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$619,900
3 Beds ⋅ 2 Baths ⋅ 992269 MLS
Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!

57 Buhleir Road, Pawling
$359,900
3 Beds ⋅ 1 Baths ⋅ 991169 MLS
Welcome to 144 Cream Street, a charming Cape Cod-style home nestled in the heart of the Hudson Valley. Built in 1951, this inviting single-family residence offers approximately 1,200 square feet of comfortable living space with 3 bedrooms and 1 full bath, all set on a generous 0.60-acre lot. From the moment you arrive, the home’s warmth and character are evident. Recent improvements, including a newly replaced side porch, enhance both curb appeal and everyday enjoyment—creating the perfect spot for morning coffee or relaxing evenings. Inside, the home features a practical layout with classic charm, an attached garage, and the timeless appeal of a well-built mid-century design. This property is especially well-suited for first-time homebuyers or those looking to make the move into the Hudson Valley lifestyle. The manageable size, expansive yard, and approachable layout provide an excellent opportunity to personalize and grow into the home over time. Ideally located in the Town of Poughkeepsie, the home offers convenient access to a wide array of local amenities. Just minutes away, the Metro-North Railroad Hudson Line at the Poughkeepsie Station provides a direct and scenic commute to New York City, making it an excellent option for commuters or weekend travelers. Residents can also enjoy nearby Hudson Valley attractions such as the Walkway Over the Hudson, one of the longest pedestrian bridges in the world, along with rail trails, parks, waterfront dining, wineries, and farm-to-table restaurants that define the region’s lifestyle. With its combination of location, charm, and recent updates, 144 Cream Street presents a wonderful opportunity to own a home in one of the Hudson Valley’s most desirable and accessible areas—perfect for those starting their homeownership journey or seeking a peaceful retreat within reach of the city.

144 Cream Street, Poughkeepsie
$365,000
3 Beds ⋅ 1 Baths ⋅ 989555 MLS
Situated on 2.45 acres of land in the Town of Amenia, you will find this three-bedroom ranch style home. The grounds are lovely, with a private, mostly level yard. The home provides single level living and the property includes a detached three bay garage with a one-bedroom apartment on the second floor. Perfect property for a first-time home buyer or an investor. Conveniently located minutes from Metro North train stations and the enjoyable Harlem Valley rail trail. Just a short drive to Millbrook or Sharon, CT.

24 Wilson Eaton Road, Amenia
$695,000
992406 MLS
Potential future subdivision! Amazing opportunity to own 10 acres of mixed used property! Great location, corner of Route 55, Clapp Hill Road and East Noxon.

Clapp Hill Road, Lagrangeville
$1,250,000
991701 MLS
Charming Hudson Valley Mixed-Use Opportunity. Ideally positioned between Beacon and Poughkeepsie, this distinctive mixed-use property blends historic character with modern versatility. Anchored by a beautifully updated 1841 farmhouse, the main building offers flexible space well-suited for professional offices, boutique retail, a creative studio, school, or showroom. Complementing the main structure is a separate two-bedroom, one-bath cottage featuring a cozy wood-burning fireplace and patio—perfect for rental income, guest accommodations, or owner occupancy. A standout feature is the expansive two-story 1800.s barn, fully equipped with heat and electricity—ideal for workshops, events, storage, or further business use. The property has been thoughtfully updated throughout while maintaining its timeless charm. A generous parking area ensures ease for clients, customers, or residents. A rare opportunity to live, work, and invest in this desirable corridor.

2321-2325 Rt-9D, Wappingers Falls
$599,000
991244 MLS
Impeccably maintained and tastefully updated City of Poughkeepsie office building features three levels of finished space. Attractive layout features welcoming lobby/reception area w/soaring ceilings and abundant natural light. Main level includes large conference room, plus multiple offices and kitchen/breakroom. Second floor features library, several offices and restroom. Lower level with conference room, storage areas and rest room plus access to courtyard. Loaded with attractive finishes and impressive architectural details such as cantilevered staircase, dentil molding and exposed brick walls. Updated infrastructure including epdm roof, boiler, 2 water heaters & a/c units. Premier office space conducive to subletting or occupying in its entirety. Ideal location in City of Poughkeepsie business district, within walking distance to court house and with easy access to municipal parking lot, Mid-Hudson Bridge and Poughkeepsie train station. A rare opportunity where location, configuration, condition and finishes converge.

9 Cannon Street, Poughkeepsie
$120,000
4 Beds ⋅ 2 Baths ⋅ 987415 MLS
SUMMER GETAWAY OR RENTAL INCOME PROPERTY?....YOU CHOOSE! A WONDERFUL SEASONAL COTTAGE (APPROXIMATELY APRIL 15 -OCTOBER 15) IN SYLVAN LAKE AREA GREAT FOR SUMMER OR WEEKEND RETREAT OR CAN BE USED AS A RENTAL INCOME PROPERTY. ALL EXISITNG KITCHEN, BATH AND AC/HEAT APPLIANCES STAY. LAUNDRY FACILITY ON SITE, AMPLE PARKING. AMENITIES INCLUDE 2 CLUBHOUSES, PLAYGROUND AND COMMUNITY POOL. SYLVAN LAKE BEACH, TENNIS,AND GOLF ALL NEARBY.

71 MILLER Road Unit #23, Hopewell Junction
$99,900
991139 MLS
Affordable building lot conveniently located in Town of LaGrange with Arlington Schools. Approved building site for a 3 bedroom home. OWNER FINANCING AVAILABLE. Filed Map attached to MLS listing or upon request. This lot #1 is part of a 2 lot subdivision. Lot #2 has been built. Driveway "right of way" passes thru Lot #1 to Lot #2. House site is located to the right of existing driveway. Lot is level and partially cleared. Conveniently located, minutes to shopping, food, parks and recreation, major roadways including the Taconic State Parkway and 10 minutes to Metro North Train. Driveway is marked by mailbox for house #24 Sedgewick Rd. Bring your own builder or ask about available builder options.

Lot #1 Sedgewick Road, Poughkeepsie
$439,000
3 Beds ⋅ 2 Baths ⋅ 990683 MLS
This property is a charming single-family home nestled in the heart of Wappingers Falls. Set on a spacious half-acre lot in a quiet residential neighborhood, this inviting property offers the perfect blend of comfort, space, and suburban tranquility. Built in 1965, this home features approximately 1,628 square feet of living space, including 3 bedrooms and 1.5 bathrooms—ideal for both everyday living and entertaining. A functional layout is complemented by a finished basement, providing additional flexible space for a recreation room, home office, or guest area. The home includes central cooling and an attached garage, while the generous yard offers ample room for outdoor enjoyment, gardening, or future enhancements. Located in a desirable Dutchess County setting, the property is just minutes from local schools, shopping, dining, and major commuter routes. Residents enjoy the charm of nearby village amenities along with convenient access to the greater Hudson Valley region, known for its scenic beauty and vibrant community atmosphere. Whether you're a first-time buyer or looking to settle into a peaceful neighborhood, 11 Sherwood Heights presents a wonderful opportunity to create your ideal home.

11 Sherwood Heights, Wappingers Falls
$109,000
990705 MLS
This breathtaking BOH approved parcel is one of the highest points in Dutchess County. Land faces east and the sunrises are breathtaking. Close to Greenfields and Peach Hill Parks, Eleanor Roosevelt National Historic Site, Hyde Park Soccer Stadium, Richard L. Skimin Memorial Baseball Fields, gas stations and eateries. Please stay on the driveway and be mindful that this is a paved private road. Road maintenance for common driveway is a verbal agreement among neighbors. Harley Tucker Hill is off of Cream Rd., between Molly's Way and Dutchess Hill Rd . Please do not walk the land without an approved appointment. Fully available unless noted here. CASH only unless you want to work with a lender to buy the land and finance the construction under one loan.

Harley Tucker Hill, Poughkeepsie
$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
$1,250,000
4 Beds ⋅ 5 Baths ⋅ 990579 MLS
Originally built in 1836, this beautifully restored Greek Revival Center Hall welcomes you with timeless charm and thoughtful updates. Set on over four acres with Willow Brook gently winding through the property, it offers a warm, peaceful retreat where historic character and modern comfort come together to create a truly special place to call home. Town historical records state it was used in the Underground Railroad, as well as a quarterly meeting place for the Quakers, who were Abolitionists during the American Civil War - all while being a vibrant and successful dairy farm in the heart of the Hudson Valley. Inside, original wide board floors, exposed hardwood beams, and intricate molding and trim work highlight the home's craftsmanship. The center hall layout leads to a stunning double parlor with two fireplaces and original pocket doors, as well as an open dining and living room boasting two additional fireplaces, perfect for gatherings both intimate and large.The heart of the home—a warm and inviting kitchen—features a wood-burning fireplace, gas stove, island, walk-in pantry, and laundry room. From here, step out to a screened porch —ideal for morning coffee, evening relaxation, or weekend entertaining. Upstairs you'll find 3 spacious bedrooms and 3 full bathrooms, as well as a room that could be used as a 4th bedroom, a custom walk-in closet/dressing room, or sitting room. The attic is a versatile space and can be reached by 2 separate staircases. The exterior boasts classic clapboard siding, metal roof, original 6-over-6 windows, raised garden beds, a fenced backyard, and several vintage outbuildings. In the basement you'll find updated mechanicals and the original milkroom with bluestone floor, echoing the home's agricultural past. Located just 3 miles from the Taconic State Parkway, this exceptional property is a beautiful blend of historic significance, and modern functionality.

36 Market Lane, Clinton Corners
$784,900
4 Beds ⋅ 3 Baths ⋅ 990233 MLS
BACK ON MARKET 6/10 Built in 1788 this home is one of the original homes in Wappinger Falls. It has been stated that one of President George Washingtons friend built the original home. This has been a family owned property for some 62 years. Wide board floors are throughout as well as original beams. There is a total of 5 large fireplaces, including one in the basement. That fireplace was used for the preparation of meals when the house was first built.. The fireplace in the living room is the only fireplace that is functioning, providing a warm winter fire in the cold winter months. The seller is leaving the original fireplace equipment and cauldron in the dining room fireplace. 22 x 18 sunroom can be used for a multiple purposes. Plants seem to like the sun coming in different times of the day. The Kitchen 20 x 16 has a center island and a breakfast area overlooking the brick patio, lined with multiple gardens and perennials. The dining room has two built in corner china cabinets, original mantled fireplace and very unique chandelier. The living room has a working wood fireplace with a decorative mantle and original storage closets. A warm, homey room that invites you to come sit and relax, especially on those cold winter nights with the fireplace warming up the room extra warm. Leading from the living room is the Library which has a closed up fireplace, wide board floors and original beams. There is a wall that has built in book shelves. The hallway both upstairs' and downstairs are wide with the downstair hall leading to the front of the house with a cozy porch overlooking the front yard. The mature trees add privacy on this porch area. The original house was built with the primary bedroom, which has a large WIC, on the second level. More than likely this WIC was used as a bedroom. It may be possible that the wall can be opened to have access to the main bath upstairs. This bedroom, too, has wide board floors under the carpeting. A wing addition was put on the mid '70's. This wing could easily be a primary ensuite with 2nd floor bedroom, bath, and 1st floor sitting area. A door from this area will lead out to the brick patio. The 7.7 acres has the potential to be horse property with a pasture and spring fed pond filled with Koi. A tranquil setting in the heart of Dutchess County. The original barn built in 1783 now has electric, water and heat. AC can be added to the duct work. It is said this barn was built before the house with the owners living in a teepee while building the house. Easily this area could make a great workshop or hobby area. The barn is heated by oil and the tank is a 275. Walkin cooler and built in cases stay. Also staying is the worktable with a marble top and has wheels for moving it from place to place. There is a 2nd barn that has one stall in it that could be used for goats, sheep, chickens. A little mini farm, if you please. There is a small pond for goldfish by the brick patio, lots of flower gardens with perennials leading to the entrance of the sunroom. Make sure you check out the pictures with all the flowers. A wonderful retreat for you and your family. Plenty of property to make it your own. This home is near all amenities along Route 9 including shopping, historical sites, restaurants, Houses of worship, Metro North, etc.

93 Widmer Road, Wappingers Falls
$7,500,000
968961 MLS
Premier 300-Acre Agricultural & Investment Estate on Route 9 – Turnkey Dairy & Creamery Operation Discover a rare and significant investment opportunity in the heart of the Hudson Valley. This expansive 300-acre property, located directly on the busy Route 9 corridor in the Town of Red Hook, offers an unparalleled combination of massive scale, modern agricultural infrastructure, and high-visibility commercial potential. The Commercial & Agricultural Engine At the center of this offering is a state-of-the-art Modern Dairy Barn, constructed in 2018. Built to contemporary standards, this 110 stall facility is ready for immediate operation, offering superior ventilation, comfort, and efficiency for livestock. Complementing the dairy operation is a separate, dedicated commercial building fully equipped for ice cream manufacturing. This facility presents a lucrative "farm-to-table" business opportunity, allowing the next owner to capitalize on the high traffic count of Route 9 for a potential creamery, farm market, slaughterhouse or agri-tourism destination. The Land & Investment Potential Spanning a massive 300 acres, the property features over a mile of road frontage across two separate roads, providing exceptional accessibility and flexibility for future potential. The land is a mix of fertile fields and scenic vistas, ideal for continuing agricultural production, equestrian use, or a long-term land-banking investment in one of Dutchess County’s most desirable towns. The Residence Anchoring the estate is a charming historic farmhouse in good condition. Whether utilized as a primary residence, a manager’s home, or converted into administrative offices for the business, this classic structure adds warmth and character to the modern commercial facilities. Property Highlights: • 300 Acres of prime Hudson Valley land. • High Visibility Location: Situated on busy Route 9, perfect for retail exposure. • Modern Dairy Barn (2018): 110 Freestall barn with a robotic milker (needs rebuilding). • Ice Cream Manufacturing Facility: Separate building housing commercial-grade equipment. • Historic Farmhouse: Well-maintained and ready for occupancy. • Exceptional Access: Over a mile of road frontage on three different roads. • Versatile Zoning Potential: Ideal for continued agriculture, agri-business, or future investment development. This is a unique chance to acquire a legacy property with the infrastructure already in place for a thriving agricultural enterprise. Perfect for investors, farmers, or entrepreneurs looking to launch a signature Hudson Valley brand. In addition to the Main Complex, included SBL's 677518 (38.4 Ac) 760494 (62 Ac) 854567 (30 Ac) 640370 (26 Ac) 670450 (10.5 Ac) to make total of 300+ Acres. Sale is real estate and equipment only, not the business; however, that is also an option.

7775 Albany Post Road, Red Hook
$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
$25,000
986565 MLS
Raw land in a yet to be built development. An opportunity to buy into this and prepare for a future build or sit on the investment. The entry road is not cut in but Access is off of Bushwick Road. All building lots are mapped out and divided on Dutchess County Parcel Access. Phil Bisesto

Arlene Road, Poughkeepsie
$345,000
5 Beds ⋅ 3 Baths ⋅ 988819 MLS
2 homes for the price of 1. This is a multi-family property on multiple structures. Two separate electrical meters. 3318 total sq ft with a flowing stream in backyard. Main house consists of 3 bedrooms and 2 baths. Bungalow house has 2 bedrooms and 1 bath. 1 hr to NYC. INVESTORS AND CONTRACTORS SPECIAL. Needs Renovation.

37 Glen Avenue, Dover Plains
$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
$495,000
3 Beds ⋅ 2 Baths ⋅ 988726 MLS
Welcome to 7 Jonathan Drive, a beautifully renovated raised ranch offering modern comfort and move-in-ready living in Staatsburg. This 3-bedroom, 2-bath home has been thoughtfully updated throughout, including a brand-new roof, energy-efficient split systems, a stylish new kitchen, and completely renovated bathrooms. The bright and inviting main level features an open flow between the living room, dining area, and kitchen, creating the perfect space for everyday living and entertaining. The finished lower level provides additional flexible living space that can be used as a family room, home office, gym, or guest area. Additional highlights include an attached garage, ample driveway parking, and a spacious yard with plenty of room to relax, play, or entertain. With major improvements already completed, all that’s left to do is move in and enjoy!

7 Jonathan Drive, Staatsburg
$849,000
6 Beds ⋅ 5 Baths ⋅ 985647 MLS
Shepherd’s Knoll offers rare privacy and flexibility, located less than two miles from the village. Set on four beautiful acres that include lawns, pastures, and lightly wooded areas, this distinctive property sits at the end of a long private drive. It includes two spacious living units that could easily be converted back into a single-family home. Unit One features four bedrooms, three bathrooms, and a finished lower level. Unit Two offers two bedrooms and two bathrooms with a strong history as a short-term rental. Both spaces include wood-burning fireplaces and a wood stove, creating a warm, inviting atmosphere. Outdoor living shines here. expansive decks and porches overlook pastoral views, while the grounds include a charming studio cottage, a former sheep barn with storage, chicken coops, and established garden areas. Located just minutes from Bard College, a campus that includes the Fisher Center, and Montgomery Place. The property blends country seclusion with access to Hudson Valley cultural life. Whether you need multi-generational flexibility, a home plus a guest setup, or a private sanctuary close to town, Shepherd’s Knoll offers a lifestyle that’s increasingly hard to find.

32 Old Route 199, Red Hook
$1,799,000
5 Beds ⋅ 6 Baths ⋅ 875119 MLS
A Quintessential Quaker Hill Estate with Guest Cottage Perched atop the storied hills of Quaker Hill, this exceptional five-acre estate embodies the romance and elegance of country living at its finest. Privately nestled amid sweeping meadows, renowned equestrian properties, and grand country estates, 43 Meeting House Road offers a rare combination of exclusivity, beauty, and refined luxury just 90 minutes from Manhattan. Thoughtfully reimagined from its original log-home roots, the residence seamlessly blends timeless character with sophisticated modern design. Wide-plank oak floors, gracious entertaining spaces, a sunlit library, and a beautifully appointed chef's kitchen with radiant-heated floors and an oversized island create an atmosphere of effortless elegance. The luxurious primary suite is a retreat unto itself, with soaring 18-foot ceilings, skylights, and a Juliet balcony overlooking rolling lawns, mature specimen plantings, and the pastoral landscape beyond. Additional ensuite bedrooms and flexible living spaces provide exceptional comfort for family and guests. Designed for an elevated indoor-outdoor lifestyle, the estate is surrounded by sweeping lawns ideal for grand-scale outdoor entertaining, garden parties, and relaxed afternoons in the countryside. Expansive decks overlook a tranquil spring-fed pond, while the resort-inspired pool area, complete with cabana, bar, and bath, evokes the atmosphere of a private countryside club. Every detail has been curated for comfort and convenience, from whole-house generators serving both residences and a heated two-car garage to integrated Sonos audio, security systems, advanced climate control, and state-of-the-art connectivity. Enhancing the estate is a beautifully renovated and completely independent two-bedroom guest cottage. Featuring its own kitchen, fireplace, lofted living area, utilities, and septic system, it offers luxurious accommodations for guests, extended family, staff, or a private home office. Rarely does a property combine such privacy, sophistication, and natural beauty. One of Quaker Hill's most compelling offerings, this remarkable estate is a turnkey country sanctuary where sweeping lawns, resort-caliber amenities, and timeless elegance create an unparalleled retreat.

41 and 43 Meeting House Road, Pawling
$2,750,000
3 Beds ⋅ 4 Baths ⋅ 987569 MLS
Milan Hall Farm circa 1750 Truly exceptional. Completely private. Set across 87 acres of open field and quiet forest, Milan Hall Farm unfolds as a rare Hudson Valley offering—where land, history, and thoughtful stewardship meet. A winding stream and natural waterfall trace the landscape, alongside a private 1.3-mile walking trail through the woods, all bordered by enduring stone walls that speak to the property's agricultural past. Protected under conservation easement with the Winnakee Land Trust and New York State forestry program, the land offers both privacy and permanence. The farmhouse, dating to the mid-18th century, has been carefully expanded to accommodate modern living while honoring its origins. Three bedrooms, each with en-suite baths, are complemented by a light-filled conservatory, a quiet library, and multiple gathering spaces anchored by wood-burning stoves. A broad porch overlooks the gardens, while bluestone patios extend living outdoors. The grounds are meticulously maintained, with layered gardens, mature plantings, and curated outdoor spaces throughout. A separate guest cottage, complete with a full kitchen, one bedroom, bath, sitting area, and wood-burning stove, provides a welcoming retreat for extended stays or visiting family and friends. Further enhancing the estate is a thoughtfully designated three-acre building envelope within the Conservation Easement, offering the rare opportunity to add complementary structures such as an accessory dwelling, swimming pool, pool house, studio, sheds, or other accessory buildings. Existing improvements also present opportunities for thoughtful expansion and adaptation, whether by enhancing the guest cottage, exploring the potential for additional space above the existing two-car garage (subject to approvals), reimagining the historic barn, or creating additional living, work, or wellness spaces. Together, these possibilities allow the estate to evolve over time while preserving its extraordinary privacy and the integrity of the surrounding landscape. The beautifully preserved 1853 post-and-beam barn, equipped with electric and water, presents endless possibilities as a studio, workshop, or future living space. Additional outbuildings, including a two-car garage, support both function and form. Modern amenities—including solar power, central air, and a whole-house generator—blend seamlessly with the home's historic character, bringing comfort and efficiency to everyday living. Just minutes from Rhinebeck Village, Amtrak, and some of the Hudson Valley's most celebrated restaurants, boutiques, and cultural destinations, Milan Hall Farm feels worlds away while remaining remarkably convenient.

457 Round Lake Road, Rhinebeck
$550,000
987492 MLS
85 Main Street Poughkeepsie is a unique opportunity to purchase a rented single-tenant restaurant/bar building PLUS the business assets, if desired. SOLD SEPARATELY OR AS A PACKAGE. The property is well-positioned for an owner-operator or investor seeking a turnkey hospitality setup with the flexibility to either lease, reposition, or activate immediately. Dual Opportunity Structure (Key Highlight): 1. Real Estate (85 Main Street) - $550,000 ±3,100 SF bar/restaurant building plus full basement Existing infrastructure for food & beverage operations Strong visibility and accessibility along Main Street 2. Operating Pizzeria + Bar (Tenant Business – For Sale) - $150,000 Fully operational pizzeria and bar concept Full commercial kitchen + state-of-the-art pizza oven Established setup with immediate revenue potential

85 Main Street, Poughkeepsie
$1,495,000
987341 MLS ⋅ Millbrook Antiques Mall BLDG.
COMMERCIAL INVESTMENT: MILLBROOK, NY: HUDSON VALLEY: Millbrook Antiques Mall: A rare opportunity to acquire a landmark income-producing property — and a thriving business — on the main street of one of the Hudson Valley’s most coveted villages. This 5,000+ square foot retail building of three levels, established in 1979, sits in the heart of the village of Millbrook. A once-in-a-generation ownership transfer: The Millbrook Antiques Mall will trade hands for the first time in over two decades. Founded in 1979 and anchored on Franklin Avenue — the village’s main commercial corridor — this is not merely real estate, it's an institution. The business enters new ownership fully operational, with immediate rental income, a loyal customer base, and decades of goodwill already in place. Four diversified revenue streams: The business generates steady income from approximately 20 dealer rentals, direct retail sales, consignment operations, and an exclusive franchise as the Hudson Valley’s only certified retailer of Made In cookware — a nationally recognized brand prized for its craftsmanship and performance. This diversified model provides resilience and meaningful upside for an owner-operator or investor. The building: Over 5,000 square feet of retail space across three levels in a distinctive, enduring structure that commands attention on Franklin Avenue. Large display windows, charming period architecture, a new roof and skylights, an attached garage, and a private office — every element reflects careful stewardship. This building has never stopped performing. ~5,000 sq ft of retail space* New roof & skylights* Large display windows* 3 levels* Attached garage* Private office* Storage* Positioned at Millbrook’s next chapter: The property sits steps from the Thorne Building, which is undergoing a landmark renaissance — exterior restoration, interior renovation, and a reimagined landscape — that will transform it into the community’s cultural anchor. The Millbrook Antiques Mall is ideally situated to benefit from the new energy, foot traffic, and visibility this revitalization will bring. https://www.millbrookbennettpark.org/the-project Flexibility: Acquire the property as a turnkey investment — step in and run a proven, cash-flowing operation from day one — or reimagine the space entirely. The building’s scale, visibility, and location make it equally compelling for retail, hospitality, gallery, or mixed-use concepts. Detailed financials, operating history, and projections will be provided to qualified buyers at the due diligence stage. DETAILS: Commercial / Retail* Forced Air Heat* Central AC* Prime Location* Built in 1920* 2 Bathrooms* Revenue Producing Property* Don't miss this once in a generation opportunity at the perfect moment in Millbrook.

3301 Franklin Avenue, Millbrook
$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
$575,000
987031 MLS
A newly subdivided 16+ acre wooded lot 10 minutes from Red Hook Village 15 to Rhinebeck village and 5 miles from Taconic Parkway . Privacy plus driveway in house location staked BOHA in progress and will deliver at closing. Owner will install fill pad for septic. NEWLY SUBDIVIDED SO TAX NUMBER AND TAXES ARE NOT AVILABLE YET .This is a world class lot offering privacy , a wonderful forest and a prime location 5 minutes from Taconic , 10 minutes from Red Hook and 15 minutes to Rhinebeck and Amtrac service at Rhinecliff . NONE NICER

765 Academy Hill Road, Red Hook
$8,600,000
986998 MLS
Set amid rolling fields and protected countryside, Hounds Pond Farm captures the essence of Hudson Valley living. Spanning 342 acres in the scenic Amenia Valley, the land unfolds across open meadows, sweeping vistas, and tranquil views over Round Pond, with the foothills of the Berkshire Mountains rising in the distance. Whether envisioned as a private estate, working farm, or recreational retreat, the property offers exceptional flexibility with 70% open land and multiple prime building sites. A newly renovated three-bedroom cottage provides an immediate foothold while future plans take shape. Located just minutes from Millerton, Silo Ridge, and Metro-North service at Wassaic—and bordering the Harlem Valley Rail Trail—this is a rare opportunity to own a significant piece of one of the region’s most beautiful and enduring landscapes.

156 Sharon Station Road, Amenia
$669,900
4 Beds ⋅ 3 Baths ⋅ 986710 MLS
Large, protective, ancient trees and handcrafted, artisan-made, stone walls beckon you towards this well-built, nearly 200-year-old, classic Red Hook farmhouse. This 4 Bedroom home has 3 full baths and a large bonus sunroom overlooking the yard, perfect as a private guest suite or home office with a designated entrance and full bath. The expansive 10.1-acre parcel boasts a cherry and peach tree, a spring-fed pond, a meandering stream, and acres of private woods to explore and make trails in. There is enough space for horses. Wood beams and historic remnants mark an old barn site near the pond. The unusually large, fully-fenced-in yard has iron fencing and a patio for entertaining, with ample space for a garden and a pool if desired. There are 3 bedrooms upstairs with a bathroom with pocket doors leading to the main bedroom. Laundry is upstairs as well. There is a bedroom on the first floor that could also be used as a den or library with the original hardwood flooring. The main floor has an open kitchen leading to the dining area and opening to the living room. Some of the many upgrades include new renovated bathrooms, a new roof with a warranty as of 2026, reinforced basement and stonework, updated hot-water heater, central-air, a full-house water filtration system, a storage shed that matches the home, and a Janelli security system. This is a genuinely solid home, built to last, on pastoral grounds filled with history and acres to explore. The location is perfectly serene and an ideal refuge, yet 10-minutes to the center of town. Williams Road is arguably one of the most beautiful roads in Red Hook and is quiet enough for long walks, biking, and jogging. Close to Tivoli, Bard, Rhinebeck, and the Taconic.

176 Williams Road, Red Hook
$80,000
985215 MLS
Turnkey, owner-operated deli located on high-visibility Route 55 with approx. 25K+ cars passing daily, offering excellent exposure. Established in 2010, this well-known, family-run business is now available as the owner steps away. Strong, loyal customer base with repeat business and consistent delivery accounts to local banks, offices, and commercial clients. Well-positioned for breakfast and lunch traffic with early opening hours. Low rent of $1,500/month. Includes 4 coolers, fully equipped kitchen, and basement storage. All equipment included. Open Monday–Saturday (closed Sunday). Confidential sale. Please do not visit without an appointment.

Poughkeepsie
$1,295,000
4 Beds ⋅ 4 Baths ⋅ 986634 MLS
**TO BE BUILT** Welcome to The Woodlands at Hyde Park, an enclave of 20 elite homes, built by a local, well known custom home builder. All lots offer a private and bucolic setting ranging from 1 to 5+ acres. Lot 14 features the Payton Model. A Modern Farmhouse situated on over 2 acres of privacy, primary first floor en suite, 3400+ finished SQFT, 4 bedrooms, 3.5 baths, an office, loft and 260 SQFT unfinished bonus room for future gym/play room/flex space! With hardwood floors throughout the common areas, 9’ ceilings in the main level, 11’ ceilings in the great room and an open concept layout. The modern kitchen with an oversized island and walk in pantry boasts plenty of space, open to the dining area and living room. The expansive primary ensuite features walk-in closet, dual sinks, custom shower, soaking tub and tons of windows allowing ample natural light. Upstairs features a princess suite with walk-in closet, Jack & Jill bath and loft area. Two car attached front load garage and full walk out basement with 8' ceilings and full sized windows allowing tons of room for future expansion! Excellent location right in the heart of historic Hyde Park, minutes to the Culinary Institute of America, Marist College, The Walkway over the Hudson, Poughkeepsie Train Station, Village of Rhinebeck and 85 miles to Manhattan! Come build your dream home today! **PHOTOS SHOWN ARE RENDERINGS AND SIMILAR MODELS BUILT WITH OPTIONS**

14 Bear Hollow Lane, Hyde Park

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