101 properties for sale in Ashokan

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 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

Tucked down a long driveway on 4.3 private, wooded acres, just outside Woodstock, this thoughtfully designed contemporary home offers the rare combination of true seclusion and effortless livability. Built with a post and beam, passive solar design, the home was constructed to work with its surroundings. Inside, 1,852 square feet are laid out across two comfortable levels, with 3 bedrooms and 2.5 baths. Both full baths were newly renovated this year. Heated floors run throughout both levels, keeping the home warm and quiet through every Catskills winter, while a cozy fireplace anchors the main living space. The eat-in chef's kitchen is a standout: a commercial Thermador range and hood, a wall-size Thermador refrigerator, a Thermador dishwasher and trash compactor make it as functional for everyday life as it is for entertaining. Every bathroom is outfitted with a TOTO heated bidet toilet and heated floors. The basement adds flexible living space, recreation space or storage. Fresh pain

Tucked down a long driveway on 4.3 private, wooded acres, just outside Woodstock, this thoughtfully designed contemporary home offers the rare combination of true seclusion and effortless livability. Built with a post and beam, passive solar design, the home was constructed to work with its surroundings. Inside, 1,852 square feet are laid out across two comfortable levels, with 3 bedrooms and 2.5 baths. Both full baths were newly renovated this year. Heated floors run throughout both levels, keeping the home warm and quiet through every Catskills winter, while a cozy fireplace anchors the main living space. The eat-in chef's kitchen is a standout: a commercial Thermador range and hood, a wall-size Thermador refrigerator, a Thermador dishwasher and trash compactor make it as functional for everyday life as it is for entertaining. Every bathroom is outfitted with a TOTO heated bidet toilet and heated floors. The basement adds flexible living space, recreation space or storage. Fresh pain

Move right into this beautifully maintained country home, thoughtfully designed with a modern open concept floor plan that is ideal for both comfortable everyday living and effortless entertaining. The custom kitchen features rich cherry cabinetry, quartz countertops which seamlessly flows into the dining area, where sliding glass doors open to a spacious deck, as well as the inviting living room with a cozy fireplace with a gas insert. Just a few steps upstairs you'll find three generously sized bedrooms, full bath and sliding doors in the primary bedroom leading to a private upper deck overlooking the garden and back yard. The bright spacious recreation room, located just a few steps below the main level, offers large windows that fill the space with natural light, a warm pellet stove and plenty of room for casual gatherings, a home office or workout area. This level also includes a bath with washer and dryer for added convenience. Upgrades include central air, security system, whole

Set on more than nine private acres just minutes from the heart of Woodstock, this elegant sprawling ranch is a rare offering where the views take center stage. Thoughtfully designed in the spirit of 1960s contemporary architecture, the home was created to celebrate its extraordinary natural setting, with sweeping vistas enjoyed from nearly every room. A substantial spring-fed pond, serene pine forest, and dramatic 180-degree Catskill Mountains views create a setting that is both tranquil and unforgettable. The open floor plan enhances the home's effortless flow and inviting, inclusive style of living. A dramatic screened porch with cathedral ceilings, along with an expansive wood deck, offers exceptional spaces for outdoor dining, entertaining, or simply taking in the surrounding beauty. Inside, a bluestone fireplace anchors the living room, while a curved glass wall, dining area, eat-in kitchen with skylight, and breakfast bar all contribute to the home's warmth, comfort, and easy li

Set on more than nine private acres just minutes from the heart of Woodstock, this elegant sprawling ranch is a rare offering where the views take center stage. Thoughtfully designed in the spirit of 1960s contemporary architecture, the home was created to celebrate its extraordinary natural setting, with sweeping vistas enjoyed from nearly every room. A substantial spring-fed pond, serene pine forest, and dramatic 180-degree Catskill Mountains views create a setting that is both tranquil and unforgettable. The open floor plan enhances the home's effortless flow and inviting, inclusive style of living. A dramatic screened porch with cathedral ceilings, along with an expansive wood deck, offers exceptional spaces for outdoor dining, entertaining, or simply taking in the surrounding beauty. Inside, a bluestone fireplace anchors the living room, while a curved glass wall, dining area, eat-in kitchen with skylight, and breakfast bar all contribute to the home's warmth, comfort, and easy li

Hidden along one of Woodstock's most coveted country roads, in the area locals call Rainbow Hill, is a remarkably intact Mid-Century Modern home, one that rarely comes to market. Set on 3.67 private acres, less than two miles from the heart of Woodstock, the property has been the cherished home of a renowned artist and his wife for the past 28 years and is now offered to its next discerning steward. Thoughtfully sited within the landscape, the home embodies everything that defines exceptional Mid-Century Modern design. Walls of glass and expansive sliding doors dissolve the boundary between indoors and out, flooding the interiors with natural light and maintaining a constant connection to the surrounding woods and gardens. Much of the home's original character remains beautifully intact. Marble floors, teak-paneled walls, custom built-ins, and a monumental bluestone fireplace create interiors that feel both sophisticated and deeply authentic. The original kitchen is a true design state

Dear buyer, I want you to know the story of this house. My family bought it three years ago and we did a total renovation to all the bathrooms and kitchen with new appliances and tile and all new fixtures. We also changed the back of the house and opened it up with a huge dormer facing the mountain since before the main view was to the expansive side meadow. We thought this was going to be our forever home so we put all the best we could into it and added mini splits throughout the house for Heating And Cooling, an on-demand hot water heater, a backup generator that comes on automatically as well as a standalone propane fireplace in case we want to look at a fire while watching TV. We also put in lots of landscaping and out door statues made by local carver extraordinaire Hoppy Quick. What we loved about the house (using past tense since we need to detach:) was that the original owner took so much time and care to build it (from 2015 to 2021) and put in many raw live edge wood features

Hidden along one of Woodstock's most coveted country roads, in the area locals call Rainbow Hill, is a remarkably intact Mid-Century Modern home, one that rarely comes to market. Set on 3.67 private acres, less than two miles from the heart of Woodstock, the property has been the cherished home of a renowned artist and his wife for the past 28 years and is now offered to its next discerning steward. Thoughtfully sited within the landscape, the home embodies everything that defines exceptional Mid-Century Modern design. Walls of glass and expansive sliding doors dissolve the boundary between indoors and out, flooding the interiors with natural light and maintaining a constant connection to the surrounding woods and gardens. Much of the home's original character remains beautifully intact. Marble floors, teak-paneled walls, custom built-ins, and a monumental bluestone fireplace create interiors that feel both sophisticated and deeply authentic. The original kitchen is a true design state

Dear buyer, I want you to know the story of this house. My family bought it three years ago and we did a total renovation to all the bathrooms and kitchen with new appliances and tile and all new fixtures. We also changed the back of the house and opened it up with a huge dormer facing the mountain since before the main view was to the expansive side meadow. We thought this was going to be our forever home so we put all the best we could into it and added mini splits throughout the house for Heating And Cooling, an on-demand hot water heater, a backup generator that comes on automatically as well as a standalone propane fireplace in case we want to look at a fire while watching TV. We also put in lots of landscaping and out door statues made by local carver extraordinaire Hoppy Quick. What we loved about the house (using past tense since we need to detach:) was that the original owner took so much time and care to build it (from 2015 to 2021) and put in many raw live edge wood features

A compact, character-filled Hudson Valley retreat just minutes from Woodstock, this newly renovated Cape offers an unconventional two-level layout designed around charm, privacy, and relaxed country living. The 934 sq ft home features wood floors throughout, a cozy wood burning stove, with built-in dining area seating, and a stylish streamlined kitchen with subway tile, copper sink, stainless appliances, and a flexible breakfast bar/workspace. The main level includes a beautifully updated full bath with glass-enclosed shower and a bedroom just off the living area. Upstairs, a spacious wood-paneled primary suite with cathedral ceilings offers a tranquil retreat, complete with a freestanding soaking tub and second bath. A full unfinished basement provides ample storage, washer and dryer, gas furnace installed in 2022, central air conditioning, and a hot water heater installed 3/23. A classic picket fence opens to a sunny tree-lined backyard with fresh landscaping, rear deck with pergola

A compact, character-filled Hudson Valley retreat just minutes from Woodstock, this newly renovated Cape offers an unconventional two-level layout designed around charm, privacy, and relaxed country living. The 934 sq ft home features wood floors throughout, a cozy wood burning stove, with built-in dining area seating, and a stylish streamlined kitchen with subway tile, copper sink, stainless appliances, and a flexible breakfast bar/workspace. The main level includes a beautifully updated full bath with glass-enclosed shower and a bedroom just off the living area. Upstairs, a spacious wood-paneled primary suite with cathedral ceilings offers a tranquil retreat, complete with a freestanding soaking tub and second bath. A full unfinished basement provides ample storage, washer and dryer, gas furnace installed in 2022, central air conditioning, and a hot water heater installed 3/23. A classic picket fence opens to a sunny tree-lined backyard with fresh landscaping, rear deck with pergola

This is a rare find - a recently built home with privacy less than 15 minutes from both Woodstock and Kingston. Built in 2022, this modern home balances thoughtful design with a connection to nature. Every aspect of the home has been done with intention, including its private location nestled in the woods, energy efficient features and open, light-filled spaces. A recently expanded backyard offers space for relaxing and dining outdoors - and potentially a pool. As you approach the house down the tree-lined driveway, you arrive at the perfect modern sanctuary with spacious, open concept living. The kitchen is outfitted with custom cabinets, solid surface countertops, and premium appliances including a Wolf range and Sub Zero refrigerator. The dining area sits next to floor-to-ceiling windows. Custom built-in bookshelves line the walls of the living area with multiple seating areas and a wood burning fireplace. On this floor, you will also find a full bath, an oversized two-car garage wi

This is a rare find - a recently built home with privacy less than 15 minutes from both Woodstock and Kingston. Built in 2022, this modern home balances thoughtful design with a connection to nature. Every aspect of the home has been done with intention, including its private location nestled in the woods, energy efficient features and open, light-filled spaces. A recently expanded backyard offers space for relaxing and dining outdoors - and potentially a pool. As you approach the house down the tree-lined driveway, you arrive at the perfect modern sanctuary with spacious, open concept living. The kitchen is outfitted with custom cabinets, solid surface countertops, and premium appliances including a Wolf range and Sub Zero refrigerator. The dining area sits next to floor-to-ceiling windows. Custom built-in bookshelves line the walls of the living area with multiple seating areas and a wood burning fireplace. On this floor, you will also find a full bath, an oversized two-car garage wi

Prime Income Property Vacant Woodstock 2-Family Opportunity Delivered Vacant-maximize your portfolio's ROI from day one. Savvy investors and owner-occupants, take note: this exceptionally located 2-family property offers immediate cash-flow potential with zero tenant transition hassle. Set your own market-rate rents right away in the high-demand Woodstock Hamlet rental market. The Units: The property consists of two highly rentable 500 sq. ft. studio units, each with an open layout. Inside, you'll find a low-maintenance, tenant-proof blend of warm hardwood and durable ceramic tile flooring. A major tenant draw is the private, south-facing sun porch included with each unit. Investor Advantages From a management perspective, this asset is designed for low overhead and ease of ownership: Infrastructure: Each apartment has separately metered electric. Municipal water and sewer obviate repair and upkeep concerns. Dedicated off street parking. Flexibility: Whether you are looking for a pure

Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in one while renting the other four. Another option is to create a warm and inviting 5-cottage compound for group living. Imagine enjoying the Woodstock lifestyle with loved ones just a door-knock away. For a writer, artist, or home-business owner, perhaps one or more of the cottages could be used as a studio or office separate from home. Cottage 1 is a delightful two bedroom/one bath with a fireplace and Craftsman kitchen. Cottage 2, with one bed and one bath, was reimagined and fully renovated in 2024. Cottage 3 is peak contemporary treehouse: a stunning two bedroom/two bath, featuring dramatic

Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in one while renting the other four. Another option is to create a warm and inviting 5-cottage compound for group living. Imagine enjoying the Woodstock lifestyle with loved ones just a door-knock away. For a writer, artist, or home-business owner, perhaps one or more of the cottages could be used as a studio or office separate from home. Cottage 1 is a delightful two bedroom/one bath with a fireplace and Craftsman kitchen. Cottage 2, with one bed and one bath, was reimagined and fully renovated in 2024. Cottage 3 is peak contemporary treehouse: a stunning two bedroom/two bath, featuring dramatic

Prime Income Property Vacant Woodstock 2-Family Opportunity Delivered Vacant-maximize your portfolio's ROI from day one. Savvy investors and owner-occupants, take note: this exceptionally located 2-family property offers immediate cash-flow potential with zero tenant transition hassle. Set your own market-rate rents right away in the high-demand Woodstock Hamlet rental market. The Units: The property consists of two highly rentable 500 sq. ft. studio units, each with an open layout. Inside, you'll find a low-maintenance, tenant-proof blend of warm hardwood and durable ceramic tile flooring. A major tenant draw is the private, south-facing sun porch included with each unit. Investor Advantages From a management perspective, this asset is designed for low overhead and ease of ownership: Infrastructure: Each apartment has separately metered electric. Municipal water and sewer obviate repair and upkeep concerns. Dedicated off street parking. Flexibility: Whether you are looking for a pure

Move right into this beautifully maintained country home, thoughtfully designed with a modern open concept floor plan that is ideal for both comfortable everyday living and effortless entertaining. The custom kitchen features rich cherry cabinetry, quartz countertops which seamlessly flows into the dining area, where sliding glass doors open to a spacious deck, as well as the inviting living room with a cozy fireplace with a gas insert. Just a few steps upstairs you'll find three generously sized bedrooms, full bath and sliding doors in the primary bedroom leading to a private upper deck overlooking the garden and back yard. The bright spacious recreation room, located just a few steps below the main level, offers large windows that fill the space with natural light, a warm pellet stove and plenty of room for casual gatherings, a home office or workout area. This level also includes a bath with washer and dryer for added convenience. Upgrades include central air, security system, whole

Tucked down a long driveway on 4.3 private, wooded acres, just outside Woodstock, this thoughtfully designed contemporary home offers the rare combination of true seclusion and effortless livability. Built with a post and beam, passive solar design, the home was constructed to work with its surroundings. Inside, 1,852 square feet are laid out across two comfortable levels, with 3 bedrooms and 2.5 baths. Both full baths were newly renovated this year. Heated floors run throughout both levels, keeping the home warm and quiet through every Catskills winter, while a cozy fireplace anchors the main living space. The eat-in chef's kitchen is a standout: a commercial Thermador range and hood, a wall-size Thermador refrigerator, a Thermador dishwasher and trash compactor make it as functional for everyday life as it is for entertaining. Every bathroom is outfitted with a TOTO heated bidet toilet and heated floors. The basement adds flexible living space, recreation space or storage. Fresh pain

Welcome to your own Catskills retreat! This beautifully renovated 2,700-square-foot farmhouse blends timeless charm with modern comfort, offering an inviting escape surrounded by the natural beauty of the Hudson Valley. Step inside to a bright, beautifully updated interior filled with natural light from large windows and thoughtfully designed living spaces. The newer kitchen features gorgeous quartz countertops, making it both stylish and functional-perfect for everything from morning coffee to gathering with family and friends. The warm, inviting living area is anchored by a wood-burning fireplace, creating the perfect cozy atmosphere after a day exploring the mountains. Outside, take in the beautiful mountain views and enjoy the peaceful setting of Shokan. Whether you're looking for a full-time residence, weekend getaway, or investment property, this home offers the ideal combination of comfort, character, and location. And the location is hard to beat! You're close to some of the Ca

Discover the charm of Catskills living at 4192 State Route 28 in Boiceville. This inviting 3-bedroom, 1-bath home is being offered fully furnished, providing a comfortable and move-in-ready opportunity in a beautiful natural setting. The interior features warm and welcoming living spaces highlighted by a wood-burning fireplace, creating a cozy atmosphere for relaxing and entertaining. Step outside and enjoy the patio with fire pit and welcoming porch, surrounded by the peaceful beauty of the Catskills. Conveniently located along Route 28 with easy access to Woodstock, Kingston, hiking trails, outdoor recreation, dining, shopping, and other popular Catskills destinations. Whether you're looking for a full-time residence or a peaceful upstate getaway, this furnished home offers comfort, character, and year-round enjoyment in the heart of the Catskills. The agent has an ownership interest in the property

Where eagles fly and mountains kiss the sky, this beautifully maintained homestead showcases quality craftsmanship and thoughtful upgrades throughout. The property also includes a 1,104 square foot barn that is perfect for equestrians or a studio, workshop, artisan/woodworker or equipment storage. Two overhead garage doors, extended wi-fi service, telephone/paging system and electricity can easily meet your needs. The property features a thriving, fenced vegetable garden with separate well and shed providing the perfect sanctuary for those who value autonomy and sustainability. Additionally, a separate, vibrant flower garden with potting shed, water, electricity and landline phone/inter-property paging system. Picturesque waterfall bubbles into the tranquil pond adding movement and sound. Beautifully constructed pergola w/Timber Tech decking off the rear stone patio. Meticulously maintained home showcases quality workmanship throughout. Handcrafted bookcases and woodwork, elegant ash w

Unique, Exciting, Warm and Inviting. Imagine a long winding driveway into your own private forested acreage with a Storybook Saltbox style home immersed in an abundance of magical perennial gardens and flowering trees enhanced with integrated rock walls, stepping stones and patio and Adirondack style arbors, all uniquely designed by the owner, a master landscaper & builder. All the gardens are eco-friendly, sustainable and encourage people to be kind to the environment. This eclectic charmer was totally transformed with custom woodwork, materials and craftsmanship, much of which was locally sourced. The Owner's renovations focused on green and sustainable building practices with non-VOC finishes, and the gardens are eco-friendly. As you wander through this one-of-a-kind home, you'll notice all the special materials and craftsmanship that give it so much warmth and character but you'll also notice how well the floor plan flows for entertaining or relaxing with family or friends. Upon en

Rare Woodstock multi-family opportunity. Three distinct, fully rented residences on one property, delivering an approximate 8 cap from day one. Just one block from the center of Woodstock, 18 Rock City Road combines an exceptional in-town location with an established income stream and three residences that each offer their own character and appeal. Originally dating to 1890, the property has evolved into a compelling three-unit investment comprising approximately 2,708 square feet, 5 bedrooms, and 5 full baths in total. Unit A is a renovated 1-bedroom, 1-bath residence of approximately 600 square feet with an open layout, expansive windows, modern kitchen and updated finishes. Unit B offers approximately 1,100 square feet with 2 bedrooms and 2 baths, high ceilings, generous living and dining space, an office area, updated kitchen and baths, plus a private patio. Unit C is a separate two-story, approximately 1,008-square-foot carriage house with 2 bedrooms and 2 baths, showcasing pine f

Framed by the mountain landscape of West Shokan, this solid brick ranch offers a practical layout, a beautiful setting, and an inviting opportunity to make each space your own. With three bedrooms, and two bathrooms, the home provides comfortable single-level living with plenty of room. The spacious kitchen offers a natural gathering place for daily meals. Nearby, the dining room features sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor living. Enjoy coffee in the morning air, dinner against a mountain backdrop, or a quiet afternoon taking in the changing seasons. Throughout the home, the existing rooms serve as a blank canvas for your preferred colors, finishes, and furnishings. Three bedrooms allow flexibility for sleeping quarters, guests, an office, or creative space. Two bathrooms add everyday convenience. A full basement with exterior access expands the possibilities. Outdoor recreation and regional attractions are within easy reac