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$499,000
3 Beds ⋅ 2 Baths ⋅ 1046807 MLS
Well maintained mid-century split-level home, privately set on over 1.5 acres at the end of a quiet cul-de-sac. Ideally located just minutes from Route 9 and conveniently situated between the New Hamburg and Poughkeepsie train stations, this home offers both privacy and accessibility. Inside, gleaming hardwood floors, vaulted ceilings, and thoughtful custom details showcase the home’s mid-century flair. The living room features custom built-in cabinetry, while the sunny family room offers additional built-ins and a cozy wood-burning fireplace. Enjoy peaceful outdoor living from the screened porch overlooking the private backyard, or step outside to the fenced patio and established gardens. The lower level is filled with natural light and provides a walk-out to the outdoor spaces. The spacious primary suite includes a private ensuite bath and walk-in closet, complemented by two additional generously sized bedrooms. A dedicated office provides a comfortable space for working from home, while the laundry and additional storage areas add everyday convenience. Unique to this neighborhood, 10 Oak Bend Rd has municipal water and sewer. With its generous acreage, peaceful setting, classic mid-century details, and inviting living spaces, this special home is ready to welcome you. Make this house your home.

10 Oak Bend Road, Poughkeepsie
$1,699,999
5 Beds ⋅ 5 Baths ⋅ 1047350 MLS
Prepare to be captivated by this one-of-a-kind 5 bedroom, 4.5 bath luxury estate in the prestigious Old Hopewell Estates—an extraordinary residence that seamlessly blends elegance, privacy, and resort-style living with town water/sewer and low taxes. Perfectly sited on a manicured 1-acre corner lot, this custom Colonial boasts over 6,000 sq. ft. of refined living space plus a fully finished 1,700+ sq. ft. walkout basement designed as a true mother/daughter or multi-generational suite with its own full kitchen, spacious living and dining areas, luxury bath, private laundry room, fireplace, and direct access to the backyard—making it completely self-sufficient for extended family or guests.ONLY For the most discerning buyers--- From its commanding brick facade, stone-accented driveway, and double-door entry to the soaring two-story foyer with dual staircases, hardwood floors, and intricate millwork, every detail radiates sophistication. The main level is designed for both grand entertaining and everyday comfort, featuring elegant formal living and dining rooms, a coffered-ceiling family room with fireplace, and a sun-filled home office. The gourmet kitchen is a showpiece with a massive quartz island, professional-grade appliances, custom cabinetry, and a garden window overlooking the lush grounds, flowing seamlessly to a dramatic breakfast area and expansive patios. Upstairs, the primary suite is a private retreat with sitting room, dual custom closets, fireplace, and a spa-inspired bath with limestone floors, soaking tub, and oversized walk-in shower, while four additional bedrooms include a princess suite and Jack & Jill accommodations. Step outside to your own resort-style paradise—a heated saltwater pool with natural stone accents, multiple stone-paver patios, an outdoor kitchen, European-style gazebo, tranquil fountain garden, and cozy firepit lounge, all surrounded by professional landscaping for ultimate seclusion. Additional highlights include a heated/air-conditioned 3-car garage, whole-house sound and security systems, and a commuter-friendly location just 5 miles to Metro-North and 75 miles to Manhattan. Combining timeless elegance with unmatched functionality, this estate is the crown jewel of Old Hopewell Estates—a forever home offering true multi-generational living, luxury, and lifestyle.

144 Shamrock Hills Drive, Wappingers Falls
$599,900
4 Beds ⋅ 3 Baths ⋅ 1043586 MLS
Pre-qualified buyers only please. This unique home is being offered for the first time in over ten years and it's a lot of house for the money. All large sized rooms on an oversized lot located at the end of a lovely street just minutes from everything. The entrance foyer has built in planters and an entire wall of custom stonework that opens up to an oversized living room with the same stonework and woodstove insert- even the wood is included for next winter's burning. There is a nice sized kitchen with a center island, and the laundry room is conveniently located right in the same room for your ease!! The dining room is there as well and has a bow window and even a built-in ironing board from the old days with a door out to the massive wrap around deck that overlooks the inground Gunite pool. There are two bonus rooms with parquet floors off of the dining area and the living room with pocket doors that are currently being used as an office and an exercise room. The home allows for anyone to choose how to use the different rooms for their individual needs and taste! The main floor has a large primary bedroom with a full bath, two additional bedrooms, and a bathroom in the hallway with double sinks. On the lower level, there is a massive fourth bedroom, a full bathroom that opens to the outside to facilitate easy access to the pool, and storage galore. There is also a large family room with a built-in bar, a non-working second wood burning fireplace insert, and a large pool table room that is not heated. There is also a large room for mechanicals and storage galore and a utility room as well. The space inside this custom home and its unique features will surprise you and the pictures don't do it justice. Outside there is a pool house, large decking overlooking the pool, and a few patios to choose from. One of the best features of this home is the detached garage with multiple doors and a full walk up to a second story. A car enthusiast or hobby person could spend years deciding on its best use or change their plans as the need arises!! The solar power is fully paid for and off sets the utility bills- we are currently looking into whether the current credit will be transferable to the new owners.

58 Ireland Drive, Poughkeepsie
$895,000
4 Beds ⋅ 2 Baths ⋅ 1039201 MLS
Private Mountain-Top Equestrian Property Only 74 miles to NYC and 2 miles to Tymor Park for riding and recreation. This is the one you've been waiting for! Tucked behind a private, gated entrance, this fantastic horse property offers the ideal combination of privacy, convenience, horses/farm animals and country living. Offered for sale for the first time ever. Appealing 4-bedroom, 2 full bath home that is ADA-compliant, thoughtfully adding accessibility without sacrificing style. Main features include: a bright, updated kitchen with stainless steel appliances and Lifeproof oak wide-board floors highlighted by a 20 year commercial warranty. The heart of the home is a spectacular living room with cherry hardwood floors, exposed beams, cathedral ceilings and a dramatic floor-to-ceiling stone fireplace that adds to the character of the property and is fantastic for entertaining. The spacious primary en-suite flows from the living room with Pergo waterproof oak floors and features double closets and a primary bathroom. The main level continues with 3 additional bedrooms, a full bath and a bonus back porch with Pella windows, cherry hardwood floors and sliding glass doors overlooking your own private backyard - and what a backyard it is! A large, manicured yard where you can sit on the porch and enjoy all that living in the country has to offer. Relax in the hot tub, gather around one of three stone fire pits, or simply enjoy the peaceful mountain setting and freshwater creek. Professional Equestrian Property! This horse farm includes a large, bright indoor arena with LED lighting and dust-free silicone sand footing (which is suitable on its own or can be mixed with discipline specific synthetic footing like GGT), four oversized rubber-matted run-out stall barns with direct paddock access in five turnout paddocks, additional pasture, three frost-free water hydrants, a 2-story hay barn, grain/feed shed, outdoor kennel, and a groomed, private trail system with obstacles right on your own wooded acreage. There is even a spacious workshop with a stone fireplace adjacent to the oversized 2-car garage, paved driveway, and private gated entrance. This property is currently in the Agricultural District and only 2 miles from Tymor Park for additional off site trails and riding opportunities. A practical setup for horse owners looking for the convenience of having their horses at home, with the added benefit of an indoor arena for year-round riding and training. Located in the Arlington Central School District - Vail Farm Elementary and Union Vale Middle School - and only 5 minutes from shopping and restaurants. A private equestrian sanctuary. A weekend getaway. A mountain-top retreat. First time offered for sale. Properties like this are hard to replicate.

2536 Wingdale Mtn Road, Poughquag
$665,000
4 Beds ⋅ 2 Baths ⋅ 1036190 MLS
Welcome to this charmer located right in the Village of Millbrook and set on one acre of beautifully landscaped land with magnificent specimen trees and a covered patio that invites one to cook, eat or just sit and admire the lush property. Abundant light streams through this cape style home which features a handsome eat-in kitchen with all modern appliances and gleaming granite counters, a spacious dining area and living room with a wood burning fireplace and a sunroom that can double as a greenhouse and laundry. The first floor also contains two bedrooms (or offices) and a full bath. The second floor features two more large sunny bedrooms and a full bath. Plenty of storage can be found in the partially finished basement and attached two car garage. A nice healthy stroll brings one to the village’s charming shops, restaurants, a fantastic library and a beautiful parks and playground.

12 Ciferri Drive, Millbrook
$895,000
3 Beds ⋅ 3 Baths ⋅ 1034739 MLS
Discover privacy, comfort, and convenience at this beautifully updated 3-bedroom, 2¾-bath home on 3.2 scenic acres in Staatsburg, NY, just six miles from Rhinebeck Village. Set well back from the road, this move-in-ready Hudson Valley property offers a peaceful country setting with easy access to dining, shopping, commuter rail, and major roadways. Inside, the light-filled home features hardwood floors, a renovated kitchen with modern appliances and gas range, a spacious primary suite with adjoining home office, and a finished walkout lower level offering flexible space for a family room, gym, recreation area, or guests. Additional features include central air conditioning, an attached garage, wine cellar, abundant storage, and a new septic system. Outdoor living is equally inviting, with a brand-new deck, powered pergola, mature landscaping, and picturesque front-yard pond creating a private setting for entertaining or relaxing. Convenient to Rhinebeck, Hyde Park, the Culinary Institute of America, Hudson River recreation, wineries, hiking, Metro-North, Amtrak, the Taconic State Parkway, and New York State Thruway, this property is ideally positioned for both full-time living and a Hudson Valley weekend retreat. A rare opportunity to own a private, updated home with acreage near Rhinebeck and enjoy everything the Hudson Valley lifestyle has to offer.

71 W Pine Road, Staatsburg
$649,000
4 Beds ⋅ 3 Baths ⋅ 1031185 MLS
Set against a backdrop of rolling green hills and mature trees on almost 2 picturesque acres, this charming updated Colonial offers a rare combination of generous living space, exceptional outdoor amenities, and a peaceful country setting just minutes from everyday conveniences. Inside, rich hardwood floors, exposed wood beam ceilings, and a striking brick fireplace bring warmth and character to the main living spaces. The thoughtfully designed floor plan offers multiple areas for gathering and relaxing. Enter off the covered front porch into a charming foyer. To the left find a spacious formal living room with oversized windows. In addition to the large living room and formal dining room, enjoy a spacious family room with exposed wood beams and brick fireplace for cozy nights at home. A half bath and main floor laundry are welcome additions. The spacious eat-in kitchen features abundant cabinetry, expansive counter space, bar countertop area and a seating area with sliding glass doors that create a seamless connection to the backyard, perfect for both everyday living and effortless entertaining. Upstairs enjoy plush carpeting in the stairway and hall and leads to 3 ample sized bedrooms, and a hall bath with the primary bedroom and en suite bath. Plenty of closet space throughout. An oversized two car garage with oversized ceilings could be a car enthusiasts dream or just provide ample storage potential. Open canvas in the large unfinished basement. The outdoor spaces are equally inviting. Enjoy quiet mornings on the welcoming front porch, host summer dinners beneath the covered pavilion, or unwind while taking in the beauty of the expansive lawn and surrounding greenery. The property's generous acreage offers endless opportunities for recreation, gardening, or simply embracing the peaceful Hudson Valley lifestyle. A standout feature is the impressive detached barn with a two-car garage and a lofted area above with its own private entrance. Turn this into a retreat of your dreams-home office, artist's studio, fitness space, guest quarters, or private retreat, this versatile addition provides exceptional flexibility to suit a variety of lifestyles. Conveniently located just minutes from Route 9, the Taconic State Parkway, and I-84, the home offers easy access to Metro-North, shopping, dining, parks, hiking trails, golf courses, and the many attractions of the Hudson Valley, all while enjoying the privacy and serenity of a truly exceptional setting. Recent updates throughout the home include new interior doors and garage doors (2025), new wall-to-wall carpeting (2025), and a beautifully updated half bath (2022). The roof is approximately 6–7 years old, offering added peace of mind. The property also features two oil tanks, providing ample fuel storage capacity.

551 Hillside Lake Road, Wappingers Falls
$1,495,000
3 Beds ⋅ 2 Baths ⋅ 1011800 MLS
Calling all dreamers, this unique, architect-designed contemporary residence is set on 25 private, wooded acres in Millbrook, New York. Located on a pastoral country road, and neighboring one of Millbrook's grand estate properties, this offering combines exceptional architectural integrity, quality construction, and future development potential. The light-filled home is defined by soaring 30-foot ceilings and a dramatic sense of volume with Greek revival motifs throughout. The grand entry to the main level flows into an open kitchen area leading to the great room, with a stunning granite fireplace and adjacent open dining area and a generous greenhouse/sunroom which extends the living space. A balcony off the dining-room anchors both sides of the house and offers a sheltered outdoor respite for coffee or cocktails overlooking the peaceful wooded landscape. The other side leads into the guest bedroom and bath, as well as the primary bedroom suite, featuring a dressing area and walk in closet. Separate loft spaces in each bedroom can be enjoyed as open galleries, sleeping areas or reimagined as another floor to expand the interior square footage. Constructed with quarried bluestone and granite, I-beams, a seamless steel roof, custom millwork, and French limestone and oak floors, the house reflects a focus on longevity and craftsmanship. Below, a large cellar is well-suited for a workshop or studio and includes multiple storage rooms including one for wine. This level also offers flexibility for conversion into additional living space. An approximately 1,000-square-foot, four-bay garage provides substantial parking and storage. Additional on-site materials, including granite pavers, brick pavers, a granite bench, and a granite lamp post base, are included in the sale and offer opportunities for future landscape or hardscape projects. The grounds are anchored by a private garden with a granite pathway encircling a grand Robinson iron fountain featuring cranes. A spring-fed brook runs along the southern border of the property, enhancing the natural setting. Approximately 20 acres on the eastern side of the property offer development potential and the possibility of creating additional vantage points. Less than 2 hours from New York City, this Millbrook estate property combines solid architectural pedigree, superior construction and significant landholding in a much sought-after Hudson Valley location, with convenient access to the amenities of Millbrook Village, Dutchess Day School, and the wider Hudson Valley region. *Some photos virtually staged.

46 Hoxie Road, Millbrook
$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
$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
$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
$3,299,000
5 Beds ⋅ 7 Baths ⋅ 888909 MLS
Welcome to Cloud Walk Estate, a once-in-a-lifetime opportunity to own the entire summit of a private mountain in East Fishkill, NY. Encompassing nearly 120 acres across three parcels, this extraordinary estate offers panoramic views stretching close to 150 miles — a setting that simply cannot be replicated. Perfectly positioned just 90 minutes from NYC, this legacy property features five distinct structures, miles of paved driveways, and extensive ATV trails — making it ideal as a family compound, luxury retreat, or creative enclave. Whether you're seeking a private oasis, an income-producing property, or a future generational estate, Cloud Walk is a canvas ready for your vision. Main House — The Historic Stone House Originally built in 1929 and once owned by Dr. Rushmore, personal physician to President Franklin D. Roosevelt, the Stone House blends timeless craftsmanship with notable provenance. Featuring 4 bedrooms, 3 full baths, 2 half baths, and over 2,600 sq ft of living space, the home is wrapped in stunning stonework and filled with historic character. Inside, you'll find 3 gas fireplaces and 2 wood-burning hearths, two staircases, and a sun-drenched stone patio with some of the most breathtaking views in the Hudson Valley. A large unfinished basement and attic invite further customization and expansion. The Guest House — Modern Luxury Meets Nature A newly constructed (2022) 816 sq ft one-bedroom residence complete with a sleek full kitchen, office/den, radiant floor heat, modern lighting, laundry, and a one-car garage with an EV charger. Ideal for hosting guests or offering complete privacy for creative endeavors or extended stays. The Country House — A Charming Renovated Escape Located at 7 Looking Rock Lane, this fully renovated 3-bedroom, 2.5-bath home is filled with rustic charm. Soaring wood beams, a beverage center, full kitchen, laundry, and your very own private pond with a fountain make it the ultimate getaway. A separate driveway and unique "Hobbit Hole" feature add to its storybook appeal. The Historic Barn — Endless Possibilities Formerly a horse barn, this structure is ready for restoration or reinvention. With strong bones, original stalls, and electricity already in place, it could become a dream event space, studio, or guest quarters. A generator is also hooked up for added peace of mind. Oversized 3-Car Garage with Loft A car lover’s dream, this 3-bay garage includes an electric car charger, two carports, and a vaulted loft — perfect for a gym, guest suite, or creative studio. A separate electric meter provides independence and flexibility. The Grounds The estate boasts nearly 1.5 miles of private, paved roads, ideal for ATVs, bikes, or scenic strolls. A massive heated 18x38 in-ground pool with a diving board awaits you, framed by serene forest and never-ending sky. With multiple build sites and subdivision potential, the property offers both luxury and legacy. Additional Features: • Backup 22kW Generator (Stone House, Guest House, Barn) • Low Taxes for Acreage of This Scale (~$37,000 annually) • Two Driveways for Optimal Access • Zoned for Maximum Flexibility This is not just a property — it’s a mountain-top kingdom with a presidential legacy. Whether you're looking to build a multi-generational compound, develop a creative or spiritual retreat, or simply own one of the Hudson Valley's most breathtaking private holdings, The Cloud Walk Compound is ready to welcome you. *Bedroom, Bathrooms, and Sqft Only reflect the Main & Guest House*

401 Woodmont Road, Hopewell Junction
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