44 properties for sale in Oakland Valley

House No. 5' is part of Philwold, a quiet five-home enclave designed by Eugene Schoen for members of the Wechsler family in the late 1930s. Schoen created a compound Usonian in spirit — channeling Frank Lloyd Wright's belief that a home should grow from its landscape. The house delivers on that promise with warm wood paneling, generous proportions, oak floors, and abundant natural light. Thoughtfully sited around Gilman Pond, No. 5 offers a rare combination of privacy, water access, and architectural pedigree. The entry sets the tone with a built-in bench-and-hook nook and powder room with bold wallpaper. Beyond, the living room opens wide — wood-paneled and anchored by a wood stove with brick surround — with a windowed dining alcove at the far end overlooking the pond. The den, clad in the same warm pine, works equally well as a media room, office, or ground floor bedroom, with a connecting full bath adding flexibility. The kitchen has been thoughtfully updated: cherry cabinetry, gran

Opportunity to get 10 acres of land while living in a spacious country residence, featuring an open kitchen, large living room, three bedrooms and office area. 2 car garage with loft and full front and back yards roll out to several acres of woods for recreational use. All on a quiet dead end road

This property has the world class charm and character of another generation. Situated on 7.1 beautiful acres on a corner lot with a stocked trout stream that runs through the property. Featuring an oversize dining room, great for holiday dinners. Living room is perfect for large family gatherings with a wood burning fireplace to keep you warm in the winter season. The kitchen opens to an eat-in-kitchen area. Take the stairs from the main foyer or from the back of the kitchen up to the second floor. Extra bedrooms can be converted to an office or den. Third floor is a large finished attic with a 1/2 bath, great for an entertainment room, movies, pool table. Etc.for your favorite pastime. Huge in ground pool and deck out back for summer entertainment and nights under the stars

This modern Colonial, built in 2005, is tucked away in the Catskills on 2.3 private acres—close to shopping, everyday conveniences, and with easy access to Route 17, yet still a world away from the noise and pace of the city. Meticulously maintained and beautifully presented, the home features 4 bedrooms, 3 bathrooms, soaring tall ceilings, an inviting open-concept layout, a chef’s kitchen, and generous entertaining spaces designed for effortless gatherings. Step outside and the expansive property becomes your own private retreat. The backyard is large enough to accommodate a pool, offering even more potential for outdoor enjoyment. Enjoy morning coffee on the porch, unwind beneath the covered gazebo, or savor warm summer evenings under the soft breeze of the overhead fan while taking in the peaceful woodland views. A whole-house generator adds an extra layer of comfort and security, ensuring year-round peace of mind. More than a home, this is a place to slow down, reconnect, and enjoy

Some homes are where you live. Others are where you finally exhale. Set along the peaceful shoreline of Forestburgh Pond, this two-bedroom, two-bathroom waterfront cabin offers something that's becoming increasingly difficult to find: privacy, water access, and a slower pace of life just 90 minutes from New York City. Whether you're searching for a full-time residence, a weekend retreat, or a property with short-term rental potential, this home is designed to make every season feel like a getaway. The open living space welcomes you with vaulted ceilings, a floor-to-ceiling stone fireplace, warm hardwood floors, and oversized windows that keep the water in view. The kitchen blends style and function with quartz countertops, stainless steel appliances, open shelving, and a cozy dining area overlooking the pond. The primary bedroom features its own updated en suite bathroom with a walk-in shower, while the second bedroom and additional full bath provide comfortable space for guests. Outsi

Not in flood zone. Must be seen. Old world charm, sits pretty back off quiet country road and property extends back off the road over 600 ft, perfect for those wishing to have a mini-farm! Has many recent updates such as roof, tilt in windows for easy cleaning, new exterior doors, furnace, hot water heater within past couple years and newly installed well pump and water tank. Exterior was painted about 5 years ago and still looks like it was just done. Great house in such a beautiful area, nature lovers paradise, and for an added bonus it is within a very short walk to parks, Neversink river for swimming, fishing (considered to be one of the best trout streams in NY) or Kayaking, tubing or rafting. Miles of hiking trails within a 1u002F2 mile of the home. Best of all, it has affordable taxes! See it today!

Tucked away on 5 private acres in the Town of Deerpark, this unique Sparrowbush property offers the kind of peaceful country setting that so many buyers dream about, while still being just minutes from convenience, recreation, and commuter access. Backing up to and neighboring a sprawling 360-acre hunting club, the property enjoys an exceptional sense of privacy and seclusion, creating the perfect retreat for outdoor enthusiasts, hunters, nature lovers, or anyone craving room to breathe and a quieter way of life. Originally built as a mobile home in 1972, a substantial addition completed in 1992 nearly doubled the home’s footprint, creating approximately 1,340 square feet of living space with a much larger feel throughout. Inside, you’ll find 3 bedrooms, 1 full bath, and a warm, inviting layout filled with character and comfort. The expansive living room is a true centerpiece, featuring vaulted ceilings with exposed beams and a brick-backed wood-burning fireplace that adds cozy charm a

Welcome to a peaceful and historic river community nestled in the hamlet of Godeffroy in the Town of Deerpark, Orange County, NY. This charming 2-bedroom, 1-bath cottage offers the perfect blend of year-round comfort and weekend retreat living. Surrounded by nature and just a short walk to the beautiful Neversink River, this cozy getaway provides deeded river access at the intersection of Shore & Ave A — ideal for fishing, swimming, kayaking, and enjoying the outdoors. Step inside this adorable cottage and discover an affordable opportunity for homeownership that’s cheaper than renting! Whether you're searching for a vacation escape, weekend retreat, investment property, or full-time residence, this home delivers tranquility, charm, and outdoor recreation in a scenic setting. Enjoy the quiet lifestyle of Myers Grove while being conveniently located near hiking, nature trails, amenities and all the beauty the Hudson Valley has to offer. Don’t miss your chance to own a slice of river com

Discover Your Dream Escape: A Cozy Ranch in Sparrowbush, NY! Nestled on a private 2+ acre parcel on a tranquil road, this well-built ranch offers ample space with vaulted ceilings in the open living/dining/kitchen, abundant natural light from large windows, hardwood floors throughout (new carpet in 3 bedrooms), and a cozy fireplace with pellet stove heating the main floor efficiently. Stay cool with four split-unit AC systems. Relax in the heated four-season sunroom off the dining area – ideal for morning coffee. Oversized 2-car attached garage doubles as workshop/storage, protecting vehicles and simplifying errands. Vast basement provides endless potential. Upgrades include both bathrooms with new toilets/sinks, new dishwasher, and a 22-ft round above-ground pool for summer fun. Spacious yard with mature trees ensures privacy and outdoor enjoyment. Just 2 hours from NYC and 10 mins to Manhattan trains – perfect for commuters. Nearby: quaint towns for dining/shopping, Delaware River ad

This stunningly expert crafted, quality and tasteful remodel makes this home brand new, top to bottom, where nothing was left to chance. Styled with calming neutrals, by experienced professionals and located in the western Orange County area of the Hudson Valley. It's an easy commute to NYC, or makes for a great weeked retreat into nature, where peace and privacy abound. The one plus acre lot is just enough to ensure privacy, without being a maintenace nightmare. The open floorplan of this home offers a contemporary vibe, with comfortable and pleasant, light filled living spaces. Take in the high ceiling and natural light of the main living space, accented with a stunning ceiling fan, and the stylish tray ceiling in the primary bedroom. The lower level living space could easily function as an in-law, home office or sports den, with extra large windows, and a full bath as well as laundry. Hardwoods throughout, a brand new HVAC system and insulation provides efficiency for heating and co

Escape to the peace and quiet countryside with this spacious 3-bedroom home nestled on nearly 4 private acres-Surrounded by nature, this property offers a beautiful mix of open yard and wooded privacy, creating the perfect setting to relax and unwind. Nestled on nearly 4 private acres in the peaceful Town of Deer Park, Enjoy the beauty of nature from the inviting enclosed three-season screened room overlooking the serene surroundings. Inside, you’ll find generously sized rooms, abundant closet space, a convenient laundry area with washer and dryer, and a comfortable layout ready for your personal touches. The kitchen and main bathroom are awaiting completion, giving you the chance to customize them to your own style and taste. Whether you’re looking for a full-time residence, a weekend getaway, or an investment opportunity, this property offers peaceful country living with endless potential. Being sold as is

Tucked along 973 State Route 42 in Sparrowbush, New York 12780, this 3-bedroom, 1-bath ranch sits on a peaceful. 59-acre parcel that offers a simple, grounded way of living in Orange County. The home is set just off the road, giving you a comfortable sense of space while still keeping daily conveniences within easy reach. Inside, the layout is practical and efficient, designed entirely for one-level living. The kitchen serves as the heart of the home, highlighted by granite countertops that bring a clean, durable finish to the space. It’s a setting that works just as well for everyday meals as it does for gathering with friends and guests. The living areas are bright and functional, with a natural flow that connects the main spaces without feeling cramped. Each of the three bedrooms offers flexibility—whether you need sleeping space, a home office, or room for guests. The full bathroom keeps things straightforward and easy to maintain, in line with the home’s overall simplicity. Outsid

Spacious custom-built Colonial set on a beautifully landscaped 1.7-acre corner lot in Sparrowbush. This well-maintained home offers 4 bedrooms, 2 full baths, and 1 half bath, with a generous layout designed for both everyday living and entertaining. The main level features new flooring, a newly finished oak hardwood staircase, a large eat-in kitchen with peninsula and sliders to the deck, a formal dining room with French doors, a sunken formal living room with 9-foot ceilings, a private sunken family room, a half bath, and a separate laundry area. The upper level includes four bedrooms, including a spacious primary bedroom with a walk-in closet and en-suite bath with whirlpool tub. A full pull-stair attic provides additional storage. The full walk-out basement offers approximately 1,250 sq. Ft. of additional space with 8-foot ceilings, Bilco doors, and a finished bonus room, creating many possibilities for recreation, storage, hobbies, or future use. A standout feature of this property

Welcome to 65 W Peenpack Trail in Sparrow Bush, NY, a spacious colonial home set on 3.5 private acres in the Town of Deerpark. Built in 2004, this well-maintained residence offers 4 bedrooms, 3 bathrooms, and approximately 2,592 square feet of living space, providing ample room for comfortable living, entertaining, and enjoying the peaceful surroundings. The home features a classic two-story colonial layout with a full basement, offering additional storage and potential for future finished space. Interior comfort is supported by central air conditioning and hot water heating, while the exterior showcases durable aluminumu002Fvinyl siding and a welcoming open porch perfect for relaxing outdoors. Situated on a generous 3.5-acre lot, the property offers privacy, open outdoor space, and the benefits of a rural setting while remaining within reach of nearby amenities and commuting routes. A two-car garage provides convenient parking and additional storage. Short Sale – Sale is subject to th

Not in flood zone. Must be seen. Old world charm, sits pretty back off quiet country road and property extends back off the road over 600 ft, perfect for those wishing to have a mini-farm! Has many recent updates such as roof, tilt in windows for easy cleaning, new exterior doors, furnace, hot water heater within past couple years and newly installed well pump and water tank. Exterior was painted about 5 years ago and still looks like it was just done. Great house in such a beautiful area, nature lovers paradise, and for an added bonus it is within a very short walk to parks, Neversink river for swimming, fishing (considered to be one of the best trout streams in NY) or Kayaking, tubing or rafting. Miles of hiking trails within a 1/2 mile of the home. Best of all, it has affordable taxes! See it today!

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

Wow! This brand new, superb, 8 room, 4 bedroom, 3 full bath contemporary colonial on 2.3 picturesque, private acres is priced to sell. It has everything, beauty & style, and is loaded with upgrades, high end finishes, smart energy efficient features and no carbon footprint. Come see this custom crafted home built in 2026 with open floor plan, gleaming hardwood floors on both levels and 2 electric fireplaces. You will adore the kitchen with center island, quartz counters, tile backsplash, smart stainless steel appliances & recessed lights that opens to a spacious dining and living room with lovely electric fireplace and has a full bedroom and upscale bath with tub on first level. Upstairs is a beautiful primary bedroom with an electric fireplace, tv wall mount, large walk-in closet & built in custom shelving and primary bath with custom rain shower, a remote control, smart, heated bidet, and also 2 additional bedrooms with great main bath with tub & linen closet. It has central air & he

Serenity and Charm built within the storied walls of this Queen Anne style home adorned with shake shingle exterior, overlooking natures wooded hills and the most perfect lake. The charm of two staircases and cute nook spaces beneath the stairs brings a smile within. Walk in to the most organized coat room and hideaway for all of your'things'. Then.Experience the'heart' of this home. The open design of the dining room with enormous windows with priceless views. The kitchen has a walk in pantry, enormous'hang out' island and so much space for cooking, baking and gatherings. This home has been gutted, renovated and brought up to perfection. Just waiting for your design eye! The main living room has the most magical oversized stone fireplace you could ever imagine, and a screened in porch for those lazy afternoons sipping your lemonade. On the other side of the home is a sweet main room with views, perfect for puzzles, card games and just hanging. Up the back staircase is the primary suit

On any lake, the lot is everything and this property delivers the kind of waterfront that is increasingly difficult to find: level to gently sloping, just three steps down from the deck to the waterfront, a natural pebble-and-sand swimming area, and a private dock, all without the steep grades or soft bottoms that define so many lakefront parcels in the region. The lake-facing wall of windows fills nearly every main living space with water views, while lakeside deck, newly built in 2025, extends the living area directly toward the shoreline. This well-maintained chalet offers 3 bedrooms and 2 full baths across 1,767 square feet, with an open layout that provides genuine first-floor flexibility. Two bedrooms and a full bath are located on the main level, allowing comfortable single-level living if desired. Upstairs, the nearly 24x17 primary suite occupies the entire second floor, complete with its own bath and an open loft-style overlook toward the great room and lake below. Major infra

Prime Location. Nestled in a vibrant community, with easy access to amenities, schools, and parks. This three bedroom and one bath home offers Large over sizes bedrooms. Vaulted high ceilings. Giant master bathroom, and tons of natural light throughout the house. Great Location! Very Attractive. Experience warmth and ambiance by the wood-burning stove in the lower level. Plus, take advantage of the proximity to Metro North and public transportation, making commuting a breeze. Three quarter fenced in backyard with tons of space. Shed for storage and 3-4 car driveway with plenty of parking. Not to mention attached storage behind house perfect for storing items in any weather or an extra room for any of your needs

Prime Location. Nestled in a vibrant community, with easy access to amenities, schools, and parks. This three bedroom and one bath home offers Large over sizes bedrooms. Vaulted high ceilings. Giant master bathroom, and tons of natural light throughout the house. Great Location! Very Attractive. Experience warmth and ambiance by the wood-burning stove in the lower level. Plus, take advantage of the proximity to Metro North and public transportation, making commuting a breeze. Three quarter fenced in backyard with tons of space. Shed for storage and 3-4 car driveway with plenty of parking. Not to mention attached storage behind house perfect for storing items in any weather or an extra room for any of your needs

Great opportunity with this 3-bedroom, 1.5-bath mobile home on 1 acre of owned land! Set in a peaceful, scenic setting, this property offers plenty of space to spread out and enjoy nature. The home features a functional layout with a spacious living area, eat-in kitchen, and dedicated laundry space. Outside, you’ll find a large yard with room for gardening, play, or future improvements. A great opportunity for buyers looking to build equity and make a home their own in a beautiful location!

Beautiful log-sided chalet on a private acre, featuring an open great room with cathedral ceilings and a stone fireplace. Modern kitchen with stainless steel appliances and granite counters. Includes 2 bedrooms, 2.5 bathrooms, and a fully finished lower level with bar/entertaining space. Peaceful setting with gardens and nature all around. Perfect year-round home or weekend escape. Close to Bashkill Winery. Easy commute to State Route 17

Attention builders and contractors, and all buyers cherishing privacy, an incredible view of the Shawangunk Mountains, and a large parcel of land, 46 acres, to hike and enjoy. This property's proximity to Orange County will be a plus for many. Located in the hills above Westbrookville, it offers a 1976 custom built ranch with a full basement. Architectural plans are in seller's file. 2 bedrooms, 2 baths, living room with fireplace, dining area, kitchen with breakfast nook and laundry room. A spacious screened porch and large enclosed porch (both 3 seasons) with deck invite you to enjoy the most beautiful long range view and to watch the sunrise in the morning. A basement family room will attract the young for movies and games. The attached 2-car garage comes in handy. There is also a large detached garage/barn for cars and toys, with a second story for storage. Update the home and create 3 parcels of approximately 15 acres each. There is plenty of road frontage. Maybe family or friends

Escape to your own secluded Hudson Valley sanctuary at 691 Peenpack Trail, an exceptional log home set on more than 7 pristine acres and accessed by a picturesque, tree-lined paved driveway. Combining rustic charm with modern conveniences, this fully furnished, move-in-ready property offers the perfect balance of privacy, comfort, and natural beauty. This stunning two-story log home features 3 bedrooms, 2 full bathrooms, and a full basement. At the heart of the home is a spectacular Great Room with soaring cathedral ceilings, abundant natural light, and a warm, inviting atmosphere that showcases the timeless character of log-home living. The home comes complete with stainless steel appliances, new Pergo flooring, and a hot tub. Relax on the covered front porch, sway on the porch swing, and enjoy peaceful views of the beautifully landscaped grounds while watching local wildlife in their natural habitat. Inside, cozy evenings await beside the wood-burning stove, while a pellet stove. Wit