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$900,000
7 Beds ⋅ 4 Baths ⋅ 1013109 MLS
Private Hudson Valley Retreat on 9.6 Wooded Acres Featuring Two Charming Homes and Exceptional Income Potential Tucked away along a peaceful country road in the heart of Clinton, this remarkable Hudson Valley retreat offers a rare combination of privacy, natural beauty, modern infrastructure, and investment opportunity. Set on 9.6 secluded wooded acres with potential subdivision possibilities, this unique estate features two separate residences, each with its own well, septic system, electric service, and oil tank, creating endless possibilities for multi-generational living, rental income, weekend escapes, or future development. Surrounded by pristine forest and abundant wildlife, this tranquil sanctuary feels worlds away from the everyday. Enjoy the sights and sounds of nature from every direction, where deer wander through the woods, wild turkeys roam freely, foxes make occasional appearances, turtles can be spotted throughout the property, and owls hoot from the trees at dusk. The setting is exceptionally quiet and serene, offering the ultimate Hudson Valley lifestyle immersed in nature. The charming circa-1924 farmhouse serves as the property's centerpiece, blending timeless character with significant recent improvements. The main residence features beautiful natural cherry hardwood floors, soaring cathedral ceilings, spacious sun-filled living areas, and 2 cozy fireplaces that creates a warm and inviting atmosphere year-round. The second residence, a thoughtfully converted stable barn, offers a distinctive open-concept design filled with character and flexibility. Perfect for guests, extended family, a home office, artist's retreat, or additional rental income, this separate dwelling enhances the property's versatility and appeal. A detached two-car garage provides ample storage, workshop space, or future expansion opportunities. Multiple outdoor areas invite relaxation, entertaining, and appreciation of the surrounding natural landscape, including a deck overlooking the peaceful wooded setting. Adding to the property's value, both homes are currently occupied by long-term tenants and generate approximately $6,000 per month in rental income. Tenants pay all utilities, providing an attractive income stream for investors while preserving future owner-occupancy options. Ideally situated near the Taconic State Parkway and conveniently located between the highly sought-after villages of Rhinebeck and Millbrook, residents enjoy easy access to renowned vineyards, hiking trails, parks, farm markets, antique shops, charming cafe's, and some of the Hudson Valley's most celebrated dining destinations.

10-12 Woodlea Road, Salt Point
$549,000
4 Beds ⋅ 4 Baths ⋅ 1014048 MLS
Wonderful center hall Colonial with timeless appeal, conveniently located in the charming Village of Millerton. Built in 1890, this home beautifully preserves its original details while incorporating thoughtful updates for modern living. The interior offers comfortable, well-proportioned, light-filled rooms and a stylish, open flow ideal for both everyday living and entertaining. The spacious eat-in kitchen opens seamlessly to a family room, creating a perfect setting for casual gatherings. For more formal occasions, the inviting living room provides a classic and elegant space. The main level also features a gracious center hall, a powder room, a mudroom with laundry, and a private en-suite bedroom—ideal for guests or flexible use. Upstairs, the second floor includes a primary bedroom suite, two additional bedrooms, a home office, and a full bathroom. A walk-up attic offers abundant storage. Outside, the property is equally inviting, with a beautiful gravel driveway, mature landscaping, and a covered side porch overlooking a level, fenced yard—perfect for relaxing or entertaining. A detached two-car garage and lean-to provide additional functionality. Added peace of mind can be had with the new roof and mechanicals, including a new propane boiler. Exciting things happening in Millerton, a community Olympic size pool will be built at Eddie Collins Memorial Park and the Village has approved and funded an upcoming sewer development project. Ideally located just a short walk to Millerton’s restaurants, shops, the Harlem Valley Rail Trail, and the Moviehouse, this home offers the best of village living. An excellent opportunity for a primary residence or a weekend retreat.

14 S Maple Avenue, Millerton
$387,000
2 Beds ⋅ 1 Baths ⋅ 1013273 MLS
A diamond in the rough! This charming 2-bedroom single-family home is ideally located in the City of Beacon, directly across from Memorial Park. Major systems have been maintained, with the roof, water heater, and furnace all less than 10 years old and everything currently in working condition. The property is being sold AS-IS and offers an excellent opportunity for buyers looking to add their own style and updates. Bring your vision, DIY skills, or contractor and transform this home into something truly special. Whether you're a first-time buyer, investor, or renovation enthusiast, this is a fantastic opportunity in a desirable Beacon location.

84 Wilkes Street, Beacon
$599,000
4 Beds ⋅ 3 Baths ⋅ 1011480 MLS
Elegant & Upscale - Completely renovated 4 bedroom, 2.5 bathroom farmhouse blending timeless charm with modern luxury. This stunning home features a chef-inspired gourmet kitchen with premium finishes, custom cabinetry, and high-end appliances, perfect for entertaining and everyday living. The luxurious primary suite offers a spa-like custom bathroom designed with exceptional craftsmanship, creating a private retreat. Thoughtfully updated throughout, this exceptional property delivers the character of a classic farmhouse with all the comforts of contemporary living. Close to the Harlem Valley Rail Trail, Sharon Playhouse, Silo Ridge, and Wassaic Metro North Train Station.

9 Depot Hill Road, Amenia
$194,999
1 Beds ⋅ 1 Baths ⋅ 1011801 MLS
Welcome to this TURNKEY, bright and inviting 1-bedroom, 1-bath condominium located in the well-maintained Tivoli Gardens community. This comfortable, 2nd floor condo offers a private balcony off the bedroom with peaceful views of mature trees and beautifully landscaped grounds, creating a relaxing setting to enjoy your morning coffee or unwind at the end of the day. The unit includes a one-car garage plus additional unassigned parking space for added convenience. Residents enjoy meticulously maintained lawns, attractive common areas, and picnic tables set up in the open green fields perfect for outdoor gatherings. Ideally situated in the heart of the scenic Hudson Valley, this condominium is just a short drive from the natural beauty of Tivoli Bays, the renowned Kaatsbaan Cultural Park, and the historic Clermont State Historic Site. Enjoy easy access to hiking, kayaking, cultural events, farmers markets, charming villages, and many of the area's most treasured attractions. Whether you're seeking a full-time residence, a weekend retreat, or an investment opportunity, this condominium offers comfort, convenience, and an exceptional location in one of the Hudson Valley's most desirable areas.

45 Tivoli Gardens Unit #C45, Tivoli
$4,950,000
4 Beds ⋅ 5 Baths ⋅ 952077 MLS
Bradford Hill Farm is a purpose-built country estate set across more than 68 acres, offering a rare combination of privacy, scale, and thoughtful design. Located near the Village of Millbrook, with easy access to Rhinebeck and within reach of New York City, the property includes a main residence with pool and terraces, a substantial auto gallery and event pavilion, equestrian facilities with a private apartment, a tennis and pickleball court, a large multi-use storage barn, and expansive grounds featuring ponds, fields, and protected views. Designed as a cohesive whole, the estate is supported by commercial-grade infrastructure and systems typically found only in institutional-scale projects. MAIN RESIDENCE & POOL: The main residence anchors the estate with classic architectural proportion and modern livability. Generous ceiling heights, expansive windows, and a natural flow to outdoor terraces create a home suited to both everyday living and entertaining. A fully restored saltwater gunite pool and surrounding stone and paver terraces extend the living space outdoors, positioned to capture views across the landscape and supported by a dedicated pool house with bath and kitchenette. AUTO GALLERY, STUDIO & EVENT PAVILION: A defining feature of the estate, this substantial structure was designed to function far beyond traditional auxiliary use. Constructed with stone masonry, timber framing, and custom mahogany doors, it offers a vaulted, light-filled interior adaptable as an auto gallery, art studio, creative workspace, or private event venue. Supporting spaces, including a dedicated wash bay with vehicle lift and an additional equipment or tractor bay, are discreetly integrated to accommodate practical use without detracting from the primary gallery space. Outdoor entertaining areas extend the pavilion’s functionality and connection to the landscape. TENNIS & PICKLEBALL COURT: Set just beyond the pavilion, the tennis and pickleball court adds an active, social element to the property. Extensive outdoor lighting allows for evening and night play, while the landscaped setting preserves the open, estate-like feel. BARN, APARTMENT & EQUESTRIAN FACILITIES: The barn complex provides fully functional equestrian infrastructure, including stalls, tack and storage areas, and fenced pastures. A private apartment above offers comfortable accommodations with vaulted ceilings and open views across the property, suitable for guests or staff. LARGE STORAGE BARN / MULTI-USE FACILITY: A substantial secondary barn provides additional scale and flexibility. Currently used for agricultural and equipment storage, the clear-span construction and generous ceiling height allow for future adaptation, including potential use as an indoor riding ring, workshop, or sports-oriented facility. INFRASTRUCTURE & SYSTEMS: Bradford Hill Farm was built with a level of infrastructure more commonly found in commercial-scale projects than private residences. The property features fully paved internal roads, underground utilities, whole-property backup power, geothermal heating and cooling in key areas, and on-site solar power designed to offset ongoing utility usage. THE LAND: The land itself is a core component of the offering. Hay fields, fenced pastures, ponds, and mature trees create a landscape that is both visually compelling and functional. Much of the surrounding acreage is protected, preserving privacy and views over time.

1963 Salt Point Turnpike, Salt Point
$624,900
3 Beds ⋅ 2 Baths ⋅ 1011126 MLS
Prepare to be impressed by this solidly built, meticulously maintained Cape Cod, offered for sale for the first time in 61 years! Nestled on a rare, sprawling 1.3-acre landscaped and luscious lot in the desirable Town of Wappinger, this charming home beautifully combines classic character with functional living and entertaining. Recent updates provide incredible peace of mind, including a new roof, premium Marvin windows, and a top-of-the-line 275-gallon Roth oil tank. The light-filled interior welcomes you with pristine hardwood floors. This move-in ready home features 3 comfortable bedrooms, 2 full bathrooms, and a versatile flex room, ideal for a home office or guest room. A full unfinished basement allows plenty of room for expansion ideas. Abundant storage spaces throughout the home. Imagine relaxing in the enclosed porch, showcasing picturesque views of your private backyard oasis. Step outside to find a sparkling 18x36 inground pool that is securely fenced in, offering the perfect blend of summer fun and safety. The expansive property features a 2-car detached garage and a private, recently sealed driveway with abundant parking space. As an incredible neighborhood bonus, membership to the Lake Oniad Lot Owners Association is available, unlocking access to community events and scenic lake recreation. Enjoy tranquility and a large private lot while being just minutes from local schools, shopping, dining, and just over 4 miles to the New Hamburg Metro-North station for an easy commute. Your forever home awaits—schedule a tour today!

28 Kent Road, Wappingers Falls
$799,000
4 Beds ⋅ 2 Baths ⋅ 1011415 MLS
You're not buying a house. You're buying a lifestyle that's already built — and it took years to create. Most buyers spend 2–3 years and $150K+ trying to build what already exists at 2 Greenwood Drive. This is the home you'd build if you had the time, the vision, and the discipline to execute. Someone already did that work for you. Start outside, because that's where this property wins. The backyard is a private resort. A full outdoor kitchen pavilion — hard metal roof, dual ceiling fans, string lights, wall-mounted TV, granite counters, stone bar face, built-in beverage refrigerator, Blackstone griddle, and seating for eight. A separate hot tub under its own covered gazebo. A large pool with volleyball net. A composite deck with outdoor dining for six under a cantilever umbrella. Stone patio, fire pit table, lounge areas in every direction. Then wrap around front: a 39-foot covered entertainment porch with ceiling fans, hanging chairs, and ambient lighting that makes your guests forget to leave. You don't have to add a thing. This is done. Inside, the home matches. Open dining room with a granite eat-in kitchen and custom cabinetry. Living room with beamed ceilings and fireplace. Main floor flex rooms — one opens directly onto the back deck through sliding glass doors. Designer barn doors throughout every floor carry a consistent, high-character design language this house wears naturally. Upstairs: three bedrooms including a spa-quality bathroom — floor-to-ceiling slate tile, double vanity with LED backlit mirrors, oversized walk-in shower with pebble floor, rainfall head, built-in bench and niche. Upper hallway features knotty pine, custom wall murals, and access to a private balcony with elevated views. Downstairs: finished basement with LVP floors, recessed LED lighting, mini-split climate control, and a barn door divider creating separate living and flex spaces. Additional bedroom with full bath — vessel sink vanity and walk-in shower. Main-level laundry with dedicated mudroom entry. The infrastructure is equally finished. Solar panels 2024 — OWNED, paid off, transfer at closing. No lease. No financing. Free electricity from day one. Whole-house generator. Mitsubishi split systems. B-Dry waterproofing with dual sump pumps and battery backup — transferable warranties. 200-amp panel. 80-gallon water heater. Replacement windows. Detached 3-car garage — oversized metal building with workshop space and overhead storage. Outdoor shed with roll top doors for plenty of extra storage. The expensive stuff? All done. Beacon Hills — minutes from downtown Beacon, one of the hottest markets in the Hudson Valley. The value. The quiet. The community. Without downtown prices. Everything done. Ready for someone that knows what they're looking at.

2 Greenwood Drive, Beacon
$299,900
917401 MLS
Two unit home featuring large two bedroom apartments with separate utilities. Gas furnaces and hot water heaters. Separate entrances as well as front and back porches. Full walk up attic and full basement for storage, laundry or whatever you would need the extra space for. The second floor is vacant for easy log and go showings, the first floor would require 24 hour notice if you would like to see both at the same viewing. Long time tenant on the first floor would be happy to stay if desired. This home is close to public transportation, schools & the main street corridor. Walk to Raymond Avenue farm market as well as restaurants in the area. Some updating needed but can provide positive cash flow quickly.

9 GRAY Street, Poughkeepsie
$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
$1,200,000
1009767 MLS
Unique offering with this LEGAL 7 unit Multifamily. Full occupancy with great reliable tenants. Unit one is 2 Bedroom, 1 full bath, Unit two is 1 Bedroom, 1 Full Bath, Unit Three is a 2 Bedroom, 1 Full Bath, Unit Four is 2 Bedroom, 1 Full Bath, Unit Five is 2 Bedroom 1 Full Bath, Unit Six is 1 Bedroom, 1 Full Bath Unit Seven a 3 Bedroom, 1Full plus 1/2 Bath. TOTAL of 13 Bedrooms and 7 plus 1 1/2 Baths. Property has been maintained to perfection, and the grounds have a Park-Like quality with Gazebo and outdoor track for recreation and is mostly fenced. There are several outbuildings that provide additional income and versatile usage. Located conveniently within 10 minutes to TSP and Villages of Red Hook and Rhinebeck in the Red hook School District. Don't miss this opportunity to invest in this turnkey money maker!

1030 Route 199, Red Hook
$498,000
3 Beds ⋅ 3 Baths ⋅ 1010116 MLS
Welcome to 2 Enderkill, a distinctive Hudson Valley retreat where natural beauty and everyday comfort come together. Nestled on a private setting surrounded by stunning rock outcroppings that create a truly one of a kind sense of character and connection to the landscape, this spacious 3 bedroom, 3 full bath home offers versatility, warmth, and room to grow. The main level features an inviting kitchen overlooking the dining area, a generous living room anchored by a cozy fireplace, and a flexible bonus room perfect as a home office, guest space, playroom, or potential first floor bedroom. Upstairs, you'll find three spacious bedrooms and two full baths, including a primary suite with its own private bath and sliding glass door leading to a secluded balcony overlooking the property. Outdoor living shines with a large deck, above ground pool, detached garage, attached carport, and an additional included .32 acre parcel, providing extra space and opportunity. Recent updates include a new roof, offering peace of mind for years to come. Perfectly positioned in the heart of the Hudson Valley, this unique property sits just minutes from Rhinebeck, Hyde Park, and Poughkeepsie, with easy access to Metro North train service for effortless commuting or weekend getaways. Enjoy the best of the region right at your doorstep, from boutique shopping and acclaimed dining to parks, hiking trails, and storied historic sites. Nature lovers and outdoor enthusiasts will love being directly across from Norrie State Park, with Dinsmore Golf Course and the iconic Mills Mansion just a short drive away. Whether you're seeking privacy, convenience, or a connection to the timeless charm and culture the Hudson Valley is celebrated for, this property delivers it all.

2 Enderkill Drive, Staatsburg
$595,000
4 Beds ⋅ 2 Baths ⋅ 1005161 MLS
-A Rhinebeck Village Classic- Nestled beneath towering shade trees in the heart of Rhinebeck Village, this charming 1933 Craftsman-inspired cottage offers the increasingly rare combination of walkability, character, and opportunity. Original hardwood floors, period details, inviting covered porches, and a detached garage speak to the home's enduring charm, while four bedrooms and two baths provide generous space for modern living. Rich in authenticity and filled with potential, this beloved home invites its next steward to thoughtfully restore, reimagine, and make it their own. Just moments from Rhinebeck's vibrant Main Street—with its celebrated restaurants, boutiques, farmers market, and cultural attractions—this is a rare opportunity to own a piece of village history while creating the next chapter of its story. A true Rhinebeck Village classic, ready for its next chapter!!

79 S Parsonage Street, Rhinebeck
$850,000
3 Beds ⋅ 3 Baths ⋅ 1006694 MLS
A rare opportunity to own a piece of Red Hook history. Offered for the first time in 117 years, this cherished family home has been lovingly maintained through generations and retains many of its original architectural details and timeless character. Located in the heart of the Village of Red Hook, the home showcases beautiful original wood floors, classic moldings, detailed staircase trim, and the craftsmanship rarely found in today's construction. The spacious floor plan features 3 bedrooms, 2.5 baths, and two dedicated office areas, providing flexibility for remote work, creative pursuits, or additional living space. Outside, an oversized detached two-car garage offers ample room for vehicles, storage, or a workshop. Conveniently situated near village shops, restaurants, parks, and schools, this exceptional property combines historic charm with everyday convenience. A truly special offering ready for its next chapter.

64 W Market Street, Red Hook
$11,500,000
5 Beds ⋅ 7 Baths ⋅ 1007235 MLS
Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance the pastoral beauty while providing a measure of sustainability. The architect Pietro Cicognani designed a home that harmoniously balances details of comfort, beauty, modernity, and history. West Meadow feels as if it’s been in place for centuries. The spacious great room boasts two 18th century stone fireplaces and floors of limestone tile imported from France. Fresh air and light pour in through six custom French doors facing both east and west. The library opens to a long covered porch and one of many stunning views. A central gathering place for friends and loved ones, the kitchen is warmed by a fireplace with pizza oven. In the summer, a wall of floor-to-ceiling windows and doors opens to fragrant gardens, thyme- and lavender-laced stone terraces, the uninterrupted panorama, and matchless sunsets. Upstairs, the primary suite features vaulted ceiling, large windows, and spacious accommodations for luxurious comfort and self-care, including steam shower and a soaking tub that has its very own view. On the bottom floor, a remarkable two thousand bottle wine cellar and tasting room offers something special for oenophiles and casual wine enthusiasts alike. Also on that level is built-in cedar storage, a full laundry, and a staff bedroom. A long, private drive leads through the natural habitat to every outdoor spot on the estate that has been designed for restful ease, comfort, and beauty. Discreetly set apart from the residence, outbuildings include a caretaker’s home, a two-bedroom guest suite, heated greenhouse, four-stall equipment garage, full shop, office, chicken house, and run-in shed. There is ample room on the property for livestock or a stick and ball polo field. Surrounding the house, the columned porch allows for seating in sun or shade, and panoramic views for watching a storm approach, an eagle cavort, or the sun lower in the painted sky.

129 W Meadow Lane, Millbrook
$495,000
3 Beds ⋅ 2 Baths ⋅ 1006885 MLS
The Ultimate Hudson Valley Retreat: Private Living Meets an Enthusiast’s Dream Escape to your own private, tree-lined sanctuary in Pleasant Valley. Tucked away in the highly desirable Arlington School District, this custom-built, 1.7-story residence offers the perfect blend of country living, efficiency, and unmatched mechanical utility. From the moment you arrive, the towering trees and serene surroundings establish a sense of total privacy. Inside, the home features 3 spacious bedrooms and 2 full baths, framed by striking A-frame commercial-grade windows that flood the main living spaces with beautiful natural light. Designed for total self-sufficiency and year-round comfort, the property features a top-of-the-line Central Boiler E-Classic outdoor wood furnace, which handles the home's heating by efficiently piping heat through the main furnace to control the lower-level baseboard system—allowing you to heat your home using the land's abundant natural timber. The main home also features central air, a central vacuum system, a water purification system, and a peaceful 3-season room perfect for taking in the wooded views. The basement features a walk-out to the lower level, offering plenty of storage. For absolute peace of mind, a premium Generac backup generator protects the property—fully connected to provide uninterrupted power to both the main home and the detached garage. For the car enthusiast, mechanic, hobbyist, or entrepreneur, the crown jewel of this property is the detached, commercial-grade 3-car garage. Fully equipped with a 4-post lift, a dedicated workshop space, and a compressor.. Combined with the attached 2-car garage on the main house, you have sheltered space for 5+ vehicles and endless projects that can continue seamlessly through any storm. Whether you are launching a business, restoring classics, or seeking a private, high-efficiency homestead, 176 Downing Road offers a lifestyle without limits. ***The personal property is being cleared every day so some pictures may be different.

176 Downing Road, Pleasant Valley
$639,000
3 Beds ⋅ 3 Baths ⋅ 1006576 MLS
Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary. A Home Infused with Warmth and Light From the moment you step inside, you are wrapped in comfort. Gleaming hardwood floors guide you through a thoughtful layout designed to soothe the soul. The Living Room: Unwind by the crackling fireplace while gazing out at beautiful lake views. The Heart of the Home: An updated, sun-lit kitchen boasts abundant countertop and cabinet space, flowing effortlessly into a lovely dining area. The Sunroom: A bright, incredibly spacious sunroom offers the ultimate spot to curl up with a good book, practice yoga, or simply watch the seasons change. Space to Grow, Create, and Breathe The second floor features two beautifully appointed full baths, ensuring ultimate convenience with 3 bedrooms. Downstairs, a full walkout basement bursts with potential, offering the ideal layout to create an accessory dwelling unit (ADU), a guest suite, or rental space. For the creator or hobbyist, the 2-car heated garage is a dream come true, complete with a workshop and a spacious loft perfect for DIY projects or studio space. Peace of mind is also guaranteed with a whole-house generator. Embrace the Great Outdoors Step outside onto your brand-new Trex porch to sip your morning coffee, breathe in the crisp Hudson Valley air, and feel the stress of the week melt away. With over 3 private acres of your own land, you can hike, explore, and connect with nature right in your backyard. Lake access on your private dock just across the street, kayak or canoe around the lake for an interesting adventure. Looking for a challenge? The breathtaking trails of Mt. Stissing are just minutes away. The Location: A Seamless Escape Located under 2 hours from NYC with a straight, scenic drive up the Taconic State Parkway, this property is incredibly versatile. Whether you dream of a permanent full-time haven, a magical summer retreat, or a lucrative short-term rental/Airbnb, this home is ready to fulfill your dreams. Best of all, you are just 15 minutes away from the historic streets, gourmet dining, and culture of Rhinebeck and Red Hook.

553 Lake Road, Pine Plains
$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
$2,999,000
3 Beds ⋅ 2 Baths ⋅ 992909 MLS
Set against the rolling hills and pastoral beauty of the Hudson Valley, 252 Crum Elbow spans more than 185 extraordinary acres, offering a rare opportunity to embrace refined country living at an exceptional scale. Surrounded by sweeping meadows, mature trees, and open skies, the property reflects the spirit of a modern agricultural estate while maintaining complete privacy and understated luxury. The residence blends timeless architectural character with thoughtfully updated interiors, featuring expansive living spaces, abundant natural light, and seamless indoor-outdoor flow. The surrounding landscape evokes the serenity of a countryside retreat, with vast open acreage ideal for equestrian pursuits, farming, recreation, or simply enjoying the quiet beauty of the land. Perfectly positioned just minutes from Rhinebeck’s celebrated dining, boutiques, farmers markets, and cultural destinations, the property offers the ideal balance of seclusion and accessibility in one of the Hudson Valley’s most sought-after locations. Whether envisioned as a full-time residence, weekend retreat, equestrian compound, or legacy estate, 252 Crum Elbow delivers a singular Hudson Valley experience where luxury and the land exist in perfect harmony.

252 Crum Elbow Road, Hyde Park
$549,000
3 Beds ⋅ 2 Baths ⋅ 1002764 MLS
Imagine soaking in those breathtaking sunsets and stunning views from your spacious deck—it’s like having a vacation every day in this beautiful Contemporary home in Staatsburg! With soaring cathedral ceilings, gorgeous wide plank wood flooring, and a double-sided stone wood burning fireplace that stretches from floor to ceiling in both the living and dining rooms, this home is truly a treat. As you step inside, you’ll be greeted by a large family room, and just a few steps up, you’ll find the main living area with the living room, dining room, kitchen, and a full bathroom. From the foyer, you can also access the lower level, which features three bedrooms, an open stone-flanked sitting area, and another beautiful full bathroom with a Grecian style bath. Plus, there’s a mudroom that connects the garage to the home on the first floor, perfect for an office or storage space. And with its convenient location near Rt 9, historic sites, the Hudson River, minutes to the Village of Rhinebeck, riding stables, a golf course, restaurants, shopping, medical facilities, the Rhinecliff Train Station, and so much more, you’ll absolutely adore this home!

12 Chaucer Road, Staatsburg
$534,000
4 Beds ⋅ 2 Baths ⋅ 1003528 MLS
Step into the charm of this 1952 Cape Cod home with distinctive mid-century flair, ideally located just minutes from the Taconic State Parkway and nearby rail trail access. Set on a picturesque acre, this unique 4-bedroom property features a detached oversized two-car garage and an inviting in-ground pool perfect for summer enjoyment. The first floor offers a spacious, sun-filled living room with hardwood floors and a wood-burning fireplace, creating a warm and welcoming atmosphere. Two bedrooms and a full bath provide convenient main-level living. The original kitchen, complete with built-in bookshelves, offers the perfect opportunity for a stylish home office or creative flex space. A step-down kitchen with vaulted ceilings opens to an additional living area with direct access to the deck and backyard, ideal for entertaining or relaxing. Upstairs, you’ll find two additional bedrooms, a full bath, and a central gathering room perfect for a family room, playroom, or home office. The basement provides walkout access to the backyard and detached garage. Outside, the in-ground pool with sundeck creates the perfect setting for enjoying long summer days. Make this one-of-a-kind home your own.

2 Merry Hill Road, Poughkeepsie
$3,850,000
7 Beds ⋅ 7 Baths ⋅ 1003365 MLS
WhistleWood Farm A rare multi-use estate set on just under 40 acres in the heart of Rhinebeck, NY. Currently operating as a successful bed-and-breakfast, event venue, and horse boarding facility, WhistleWood Farm offers exceptional flexibility for both residential and commercial buyers seeking a true Hudson Valley destination property. Comprised of three parcels totaling nearly 40 acres, the property is equally suited as a private compound, gentleman’s farm, equestrian retreat, boutique hospitality venture, or wellness-focused escape. Existing hospitality and equestrian infrastructure provide a strong foundation for continued or expanded use. The main residence spans approximately 4,500 square feet and features 5 bedrooms, 5 full baths, and 2 kitchens—offering remarkable flexibility for private living, guest accommodations, or hospitality operations. Complementing the main house is an beautifully appointed 1,500-square-foot carriage house with three bedrooms and three baths, rich in character and perfectly suited for guests, extended stays, or expanded event and hospitality use. Walking trails through the woods create a rare sense of privacy and connection to the landscape just moments from the heart of Rhinebeck Village—with its celebrated dining, farm-to-table restaurants, boutiques, and nearby Amtrak access. For the tennis enthusiast, premier tennis facilities conveniently located next door further enhance the property’s lifestyle appeal. Open meadows, mature trees, and a coveted Village-adjacent setting make WhistleWood Farm a truly rare offering—equally compelling as a private estate, hospitality investment, or legacy property in the Hudson Valley. Additional features include solar power, further enhancing the property’s efficiency and long-term sustainability.

52 Pells Road, Rhinebeck
$379,000
3 Beds ⋅ 2 Baths ⋅ 998179 MLS
Step into timeless charm with this 3 bedroom, 1.5 bathroom brick and stone Cape Cod, where classic architecture meets warm, inviting living spaces. From the moment you arrive, the home’s solid masonry exterior and steeply pitched roofline create unforgettable curb appeal that speaks to craftsmanship and character. Inside, rich hardwood flooring flows throughout, adding warmth and elegance to every room. Original features—including vintage hardware, and thoughtfully preserved architectural touches—celebrate the home’s heritage while offering a distinctive sense of style you simply can’t replicate. Natural light fills the cozy yet spacious living areas, highlighting the home’s character and creating an inviting atmosphere perfect for both everyday living and entertaining. The traditional layout offers comfortable bedrooms tucked beneath charming rooflines, along with welcoming common spaces designed for gathering. This Cape Cod is more than a home—it’s a rare opportunity to own a piece of enduring design, where solid construction and original details come together in perfect harmony.

208 S Grand Avenue, Poughkeepsie
$899,000
999699 MLS
Seeking An Investment Property? Looking To Perhaps Retire....Retire Early And Have Additional Income? For Sale Is This Six Family Building Consisting Of (5) Three Bedroom Apts And (1) Two Bedroom, All With Separate Utilities (Gas & Electric). This Turnkey Property Also Includes Off The Street Parking In The Form Of A Driveway From The Front To The Rear Of The Bldg Opening Up To A Parking Area Plus (8) Garages. The Apartments Are Moderately Priced, As This Income Generated Has Been As Such For Years; With Pro Forma, The Numbers Have The Potential To Go Up. This Is An AS IS SALE Please Read Other Remarks For More Information.

242 Mansion Street, Poughkeepsie
$745,000
3 Beds ⋅ 2 Baths ⋅ 999749 MLS
Welcome to 32 Dutchess Terrace — a fully renovated Beacon gem just moments from vibrant Main Street. This stunning home has been completely transformed with bold modern design, high-end finishes, and timeless character throughout. From the striking black-and-white exterior to the designer interior details, every inch has been thoughtfully curated. Highlights include refinished dark hardwood floors, custom millwork, statement lighting, and a showstopping new kitchen featuring sleek black cabinetry, quartz countertops, and stunning black-and-white Italian marble flooring. Both bathrooms have been beautifully redesigned with marble finishes, including a spectacular Italian marble shower in the downstairs bath off the porch. Bright, sun-filled living spaces, generously sized bedrooms, updated systems, a spacious basement, and an unfinished attic with future potential make this home as functional as it is stylish. Outside, enjoy refreshed landscaping, new fencing, and inviting outdoor spaces perfect for relaxing or entertaining. Completely turnkey and impeccably designed, 32 Dutchess Terrace offers modern Beacon living at its finest.

32 Dutchess Terrace, Beacon
$595,000
2 Beds ⋅ 2 Baths ⋅ 995827 MLS
Welcome to Turtle Pond Gully, a delightful property in the Hudson Valley. Enjoy country life in this sweet colonial farmhouse located in the town of Pleasant Valley. This 1930s cottage offers immense charm and is the perfect retreat for weekenders or year-round residents. The light-filled home offers a cozy and comfortable interior with beautiful wood floors. Many original details have been preserved and the home has been updated and is well maintained. It has a wonderful dining room with a pellet stove and a French door to a peering porch and another to a lovely sunroom; a stylish kitchen with tin ceiling; a living room with a French door to an attractive side porch. Many recent improvements, including new metal roof, new siding, and an automatic Generac generator. The grounds, with fine plantings, a pond and stone wall borders, have a lovely park-like feel. There is a detached two car barn style garage with a large game room and woodshop. Centrally located in Dutchess County this is a convenient location, within a mile to the Taconic Parkway, 10 miles to Poughkeepsie train station and only a 12 minute drive to Millbrook.

145 Drake Road, Pleasant Valley
$599,408
4 Beds ⋅ 2 Baths ⋅ 996401 MLS
Sophisticated country living in the desirable Millbrook area within the highly regarded Millbrook Central School District. Ideally located close to the charming village, local amenities, and the Wassaic Station for convenient Metro-North access to New York City. Privately set on 2.06 picturesque acres, this light-filled 4-bedroom, 2-bath Cape offers the perfect blend of comfort, versatility, and lifestyle. Designed to accommodate a variety of needs, the exceptional heated three-bay garage with soaring ceilings and expansive upper level creates endless possibilities for car enthusiasts, artists, writers, entrepreneurs, fitness enthusiasts, or those seeking a spacious home office or creative studio. The inviting interior features wood floors and tile throughout the main level, with an effortless open-concept layout ideal for both everyday living and entertaining. The vaulted-ceiling family room is filled with natural light and showcases tile flooring, a custom built-in entertainment cabinet, and a chimney ready for a pellet or wood stove. The adjoining kitchen flows seamlessly into the living and dining spaces, creating a warm and welcoming atmosphere. A formal dining room and spacious living room continue the home’s airy, connected design, while a first-floor bedroom and full bath with laundry closet provide flexibility for guests or one-level living. Upstairs, the primary suite offers vaulted ceilings and a private ensuite bath, accompanied by two additional bedrooms. Step outside to the rear deck overlooking the peaceful grounds—perfect for outdoor dining, entertaining, or simply enjoying the tranquil setting. A storage shed adds additional convenience to this thoughtfully designed property. A rare offering combining refined country style, functional workspace, and an ideal location in the heart of the Hudson Valley.

810 ROUTE 343, Dover Plains
$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
$825,000
3 Beds ⋅ 3 Baths ⋅ 985648 MLS
Experience extraordinary at The Arboretum—more than a residence, it is a botanical sanctuary defined by a living landscape of specimen trees, perennial gardens, and the soothing sound of a year-round stream. From the moment you pass through the gated entrance framed by hydrangea-lined fencing and continue down the drive bordered by majestic Metasequoia and fragrant linden trees, you are transported into a world of complete tranquility. Spanning 3,656 square feet, this circa-1840 Colonial has been carefully preserved and thoughtfully expanded, showcasing wide-plank floors, period moldings, and three fireplaces throughout. At the heart of the home, a chef’s kitchen with custom cabinetry and premium appliances flows effortlessly into an inviting living area with a fireplace and a sun-filled dining nook—capturing picturesque views of the manicured lawn, gardens, and water beyond. A pergola-covered back deck extends the living space outdoors, offering the same serene outlook. The main level is well-suited for today’s lifestyle, featuring a gracious covered front porch framed by a wisteria-draped arbor, a formal dining room, living room, a library with fireplace, and a home office. The upper level serves as a peaceful escape, highlighted by a primary bedroom with dual walk-in dressing rooms with natural light, two additional bedrooms and a renovated bath featuring a Jacuzzi tub and walk-in shower. For guests, a private lower-level suite offers original architectural details, a fireplace, and direct access to a secluded bluestone patio. Beyond the main house, the grounds offer endless inspiration with a greenhouse and a detached barn-style garage. This versatile structure features a work area and upper loft perfectly suited for an office, studio, or gym, complemented by an additional storage shed. Modern comforts are seamlessly integrated, including central air conditioning, a generator, an irrigation system, and Pella windows. This property offers the serenity of country living and is conveniently located just minutes from shopping and dining, the Taconic State Parkway, I-84, and the Pawling train station, providing an easy commute to New York City. The Arboretum is a remarkable property, offering an ever-changing landscape where each season unveils its own distinct beauty.

212 Pleasant Ridge Road, Poughquag
$499,000
3 Beds ⋅ 2 Baths ⋅ 996553 MLS
Privately nestled on 3 serene acres in the rolling hills of Dover Plains, this beautifully reimagined country retreat offers an exceptional blend of privacy, refined modern updates, and effortless indoor-outdoor living. Set far back from the road and surrounded by mature trees and picturesque natural scenery, 256 Hammond Hill Road delivers a peaceful lifestyle with extraordinary entertaining space both inside and out. Accessed via a deeded right-of-way, the property offers a uniquely private setting while maintaining convenient accessibility. This inviting 3-bedroom, 2-bath residence spans approximately 1,788 square feet and features a bright, open-concept layout filled with natural light and thoughtfully curated finishes throughout. Completely renovated kitchen and bathrooms elevate the home with a sophisticated, modern aesthetic while preserving its warmth and timeless character. The stunning kitchen flows seamlessly into the dining and living areas, creating an airy atmosphere ideal for both everyday living and entertaining on any scale. Rich hardwood flooring, oversized windows, freshly painted interiors, and newly installed designer light fixtures throughout the kitchen, bathrooms, exterior, and hallways further enhance the home’s polished presentation. Major mechanical and functional improvements provide additional peace of mind, including newer appliances with most approximately two years old, a refrigerator replaced within the last year, and a recently updated well pump. The home also includes a newer pellet stove, approximately 3–4 years old, accompanied by both pellets and wood for the wood-burning stove, offering warmth and ambiance throughout the colder seasons. In addition to the primary living spaces, the home features an expansive bonus room offering remarkable versatility for a home office, guest accommodations, recreation space, fitness studio, or additional lounge area tailored to a variety of lifestyle needs. One of the property’s most captivating features is the oversized rear deck spanning the back of the home, creating a spectacular extension of the living space with multiple seating and dining areas overlooking tranquil wooded surroundings. Whether hosting summer gatherings, enjoying quiet mornings with coffee, or relaxing beneath the stars, the outdoor setting captures the essence of refined country living. Additional highlights include central air conditioning, included washer and dryer, a SimpliSafe security system that may be expanded by future owners, and an oversized garage with an additional oil tank for supplemental heat. Town of Washington documentation reflects updated approvals and retroactive Certificates of Occupancy for prior improvements, with no known violations currently on file. Conveniently located in the heart of Dutchess County, just moments from local shops, restaurants, hiking trails, Metro-North, and the charming nearby towns of Pawling, Millbrook, and Amenia, this exceptional offering combines modern enhancements, flexible living space, expansive outdoor entertaining, and timeless country elegance less than two hours from Manhattan.

256 Hammond Hill Road, Dover Plains
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