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$4,250,000
4 Beds ⋅ 5 Baths ⋅ 1012988 MLS
Completely reimagined and renovated in 2026, this exceptional Millbrook compound offers an extraordinary blend of timeless architecture, modern luxury, and refined craftsmanship. Set on 18.92 private acres, the property encompasses a beautifully updated four or five bedroom, three full and two half bath main residence and a separate two bedroom, two and a half bath guest house. A dramatic formal entry with a 19-foot vaulted ceiling creates a grand first impression. Walnut-stained wood floors run throughout much of the home, leading to beautifully designed living spaces designed for both elegant entertaining and everyday comfort. The spacious living room features a fireplace and four sets of French doors opening to the flagstone terrace, while the formal dining room, family room, and double parlor provide a variety of inviting gathering spaces. The chef's kitchen serves as the heart of the home, showcasing custom Plain & Fancy cabinetry, quartz countertops, a Viking six-burner range with grill, Liebherr refrigerator, Bosch dishwasher, and a brick fireplace. A large pantry and first-floor laundry room add convenience and functionality. Upstairs, the primary suite offers a luxurious retreat with a spa-like bath featuring an oversized shower, double vanities, water closet, and an impressive walk-in closet. Three additional bedrooms, a second-floor family room with fireplace, and a library with built-in shelving provide ample space. A third-floor bonus room offers flexibility for a studio, gym or playroom. The guest house is equally appealing, featuring a two-car garage below and a thoughtfully designed upper level with a great room, kitchen, two bedrooms, two baths, loft space, and private deck. Outdoor living is enhanced by a beautiful flagstone terrace that spans the entire length of the home and extensive new landscaping with approximately 300 salvia and 130 limelight hydrangeas. A 18' x 36' gunite pool is being constructed, adding to amenities. This turnkey Hudson Valley estate is located just minutes from the charming Village of Millbrook.

296-302 Stanford Road, Millbrook
$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, a beautiful area of the Hudson Valley, known for its scenery. This listing is minutes from one of the best known bike rides, a paved 25 mile stretch of the Harlem Valley Rail Trail where one can ride through marshlands, forests and amid farms and the Taconic Range. 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 with electric and a 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
$550,000
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
$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
$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
$1,199,000
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
$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
$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
$509,000
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. HOME FEATURES: • Approx. 4,600-square-foot main residence • Five bedrooms • Multiple gathering and entertaining spaces • Apartment within the main house • Two kitchens • Beamed and cathedral ceilings • Fireplaces • Separate 1,500-square-foot carriage house • Two-bedroom, two-bath carriage house • Additional apartment above the barn • Country views from many rooms • Flexible layout for private residential • Minutes to Rhinebeck Village and Rhinecliff Amtrak LOT FEATURES: • Nearly 40 acres in Rhinebeck, New York • Original stone walls throughout the property • Seven fenced pastures and one paddock • Two ponds • Over two miles of walking and riding trails • Keep Safe fencing throughout • Grass riding ring • Riding arena with TravelRight footing • Mature trees and open meadows • Minutes to Rhinebeck Village and Rhinecliff Amtrak HORSE FACILITY FEATURES: • Up to 12 stalls • Southern pine stalls with rubber stall mats • Stalls configured as 12x12 or 12x24 • Dutch doors from each stall leading outdoors • Wash racks • Tractor barn with four bays • Grass riding ring • Riding arena with TravelRight footing • Seven pastures and one paddock • Keep Safe fencing throughout • Apartment above the barn for staff, guests, or caretakers

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
$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
$4,750,000
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
$795,000
3 Beds ⋅ 3 Baths ⋅ 985648 MLS
A remarkable opportunity to own a beautifully maintained circa-1840 Colonial set on 12 acres in the town of Beekman. With 3,656 square feet, 3 bedrooms, 2.5 baths, multiple fireplaces, and a thoughtful blend of historic character and modern amenities, this distinctive property offers exceptional space, flexibility, and value. Enter through the gated drive to a gracious residence featuring wide-plank floors, period moldings, and original architectural details throughout. The heart of the home is a beautifully appointed chef's kitchen with custom cabinetry and premium appliances, opening to an inviting living area with fireplace and sun-filled dining nook. The main level also offers a formal dining room, living room, library with fireplace, home office, and a welcoming covered front porch. Upstairs, the primary bedroom features two naturally lit walk-in dressing rooms, accompanied by two additional bedrooms and a renovated bath with Jacuzzi tub and walk-in shower. A private lower-level guest suite offers additional living space, original architectural details, a fireplace, and direct access to a bluestone patio, with its own exterior entrance. The 8-foot heavy-wire deer fence encloses roughly one-third of the property, creating a secure area for gardens, pets, and outdoor enjoyment. Mature specimen trees, perennial gardens, a greenhouse, and a year-round stream add beauty and character to the grounds. Beyond the main residence, a substantial detached barn-style garage includes a work area and upper loft with excellent potential for an office, studio, gym, or creative workspace. An additional storage building provides further utility. A pergola-covered rear deck extends the home's living space outdoors and overlooks the grounds. The 12 acres offer room to garden, entertain, explore, and enjoy the changing seasons, with both open and wooded areas providing a variety of possibilities. Modern conveniences include central air conditioning, generator, irrigation system, and Pella windows. Ideally situated minutes from shopping and dining, the Taconic State Parkway, I-84, and Pawling train station, the property combines the character and space of a historic country home with convenient access to everyday amenities and New York City.

212 Pleasant Ridge Road, Poughquag
$719,000
5 Beds ⋅ 4 Baths ⋅ 993548 MLS
WALK TO THE VILLAGE OF RHINEBECK! FABULOUS RHINEBECK INVESTMENT OPPORTUNITY! Rare three family rental property in the Village of Rhinebeck! Fully occupied by long term tenants. Washer and Dryer in every unit! Separate electric meters. This three-family home in the charming Village of Rhinebeck presents a fantastic investment opportunity. Located in a quiet, neighborhood with a park directly across the street, it’s an ideal location for tenants. The property is fully occupied, ensuring immediate rental income from day one. Rhinebeck is an area with a mix of small-town charm and proximity to larger metropolitan hubs, making it an attractive option for renters. With its well-maintained structure and peaceful surroundings, this property offers the potential for steady returns and long-term growth. Access to Landsman Kill for great fishing. Unit 1 is a 1 bedroom ground floor apartment with a bonus room. Unit 2 is a 2 bedroom second floor unit with updated kitchen. Unit 3 is a two floor, 2 bedroom unit with an updated kitchen.

12 S Parsonage Street, Rhinebeck
$3,750,000
7 Beds ⋅ 7 Baths ⋅ 990563 MLS
Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty—three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for modern living. A spacious chef’s kitchen anchors the home, flowing seamlessly into elegant dining and living rooms, a relaxed family room, and expansive outdoor entertaining spaces. Details such as a wood-burning fireplace, rich hardwood floors, bluestone terraces, and a gracious screened porch elevate the experience. An in-ground pool and tranquil wildlife pond complete the idyllic setting. A stately circular drive leads to the 1860s carriage house, offering a beautifully appointed two-bedroom guest residence. Further along, the 1929 Barn House provides yet another charming haven for hosting gatherings. Winding paths traverse a landscape of remarkable diversity—open meadows, mature woodlands, and picturesque waterways—while multiple elevated sites offer breathtaking panoramic views and future possibilities. Surrounded by over 1,000 acres of protected farmland along the Ten Mile River watershed, the estate ensures privacy without isolation. Just five minutes from Metro-North access in Dover Plains and Ten Mile River, Honey Lane Farm represents a rare convergence of history, scale, and enduring elegance.

151 Benson Hill Road, Dover Plains
$2,294,000
4 Beds ⋅ 6 Baths ⋅ 988928 MLS
Nestled in the heart of the Hudson Valley, this exceptional custom-built compound offers a rare blend of elegance, privacy, and ease. Set on 3.15 acres of beautifully landscaped grounds, the property unfolds as a true retreat—featuring a main residence with a heated three-car attached garage, a legal guest house, a commercial-sized detached garage, a heated in-ground pool, pool pavilion, and multiple outdoor living spaces designed for both quiet enjoyment and memorable gatherings. The 4,900+ square foot main residence is rich in detail and thoughtful design. A gracious entry foyer welcomes you into formal living and dining rooms, while the expansive open-concept family room, with its inviting fireplace, creates a warm and natural gathering place. The gourmet kitchen, appointed with granite countertops and stainless-steel appliances, is both functional and refined. A charming breakfast nook overlooks a spacious deck and the beautifully landscaped pool complex, offering a serene backdrop for everyday living. The first-floor primary suite is a private sanctuary, with tray ceiling, custom closets, a spa-like bath with soaking tub and separate shower, and private access from the bedroom to the rear deck. A formal dining room with winscot, crown molding and hardwood floors, a well-placed laundry room, powder room, and secondary staircase leading to the heated three-car garage complete the main level. Upstairs, three generously sized bedrooms and three full baths are complemented by a comfortable sitting nook and a dedicated home office, perfectly suited for remote work or creative pursuits. The fully finished walk-out lower level expands the home’s versatility, offering a second full kitchen, fitness area, home theater with seating for nine, and a full bath, along with ample storage and dedicated mechanical spaces. The detached 36' x 32' heated garage offers exceptional flexibility, complete with a second-floor office and full bath, ideal for workspace, hobbies, or additional storage. Attached, the beautifully designed two-story guest house provides a fully self-sufficient living experience, featuring a private entrance, covered stone patio, full kitchen, living room with a striking stone fireplace, laundry, and two and a half baths. With its own garden and dedicated parking, this space presents an outstanding opportunity for extended living or supplemental income (Airbnb approval was never used, but can be renewed). Outdoors, the property truly shines. The backyard is a private oasis centered around a 38' x 30' heated in-ground pool, framed by custom stonework, walkways, and mature plantings. The pool house, both heated and air-conditioned, includes a changing room and a well-appointed bath. A striking covered cabana/gazebo features built-in seating and a full outdoor kitchen, complete with gas grill, refrigerator, microwave, and sink ... creating an effortless setting for summer entertaining. Additional features enhance both charm and functionality, including a small vegetable/herb garden, a gas fire pit, invisible fencing, and a custom-built kennel or chicken coop. A second gated driveway, discreetly positioned behind a stacked-stone retaining wall, provides convenient access for RV, boat, or guest parking. Extensive upgrades include 9-foot and vaulted ceilings, radiant floor heating on levels 1 and 2 (including the attached garage), Marvin Integrity windows, a high-efficiency Viessmann boiler, crown molding, LED recessed lighting, and spray foam insulation—ensuring comfort and energy efficiency year-round. Ideally located just minutes from the Taconic Parkway, Rhinebeck, and Red Hook, as well as area golf courses, wineries, spas, and fine dining, this one-of-a-kind property offers a seamless balance of seclusion and accessibility. Situated within the Red Hook Central School District.

163 Hapeman Hill Road, Red Hook
$749,900
5 Beds ⋅ 2 Baths ⋅ 988846 MLS
Welcome to 1141 Beekman Road! Brookside Circa 1804 Farmhouse Colonial Home Sited on 2.73 Private Parklike Acres. The Home was Fully Restored in 2016 with eco-friendly, money saving Geothermal Central Heat & Air, New Duct Work, Updated Electric, New Hot Water Heater, and Two Wood Pellet Burning Stoves. The house also has Two Additional Fireplaces. 5 bedrooms/office/den, 2 of which have walk-in closets. There is a New Eco-Friendly High Speed Electric Vehicle Charger installed and a Carriage House that was recently renovated to accommodate at least four cars. Several Additional Outbuildings include the Quaint Writing Cottage with it's own Patio Seating Area overlooking the Babbling Brook. Original details throughout the home include Wide Plank Floors, Wood Bannister, Beautiful Lighting fixtures and Moldings. Walk-Up Attic and large Basement, provide plenty of storage, in addition to a devoted storage area in a second attic. Local Custom Made Built-in Bookcases, Window Shutters, and Amish Swing with Frame enhance the properties enjoyment. The Kitchen Island, 1st Floor Vanity and Birdhouse (by the large exterior patio) were all Handmade by Robert Sherman out of Antique Barn Wood. While Enjoying your Visit to this Beautiful Home, Have the Privilege of viewing Paintings by the Owner's Grandfather, Bert Lahr, who Played the Lion in the Wizard of Oz.

1141 BEEKMAN Road, Hopewell Junction
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 987176 MLS
Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef’s kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover's dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn't just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.

617 BEAN RIVER Road, Pine Plains
$425,000
3 Beds ⋅ 3 Baths ⋅ 964337 MLS
Bring new life to a home rich with character and history. Original details such as hardwood floors, stained glass and chandeliers reflect its timeless charm and craftsmanship while offering a strong foundation for renovation and customization. The layout includes large sized rooms and the convenience of first floor laundry, with the washer and dryer already in place. Set on a level, double lot, the property features a fenced backyard, long driveway and a detached two car garage, providing amble outdoor space and parking. The home is ideally located with easy access to transportation, shopping, dining, medical facilities and other local amenities. Please note that the photos were taken when the home was furnished. The property will require updates, mostly on the outside of the home and the garage, and may be best suited for a renovation/rehab loan or cash. Buyer will be responsible for obtaining a certificate of occupancy, agent has the list of requirements. Current condition of home is not reflected in these photos, photos are from a previous listing. Home is being sold AS IS.

105 Hooker Avenue, Poughkeepsie
$4,900,000
3 Beds ⋅ 4 Baths ⋅ 956925 MLS
Perched atop 40.9 private acres, this exceptional custom-built estate offers unrivaled privacy and sweeping panoramic views of the Catskill Mountains. Blending timeless craftsmanship with modern luxury, this hilltop retreat embodies refined living in a breathtaking natural setting. Inside, antique teak flooring flows throughout the home, adding warmth and character to every space. The open floor plan features a gracious living room that opens to a library with a fireplace and a full bath, creating an inviting centerpiece for both relaxation and entertaining. At the heart of the home, the eat-in kitchen is both functional and striking, featuring a scullery and a distinctive modern Rumson fireplace. The kitchen opens effortlessly onto a stone terrace and pergola, offering a breathtaking setting for alfresco dining while overlooking beautifully landscaped gardens that evolve with the changing seasons. Adjacent, the formal dining room provides a refined space for hosting memorable gatherings. The lower level includes three bedrooms and four full baths, along with a music salon featuring expansive glass doors that open to a stone terrace with breathtaking panoramic views. Additional amenities include a wet bar, laundry room, and wine cellar, offering both convenience and luxury. A detached two-car garage complements the home’s timeless architecture while adding everyday practicality. Experience the epitome of serenity, artistry, and mountain living in this extraordinary hilltop estate—where every sunset paints a masterpiece across the western sky.

1135 Duell Road, Stanfordville
$850,000
4 Beds ⋅ 3 Baths ⋅ 980223 MLS
This extraordinary colonial is a rare Hudson Valley find, where over a century of craftsmanship forms the foundation for a lifestyle that has to be seen to be believed. This 4 bedroom home has bones that simply cannot be replicated, while an extensive list of upgrades throughout has transformed every inch of the property into something truly exceptional. Inside, original hardwood floors flow through light filled living spaces, a chef's kitchen, center island with cooktop, custom cabinetry, exposed brick, and a primary suite with soaking jetted tub, travertine tile, and frameless glass shower. A two story 3 car garage and an additional detached barn-style garage.

23 S Creek Road, Staatsburg
$1,695,000
4 Beds ⋅ 5 Baths ⋅ 969504 MLS
Set in a beautiful rural landscape on 20.677 acres with seasonal views of Silver Lake, this inviting property captures the essence of Hudson Valley living—peaceful, scenic, and just a short drive to the Village of Rhinebeck. Built in 2007, the thoughtfully designed home offers over 4,000 square feet of comfortable living space with 4 bedrooms and 4.5 baths, complemented by a detached 8 car garage with studio space above. A covered porch welcomes you into the home’s entry, opening to a spacious living room that serves as the heart of the house. Here, soaring 18-foot ceilings, a dramatic two-story slate-surround fireplace with woodstove insert, and two French doors leading to a large wraparound deck create an ideal setting for both everyday living and entertaining. The chef’s kitchen provides a large center island, high end appliances, and looks out into the dining/living room. The first-floor primary suite provides a private retreat with two walk-in closets and a spa-like bath featuring a large walk-in shower and Jacuzzi tub. The main level also includes a den, half bath, laundry room, and accesses the attached 2-car garage. Upstairs are two additional bedrooms, a full bath, and a generous 12’ x 23’ bonus room well suited for a home office, studio, or media space. The finished basement further expands the living area with a family room, wine room, sauna, and full bath. A standout feature of the property is the impressive 1,728 square foot detached two-bay garage with capacity for 8 cars plus a carport, constructed in 2021. Ideal for car enthusiasts, collectors, or those seeking flexible workspace, one bay features two lifts and an exceptional 14’8” ceiling height. The entire structure is equipped with heat and AC, has a rear covered porch, expansive loft/attic storage, and its own Generac generator. Additional highlights include a fenced dog run, shed, whole-house Generac generator and rights to Silver Lake—making this a rare offering that blends comfort, privacy, and ideal location.

203 Silver Lake Road, Rhinebeck
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 967644 MLS
Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire property! Set on 0.21 acres just steps from Millbrook's boutiques, restaurants, galleries, and everyday conveniences, the property offers an increasingly rare combination of village living and income-producing potential. Originally built in 1910, the main residence was extensively renovated in 2002 with new windows, updated heating systems, a new oil tank, and two-zone central air conditioning, blending modern comfort with historic character. The guest apartment was constructedin 2018 and provides excellent flexibility for rental income, guests, or extended family. The private fenced backyard serves as a peaceful retreat, featuring two bluestone patios ideal for outdoor dining, entertaining, or relaxing. Ideally located near highly regarded public and private schools, summer camps, and premier sporting clubs, including the Millbrook Golf & Tennis Club, Tamarack Preserve, and Mashomack Preserve Club. The region is renowned for its equestrian lifestyle, with access to horse shows, fox hunting, riding trails, and top-tier equestrian facilities. Hiking, fly-fishing, polo, and skiing are all nearby. Millbrook's central location provides convenient access to Rhinebeck, Red Hook, Pine Plains, Millerton, Hudson, Litchfield County, and the Berkshires, home to Tanglewood and a wealth of cultural attractions. Just 1¾ hours from Manhattan by car or via Metro-North Railroad, this unique property offers the perfect blend of village convenience, country charm, and income-producing flexibility.

3311 Franklin Avenue, Millbrook
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