97 properties for sale in Upper Red Hook

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This Adorable 1950's Cottage Style Ranch located in the Barclay Heights Area of Saugerties welcomes you with a covered front porch perfect for the morning coffee or winding down in the evening. There are also some original mid-century details including the front door, kitchen and a curved archway. This home has been well loved by its current owners, and some of the updates include a newer roof, high efficiency boiler and 200 Amp electric panel, all installed in approx. 2018. There is wood flooring and newer kitchen appliances as well. The lower level has a nice sized family room/home office, laundry area and a guest room. A spacious fenced backyard with a patio area is nice and private and there is plenty of room for gardening, gathering, pets and play. Just move right into this Sweet Home on a low traveled dead-end road that is minutes to everything. The Saugerties Village, Woodstock Town Center and Historic Kingston are all close by for shopping and wonderful restaurants. 2 hours out

A true mid-century time capsule, 17 Chamberlain Hill Road is a rare opportunity to own a piece of Red Hook history. Built in 1956, this thoughtfully preserved ranch has been held by the same owner since its completion and retains the details that make its era so enduring: original redwood paneling, warm oak floors, birch cabinetry, and western-facing windows that welcome the afternoon light. Set on. 69 acres along a private dead-end road, the property has a quiet, established feel. Its history is closely tied to the Red Hook community, where the original owners spent decades, including years teaching in the Red Hook School District. The grounds are just as special, with thoughtfully established plantings that bring color and interest throughout the seasons. A kousa dogwood welcomes you at the driveway, with a redbud, flowering crabapple, and weigela adding to the landscape. In the backyard, a large pink azalea, an impressive hydrangea, and established perennial gardens create a lovely

A true mid-century time capsule, 17 Chamberlain Hill Road is a rare opportunity to own a piece of Red Hook history. Built in 1956, this thoughtfully preserved ranch has been held by the same owner since its completion and retains the details that make its era so enduring: original redwood paneling, warm oak floors, birch cabinetry, and western-facing windows that welcome the afternoon light. Set on. 69 acres along a private dead-end road, the property has a quiet, established feel. Its history is closely tied to the Red Hook community, where the original owners spent decades, including years teaching in the Red Hook School District. The grounds are just as special, with thoughtfully established plantings that bring color and interest throughout the seasons. A kousa dogwood welcomes you at the driveway, with a redbud, flowering crabapple, and weigela adding to the landscape. In the backyard, a large pink azalea, an impressive hydrangea, and established perennial gardens create a lovely

Set on a sunny corner lot in the heart of Red Hook Village, just moments from its charming shops, cafes, and restaurants, this inviting 1900 home has a character all its own. Natural light pours through the windows throughout the day, illuminating warm, welcoming interiors and the thoughtful details that make the home so appealing. A bright and welcoming entry leads into an elegant parlor, where crown molding adds a lovely architectural detail. From here, the home opens into a generously proportioned kitchen and dining room, a wonderful space for cooking, entertaining, and everyday living. Hardwood floors, exposed brick, and abundant cabinetry lend texture and warmth, creating an atmosphere that feels both comfortable and full of charm. Upstairs, three bedrooms and a full bathroom offer peaceful, light-filled spaces, while the partially finished walk-out lower level provides an additional half bathroom and flexibility for a home office, creative studio, or recreation room. Outside, a c

Bring your vision to this sweet two-bedroom home in the Village of Saugerties. Set on an extra-large lot in a wonderful neighborhood, it features wood floors throughout, an eat-in kitchen, and a one-car garage. The generous yard offers room for gardening, gathering, or simply enjoying a little extra green space. Ready for your updates and personal touches, this home has good bones and offers a lovely opportunity to make it your own. A mere mile into the center of Saugerties to enjoy great shops and local restaurants

Welcome to affordable living. Whether you are a first time home buyer or looking to downsize. Spacious living room with eat in kitchen. Complete with 3 bedrooms and 2 bathrooms. Central Air. Lot rent is 605.00 a month. Buyer must be approved by park management

Charming 1940 Home Near Red Hook Village Full of character and original architectural details, this move-in-ready 1940 Sears home offers 3 bedrooms, 1 bath, and 1,792 square feet of living space flooded with natural light, including a flexible rear extension. Hardwood floors, wood trim, and timeless details add warmth and charm throughout, while modern amenities like an EV charger and mini-split heat/cooling systems provide upgraded functionality. House is wired for both fiber and cable internet. Minutes from charming Red Hook Village, the Taconic Parkway, and Bard College, the location marries convenience with expansive outdoor space. Set on a level. 86-acre parcel, the property features a detached two-car garage and a wonderful outdoor retreat with a 16’ x 32’ in-ground pool, an inviting cabana, and a beautifully upgraded pool patio completed in fall 2025. The back porch and firepit provide opportunities to relax and entertain, and the yard features garden beds and a fence. Mature oa

A Modern Retreat in The Hudson Valley. Tucked away on six secluded and lightly wooded acres, this architect designed mid-century style home is a study in light and space. With a deep connection to the natural landscape, the project was conceived and constructed in 2025 by the architectural and build firm Upstate Modernist. Offering an elegant and open floor plan, the house centers on a striking and exposed floating staircase. 16 foot ceilings and large expanses of glass flood abundant sunlight deep into the interiors. The public and private rooms are all wonderfully scaled and designed to emphasize an effortless flow and sequencing. Outside, a stunning in-ground swimming pool with adjacent outdoor shower and changing room is perfectly set within a handsome stone terrace. The surrounding lawn, grounds and trees are a natural extension of the house and provide an invitation to enjoy the beautiful and blended grounds. With distinctive architecture, thoughtful design, and a peaceful settin

Set just steps from the center of Tivoli, 16-18 Broadway is a rare village compound comprising two complete residences, a heated saltwater pool and a remarkable level of craftsmanship throughout. It offers something particularly unusual for one of the Hudson Valley's most charming small villages: the flexibility and privacy of a country property, with the restaurants, shops and everyday life of Tivoli just outside the door. The 2,170-square-foot main house offers three bedrooms and two-and-a-half baths and has been thoughtfully renovated by a master carpenter, whose work can be felt throughout. Handmade wood windows, beautifully executed plaster walls and ceilings, wide-plank floors and original details give the interiors a quiet, elemental quality. The renovation is restrained, preserving the age and character of the house while introducing a new kitchen and baths and thoughtfully updated systems. Rooms are simple, warm and filled with natural light, with old wood, softly textured pla

Welcome to 118 Hudson Street, a beautifully appointed home with views of the Hudson River, and moments from the charm of Saugerties Village, Kingston, and the highly anticipated Soho Farmhouse Hudson Valley in Rhinebeck slated to open in 2028. Built in 2004, this spacious residence offers approximately 2,700 square feet of living space, with 4 bedrooms and 3.5 bathrooms, creating an inviting setting for comfortable everyday living and entertaining; or a profitable investment property (annual revenue available upon request). Renovations and interiors were custom designed by a local interior decorator with no detail overlooked. Stunning chef's kitchen with a Viking range, beautiful custom kitchen island, and walk-in pantry are some highlights. The living room features double height ceilings, views of the Hudson River, and goregous gas fireplace. The real showstopper is the landscaped and completely fenced in backyard with a heated inground pool, lounge seating, outdoor dining, hot tub, a

In Saugerties, where the Esopus Creek winds through the Hudson Valley and the Catskill Mountains rise in the distance, a new chapter unfolds. Eleven handcrafted townhomes rise along the creek, each built from the land itself. Local timber milled on site, stone from nearby quarries, and mantels carved from reclaimed barn beams. Local builder John Mullen & Sons, longtime valley neighbors, honors the region's heritage in every detail. From wood floors milled from Saugerties trees to weathered stone foundations. Ensuring no two homes are alike. These creekside row houses weave a narrative of authenticity and craftsmanship, inviting residents to become part of a story as enduring as the mountains and as timeless as the creek

Classic Split Level Barclay Heights three bedroom, 1.5 bath home in Saugerties. First time on the market since the home was built in 1958. Hardwood floors in the living room with high ceilings and bay window. Eat in kitchen with butcher block counter and new gas range. Three bedrooms, all with hardwood floors and a full bathroom located upstairs. Second living room, half bath with laundry and den on lower level. Three season room with skylights lead to the fully fenced in backyard. Well maintained lawn and gorgeous maple tree adorn the front yard. One car detached garage and shed for storage. Walking distance to the Esopus Bend Nature Preserve. Minutes to the Village of Saugerties and a short drive into Kingston

Welcome to Madalin Estate, a 79-acre compound across three parcels at the end of a private dead-end gravel road in Clermont, just minutes from the village of Tivoli, with 500 feet of frontage along the Roeliff Jansen Kill. At its heart is a sun-filled 1960 contemporary, a 3,370-square-foot home with five bedrooms and three baths. A 70-foot heated in-ground pool sits low in the meadow, a deep spring-fed pond is stocked with largemouth bass, and a grove of more than 100 dogwoods blooms each spring. A separate two-bedroom, one-bath cottage stands on a neighboring parcel beside the pond. The three tax parcels include 26.20 acres with the main house, 19.13 acres with the cottage and pond, and 33.67 acres of mature hardwood forest. Clean, light-colored walls, sloping rooflines, and a tall sculptural chimney give the main house a distinctly modern look. A curved wall encloses the front courtyard, where an outdoor fireplace is built into the base of the chimney, and leads to a deeply recessed

Note that the list price is NOT indicative of the seller's final reserve amount; it is just the starting auction bid amount*. This 2345 SF ranch home sits on an 1.32 acre lot. This property is eligible under the Freddie Mac First Look Initiative through 10/27/2026. It is sold only to owner-occupants, non-profit organizations, and government entities during the First Look period. This property is part of an online bidding event; please visit the Auction company's website to place a bid and contact your real estate agent for auction bidding instructions. Inspections of this property and contact with occupants are strictly prohibited. Property is sold'as is' with NO interior access and no'for sale' sign allowed. Cash offers only! The seller will not complete any repairs to the property. *Agents. See private remarks for offer presentation instructions

Built in 2019 and privately situated on 3.1 picturesque acres, this beautifully appointed 3-bedroom, 2.5-bath home offers an exceptional blend of modern comfort and Hudson Valley country living, just minutes from Red Hook Village. Offering an expansive floor plan with an inviting interior features soaring vaulted ceilings, abundant natural light, warm wood accents, and an open-concept design. The spacious kitchen with center island flows seamlessly into the main living area, ideal for everyday living and entertaining. A finished lower level provides additional versatile space, while an expansive patio extends the living area outdoors. The beautifully landscaped grounds offer a private retreat complete with an inground pool, charming heart-shaped pond, sweeping lawns, and mature trees. This retreat like property also features an oversized detached garage with loft providing exceptional flexibility for storage, hobbies, or workshop use. Enjoy convenient access to Red Hook’s charming shop

Set along a quiet country road in a breathtaking part of the Hudson Valley just minutes from Rhinebeck Village, one arrives at Sylvan Rock, the first single family compound designed and built by Aston Martin in collaboration with S3 Architecture and one of the most exciting and sophisticated modernist estates ever built in the Hudson Valley. Reached via a gated, 2,000-foot-long driveway that winds through mature trees, natural rock outcroppings and Revolutionary-era stone walls, the property unfolds onto a dramatic and secluded luxury retreat. With a sense of tranquility combined with unparalleled design & craftsmanship, one is immediately struck by the jagged edges of the roofline, the black cedar facade, floor-to-ceiling glazing and the cantilevered primary suite. Centered on 55 incredible acres, the 7,773 square foot main residence rises like a dramatic geological rock formation, perfectly blending a modern aesthetic with its rural location and connection to nature to create a uniqu

Discover the potential of this charming 1940 mid century home nestled on a 15.82 acre parcel with lots of mature trees & gardens. This house has 3 Bedrooms 3 bathrooms and a detached garage. This property is a rare opportunity to restore a home rich in character while enjoying an extraordinary natural setting. Step inside to find wood moldings, and large rooms, the perfect canvas for creating something special. The enchanting trees and gardens and fenced in yard offer a space for peaceful outdoor living. Bring your imagination and discover the charm this Red Hook gem has to offer

Village of Red Hook home is located in Red Hook Estates. This property is situated with a private back yard that has a deck that wraps around to the backyard. Perfect for all your barbeques and the yard is ideal for all your outside activities. This home is well maintained and has updated appliances and updated bamboo flooring. The kitchen has a sliding glass door that over looks your back yard. A side door gives you access to the back deck. There are 3 bedrooms that are very spacous with windows that let in lots of bright lights. The bathroom has an updated fixture, sink an toilet. There is a full basement for storage that could be updated for future living space. There is room for a future garage if so desired. The heating is electric and is a hybrid electric hot water heater with a heat pump. There are 18 solar panels on the roof and the system is A 6 KW system. This home in Red Hook is walking distance to many businesses. The village offers many ameinities from garbage pick up to m

Set on a spacious 0.63-acre lot just minutes from the heart of Tivoli Village, this well-maintained 3-bedroom, 2-full-bath ranch offers the rare combination of easy one-level living, a large private yard, and convenient Hudson Valley location. The bright, comfortable interior features an open kitchen and dining area, generous living room, three bedrooms and two full baths, all on one level. A back deck overlooks the expansive fenced yard, with plenty of room for gardening, play, entertaining or simply enjoying the privacy of the property. An attached two-car garage and ample driveway parking add everyday convenience and valuable storage. Public water and sewer, propane heat, and a full attic with pull-down stairs provide additional practical features. Located in the Red Hook Central School District and close to Tivoli's restaurants and shops, Bard College, Kaatsbaan and the Hudson River, with Rhinecliff Amtrak less than 20 minutes away. A wonderful opportunity to enjoy village living w

One of those rare finds that is often sought and seldomly available! This beautifully maintained end-unit townhouse offers the convenience of one-level living with plenty of additional space upstairs. Featuring 3 bedrooms and 2½ baths, this home offers a flexible layout with a first-floor bedroom and full bath, plus two additional bedrooms and a full bath upstairs. The spacious living area features soaring ceilings and a real wood-burning fireplace, creating a warm and inviting space to relax and entertain. The kitchen and dining areas flow easily into the main living space, while the newer carpet and Autumn Cherry laminate flooring add warmth and style throughout. Numerous updates include a new hot water heater and new central A/C. Enjoy the outdoors in the gorgeous, fenced backyard, offering a wonderful private space for relaxing, gardening, entertaining, or simply enjoying the seasons. A 2-car attached garage provides convenience and plenty of storage, and best of all-NO HOA! Munici

Pondside” takes its name from the view that defines it: a broad, beautiful pond framed by open meadow and visible through a wall of sliding glass doors. Set on 4.06 peaceful acres near the end of a private road in Red Hook, this modern country retreat is a place to watch the light move across the water, birds settle into the meadow, and a resident blue heron make its rounds. Koi and carp inhabit the pond, and nature is always just outside the glass. Built in 2021, the thoughtfully designed 1,152-square-foot, 2-bedroom, 2-bath home makes the most of its setting. An open floor plan keeps the focus on the outdoors, with the living, dining, and kitchen areas flowing together against the backdrop of pond and meadow views. The kitchen features granite countertops and an induction range, while concrete floors with radiant in-floor heat lend a clean, understated simplicity throughout. The primary bath offers its own connection to the landscape, with a soaking tub positioned to take in views ac

Twenty-One North Road was built in 1894. For nearly half a century, it was home to its most recent owner, who served for a time as mayor of Tivoli. Its five-color exterior palette, at once playful and understated, was one he chose and painted himself. The vines he tended still run along the wraparound porch, and a mowed path leads through the property to Stony Creek. The house sits on 2.21 acres in the village of Tivoli, with four bedrooms and one-and-a-half baths. Inside, the rooms are gracious without being grand, with floor-to-ceiling windows in the front parlor and two marble mantels, each with its own pattern and ornament. There are wide. And narrow-board floors, pocket doors, built-ins, and other details that reveal themselves as you move through the house. The property runs all the way to Stony Creek and continues onto the far bank, with a mowed path to take you there. At the water's edge, a small cascade runs over stone. Beside the house is a two-story outbuilding with electric

Cape Cod homes can be deceiving-they often look modest from the outside, yet offer surprisingly spacious interiors, and this home is no exception! Designed with family and entertaining in mind, the front living room has been transformed into a welcoming dining room, perfect for enjoying family dinners. The kitchen offers an abundance of cabinetry, a floating island, and additional space for casual dining. Follow the long hallway into the huge family room, featuring a wood-burning fireplace and a heat pump for year-round comfort. From the family room, step into the three-season room, which leads outside to a Trex deck and a fenced-in yard-perfect for relaxing, entertaining, and letting the pups enjoy the outdoors. The home offers four bedrooms total, with two bedrooms on the main level and two upstairs. One of the downstairs bedrooms is currently being used as a home office. And there's still more! The finished basement features a B-Dry system and a dry bar, creating even more flexible

Home Sweet Home! This pretty 3 Bedroom 1 Bath Ranch style located in wonderful, friendly neighborhood is the perfect place if you want easy maintenance and one level living. Very well loved and cared for with; new updates, gleaming hardwood floors, Nice sized Living Room that are flooded with natural light, Country Style Kitchen with access to Deck and Garage. Full Dry Basement allows for future growth. Lovely corner lot with beautiful Silver Maple centerpiece as well as mature landscapes with flowering shrubs. Baby Barn holds all your tools and toys. Minute stroll to Village of Red Hook, Hannaford, Movies, Holy Cow. Quick commute to Rhinebeck and Kingston Rhine cliff Bridge and all things The Hudson Valley offers

With exceptional privacy, scale and location, Hemlock Hill. A sprawling multi-level home with resort style amenities, is tucked away just minutes from the charming town of Rhinebeck, one of the Hudson Valley's top destinations. The 30-acre estate with Catskill Mountain views is designed as the ultimate get away with a heated salt water pool with cascading waterfall, 6 person hot tub with 47 jets, stunning pergola with gas fire pit, stocked pond, hiking trails, and a professional-caliber outdoor kitchen, perfect for large outdoor gatherings. This contemporary estate is accessed via a stone gate with a winding quarter mile long tree lined driveway for privacy and seclusion. The home is perched on a crest to take full advantage of the stunning Catskill Mountain views to the west. Inside you will find nearly 9000 sq. Feet of clean lines and open airy spaces with dramatic soaring ceilings. The home boasts five bedrooms and seven bathrooms. 4 full and 3 half bathrooms. The oversized dining r

Perfect get away to serenity! Charming Rhinebeck Cottage & Modern Updates. Tucked away on a peaceful, wooded hillside at 6 Woods Road, this updated 2-bedroom plus a BONUS room cottage perfectly balances tranquil country living with everyday convenience. Located just 8 minutes from downtown Rhinebeck world-class dining and shops, and a quick 11-minute drive from the Taconic State Parkway, it is an ideal weekend retreat or full-time residence. Step inside to find a beautifully refreshed interior boasting extensive modern updates. The primary bedroom serves as a private sanctuary, complete with its own private deck—the absolute perfect spot to enjoy your morning coffee surrounded by nature. Outside, you'll find plenty of parking for guests. Enjoy the best of the Hudson Valley right from your doorstep!

Amazing property overlooking the Beautiful Hudson River. This could be your Dream Home. It's a Must See. Bright and Spacious 4545 square feet' Built'Eye to Detail' Perfect for entertainment. Whether it's the spa, sauna, hot tub, gym, movie theater or the apartment for extended family/friend stay. Close to all the shops and dining in the Village of Saugerties. Within 30 minutes to Woodstock, Kingston, Commuter Train station, 87 Thruway, Catskill with ski destinations in Windham, Hunter