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$1,999,000
3 Beds 3 Baths 1041154 MLS
Spectacular 100+ Acre Equestrian Estate | Premier Horse Farm Opportunity Within Approximately 90 Minutes of NYC A truly exceptional 100+ acre equestrian estate offering a rare combination of historic character, modern amenities, exceptional equestrian facilities, and expansive acreage. This remarkable property presents an outstanding opportunity for a private equestrian estate, professional training operation, boarding facility, equestrian center, or other income-producing use, all within approximately 90 minutes of New York City. At the heart of the property is an iconic 1720s cattle barn masterfully transformed into a stunning residence. The beautifully renovated open-concept home features 3 bedrooms and 2.5 baths, dramatic cathedral ceilings accented by rough-sawn chestnut, hand-scraped oak floors, and a custom staircase crafted from chestnut wood harvested on the property. The residence beautifully blends historic character with modern luxury. The expansive kitchen features high-end finishes, a center island, pantry, and wet bar, while three decks overlook the spectacular grounds and surrounding countryside. The equestrian facilities are equally impressive. A custom 13-stall modern barn features 12' x 12' matted stalls, a dedicated wash and grooming stall, approximately 24' x 12' tack room/kitchen/break room, laundry/feed room, and bathroom. The upper level includes a spacious hay loft, fully functioning office, partially finished caretaker's apartment, and large great room, offering tremendous flexibility for equestrian and residential uses. Additional facilities include an 8-stall shed row, four oversized paddocks with Nelson automatic waterers that can be divided into as many as eight individual turnout areas, and a separate barn providing extensive storage for equipment, vehicles, trailers, and farm necessities. Approximately 4–6 wells provide substantial water infrastructure throughout the property. The expansive acreage offers privacy, room for additional improvements, and extensive opportunities for riding, turnout, recreation, and continued development of the equestrian operation. Rare Opportunity to Expand to Nearly 125 Acres An extraordinary opportunity exists for a buyer to acquire this property together with the contiguous equestrian facility at 5 McCarthy Road, Listing #1003257. Purchased together, the two properties would create a nearly 125-acre equestrian compound with an exceptional collection of facilities. The combined properties would offer two residences, two exceptional barns, approximately 31 stalls, an indoor riding arena, an outdoor riding arena with ESI footing, extensive paddocks and turnout, miles of riding trails, and a large pond—creating an exceptional foundation for a professional training and boarding operation, multi-disciplinary equestrian center, horseman's estate, or premier private equestrian compound. The ability to combine two contiguous, established equestrian properties of this caliber is extraordinarily rare. For the serious equestrian buyer, the combined offering provides remarkable scale, infrastructure, and flexibility while maintaining the privacy and character of a spectacular Hudson Valley estate. Whether purchased individually or together with 5 McCarthy Road, this is a once-in-a-generation opportunity to acquire a substantial equestrian property with the acreage, facilities, and infrastructure to support virtually limitless possibilities. Note: The owner would consider selling the home with a few acres without the barn should someone be interested in the home only.

42-45 Blackstone Ridge, Holmes

$1,475,000
4 Beds 5 Baths 1029458 MLS
**Do not walk or go to the property without an agent**Set privately on more than 22 acres just minutes from the quaint Village of Pawling, this exceptional country estate captures the essence of Hudson Valley living with breathtaking mountain views, extraordinary privacy, and timeless elegance. Designed for both sophisticated entertaining and comfortable everyday living, this exquisite Colonial showcases refined craftsmanship and beautifully appointed living spaces throughout. A dramatic two-story foyer welcomes you with a sweeping staircase, cathedral ceiling, gleaming ceramic tile flooring, and an elegant chandelier. Bathed in natural light, the gracious living room features a tray ceiling, oversized windows, hardwood floors, and a handsome wood-burning fireplace, while the formal dining room offers rich hardwood flooring, expansive windows, and a tray ceiling, creating an elegant setting for intimate dinners and memorable celebrations. The heart of the home is the open-concept kitchen and family room. The eat-in kitchen boasts abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting, hardwood floors, and a large center island, making meal preparation and casual gatherings effortless. The adjoining sunken family room impresses with soaring ceilings, a dramatic floor-to-ceiling brick fireplace, wet bar, oversized windows, and glass doors leading to a freshly painted deck overlooking beautifully landscaped grounds, mature trees, and peaceful vistas. Whether hosting or enjoying a quiet evening at home, this inviting space offers warmth, comfort, and spectacular year-round views. The first-floor primary suite offers a luxurious retreat with a spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, dual marble vanities, and generous natural light. A private home office, powder room, laundry room, and access to the oversized three-car garage complete the main level. Upstairs, a spacious bonus room provides endless possibilities as a media room, playroom, library, or additional gathering space. Three generously sized bedrooms with hardwood floors and generous closets are served by two full baths, providing comfortable accommodations for all. The walk-out lower level offers exceptional flexibility with a recreation room featuring a full bar, den with walk-in closet, sitting area, exercise space, game room, full bath, and abundant storage—ideal for multigenerational living, extended guests, or an au pair suite. Beyond the beautifully maintained lawn, the property unfolds into acres of rolling countryside where open meadows, mature trees, and sweeping mountain views create an unforgettable backdrop. The expansive acreage offers endless possibilities for a pool, cabana, gardens, equestrian pursuits, or simply preserving the serenity and remarkable natural beauty that surrounds you. Spectacular sunsets paint the western sky, providing a breathtaking finale to each day. Additional amenities include hardwood flooring, recessed lighting, a generator, brick walkway, storage shed, tray ceilings, decorative columns, transom and bow windows, and dramatic floor-to-ceiling windows that beautifully frame the surrounding landscape. Conveniently located just 90 minutes from New York City with easy access to Metro-North, Routes 22, 311, I-684 and I-84, and just minutes from Thunder Ridge Ski Area, the Harlem Valley Rail Trail, golf, parks, shopping, dining, and the charming Village of Pawling. This extraordinary estate offers a rare opportunity to enjoy refined country living where timeless architecture, breathtaking scenery, and exceptional privacy create an unforgettable Hudson Valley retreat. Whether enjoyed as a full-time residence or an exceptional weekend escape, this is a place where luxury, nature, and tranquility exist in perfect harmony.

7 Herd And Tanner Road, Holmes

$879,800
3 Beds 3 Baths 1021432 MLS
Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property is a must see. Privacy awaits in a pristine area with nearly 5 acres. Once a horse farm, this unique home offers enchanting landscapes that surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house has been meticulously selected to evoke a perfect blend of elegance and timeless design. The open-concept design connects the great room, featuring custom bookcases and granite fireplace which flows into a stunning chef’s kitchen. This chef designed kitchen encompasses a huge granite workspace which has also developed & recipe tested numerous successful cookbooks. Featuring three spacious bedrooms and a studio/office which can easily be transformed to a 4th. This charming home offers ample space for life, living and entertaining. Opportunity to own a home with this much heart and elegance rarely comes along. Additional Information: Cooling: SEER Rating 14+, Marble Bath, 2 Soaking Tubs, Storage, Heating Fuel :Oil & propane gas fireplace, 2 Car garage (oversized). New Heat system, 10/24, new Miele dishwasher racks, new gas lines for Professional Wolf 8 burner range, new kitchen sink faucet including new plumbing, new baths vanities, new shower fixtures, exterior; new gutter system 10/25, new washer, backed with warranty and much more... 08/26 New Sub-Zero state of the art Cove dishwasher, 2 year warranty. Home warranty, SEPARATE warranty on Lux-Care W&D. Conveniently located to Manhattan & Connecticut. Enjoy activities of the Hudson Valley, historical sites, enjoy over 450 Wineries in NYS, unique shopping and hike the Hudson Valley Trail. SURVEY AVAILABLE. Engineered to accommodate a 4th bedroom.

57 S White Rock Road, Holmes

$2,500,000
4 Beds 4 Baths 1003257 MLS
Nestled in a tranquil and picturesque setting, this exceptional equestrian facility offers everything a rider could desire, along with a beautiful home to live in. Spanning 21 acres of mostly open land, the property features expansive pastures enclosed by charming 3-board post and rail fencing. Equestrian amenities include a main barn with 8 spacious 12x12 stalls, each with individual water, a heated tack room, wash stall, feed and storage room, a half bath, and laundry facilities. The indoor also has an additional 6 stalls and two, double run-in sheds on the backside of the barn, that could easily be moved to one of the paddocks, if wanted. Above the barn, you'll find a large space perfect for a caretaker's apartment or viewing area and huge hayloft. The property also boasts a 72x160 indoor riding ring connected to the barn with new footing, a new roof and new LED lighting, as well as a 100x200 outdoor ring equipped with ESI footing, providing an ideal environment for year-round training. Six large paddocks and an another 3+ acres that could have additional paddocks added. The charming 4,000 sq. ft. farmhouse-style home, featuring 4 bedrooms and 3.5 bathrooms, overlooks the entire facility. The home is designed for comfort and luxury, with beautiful views from every window. Outside, enjoy an in-ground pool, an one bedroom apartment above the 3-car garage, a patio with a pergola, and breathtaking sunsets. This turnkey equestrian estate is conveniently located, with easy access to I-84/684, Metro North, and just 90 minutes from New York City. Rarely does a property of this caliber, combining world-class equestrian facilities and a luxurious home, become available. Whether you’re looking to train, ride, or simply enjoy a peaceful country lifestyle, this estate offers it all. Rare Opportunity to Expand to Nearly 125 Acres An extraordinary opportunity exists for a buyer to acquire this property together with the contiguous equestrian facility located at 42-45 Blackstone Ridge, Listing #1041154. Purchased together, the two properties would create a nearly 125-acre equestrian compound with an exceptional collection of facilities. The combined properties would offer two residences, two exceptional barns, approximately 31 stalls, an indoor riding arena, an outdoor riding arena with ESI footing, extensive paddocks and turnout, miles of riding trails, and a large pond, creating an exceptional foundation for a professional training and boarding operation, multi-disciplinary equestrian center, horseman's estate, or premier private equestrian compound. The ability to combine two contiguous, established equestrian properties of this caliber is extraordinarily rare. For the serious equestrian buyer, the combined offering provides remarkable scale, infrastructure, and flexibility while maintaining the privacy and character of a spectacular Hudson Valley estate. Whether purchased individually or together with 42-45 Blackstone Ridge, this is a once-in-a-lifetime opportunity to acquire a substantial equestrian property with the acreage, facilities, and infrastructure to support virtually limitless possibilities. Schedule a showing.

5 McCarthy Road, Holmes

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.