333 properties for sale in Baileys Gap

Fully available! Welcome HOME to 25 Park Ave – this adorable and well-maintained ranch-style home located in the Town of Poughkeepsie within the highly desirable Arlington School District, offering easy one-level living, this charming 3-bedroom, 1-bath home is perfect for first-time buyers, downsizers, or anyone seeking comfort, convenience, and character. Step inside to find a unique and functional kitchen featuring an island and pantry closet that flows seamlessly into the spacious living room with a cozy fireplace and adjacent formal dining area, creating an open and inviting layout ideal for both everyday living and entertaining. Refinished hardwood floors, abundant natural light, fresh paint, and updated LED lighting add warmth and a bright, cheerful atmosphere throughout the home. Down the hall, you’ll find three generously sized bedrooms and a full bathroom, all conveniently located on the main level for effortless living. Outside, enjoy a level, fully fenced backyard perfect fo

Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N. Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living-ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom kitchen offers contemporary cabinetry, quartz countertops and premium appliances. The spacious bath includes a deep soaking tub, heated towel racks and generous built-in storage, while the in-unit washer and dryer add everyday convenience rarely found at this size. Building common areas are powered by on-site solar with solar water pre-heating supporting energy efficiency. Each residents includes dedicated off-street parking (based on bedroom count) with EV charging available plus a separate private on-site storage unit. Thoughtful finishes and quality construction complete this move-in-ready

Located on a tidy half-acre lot in the town of New Paltz, this sunny 3-bedroom ranch home features hardwood floors, a spacious 2-car garage, and a lovely sunroom addition. Following the front curving walkway, Norwegian maples stand tall to the right and left of the house, while a classic planting of boxwoods are at home under the front windows. The cozy living room features a large picture window and a clean aesthetic with neutral tones of gray and white extending to the adjacent dining area, all with hardwood floors underfoot. The kitchen's original 1950's cabinets bring the charm, while the modern appliances provide convenience. There's a Bosch dishwasher, Samsung induction glass-top range with range hood, Samsung french-door fridge, and large double bowl stainless sink overlooking the sunroom. Down a half-staircase, the sunroom addition offers extra space for relaxing, exercising, and even work-from-home. There's a wall of double paned casement windows facing east, painted wood pane

An inviting old-style updated home set in the historic hamlet of Milton, just steps above the majestic Hudson River. Surrounded by period architecture and tree-lined streets, this residence offers partial river views and a timeless sense of place. The home features 4 bedrooms and 2 baths, along with a charming butler's pantry and two staircases leading to the second level. A former third bath has been thoughtfully converted into a laundry room conveniently located on the bedroom floor. The first level blends classic character with modern updates, including a remodeled kitchen with granite countertops and an airy, light-filled living room with sliding doors that open to a custom stone patio. A formal dining room adds a touch of traditional charm. A standout feature is the two-level, two-car garage. Its expansive upper floor offers endless potential-studio, art room, private office, entertainment space, playroom, or hobby workshop. Just one block from the heart of the hamlet, you'll have

Located on a quiet street in a neighborhood with no thru-traffic, this modernized raised ranch offers a comfortable layout that feels like home. Upstairs the spacious living room with a large bay window and hardwood floors shares an open floor plan with the dining room and the updated kitchen, with its stainless appliances, gas range, and elegant slate-tiled floor. Beyond the dining room is a bright, airy sunroom, full of windows overlooking the backyard. This space is a perfect flex room, and opens to the elevated deck with stairs to the side yard. Down the hall you'll find 3 bedrooms, and a crisp, newly renovated bathroom with double vanity and glass shower door. Downstairs there's a cozy den and an additional room perfectly suited for an office or guest space. This level also includes a second newly renovated bathroom, laundry closet, and access to the 2-car garage. Recent improvements of note include a high-efficiency boiler, EV charger, new garage doors, and Nest thermostats. The

Beautiful well maintained multi-family property offer, a rare opportunity for both owner-occupant & investors. Two houses that sit on 15 acres with endless revenue generating opportunities. The deed allows for the property to be subdivided & extending the private road along northern property line. The main house is a single family that features 2 bedrooms, 2.5 bathrooms with a full finished basement. There is a lifetime warranty for a B-dry drainage system. It has central a/c with a heat pump, above ground pool with a wrap around deck, movable patio with electric service, and two storage sheds equipped with electric. Second home has 3 bedrooms, 2 full bathrooms with central a/c, deck, side yard & is surrounded by nature, secluded with a wooded backyard. Great tenants that would like to stay. It is a rare opportunity to enjoy natural beauty, income potential & the serene Hudson Valley

Welcome to 152 N Clinton Street, a beautifully renovated home in the heart of Poughkeepsie offering the perfect blend of modern style, comfort, and convenience. This move-in-ready 2-bedroom, 2 full bathroom home has been thoughtfully updated from top to bottom with contemporary finishes and functional living spaces throughout. Step inside to find a bright open-concept layout featuring brand-new flooring, recessed lighting, fresh paint, and a stunning modern kitchen complete with sleek cabinetry, stainless steel appliances, and stylish countertops. The spacious living area is filled with natural light and centered around a charming decorative fireplace that adds warmth and character to the space. Both full bathrooms have been tastefully redesigned with modern tilework and updated fixtures, while the generously sized bedrooms offer comfort, flexibility, and ample closet space. Additional upgrades include updated mechanicals, and off-street parking with a private driveway. Outside, enjoy

Prime Investment Opportunity in Poughkeepsie: Discover an exceptional investment in this charming three-family Colonial, ideally located in the heart of Poughkeepsie. Each unit boasts a spacious floor plan, a bright and airy living room, a well-appointed eat-in kitchen, and a full bath. The property has undergone complete renovation for a long term investment, including the exterior, utility systems, and each complete unit. All units have separate utilities, with the landlord covering only common area lighting and water, while tenants are responsible for their individual electric (heating, cooking, and hot water), and other utility costs. Centrally located with convenient access to local amenities, schools, and transportation. Coin Operated Laundry, Security Lighting, and Exterior Camera System in place. Fully leased

Welcome to 8 Mildred Avenue! This well-maintained home offers the perfect blend of character, space, and convenience. Step inside to find bright living areas, hardwood floors, an updated kitchen with stainless steel appliances, and spacious rooms throughout. The formal dining room provides a great space for entertaining, while the large windows fill the home with natural light. Upstairs you'll find comfortable bedrooms and plenty of storage, while the full basement offers additional space for storage, hobbies, or future possibilities. Outside, enjoy a level backyard with room to relax, garden, or host summer gatherings. Conveniently located near shopping, restaurants, schools, hospitals, Metro-North, and major commuter routes, this home is a fantastic opportunity for both owner-occupants and investors alike. Don't miss your chance to make this charming Poughkeepsie property your next home!

Step into the potential of this 952 sq ft railroad-style home, featuring 2 cozy bedrooms and 1.5 bathroom. This classic layout, known for its linear flow and vintage character, offers a unique opportunity for those looking to restore or reimagine a timeless space. While the home needs renovation, its solid structure and charming original details provide the perfect canvas for customization. Whether you're an investor, first-time buyer, or renovation enthusiast, this property holds great promise. With the right vision, this house could become a beautiful blend of historic charm and modern comfort. Don't miss your chance to bring this diamond in the rough back to life!

This bold custom built home sits atop a hill like a postcard extolling the beauty of the Hudson Valley. Built to exacting specifications and with an understanding of how people live best by a master craftsman, this is a post and beam masterpiece in an inspiring setting. Uniquely, it offers all the bells and whistles you expect in a new luxury home while also feeling like an heirloom. Set on 4 acres in Highland, NY it's surrounded by rows of apple trees (planted purely for aesthetics), beautiful stonework, and patios that are the perfect perches from which to enjoy the beautiful valley views (you can actually see Mohonk from the street), sunrises, and sunsets. Inside, the house delivers the romantic visions the exterior conjures. The exposed timber-frame structure feels like a cathedral, matching wood-clad walls and ceilings are wonderfully warm, and the whole house smells like a fresh pine forest. Black metal railings, black windows, and black French doors bounce light around and add e

This charming three-bedroom, two-bathroom home offers spacious living with timeless character and endless potential. Step into the inviting enclosed sunroom entrance, the perfect place to relax and enjoy natural light year-round. Inside, you’ll find the home is freshly painted with refinished hardwood floors and the kitchen featuring beautiful NEW wood cabinetry, NEW gas stove, recess lighting and a doorway onto the rear deck overlooking the property. The living room is open to the formal dining room, and a spacious and impressive entryway that welcomes you home. The home boasts generously sized rooms, hardwood floors throughout, natural gas heat, city water, and city sewer for added convenience. A side entrance provides easy access, while the unfinished walk-up attic offers excellent storage space and includes a window, creating possibilities for future use and storage space. Unfinished basement with utilities and storage space. Outside, enjoy a beautiful flat garden property with amp

Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N. Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living-ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom kitchen offers contemporary cabinetry, quartz countertops and premium appliances. The spacious bath includes a deep soaking tub, heated towel racks and generous built-in storage, while the in-unit washer and dryer add everyday convenience rarely found at this size. Building common areas are powered by on-site solar with solar water pre-heating supporting energy efficiency. Each residents includes dedicated off-street parking (based on bedroom count) with EV charging available plus a separate private on-site storage unit. Thoughtful finishes and quality construction complete this move-in-ready

Impeccably maintained and thoughtfully updated, this move-in ready Colonial is the one you've been waiting for. Freshly painted throughout, this beautiful home showcases a newly updated kitchen and bathrooms, offering the perfect blend of timeless charm and modern convenience. Enjoy peace of mind with major improvements already completed, including a new roof (2024) and hot water heater (2019). Andersen double-hung tilt-wash windows provide energy efficiency and effortless cleaning. Designed for both everyday living and entertaining, the spacious layout includes an eat-in kitchen as well as a dining room. The large bonus room can easily accommodate a home office, playroom, media room, gym, or guest space to fit your needs. Storage is abundant throughout the home, with generously sized bedroom closets, a spacious walk-in closet in the primary suite, and plenty of room to keep everything organized. The private primary suite offers a relaxing retreat complete with a walk-in closet and an

Absolutely stunning, custom-built expanded ranch situated on a little over an acre, with views of Dutchess County. You'll love the ease of single-level living and will enjoy all of the special features throughout! Amenities include: Hardie Board siding, wonderful metal roofing, covered front porch and rear patio, 9ft ceilings, radiant-heated flooring, spacious living room with a masonry fireplace, three bedrooms, laundry room on the main living level, ADA bathrooms, and pass-throughs. The custom-designed kitchen is appointed with a gas cooktop, oversized island, Tile backsplash, recessed lighting, and plenty of prep space for the chef! The primary suite includes a beautiful custom-designed bathroom complete with a soaking tub and large shower. There is also a generous walk-in closet-a clothing lover's dream! The second level of the home has a staircase in place, though it is not yet finished but is waiting for you to do what fits your needs! Wonderful space that is plumbed for a full b

Wake up to mountain views and picturesque apple orchards in this beautifully situated Marlboro home, privately set back along a quiet private road. Built in 2017 and offering approximately 2,700 square feet of living space, this three-bedroom, three-full-bath home delivers the space, privacy, and modern comfort today's buyers are searching for. From the moment you step inside, natural light fills the home, highlighting an open and inviting layout designed for both everyday living and entertaining. The pellet stove adds warmth and character to the main living space, creating the perfect place to gather on crisp Hudson Valley evenings. The kitchen combines style and functionality with extra-tall soft-close cabinetry, generous storage, and ample workspace. Directly off the dining area, a grilling deck extends the living space outdoors; ideal for summer dinners, weekend entertaining, or simply enjoying the surrounding scenery. Three spacious bedrooms and three full baths provide flexibilit

Great opportunity to own a multi-family property in the heart of Poughkeepsie! Perfect for investors or owner-occupants. This turn-key, well-maintained property offers strong rental potential in an area with high rental demand. Conveniently located close to shops, restaurants, public transportation, and the Mid-Hudson Bridge, making it an ideal location for commuters and tenants alike. Schedule your showing today! Property being sold as-is. Buyer’s agent to verify all information

Step back in time without sacrificing modern luxury in this lovingly restored 1890s Victorian duplex. Located on the historic Balding Avenue, this property perfectly blends late-19th-century craftsmanship with a complete 2019 top-to-bottom renovation. This home was renovated in a way that lends itself to an easy single-family conversion. A bonus is the huge walk-up attic, great for storage or future expansion. As you approach, the classic facade and inviting porch hint at the character within. Inside, soaring ceilings and oversized windows flood the massive 3,600+ square foot interior with natural light, highlighting original hardwood floors and intricate period woodwork. The dual-unit layout offers incredible versatility for an investor seeking premium rents or an owner-occupant looking to live for free while renting the other half. Each unit features a nice kitchen with gas cooking and a dishwasher on the first floor, plus the rare convenience of in-unit laundry hookups. (Only the up

2 Family within walking distance to Metro North, the Main Street Restaurant District and the waterfront. Solid rental history with very low turnover. This home features separate utilities and a driveway for off street parking. Perfect for the investor or a live in one unit and rent out the other unit type situation

Opportunity awaits in this spacious 3-bedroom, 2-bath home that offers the flexibility to live like a 4-bedroom. Ideally located just minutes from Poughkeepsie’s waterfront, Metro-North, restaurants, and local amenities, this property is perfect for buyers looking to build equity. The home needs updating and is being sold as-is, making it a great opportunity for an owner-occupant or investor ready to bring their vision to life

Welcome to 549 Gregory Ct, a bright, spacious, and impeccably maintained condo located in the desirable Woods at Bridgeview community in Highland, NY. Designed with both comfort and functionality in mind, this open-concept layout is ideal for everyday living and entertaining. The home features a spacious kitchen with breakfast bar seating, a large dining area, and an inviting living room with access to a private deck. Offering two bedrooms plus a versatile den/home office or possible third bedroom, this move-in ready condo also includes newly installed flooring, fresh paint, natural gas heat, central air, and in-unit washer/dryer hookups for added convenience. Residents of Bridgeview enjoy a variety of amenities including a clubhouse, in-ground pool, playground, tennis courts, basketball courts, and dog-friendly outdoor spaces. Ideally situated within walking distance to the Rail Trail and the Walkway Over the Hudson, and conveniently located near Route 9, Route 9W, I-84, the Mid-Hudso

Fully occupied and income producing two-family home in a convenient Poughkeepsie location, situated between Marist College and Vassar College. Each unit features 2 bedrooms, 1 bathroom, an updated kitchen, separate entrance, and separate utilities paid by the tenants. This detached property also offers a driveway and backyard, adding extra value and convenience. A great opportunity for investors looking to add a rented multi-family property to their portfolio, or for future owner-occupants seeking rental income potential

This charming, recently updated home is ideally situated on a quiet dead-end street, offering a serene escape without sacrificing convenience. The location provides easy access to local amenities and transportation options. Step inside to discover a freshly revitalized interior featuring new flooring and paint throughout, creating a bright and welcoming atmosphere. The spacious living area is bathed in natural light and anchored by a cozy fireplace, perfect for relaxing evenings. The heart of the home, the kitchen, has been thoughtfully updated with sleek quartz countertops, stylish subway tile backsplash, and modern finishes. The flexible layout offers two generously sized bedrooms and a full bathroom on the main level, with an additional two bedrooms and full bath upstairs, providing ample space and privacy for everyone. Adding significant value and flexibility, a legal accessory studio apartment is situated above the garage, complete with its own private bathroom—perfect for guests,

This bold custom built home sits atop a hill like a postcard extolling the beauty of the Hudson Valley. Built to exacting specifications and with an understanding of how people live best by a master craftsman, this is a post and beam masterpiece in an inspiring setting. Uniquely, it offers all the bells and whistles you expect in a new luxury home while also feeling like an heirloom. Set on 4 acres in Highland, NY it's surrounded by rows of apple trees (planted purely for aesthetics), beautiful stonework, and patios that are the perfect perches from which to enjoy the beautiful valley views (you can actually see Mohonk from the street), sunrises, and sunsets. Inside, the house delivers the romantic visions the exterior conjures. The exposed timber-frame structure feels like a cathedral, matching wood-clad walls and ceilings are wonderfully warm, and the whole house smells like a fresh pine forest. Black metal railings, black windows, and black French doors bounce light around and add e

Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N. Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living-ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom kitchen offers contemporary cabinetry, quartz countertops and premium appliances. The spacious bath includes a deep soaking tub, heated towel racks and generous built-in storage, while the in-unit washer and dryer add everyday convenience rarely found at this size. Building common areas are powered by on-site solar with solar water pre-heating supporting energy efficiency. Each residents includes dedicated off-street parking (based on bedroom count) with EV charging available plus a separate private on-site storage unit. Thoughtful finishes and quality construction complete this move-in-ready