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$749,900
4 Beds 4 Baths 1029051 MLS
Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted by soaring nine-foot and vaulted ceilings, gleaming hardwood and ceramic tile floors, crown moldings, French and pocket doors, recessed lighting, and striking Palladian windows that fill the home with natural light. The heart of the home is a spacious maple kitchen complete with a center island, abundant cabinetry, and a full suite of appliances, opening seamlessly to the home's inviting living and entertaining spaces. The luxurious primary suite offers a vaulted ceiling, a private sitting room, and a spa-inspired bathroom with a whirlpool tub, creating the perfect private retreat. The finished, walk-out lower level is at grade and offers exceptional versatility with a summer kitchen, full ADA-compliant bathroom, spacious den or recreation area, abundant storage and utility space, making it ideal for extended family living, guests, a home office, or flexible multi-generational living. Additional highlights include central air conditioning, a security system, computer networking, an attached two-car garage, and a picturesque setting with a combination of level and gently sloping land that provides privacy and room to enjoy the outdoors. Offering quality craftsmanship, thoughtful design, and an ideal commuter location, this exceptional property delivers the perfect balance of privacy, functionality, and convenience

26 E Forest Trail, Holmes

$1,150,000
5 Beds 4 Baths 1024239 MLS
Introducing a stunning to-be-built farmhouse by respected local builders known for exceptional craftsmanship, thoughtful design, and quality construction. Perfectly positioned on more than 11 private acres, this custom home blends timeless farmhouse charm with modern comfort, offering a peaceful retreat in one of the Hudson Valley's most desirable settings. Designed with today's lifestyle in mind, the open-concept floor plan is filled with natural light and offers an effortless flow for both everyday living and entertaining. At the heart of the home, the dramatic vaulted family room with a gas fireplace opens to a sun-filled eat-in kitchen featuring a large center island, abundant cabinetry, and direct access to a covered porch—creating the perfect setting for seamless indoor-outdoor living. The thoughtfully designed main-level primary suite is privately situated away from the secondary bedrooms and offers a luxurious escape with a spacious walk-in closet and spa-inspired bath. Two additional bedrooms and a full bath complete the first floor, although the floor plan can easily be customized to create a second primary suite with a sitting area, accommodate multi-generational living, or provide dedicated home office space. The second level expands the home's versatility with plans for a fourth bedroom, full bath, an optional fifth bedroom or office, and a generous bonus room ideal as a media room, fitness studio, recreation room, playroom, or additional living space. The flexibility of the design allows you to tailor the home to your lifestyle. Quality finishes include hardwood flooring, high ceilings, energy-efficient insulation, central air conditioning, a welcoming Trex front porch, and an attached three-car garage. Although privately tucked away, the property is just minutes from the charming Village of Pawling, Metro-North, shopping, restaurants, major commuter routes, and the area's many hiking trails, golf courses, and cultural attractions. Whether you're searching for a full-time residence or a refined country retreat, this exceptional to-be-built home presents a rare opportunity to create a custom residence where privacy, elegance, and convenience come together. Photos include virtual renderings and images of a recently completed similar home and are for illustrative purposes only. Finishes, specifications, and features are subject to change during construction.

Lot 5 S White Rock 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. Enchanting landscapes 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... 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

$995,000
3 Beds 3 Baths 1017929 MLS
Renovated Colonial near Quaker Hill, less than two hours from NYC and minutes from Metro-North. Board-and-batten exterior with black-trimmed windows set the tone: clean lines and deliberate detail. Inside, the kitchen anchors the main level - marble island with seating, patterned tile backsplash behind the range, double wall ovens, and a layout that opens naturally to dining and living spaces. Brick fireplace with a reclaimed wood mantel. The den, with exposed timber ceiling beams, black-framed windows on three sides, and hardwood floors, overlooks the backyard and pool. The primary suite is on the main floor, making an easy option for single-floor living, and includes luxurious private bath with a marble-topped double vanity, walk-in tile shower with steel-framed glass, freestanding soaking tub, and brass fixtures throughout. Three bedrooms upstairs, all with vaulted ceilings, share a full bath. Outside, there’s the heated gunite pool and spa with lounge surround, pool shed, basketball court, fire pit, and dining patio with stone retaining walls. The yard is open and level with room for a game of any kind, or just the quiet that brought you here in the first place.

6 Byrds Hill Road, Pawling

$499,000
3 Beds 2 Baths 1006794 MLS
Pure perfection! This beautifully and fully renovated 3-bedroom, 2-full-bath home offers modern luxury and total peace of mind. Step inside to an open, sun-drenched living space featuring high ceilings and gleaming hardwood floors throughout. The stunning kitchen boasts sleek quartz countertops, stainless steel appliances, and a spacious pantry for all your storage needs. Convenience is key with a dedicated laundry room, a linen closet, and additional closet space. Stay comfortable year-round with an efficient heat pump and central air. Outside, enjoy your private back deck overlooking just under an acre of park-like manicured lawn surrounded by a serene, partially wooded backdrop. Complete with a brand-new blacktop driveway offering plenty of parking. This gem offers easy access to I-684, I84, Thunder Ridge Ski Area, bike trails and Metro North. Just minutes from dining and shopping and a short drive to the Village of Pawling A truly turn-key property— Absolutely nothing to do but move right in and enjoy!

358 Route 292, Holmes

$1,350,000
11 Beds 8 Baths 1004618 MLS
Multi-generational housing opportunity with 3 distinctly different homes on one property providing plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well. Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with abundant light, Formal Dining Room with chair rail accent and beautiful chandelier. Eat in Kitchen with center island, Bosch oven, stainless steel appliances with breakfast nook and bay window. Convenient First floor laundry with 2nd laundry on lower level. Sunroom with tile floor and fireplace. Primary Bedroom Suite with two walk-in closets plus private bonus space could be nursery, craft area or small office. Primary En Suite Bathroom including jetted tub, shower with ceramic tile and double vanity. 2 generous sized bedrooms with ceiling fans and more than ample closet space. Full, walk out basement with kitchenette and 2 rooms to fit your personal lifestyle or In-law Suite. Outdoor living on both upper and lower deck areas with built-in benches for entertaining and enjoying a panoramic view. Unit B: Architecturally inviting 3 bedroom, fully renovated ranch style home. Living Room boasts a cathedral ceiling, hardwood floors, exposed brick & beams and abundant light. Stairway to loft space for kids hideaway, simple storage or use your imagination. Eat in Kitchen with recessed lights. All appliances and Washer/Dryer included. Primary Bedroom Suite with En Suite Bathroom – shower with ceramic tile and built in shelving. 2 additional bedrooms with hardwood floors, ceiling fans and great closet space. Spacious deck with built in bench for relaxing or entertaining. Unit C: Contemporary modular home that is almost brand new. Open concept Living Room and Kitchen with propane heated radiant floors to keep the living space warm and cozy. Gather around the oversized island for meals and conversation. First floor bedroom and full bathroom for often sought after one floor living. Laundry Room on 1st floor with full size washer/dryer. Second floor uses electric heat, hosts 3 bedrooms and den plus another full bathroom with tub/shower and double sinks, 2 good sized linen closets and attic access for additional storage. New boiler and gutters added to home in 2025. All this on a rolling grassy 3.8 acres with large open area and fire pit - consider a pool or other outdoor games and activities. 3 car garage with deck for grilling or congregating with huge loft space for all the additional storage you’ll need. If you have the vision, this is the one!

750 Route 292, Holmes

$469,900
4 Beds 2 Baths 997863 MLS
Well maintained raised ranch offering 4 bedrooms and 2 bathrooms. This inviting home features spacious bedrooms, hardwood floors, and a bright living room filled with natural light. The finished lower level provides additional living space and laundry room, perfect for guests, a home office, or recreation. Sliding doors from the dining room lead to a deck overlooking a spacious backyard, ideal for entertaining and outdoor activities. Conveniently located right by the beautiful Whaley Lake, where you can enjoy private beaches, fishing, swimming, kayaking, boating, and motor boats are allowed. Just minutes from the charming Town of Pawling, with easy access to dining, shopping, Metro north train station, Thunder Ridge Ski Area, Trails to Walk, Bike or Hike. A wonderful opportunity to enjoy both comfort and outdoor living!

23 Lakeview Drive, Holmes

$990,000
4 Beds 4 Baths 964060 MLS
Currently being crafted by skilled local builders, this distinguished rocking chair porch Colonial sits gracefully on more than nine private acres, offering an exceptional blend of elegance, comfort, and modern design. Once complete, the home will be bathed in natural light, showcasing gleaming hardwood floors, 9 foot ceilings, and a sophisticated chef’s kitchen appointed with recessed lighting, granite countertops, and a large island that invites both culinary creativity and effortless gathering. The formal dining room provides a lovely setting for memorable celebrations and intimate dinner parties. Just beyond the kitchen, a maintenance free Trex deck extends the living space outdoors, connecting seamlessly to the enclosed side porch and yard. It’s an ideal retreat for al fresco dining, morning coffee, or simply savoring the quiet beauty of the changing seasons. The family room offers a warm, inviting ambiance centered around the soft glow of the gas fireplace—perfect for relaxed evenings and cozy gatherings. The finished walkout basement area adds versatility, featuring laminate flooring, nine foot ceilings, a full bath, and an energy efficient mini split system. Whether envisioned as a private office, fitness studio, media lounge, or place for guests, this space adapts effortlessly to your lifestyle. Upstairs, three well appointed bedrooms and a full bath accompany a serene primary suite designed as a personal sanctuary. A walk in closet, standalone soaking tub, large glass enclosed shower, and dual vanities create a spa like experience that elevates everyday living. Thoughtful amenities throughout the home include nine foot ceilings, hardwood floors, Anderson windows, central air, abundant recessed lighting, foam and batt insulation, a two car garage, paved driveway, and a bluestone walkway enhances the home’s design. The location offers the luxury of seclusion just minutes from the charming Village of Pawling, Metro North, major routes, shopping, restaurants, and the many cultural and natural treasures of the historic Hudson Valley. For those seeking a weekend escape or a year round haven, this soon to be completed Colonial presents a rare opportunity to own a beautifully designed home where privacy, elegance, and convenience meet.

194 South 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.