86 properties for sale in Olivebridge

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

Nestled among the trees and tucked back from the road, this immaculate Olivebridge retreat offers the kind of peace and privacy people move upstate for. Quiet, serene, and thoughtfully updated throughout, the property feels effortlessly welcoming from the moment you arrive. Inside, the home feels bright, comfortable, and incredibly well cared for. Sun pours through the windows, the wood stove adds a cozy touch in colder months, and the entire space has an easy, relaxed flow. Recent upgrades include a whole house generator, new driveway, and numerous improvements throughout, making the home feel completely move in ready. A small private deck off the primary bedroom overlooks the beautiful backyard, the perfect spot for slow mornings, evening wine, or listening to the trees move in the breeze. The expansive yard offers endless potential for a pool, gardens, or outdoor entertaining while still feeling incredibly private. One of the standout features of the property is the impressive 1,600

Set in the quiet, storied hills of West Shokan, 269 Watson Hollow Road offers a rare blend of historic character and natural beauty. Originally constructed in the 1800s as a barn, this distinctive home was thoughtfully relocated across the stream approximately 40 years ago, where it now rests gracefully against the mountain backdrop. 16.5 acres extend to the top of the ridge behind the house. Beyond that is NYC property. Inside, the home showcases its heritage with stunning original chestnut beams-many of which remain structural and weight-bearing-bringing warmth, authenticity, and architectural significance to the living space. A striking chimney, masterfully crafted both inside and out by a local mason, serves as a centerpiece, anchoring the home with timeless craftsmanship. The setting is equally compelling. A pristine, swimmable spring-fed pond invites peaceful afternoons and reflects the surrounding mountain landscape, creating a private retreat-like atmosphere. The property is ac

Offered for the first time in 20 years, this hemlock post-and-beam modern farmhouse is a rare retreat designed for those seeking something far beyond the ordinary. Set on 5.3 acres along a quiet dead-end road, the property offers a remarkable sense of privacy while remaining close to the Ashokan Reservoir, Woodstock, Kingston, and the best of the Catskills. The setting feels peaceful and secluded, with open forest trails, mature trees, and multiple outdoor spaces designed for gathering, relaxing, and enjoying the natural surroundings. The home blends modern loft-style living with the warmth of natural materials. Soaring ceilings, exposed post-and-beam construction, hickory wood floors, and oversized Pella windows create interiors that feel open, bright, and deeply connected to the landscape. A custom steel and bluestone staircase anchors the home with a striking architectural presence, while the changing light throughout the day brings softness and movement to the living spaces. The ki

Tucked into a dramatic rock ridge with sweeping views of the Catskill Mountains, this renovated farmhouse invites you to slow down and savor country living at its finest. Spanning just over 3,000 square feet, the home balances rustic character with thoughtful modern updates throughout. The renovated kitchen, anchored by warm butcher block counters, flows gracefully into a generous dining room. From there, step into the cozy living room, where windows on every side pull the outdoors in. It's the kind of layout that makes both quiet mornings and lively gatherings feel effortless. Upstairs, the primary suite steals the show with spectacular mountain vistas, a walk-in closet, and a beautifully renovated bathroom featuring a soaking tub perfectly positioned to enjoy the view. An additional bedroom and full bath share this level, along with a spacious flex room and sleeping loft ready to serve as a home office, gym, or guest quarters. The finished third-floor attic opens up even more possibi

Welcome to the Delamater-Davis House, a tastefully restored stone home on over 4 acres with a lovely creek in the hamlet of Marbletown. Built circa 1750 and later operated as a tavern on the road from Kingston into the Catskills, this four-bedroom, two-and-a-half-bath residence is one of the Hudson Valley's most significant examples of 18th-century stone architecture. Comprehensively restored from the studs for the first time in over a century, it features five fireplaces, hand-hewn beams, wide-plank floors, and a restored beehive oven. The Stony Kill runs through the property, dropping over a natural waterfall. The sound of the falls drifts through the house. Only 15 minutes to Kingston and two hours to New York City

Affordable Two-Family Opportunity in Shokan! Set on 2 acres with frontage along Route 28, this two-family home is ready for its next chapter. The first-floor unit features 2 bedrooms and 1 bath; the second-floor apartment includes 1 bedroom and 1 bath—ideal for extended family, rental income, or offsetting your mortgage. The property needs renovation, but the potential is real for first-time buyers, handy homeowners, or investors alike. Conveniently located near Woodstock, Phoenicia, and the Ashokan Reservoir, with easy access to hiking, skiing, shops, and dining. Check with the Town of Olive about possible business use

Set in the quiet, storied hills of West Shokan, 269 Watson Hollow Road offers a rare blend of historic character and natural beauty. Originally constructed in the 1800s as a barn, this distinctive home was thoughtfully relocated across the stream approximately 40 years ago, where it now rests gracefully against the mountain backdrop. 16.5 acres extend to the top of the ridge behind the house. Beyond that is NYC property. Inside, the home showcases its heritage with stunning original chestnut beams-many of which remain structural and weight-bearing-bringing warmth, authenticity, and architectural significance to the living space. A striking chimney, masterfully crafted both inside and out by a local mason, serves as a centerpiece, anchoring the home with timeless craftsmanship. The setting is equally compelling. A pristine, swimmable spring-fed pond invites peaceful afternoons and reflects the surrounding mountain landscape, creating a private retreat-like atmosphere. The property is ac

Trade traffic for trails. Replace skyscrapers with towering trees. Swap city lights for star-filled skies. Welcome to 630 Ashokan Road, Marbletown Tucked away on 6.4 wooded acres in the heart of Marbletown, this well maintained, original owner home offers the perfect balance of comfort, privacy, and adventure. With 3 bedrooms, 2 full baths, and 1,792 square feet of living space, this move-in-ready escape is designed for those who appreciate room to breathe. Spend summer afternoons lounging by the swimming pool, entertaining on the large rear patio, and gathering around the fire pit as the stars emerge overhead. Inside, the spacious layout and enormous full basement provide endless possibilities for storage, hobbies, a workshop, recreation space, or future expansion. The massive garage provides plenty of room for all your outdoor toys. Whether you're escaping the pace of New York City for weekends in the country or searching for a place where hunting season, hiking boots, ATVs, and camp

You'll understand just how special this 41 Acre property is once you arrive. Just driving down the country road to get here is already a treat. Situated at the base of the majestic High Point Mountain you'll find a private driveway that takes you through a beautiful forest and then it opens up to acres of your own open farmlands. The open fields are perfectly suited to horses and with an amazing newly painted Gambrel Roof Horse Barn, you can move them right in and start enjoying every aspect of country life. The peaceful feeling this private property gives is unmatched. The home is nestled perfectly along the woodlands with great views of the open fields. Watch your horses, cows or goats grazing or just relax on the open front porch and breath in all the fresh air! The home has been very well maintained and features a charming stone fireplace, pretty solid wood six panel doors, a kitchen with multiple wood cabinets including an integrated pantry, Corian countertops, a gas stove and pen

Your storybook ending begins now. Tucked away on 2.3 private acres in Stone Ridge, this spirited 1980s passive home, three bedrooms, two baths, 2,037 square feet, strikes a balance that's increasingly hard to find: genuinely charming without trying too hard, and quietly stylish in every detail. Fully enclosed by fencing, the grounds are yours to claim completely, a haven for gardens cultivated over many years, for four-legged companions to roam freely and everyone to exhale. The first floor opens with intention. A mudroom and three-season storage room ease you in, a small but meaningful buffer between the world outside and the life within. Beyond it, the main level unfolds with a rare sense of spatial intelligence with distinct zones that breathe independently without ever losing their conversation with one another. A flexible front room currently serves as a home office, though it wears its versatility openly: reading room, yoga studio, creative den. The living room anchors the heart

Low-Tax Olive Haven Set on 6.5 picturesque, quiet acres with the Shawangunk Ridge rising to the east, this beautifully renovated 18th century farmhouse feels like the place you've been looking for. Wide board floors, post and beam construction. The chef's kitchen includes a center island for prep and conversation, a dining table ready for long Sunday breakfasts, game night, or entertaining guests. The heart of the home is the great room, where picture windows flood the space with light and a woodstove waits for the first cold snap. On the third floor, a light-filled loft becomes whatever you need: a yoga studio, a home gym, or the writing retreat you've always wanted. With amazing views that make it hard to leave. The updates are already done for you: a new roof in 2018 with 50-year shingles, a new septic system in 2015, and mini-splits that handle heating and cooling year-round. Living in Olivebridge means having the best of the Hudson Valley right outside your door. Everyday errands

Motivated Seller*. Tucked away on a quiet dead-end road, this charming 3-bedroom, 2-bath ranch offers peaceful living on over 3 private acres. Built in 2005, the home features convenient one-level living with a well-designed layout, including central living spaces, a spacious primary suite with walk-in closet and private bath, and two additional bedrooms with a full guest bath. The kitchen provides ample cabinet space, dishwasher, and a convenient washer/dryer closet with access to the back deck. Enjoy the tranquil setting surrounded by nature, where wildlife sightings are a regular part of the landscape. The walk-out unfinished basement offers excellent potential for additional living space such as a media room, home office, or gym, and includes access to the one-car drive-under garage. Ideally located in the heart of the Catskills, this home offers the perfect balance of privacy and convenience. Enjoy being just 6 miles from the Ashokan Reservoir and only minutes from scenic hiking t

This charming cottage in Olivebridge NY proves that great things really do come in small packages. Thoughtfully designed for easy living, it's the kind of home that lets you spend less time maintaining and more time enjoying everything the Hudson Valley has to offer. Inside, warm and inviting spaces feel instantly welcoming, while an airy loft provides the perfect spot for a home office, creative studio, or cozy reading nook. Whether you're working remotely or simply looking for a quiet place to unwind, this home offers just the right amount of space and versatility. Outside, the beautifully established gardens create a private retreat that bursts with seasonal color, offering plenty of room to relax, entertain, or indulge your green thumb. Set on an easy-to-manage 1.3-acre lot with low property taxes, this is a home that's as practical as it is charming. Whether you're searching for a full-time residence, a weekend escape, or a low-maintenance country retreat, this magical home offers

203 Watson Hollow Road is a Creekside Gem Close to Woodstock, NY. A beautiful and impeccably maintained single-family home tucked away on a quiet road near the Ashokan Reservoir includes three bedrooms and one bathroom. The property is a tranquil paradise for outdoor enthusiasts. The gorgeous creek flows year-round and is surrounded by lovely trees and foliage. This exceptional cottage residence is warm and inviting with two wood-burning fireplaces. A stone, wood-burning fireplace is in the living room and another wood burning fireplace in the primary bedroom. A delightful sunroom is ready for entertaining, or reading your favorite book. The kitchen has all the appliances you will need for home cooking. A dishwasher can be added, if desired. There is a washer and dryer, the heating source is propane and central air conditioning was added in 2026, The roof is also new. Effortless convenience to Woodstock, Kingston, and the NY State Thruway makes this dream home in the Hudson Valley the

This charming Olivebridge cottage on a full acre is ideal as both a peaceful full-time residence or a perfect weekend escape. Step out onto the rear deck, which overlooks a serene, private green haven complete with its own organic garden. In the winter months, enjoy lovely seasonal views of Ashokan High Point. Conveniently located just minutes from the Ashokan Reservoir, the Ashokan Quarry Trail, and Tetta's Market, this inviting retreat has had a number of thoughtful upgrades. Come experience the best of upstate living in a prime location

There is something instantly comforting about this home. Warm, welcoming, and lovingly maintained, it offers the kind of easy living that never goes out of style. Whether gathering around the fireplace with friends, enjoying a quiet morning coffee, or unwinding after a long day, every space feels inviting, functional, and meant to be lived in. Set amidst peaceful natural surroundings with views across an open meadow, the property offers a sense of calm. A welcoming front porch invites you to slow down and savor the changing seasons, while the charming gazebo creates the perfect setting for outdoor dining, afternoon reading, or evenings spent enjoying the fresh country air. Offering approximately 1,900 square feet of living space, the interiors balance warmth with practicality. Engineered cherry floors flow throughout the main level, where radiant heat beneath your feet and a wood burning fireplace with electric fan create comfort in every season. Large Andersen double-pane windows fram

Tucked away on a sleepy country road, this gut-renovated and completely re-imagined 1930s retreat offers the perfect blend of privacy, natural beauty, and modern comfort. The main house is defined by a copious amount of windows and skylights which drenches the home in natural light and creates a perpetual connection to the outdoors. The kitchen boasts new appliances, soapstone counters and a pantry with custom shelving. It's a study in clean lines with massive picture windows that stare out to one of the many gardens. The open floor plan includes a dining nook and a large high-ceilinged living room anchored by a wood stove. Three ensuite bedrooms, with heated bathroom floors sit in separate areas of the home offering peaceful and private sleeping quarters. A spectacular sunroom complete with slate floors and stone walls offers flex space that can serve as an additional dining area, lounge space or a home office. Above the detached two-car garage, a stylish guest studio provides a self-

Set in the quiet, storied hills of West Shokan, 269 Watson Hollow Road offers a rare blend of historic character and natural beauty. Originally constructed in the 1800s as a barn, this distinctive home was thoughtfully relocated across the stream approximately 40 years ago, where it now rests gracefully against the mountain backdrop. 16.5 acres extend to the top of the ridge behind the house. Beyond that is NYC property. Inside, the home showcases its heritage with stunning original chestnut beams-many of which remain structural and weight-bearing-bringing warmth, authenticity, and architectural significance to the living space. A striking chimney, masterfully crafted both inside and out by a local mason, serves as a centerpiece, anchoring the home with timeless craftsmanship. The setting is equally compelling. A pristine, swimmable spring-fed pond invites peaceful afternoons and reflects the surrounding mountain landscape, creating a private retreat-like atmosphere. The property is ac

Tucked into a dramatic rock ridge with sweeping views of the Catskill Mountains, this renovated farmhouse invites you to slow down and savor country living at its finest. Spanning just over 3,000 square feet, the home balances rustic character with thoughtful modern updates throughout. The renovated kitchen, anchored by warm butcher block counters, flows gracefully into a generous dining room. From there, step into the cozy living room, where windows on every side pull the outdoors in. It's the kind of layout that makes both quiet mornings and lively gatherings feel effortless. Upstairs, the primary suite steals the show with spectacular mountain vistas, a walk-in closet, and a beautifully renovated bathroom featuring a soaking tub perfectly positioned to enjoy the view. An additional bedroom and full bath share this level, along with a spacious flex room and sleeping loft ready to serve as a home office, gym, or guest quarters. The finished third-floor attic opens up even more possibi

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

Welcome to Galloway House, a circa 1924 Craftsman residence set well back from the road on a corner acre in the historic hamlet of Stone Ridge, with sweeping lawns, mature flowering trees, and far-reaching views of the Shawangunks. Tucked along one of the areas most beloved country roads, this classic home offers a sense of quiet privacy just minutes from the heart of town, with an original bluestone front porch that sets the tone for whats to come.The interior is warm and beautifully proportioned, with hardwood floors, high ceilings, and preserved period details throughout. The living room is anchored by a working gas fireplace with an adjoining nook suited to a library or home office. A sunlit dining room with a built-in window seat creates an easy setting for long meals and quiet mornings.The kitchen connects naturally to an expansive rear deck with pergola, making indoor and outdoor living feel continuous across the warmer months, with a well-placed half bath just off the kitchRefe

Set on a quiet street in one of Marbletown's most desirable areas, this well-maintained rustic ranch offers a rare opportunity to create your ideal Hudson Valley escape. Just two hours from NYC, the home is perfectly suited as a weekend getaway, full-time residence, or investment property.Inside, the one-level layout features two bedrooms and one full bath, along with a comfortable living area anchored by a wood-burning stove. A bright sunroom addition provides the perfect spot to relax year-round, bringing in natural light and views of the surrounding landscape.The property has been lovingly cared for by the same family for over forty years and is ready for its next chapter, offering a solid foundation with room to personalize and make your own. A detached garage adds convenience and additional storage.Ideally located just minutes to Stone Ridge, under 15 minutes to Uptown Kingston and High Falls, and 30 minutes to New Paltz. Spend your days exploring nearby favorites likeReference: 3