333 properties for sale in Baileys Gap

Set back on nearly two acres, this architecturally inspired ranch captures the best of mid-century design with a dramatic wall of windows, soaring beamed ceilings, a floor-to-ceiling stone fireplace, and seamless indoor-outdoor living centered around a large in-ground pool. Natural light pours through the expansive windows, giving the main living space an open, airy feel while framing peaceful views of the surrounding property. The stone fireplace elegantly separates the great room from the dining area, creating distinct spaces while maintaining an easy flow for everyday living and entertaining. Just beyond, a spacious three-season room lives like a second family room, opening directly to the patio and pool for the kind of summer living Hudson Valley buyers dream about. The kitchen is thoughtfully designed with stainless steel appliances, generous cabinetry, and a functional layout with everything within easy reach. A dedicated laundry room connects the kitchen to the attached two-car

This home is completely remodeled. New roof, new siding new windows new Insulation all new electrical all new plumbing. All new flooring throughout the home. Brand new kitchen with quartz countertops, completely remodeled bathrooms. Brand new central air unit brand new furnace, brand new hot water heater. This Home is just minutes away from the mid Hudson Bridge and the Minnewaska mountains

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

Investor opportunity in the Town of Lloyd! Situated on 1.4 private acres, this 4-bedroom home offers tremendous potential for renovation, customization, or resale. The property is in need of significant rehabilitation and is ready for its next owner to bring it back to life. Features include a full basement, attached garage, and a desirable location just minutes from New Paltz, the Mid-Hudson Bridge, shopping, dining, and major commuter routes. Whether you’re an investor, contractor, or buyer looking to create your dream home, this property presents a rare chance to add value and build equity. Sold as-is

Single-Level Living at Its Finest This 1,456 sq. Ft. ranch, situated on a. 69-acre lot just steps from the beautiful Twin Star Farms, offers an ideal location and a thoughtfully designed layout. Featuring three generously sized bedrooms and a full bath, this home provides comfort and functionality. Upon entering, you are welcomed into a spacious den with vaulted ceilings-a versatile area that can be tailored to your lifestyle. The open kitchen boasts abundant natural light, a breakfast nook, and space for an island. Just off the kitchen, the inviting living room features a large bay window and a brick wood-burning fireplace, creating a cozy atmosphere during fall and winter months. In the summer, the central HVAC system keeps the home cool and comfortable. Down the hallway, you'll find three bedrooms with hardwood floors and the main bathroom, conveniently located and ready for your personal touch. The full basement runs the entire length of the house, offering higher ceilings and exce

Hudson River Views! This inviting home combines comfort, character, and convenience with a dramatic two-story foyer and open floor plan. Enjoy a cozy living room with a gas fireplace, formal dining area overlooking the river, and a kitchen with custom cherry cabinets, granite counters, and Jenn Air cooktop. A flexible room with French doors makes a great office or fourth bedroom. Bathroom and laundry room on first floor. Hardwood floors throughout the first level. Upstairs, the primary suite, with large walk-in closet, offers a Jacuzzi tub and separate shower, plus two bright spacious additional bedrooms. All bedrooms have walk in closets. The finished lower level, approximately 1100 sq. Ft. with radiant heat in the floor, and walkout access, adds extra living space. Attached heated two-car garage and a separate insulated two-story garage with electric-perfect for a studio or workshop. Ideal location near the Mid-Hudson Bridge, Metro-North, New Paltz, and major hospitals. A 3D Walkthro

Set back on two private acres in the heart of Milton, this beautifully maintained Colonial offers the kind of Hudson Valley lifestyle buyers dream about, where peaceful mornings, wide open space, and timeless design come together just minutes from some of the region’s most beloved wineries, orchards, hiking trails, and farm markets. Offering nearly 3,000 square feet of thoughtfully designed living space, this four-bedroom, two-and-a-half-bath home welcomes you with an impressive two-story foyer, soaring ceilings, abundant natural light, and an effortless flow designed for both everyday living and memorable gatherings. The spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and opens seamlessly into the home’s inviting living spaces, where a cozy fireplace creates the perfect backdrop for crisp Hudson Valley evenings. A formal dining room provides an elegant setting for holidays and celebrations, while tasteful details including crown molding,

This write up for this home has been such a challenge for me due to the exceptional total transformation of labor of love and proud ownership these homeowners have poured in. Had the pleasure of helping them acquiring this home years ago. No expense has been spared from ground to roof top, exterior and interior. Above and beyond basic build that the eye can see and not see behind walls. Outside entertainment is of high quality throughout, walk-ways of pavers, stone entry columns with electric for even more lighting if you wish, Built in Fire-Pit, Barbecue and enhanced with a Luxury entry into your home! Front covered porch to sit and relax in the evening with an tall living fence for privacy. Upon entering you have a ballroom size entry with an open bright feeling leading to the main living areas. Kitchen is designed for functionality and modern appliances like a convention oven that is also an air-fryer is one example. So much to say about the main house. The accessory apartment has t

Discover the perfect Hudson Valley retreat in this beautifully crafted modern home offering high-end finishes, energy-efficient construction, and effortless indoor-outdoor living just a short trip from NYC. Designed with a fresh, contemporary aesthetic and filled with natural light, this move-in ready home blends sophisticated style with the peaceful setting today’s buyers are seeking. At the heart of the home is a custom Apuzzo kitchen featuring white cabinetry, stainless steel appliances, quartz-like countertops, and a large center island ideal for entertaining after a day exploring the Hudson Valley. Wide-plank flooring and an airy open-concept layout create seamless flow between kitchen, dining, and living spaces, complemented by a dedicated home office and main-level laundry. Upstairs, the serene primary suite offers a private retreat, joined by two additional spacious bedrooms and beautifully finished baths. Every space reflects quality craftsmanship and modern design. The finish

Great investment opportunity in the heart of downtown Highland. This well-maintained 2-family property features one fully renovated unit and one unit with value-add potential—ideal for investors or owner-occupants looking to increase rents over time. Situated on a generous. 75-acre lot on a quiet street, the property offers plenty of space to entertain, relax, and enjoy the surrounding setting. Each unit offers a spacious layout with abundant natural light. The renovated unit showcases updated flooring, modern finishes, and a beautifully upgraded kitchen with new appliances, sleek cabinetry, and ample counter space, along with a stylishly updated bathroom. The second unit provides a solid layout with the opportunity to renovate and add value, making this a compelling blend of immediate usability and future upside. Located just steps from Highland’s shops, restaurants, and local conveniences, with easy access to major roadways and the Walkway Over the Hudson, this property sits in a des

Jackpot! Recently renovated ranch in the charming town of Marlboro. Walking through the front door you are welcomed into a spacious family room. The natural light in the family room illuminates the way to the updated kitchen with dazzling new cabinetry, granite countertops and stainless steel appliances. Throughout the home there are hardwood floors along with new roofing, siding, windows, doors, paved driveway, washer/dryer, boiler Plus a one car garage. This home offers a vast backyard space along with an awesome deck that is perfect for backyard entertaining. The property has been well taken care of and is ready for its next adventure

Nestled on a quiet road in the heart of the Hudson Valley, this well maintained raised ranch at 85 Bellevue Road in Highland offers comfortable living with a spacious layout and peaceful surroundings. Built in 1987, the home features approximately 1,800+ square feet of living space with 3 bedrooms and 2 full bathrooms on over half an acre of property. The main level offers a bright and inviting floor plan with generous living and dining areas. Large windows bring in natural light. The lower level offers additional finished space perfect for a family room, home office, gym, or guest area. Outside, the property enjoys a private backyard setting with mature trees and room for outdoor gatherings, gardening, or relaxing by the river community atmosphere Highland is known for. Conveniently located near local shops, schools, parks and commuter routes, the home combines suburban comfort with easy access to nearby Poughkeepsie, the Hudson River waterfront, and the Walkway Over the Hudson, as we

Privacy and seclusion await in this well maintained home. The gourmet eat-in kitchen features vaulted ceilings, granite island, wine bar, double ovens, stainless steel appliances, and abundant cabinetry, and sliding glass door leading to a deck. The open concept living flows into the formal dining room with a bay window and hardwood floors. Upstairs, the primary suite boasts vaulted ceilings, a dressing room, and spa-like bath with dual vanities and jacuzzi tub. Two additional bedrooms and a full bath complete the second floor, including one with a private three-season porch. The finished walk-out lower level offers a cozy den with wood burning fireplace, garage access, utility room, office and another three-season room. Outside, enjoy a private backyard oasis with a fenced yard, in-ground pool, hot tub, covered pavilion, and landscaped flowering gardens throughout. Additional highlights include a whole. House generator, upgraded electric, and a two car attached garage. A must see!

Hudson River Views! This inviting home combines comfort, character, and convenience with a dramatic two-story foyer and open floor plan. Enjoy a cozy living room with a gas fireplace, formal dining area overlooking the river, and a kitchen with custom cherry cabinets, granite counters, and Jenn Air cooktop. A flexible room with French doors makes a great office or fourth bedroom. Bathroom and laundry room on first floor. Hardwood floors throughout the first level. Upstairs, the primary suite, with large walk-in closet, offers a Jacuzzi tub and separate shower, plus two bright spacious additional bedrooms. All bedrooms have walk in closets. The finished lower level, approximately 1100 sq. Ft. with radiant heat in the floor, and walkout access, adds extra living space. Attached heated two-car garage and a separate insulated two-story garage with electric-perfect for a studio or workshop. Ideal location near the Mid-Hudson Bridge, Metro-North, New Paltz, and major hospitals. A 3D Walkthro

Offering a comfortable layout, versatile living spaces, and a location just minutes from everything New Paltz has to offer, this inviting 4-bedroom, 2-bathroom home is ready to welcome its next owner. As you step inside, you are welcomed into the living room, which flows naturally into the rest of the main living area. The kitchen and dining area/sunroom truly serve as the heart of the home, creating a connected and inviting space for everyday living and entertaining. The kitchen overlooks the bright four-season sunroom, allowing natural light to fill the space while maintaining an open feel. From here, sliders provide a seamless indoor/outdoor flow to the rear deck, extending your living space into the outdoors and making it easy to enjoy gatherings or quiet evenings at home. The outdoor area features an oversized backyard, offering plenty of room for recreation, gardening, pets, or future enhancements, all while maintaining a sense of privacy and space. The main level also features t

Tucked away on a lovely lot surrounded by mature trees, this charming 3-bedroom, 1.5-bath cottage is filled with character and warmth. From the moment you arrive, you'll appreciate the home's inviting atmosphere, where original details tell the story of years gone by while offering endless possibilities for your personal touch. Imagine starting your day with a cup of coffee in the peaceful, private backyard, listening to the sounds of nature and enjoying the wooded setting that creates a true sense of retreat. Inside, comfortable living spaces provide the perfect backdrop for everyday living, gathering with friends, or creating lasting memories. Conveniently located close to shopping, dining, and everyday amenities, this home also offers easy access to outdoor recreation. The Rail Trail is just a mile away, perfect for walking, biking, and exploring the beauty of the area. Nearby you'll also find the university, Trailways bus station, and Metro-North, making commuting and travel a bree

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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