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$699,000
3 Beds 3 Baths 1029600 MLS
A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your favorite beverage looking out into the vibrant sunset, or lounging by the crystal-clear in-ground pool, sunbathing while overlooking nearby farms and sparkling lakes. This property was built for unforgettable outdoor living and limitless entertaining. Inside, the home is a clean-cut, light-filled ranch featuring three bedrooms and two-and-a-half bathrooms. The expansive living room serves as the heart of the home with its classic brick wood-burning fireplace, two huge picture windows framing the valley skyline, and sliding glass doors that open directly onto the massive patio. Adjacent, the kitchen is outfitted with high-end cabinetry and modern stainless steel appliances, opening seamlessly to a bright dining area framed by another impressive picture window. The primary bedroom offers its own private half bath, while a hallway closet conveniently houses the main-level laundry. Downstairs, the finished walk-out basement expands your living space with two versatile rooms perfect for a home theater, gym, or guest quarters, complemented by a full bathroom and abundant storage space. Spanning over 4.5 acres, the grounds offer exceptional privacy along with rare long-term flexibility. Whether you envision expanding the existing home or exploring options to subdivide and sell or build a second residence, this property delivers a quintessential Pawling sanctuary where indoor ease meets endless horizon.

21 Overlook Drive, Pawling

$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

$575,000
3 Beds 2 Baths 1022255 MLS
Welcome to 17 Spring Street, a beautifully maintained 1890 Victorian in the heart of the Village of Pawling. Rich in character and timeless charm, this inviting home features hardwood floors, crown molding, and a classic rocking chair front porch. The bright Living Room opens to an elegant Dining Room with bow windows, hardwood floors, chair rail, and a chandelier, creating the perfect setting for gatherings. Just off the Dining Room is a spacious Laundry Room with custom built-ins, abundant storage, and a full bath with a walk-in shower. The generously sized Kitchen offers plenty of workspace, a corner breakfast bar, and access to a mudroom/enclosed porch leading to a private rear patio.Upstairs, you'll find three bright bedrooms with hardwood floors, including a spacious primary bedroom with a walk-in closet. A beautifully appointed hall bath features a classic claw-foot tub and a separate walk-in shower. Additional highlights include a one-car garage, storage shed, and a private backyard. Ideally located within walking distance to the Pawling Village shops and restaurants, Metro-North, parks, and more, this charming Victorian offers the perfect blend of historic character and everyday convenience.

17 Spring Street, Pawling

$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

$619,900
3 Beds 3 Baths 1024161 MLS
TO BE BUILT – Build your dream home in the charming Village of Pawling! Ideally located just minutes from downtown Pawling, you'll enjoy convenient access to local shops, restaurants, schools, parks, and the Metro-North train station, making commuting and everyday living a breeze. The homesite is serviced by municipal water and sewer, offering added convenience and peace of mind. Pricing and listing details, such as square footage, bedroom count, etc., is based on LMD’s Bennet model. Looking for something different? Buyers have the opportunity to select from several of our available floor plans and personalize their home with structural options and designer interior finishes to create a space that fits their lifestyle. Whether you're looking for additional living space, a first-floor owner's suite, a gourmet kitchen, or upgraded finishes throughout, our team will guide you through the customization process. Don't miss this opportunity to build a brand-new home in one of Dutchess County's most desirable communities!

Prospect Street, Pawling

$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

$650,000
3 Beds 3 Baths 1017740 MLS
**Lakefront Living at Its Finest on Private Sunset Lake Just over an HOUR to NYC*** Newly priced at $650,000, this beautifully maintained 3-bedroom, 2.5-bath lakefront home offers four-season living on private Sunset Lake. Located in Holmes, a hamlet of Pawling, this waterfront retreat combines peaceful surroundings, inviting indoor and outdoor spaces, and convenient access to everything the Hudson Valley has to offer. Are you a runner or a walker? This house in conveniently located moments from the local rail trail as well! Inside, you’ll find gleaming hardwood floors, elegant crown molding, two fireplaces, and central air. The thoughtfully designed kitchen features concrete countertops, tile flooring, radiant heat, propane cooking, and an adjoining mudroom with radiant heat—an especially welcome feature during Hudson Valley winters. The screened-in porch is the perfect place to enjoy morning coffee or unwind while overlooking the lake. A spacious open-air deck provides even more room for barbecues, outdoor dining, and entertaining. Gather around your private fire pit or enjoy the community fire pit with neighbors and friends. Sunset Lake residents also enjoy access to a private sandy community beach and pavilion. Spend summer days swimming, fishing, kayaking, or paddleboarding, then enjoy ice skating when winter transforms the lake. The property also offers the potential for a private dock, subject to applicable community and municipal approvals. A invisible fenced yard provides a secure outdoor space for pets, while high-speed internet makes working from home easy. The attached two-car garage offers plenty of room for vehicles, kayaks, paddleboards, and other recreational equipment. Located in the Pawling School District and just minutes from the Village of Pawling, Metro-North, restaurants, shops, hiking trails, golf courses, wineries, breweries, farms, and Interstate 84. Whether you’re searching for a year-round home or a weekend escape, 45 Willow Lake offers the opportunity to enjoy lakefront living in every season.

45 Willow Lake Drive, Holmes

$1,235,000
5 Beds 4 Baths 1010537 MLS
Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living space 1 bedroom, living room and a full bathroom above. Inside, much of the home’s original character remains with hardwood floors, crown molding, fireplaces, and hidden staircases throughout. The inviting main level features a quiet library or office with fireplace, a bright sunroom overlooking the yard and patio, a spacious living room with fireplace, and a large dining room ideal for entertaining. The kitchen is ready for your personal vision. Upstairs offers 4 unique guest bedrooms along with a spacious Primary Suite featuring hardwood floors, private staircase, large bath, and ample closet space. With room for horses, gardens, or simply enjoying the beauty and privacy of the outdoors, this special property is full of opportunity and old-world character.

64 S Quaker Hill Road, Pawling

$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

$3,100,000
3 Beds 3 Baths 1005064 MLS
Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property’s idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling meadows. The seat of the estate, a traditional gentleman’s farmhouse, lies at the end of a long gravel driveway lined with historic sugar maples on both sides. The original barn has been renovated, with a charming cedar-shake roof and an attached fenced kitchen garden, and a sweet cottage nestled into the hills above the house has an interior wood-burning sauna and wellness space. The nearly 300 year old, three bedroom, three bath home has been thoughtfully preserved, without compromising the authenticity of the original details, including the wide board wood floors, long beams, and five wood-burning fireplaces. The kitchen was created in tandem with a masterful local craftsman and woodworker, featuring DeVOL fixtures, La Cornue sinks, a dual Wolf range, top-quality appliances, aged brass hardware, and entirely custom cabinetry. The kitchen connects to a light-filled family breakfast nook that overlooks, through walls of French doors, the property’s outdoor dining terrace and picturesque gardens. Off the kitchen, on one side, is the formal living room with a wood-burning stone fireplace, and on the other is the light-filled dining room with the original cooking hearth and a butler’s pantry. A wallpapered full bath and a quintessential mudroom finish the first floor. Upstairs, the family room has tall, vaulted ceilings with wood beams, a fireplace, built-in window benches with storage, and some of the prettiest views of the property from its tall windows and French doors. Off the family room is a richly colored office with custom cabinetry, paneled walls, and a skylight that streams in light throughout the day. The primary suite is tucked away in its own wing of the house, and has a hearth fireplace, a large walk-in closet with beautiful cabinets and extensive storage, and a tastefully appointed bathroom. The remaining two bedrooms look out over the meadows surrounding the home, and share the third bath with a claw-foot soaking tub. Farm Nord is bordered by hundreds of acres of conserved land, making for an abundantly peaceful setting. The original barn, fully restored, has a workshop/studio space, gym, and plenty of additional storage. There is an established herb garden with installed irrigation next to the barn and tall fencing. A small building nestled atop the property’s hills has been converted into a wood-burning sauna. Trails meander through the property’s twelve acres, and a truly incredible number of stone walls line the lush meadows. Farm Nord is conveniently located less than 90 minutes from New York City and just 10 minutes from the Metro North station in the quaint village of Pawling. The area is filled with bucolic farms, rolling hills, and stretches of the Appalachian Trail, making it an excellent area for anyone who loves hiking, wild swimming, and biking.

809 QUAKER HILL Road, Pawling

$2,790,000
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.

5 McCarthy Road, Holmes

$5,000,000
8 Beds 13 Baths 968589 MLS
Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations. Quaker Hill has long been known as one of the Hudson Valley’s most distinguished enclaves. For more than a century it has quietly attracted artists, writers, diplomats, and those seeking privacy, landscape, and a connection to history. Elmwood Farm stands among the hill’s most recognizable estates, shaped by generations of stewards who helped define the character of this remarkable hamlet. Owning Elmwood Farm is not simply about acquiring a home. It is about becoming part of the long story of Quaker Hill and carrying that legacy forward. The manor itself reflects the craftsmanship and romance of another era. Leaded glass windows cast soft light throughout the interior, while hand carved pilasters and hand painted plaster ceiling motifs reveal the artistry and attention to detail that defined the estate’s original design. Dramatic rooflines with carved timber fascia and Gothic inspired spires create a striking architectural silhouette that rises above the surrounding landscape. At the center of the home, a magnificent figured oak staircase ascends through the interior, its hand carved newel posts adorned with whimsical animal figures that speak to the individuality and charm of the residence. Gracious gathering rooms anchored by ten fireplaces provide spaces that feel both intimate and grand, equally suited for quiet evenings by the fire or lively gatherings with friends. A charming upper wing with hand painted storybook murals adds an unexpected and delightful layer of character that reflects the estate’s long and colorful history. Beyond the main residence, Elmwood Farm unfolds as a true country compound. The property includes two caretaker homes, a carriage house with groom’s quarters, a yoga studio, and a greenhouse, offering extraordinary flexibility for guests, staff, creative pursuits, or wellness focused living. The grounds themselves are equally compelling. Rolling lawns, mature trees, and sweeping views across the surrounding countryside create a sense of scale and serenity that is increasingly rare in today’s world. The landscape feels timeless, a place where mornings begin with mist rising over the hills and evenings conclude with golden sunsets stretching across the valley. For the next owner, Elmwood Farm offers something truly rare. It is an opportunity to become the next steward of one of Quaker Hill’s historic estates and to preserve a remarkable piece of Hudson Valley history while shaping its next chapter for generations to come.

618 Quaker Hill Road, Pawling

$629,900
3 Beds 2 Baths 992269 MLS
Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Ready For Your Ideas Without Having To Start With Unfinished Space. Very Flexible Space! Both Bedrooms In The Upper Level Are Very Large and The House Has Room To Grow As Your Spatial Needs Grows -- Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Summers Are The Best While Enjoying The South Facing Deck Off The Kitchen That Leads To The In-Ground Pool In The Backyard. Excited To Host Summer BBQs & Pool Parties? You Could Pack + or -- 50 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, A Camper / RV, OR For Those Fantastic Summer Parties! To The Left Of The House Is Included In The <3 Acres & Its 1 Acre Of Land That Is Part Of The Privacy. It Could Be Turned Into An Additional Detached Garages, Cute Cottage To Rent Full or Part Time (Abnb) or House an In-Law, A Garden With A Garden Potting Shed, A Work Shop, Or Whatever Your Vision Can Imagine. Cozy Up To The Fire In The Winter OR The Summer's Sun & Moon's Reflection From The Salt Water Pool As You Enjoy Your Morning Coffee & Your Evening's Glass Of Wine. Come! Relax, Unwind, & Enjoy Life!

57 Buhleir Road, Pawling

$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

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