in 2005, is on over 9 acres of open, level land with a bridge crossing your private pond. The property is private and secluded. The house has a grand floor plan with gracious formal and family spaces for entertaining inside and out. This majestic house has an impressive two-story entry with a bifurcated staircase. There are six generously sized bedrooms, four full bathrooms, and two half bathrooms. The lower level contains a large wine room. There is a three car garage and a carport. Also available for rent at $19,000 monthly.

180 Stone Hill Road, Bedford

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.