Sleepy Hollow Real Estate Search

Sleepy Hollow Properties between $500,000 and $600,000 for Sale

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Newest Sleepy Hollow Properties between $500,000 and $600,000 for Sale

$569,999
6 Beds 2 Baths 984045 MLS
A rare and remarkable multi-family opportunity nestled in the heart of the Catskills, 2 Mountain Valley Road, Boiceville, New York presents two fully self-contained units, each delivering a level of space, privacy, and independence that is hard to find in the multi-family market. Set against the stunning natural backdrop of Ulster County’s Catskill Mountains, this 1,842 total square foot 2-family home offers two generously sized 3-bedroom, 1-bath units, each thoughtfully equipped for comfortable, independent living. Each Unit Features: 3 Bedrooms | 1 Full Bath Private Deck, ideal for enjoying the natural Catskills surroundings Attached Garage, offering dedicated parking and storage In-Unit Laundry Room in the basement, adding convenience and functionality For the investor, two 3-bedroom units in the Catskills region offer exciting income potential in a highly desirable Upstate New York market. The combination of private garages, individual decks, and dedicated laundry adds significant appeal for tenants and helps set this property apart from typical multi-family offerings. For a future owner-occupant, this property also offers the potential for a smart house-hacking opportunity, with the ability to enjoy a spacious 3-bedroom residence while generating rental income from the additional unit, subject to existing occupancy and lease terms. Located in Boiceville, New York within the Onteora School District, this property sits at the gateway to the Catskills, just minutes from Woodstock, Phoenicia, and the natural beauty that makes Ulster County one of the most desirable destinations in the Hudson Valley. Easy access to Route 28 connects residents to Kingston, the I-87 corridor, and beyond. Multi-family properties offering this combination of space, private garages, individual decks, and laundry for each unit are a unique find in the Catskills region of Ulster County. Whether you’re building your investment portfolio, purchasing your first multi-family property, or planning for future owner occupancy, 2 Mountain Valley Road deserves a closer look.

2 Mountain Valley Road, Boiceville

$599,408
4 Beds 2 Baths 996401 MLS
Sophisticated country living in the desirable Millbrook area within the highly regarded Millbrook Central School District. Ideally located close to the charming village, local amenities, and the Wassaic Station for convenient Metro-North access to New York City. Privately set on 2.06 picturesque acres, this light-filled 4-bedroom, 2-bath Cape offers the perfect blend of comfort, versatility, and lifestyle. Designed to accommodate a variety of needs, the exceptional heated three-bay garage with soaring ceilings and expansive upper level creates endless possibilities for car enthusiasts, artists, writers, entrepreneurs, fitness enthusiasts, or those seeking a spacious home office or creative studio. The inviting interior features wood floors and tile throughout the main level, with an effortless open-concept layout ideal for both everyday living and entertaining. The vaulted-ceiling family room is filled with natural light and showcases tile flooring, a custom built-in entertainment cabinet, and a chimney ready for a pellet or wood stove. The adjoining kitchen flows seamlessly into the living and dining spaces, creating a warm and welcoming atmosphere. A formal dining room and spacious living room continue the home’s airy, connected design, while a first-floor bedroom and full bath with laundry closet provide flexibility for guests or one-level living. Upstairs, the primary suite offers vaulted ceilings and a private ensuite bath, accompanied by two additional bedrooms. Step outside to the rear deck overlooking the peaceful grounds—perfect for outdoor dining, entertaining, or simply enjoying the tranquil setting. A storage shed adds additional convenience to this thoughtfully designed property. A rare offering combining refined country style, functional workspace, and an ideal location in the heart of the Hudson Valley.

810 ROUTE 343, Dover Plains

$555,000
5 Beds 3 Baths 994440 MLS
3 PRIVATE ACRES + ULTIMATE VERSATILITY + POSSIBLE INCOME POTENTIAL = A RARE MIDDLETOWN OPPORTUNITY Set on 3 serene, wooded acres, this beautifully maintained raised ranch offers an expansive 2,202 sq. ft. of living space designed with a unique, highly adaptable layout that can help with your financial goals or adapt to your lifestyle. The main level features a bright open-concept main floor with gorgeous hardwood flooring and a seamless flow. The updated kitchen is a home chef's dream, appointed with granite countertops and stainless steel appliances. This level hosts three comfortably sized bedrooms, including a primary suite complete with a walk-in closet and ensuite bathroom. The lower level is a legal 2-bedroom apartment with endless options. The fully finished lower level expands your options immensely. Featuring a seperate entrance, kitchen, 2-additional bedrooms, living room, and bathroom - this legally compliant space offers incredible flexibility. It's perfectly set-up for you to earn an income to offset your mortgage or for a variety of other uses such as multi-generational living, the ultimate entertainment area, guest wing, massive home office, studio, gym space, or whatever fits your needs and imagination. TURN-KEY AND HIGH VALUE- the sellers have already taken care of the major expenses so you don't have to. Enjoy peace of mind with the newer roof, addition of a new Rehem water system, and a redone driveway. Rounding out the property is a large heated 2-car garage - perfect for a personal workshop or storage area. Combining total privacy, recent updates, and an adaptable footprint that can earn you some money or scales with your family, this property is a must-see. Schedule your private tour today.

29 Murray Road, Middletown

$559,000
2 Beds 2 Baths 996250 MLS
Welcome to resort-style living at The Manors at Colony Preserve — an exceptional 55+ community where luxury, comfort, and lifestyle come together beautifully. This stunning builder’s model is spacious and elegantly appointed, featuring 2 bedrooms, 2 full baths, a versatile bonus room perfect for a home office or den, an inviting living room, formal dining area, and an eat-in kitchen ideal for everyday living and entertaining. The private guest quarters provide the perfect retreat for visiting friends, while the in-unit washer and dryer and private elevator offer everyday convenience and comfort. Beautiful designer touches throughout include crown molding, classic wainscoting, stunning coffered ceilings, and recessed lighting, creating a sophisticated and welcoming atmosphere in every room. Enjoy breathtaking views and peaceful surroundings with beautifully maintained walking trails and scenic outdoor spaces right outside your door. Residents of this vibrant community enjoy an unmatched lifestyle with outstanding amenities including a heated pool, whirlpool spa, bocce courts, picturesque lake with row and paddle boats, charming gazebo, and tranquil walking paths throughout the grounds. The stunning clubhouse offers everything you could want and more — featuring a state-of-the-art Life Fitness Center, game rooms, elegant great room, bar and kitchen facilities, and a cozy gas fireplace perfect for gathering with neighbors and friends. Experience the feeling of being on vacation in a luxury resort all year long at The Manors at Colony Preserve — where every day feels like a getaway.

17 Greentree Court, Shirley

$520,000
2 Beds 1 Baths 996196 MLS
Enter the Madison at Berkeley Towers doorperson building and ride the elevator up one floor to this bright and airy corner two bedroom unit. Open the door to be greeted by a large window offering front exposure with park and tree views. The living room is situated adjacent to a dining area and the kitchen to offer great flow for entertaining. Two closets in the entry way allow one to set outside belongings prior to retreating to the home. Several closets-- including a walk-in-- allow for great hanging and folding space for those with a discerning wardrobe, plus linens, dried food items, toiletries, and recreational items. The bathroom has updated finishes and hardware and a full shower/tub combination ideal for a relaxing bath at the end of the day or refreshing power shower to start the day with glass doors. The primary bedroom is situated on a corner and offers two exposures with cross-ventilation with space for complete furnishings. The second bedroom contains a large window and can accommodate an array of items for sleeping/seating/working-- a great multi-use purpose in this post 2020 work from home/multi-generational living environment! The Berkeley Towers is an original co-operative with fire/sound-proofing between units. It is pet friendly and in-zone for Sunnyside Gardens Park-- one of the only two private NYC parks. Situated proximate to Skillman Avenue, shops, cafes, bars and restaurants are within easy reach. Located North of Queens Boulevard and South of Northern Boulevard, this location is ideal for travel throughout the area with its proximity to mass transit and major roadways. Easily reachable by the Flushing (7) local and express, plus M & R trains, and the Long Island Railroad. The B.Q.E., L.I.E., Triboro Bridge, 59th Street/Queensboro Bridge, Midtown Tunnel, and Grand Central Parkway offer various travel routes in multiple geographic directions. Maintenance includes heat, hot water, cooking gas, and electricity. Surcharge for air conditioning. Indoor and outdoor parking on a wait-list basis at additional monthly rate. Community patio area great for sitting to enjoy fresh air and sunshine plus social gathering. Priced to sell! Here's your chance to live in a modernized luxury style building adjacent to an historic enclave to enjoy a combination of two great styles of New York City living.

52-30 39 Drive Unit #1G, Woodside

$600,000
2 Beds 2 Baths 995742 MLS
Located in the heart of Saugerties' vibrant and walkable village, 230 Partition Street presents a prime mixed-use opportunity on a highly visible corner lot. This property features a bright commercial storefront with expansive wraparound windows, offering excellent exposure and natural light, along with a spacious two-bedroom apartment above. The building is currently under renovation, providing a unique opportunity for a buyer or tenant to step into a refreshed space. The foundation has been fully rebuilt to code, and the property features brand new electrical service, including a 200-amp service along with two additional 100-amp panels, offering flexibility for a variety of commercial and residential needs. The flexible layout of the commercial area makes it ideal for retail, office, studio, or service-based businesses, while the residential unit offers the option for owner-occupancy or additional rental income. The property also benefits from off-street parking, a rare and valuable feature within the village, adding convenience for both business owners and customers. Offered as-is or with the option to build-to-suit at an adjusted price, this is an excellent opportunity to tailor the space to your specific needs while capitalizing on an already strong location and upgraded infrastructure. Positioned just steps from popular restaurants, cafes, boutique shops, and local attractions, the property is surrounded by steady foot traffic and year-round activity. Nearby amenities include Cantine Field, the Saugerties Lighthouse, HITS Equestrian Facility, local theaters, fine dining, shopping, and the Hudson River waterfront, along with a variety of community events and festivals that draw both locals and visitors alike. With easy access to Route 9W, Route 32, and the New York State Thruway, this location offers both convenience and visibility, making it an ideal setting for a thriving business and a smart investment in the heart of the Hudson Valley.

230 Partition Street Unit #2, Saugerties

$519,000
5 Beds 3 Baths 994006 MLS
A lifestyle. A place to gather. A place to call home Tucked away on a picturesque 1.3-acre property in the heart of Accord, 59 Cooper Street offers the space, privacy, and peaceful setting that define Hudson Valley living. Surrounded by mature trees and open skies, this five-bedroom, two-and-a-half-bath home is an inviting retreat where everyday life feels just a little slower and a little more meaningful. Inside, nearly 2,400 square feet of thoughtfully designed living space provides room for every stage of life. Sun-filled living areas invite conversation and connection, while the flexible floor plan offers endless possibilities for remote work, guest accommodations, creative pursuits, or multigenerational living. With five true bedrooms, there’s space for everyone without sacrificing comfort. Step outside and imagine mornings with coffee on the deck, afternoons gardening or playing in the expansive yard, and evenings gathered with friends beneath the stars. The property offers privacy, room to roam, and the opportunity to create the outdoor lifestyle you’ve been dreaming about. Perfectly positioned in one of the Hudson Valley’s most sought-after communities, you’ll enjoy easy access to Mohonk Preserve, Minnewaska State Park, Stone Ridge, Inness, local farm stands, wineries, breweries, and some of the region’s finest restaurants. Kingston, New Paltz, Woodstock, Arrowood and the NYS Thruway are all within easy reach, making this an ideal full-time residence or weekend escape. This is more than a house—it’s an opportunity to embrace the Hudson Valley lifestyle, where natural beauty, small-town charm, and modern convenience come together. Whether you’re searching for your forever home, a peaceful country retreat, or simply more room to live the life you’ve imagined, 59 Cooper Street is ready to welcome you home. Schedule your private showing and experience everything this special property has to offer.

59 Cooper Street, Accord

$564,000
4 Beds 2 Baths 994026 MLS
Step into a one of a kind Goshen farmhouse rich in history at 14 Maple Avenue, a captivating late-19th-century farmhouse set on over 5 picturesque acres in the heart of Goshen. The original structure was built in 1887 (later completed in 1940) by Kenneth Sinsabaugh: respected craftsman, town supervisor, and contributor to the First Presbyterian Church. This home offers a rare blend of historical significance and modern-day comfort. Notably, the home features authentic Tiffany stained-glass windows, mirroring those found in the church itself. A welcoming front porch leads to impressive double entry doors, opening into a grand foyer with soaring ceilings and an original gas lamp thoughtfully converted to electric. The main level features a spacious formal dining room and an inviting living room highlighted by oversized windows and a striking brick wood-burning fireplace. The kitchen is well-appointed with a large center island, gas range, stainless steel appliances, and its own side entrance leading to a charming second porch. The home’s original 1887 structure, which was seamlessly incorporated to the overall 1940 structure, serves as a versatile family room or ideal first-floor primary suite, complete with a full ensuite bathroom. Upstairs, you’ll find four generously sized bedrooms, each with unique character, along with a full bath offering a dual vanity, shower stall, tub, and abundant storage. Additional highlights include a walk-up attic ready to be transformed into a home office, media room, or play space, and an unfinished basement offering excellent storage and updated mechanicals, including washer/dryer, water softener, new electric panels, furnace, and hot water heater. Outdoors, the property truly shines: enjoy a spacious back patio with dual gas hookups for grilling, and explore your own private walking trail leading to a scenic hilltop clearing, perfect for gatherings around the firepit. Conveniently located just minutes from the shops, restaurants, and parks of the Village of Goshen, with easy access to Route 17 for commuting—approximately 55 minutes to NYC via the George Washington Bridge. Nearby attractions include LEGOLAND New York Resort and Resorts World Catskills. This is more than a home, it’s a legacy property rich in character, history, and opportunity. Schedule your private showing today!

14 Maple Avenue, Goshen

$524,999
6 Beds 2 Baths 984037 MLS
Investor Opportunity in the Village of Saugerties, New York – 2-Family Property with Strong Rental Potential Calling all investors! This 2-family investment property in Saugerties, New York is a prime opportunity to expand your rental portfolio in one of the Hudson Valley’s most desirable and growing markets. What makes this property a smart investment? Two units — each offering 3 bedrooms and 1 full bath Separate utilities/meters for easier management and tenant responsibility Shared yard for outdoor enjoyment Unfinished basement with Bilco doors — ideal for storage or future value-add potential Shared driveway + street parking Why this location stands out: Situated in the heart of the Village of Saugerties, New York and within the Saugerties School District, this property is surrounded by convenience and lifestyle appeal. Enjoy close proximity to local restaurants, shops, and everyday essentials, plus outdoor destinations like Esopus Creek and Saugerties Marina. Commuters and tenants alike will appreciate being less than 10 minutes from Route 9W and Interstate 87, providing easy access throughout the Hudson Valley and beyond. Who is this ideal for? Investors looking for multi-family rental income Buyers seeking a live-in-one, rent-the-other opportunity Those wanting a property with long-term appreciation potential in Ulster County With strong rental demand in the Hudson Valley, properties like this don’t stay on the market long. Whether you’re adding to your portfolio or entering the investment space, this is an opportunity worth exploring.

252-254 Partition Street, Saugerties

$575,000
7 Beds 5 Baths 993929 MLS
Stunning renovated Colonial farmhouse set in a peaceful country setting with beautiful pastoral views, just minutes to the Village of Pine Plains. Completely updated in 2020, this spacious home offers the perfect blend of classic charm and modern finishes. The main residence features 4 large bedrooms and 3 full bathrooms, a gracious formal dining room, and a bright, open kitchen with tile flooring and an electric fireplace for a warm, inviting feel. The oversized living room is filled with natural light and highlighted by a beautiful bay window. A finished attic provides additional flexible space, ideal for a home office, studio, or a fun hang out space for teenagers. A standout feature is the separate in-law suite or legal rental, offering 3 bedrooms and 2 full bathrooms with upscale finishes and tile work throughout—perfect for extended family, guests, or income potential. Enjoy quiet country living with easy access to everything the area has to offer—just minutes to Pine Plains and a short drive to Millerton. Spend your weekends exploring local farm stands and farm-to-table dining, walking trails, and scenic hiking. Stissing Lake is nearby for kayaking, swimming, and relaxing summer days. Conveniently located just 10 minutes to Millerton and within 20 minutes to both Red Hook and Rhinebeck. A rare opportunity to own a versatile and beautifully updated property in one of the Hudson Valley’s most charming countryside settings.

80 County Route 7, Pine Plains

$595,000
7 Beds 5 Baths 993710 MLS
Welcome to The Gather House located at 8643 New York 28 in Big Indian - a Four-Season Mountain Retreat in the Heart of the Catskills. There's a certain kind of quiet you only find in the Catskills - the kind that settles in your shoulders, slows your breathing, and reminds you that life can be simpler, softer, more intentional. As Route 28 winds through the valley, the mountains rise around you like old friends, and the Esopus Creek flashes between the trees. By the time you reach Big Indian, you're already somewhere else entirely. Tucked along the water's edge on 1.7 acres, this nearly 4,000 sq ft retreat feels less like a house and more like a place where stories take root. Morning sunlight filters through the windows and spills across the deck. The creek moves over the rocks while the sounds of wildlife layer into a natural harmony - a melody that will linger in your heart long after you leave. Inside, a large wood-burning fireplace anchors the great room creating the kind of hearth that pulls everyone together after long days on the mountain. Life here has its own rhythm. It's where you know all the farmers market locations, where the best swimming holes are tucked between boulders, and which trailheads catch the first light. Adventure is always close, but so are the moments of stillness; and that balance is what makes The Gather House so special. With space to host up to 20 guests, the home adapts to whatever your life calls for. The layout offers two distinct yet connected living spaces: A main residence with 5 bedrooms, 3 baths, sleeping lofts, and a game room/loft where late-night card games and laughter tend to stretch longer than planned. A private 2-bedroom, 2-bath apartment that can stand alone or open seamlessly to the main home through a shared interior door located off the laundry room. Open it up for one expansive retreat or close it for privacy and flexibility. It's a rare setup that works equally well for personal use or a multi-family income property (zoned as a legal 2-family). A detached second structure, already equipped with electric, plumbing, and septic, stands ready for its next chapter. A guest cottage, studio, workshop, or additional income unit - the infrastructure is in place for your vision to unfold. And for those who want even more yard space or an additional build site, the neighboring vacant parcel could be available for purchase. With ample parking, easy access along Route 28, and proximity to some of the region's most iconic destinations, The Gather House provides a true charm to Catskills living. Rooted in nature, shaped by seasons, and ready for you to call home.

8643 State Route 28, Big Indian

$599,000
991859 MLS
Business Opportunity (Restaurant Sale) Exceptional opportunity to acquire OTTO Full Service, a fully built-out and operating restaurant in the heart of Piermont’s highly desirable riverfront corridor. This is a true turnkey offering with significant value driven by its prime location, strong lease structure, and extensive existing improvements. The business benefits from a favorable long-term lease in place, providing stability and a solid foundation for future growth. Recreating this restaurant today would require substantial capital, as construction, labor, and equipment costs have risen dramatically—making this an attractive acquisition versus building from scratch. Strategically positioned in Piermont, a well-known destination market drawing clientele from both New Jersey and New York City, the location enjoys consistent traffic driven by dining, tourism, and weekend visitors. As the saying goes in real estate—location, location, location—and this property delivers. The space includes a fully approved outdoor patio (no additional approvals required), a major advantage for revenue generation, along with dedicated parking, a rare and valuable feature in this area. The layout supports full-service dining and offers flexibility for private events, live music, and entertainment concepts—an increasingly popular trend as consumers seek high-quality local experiences outside of NYC. Ideal for an experienced hospitality operator or investor looking to capitalize on an established setup in a thriving market. With the right vision and execution, this location offers substantial upside potential.

505 Piermont Avenue, Piermont

$550,000
4 Beds 3 Baths 991436 MLS
Welcome to your brand-new sanctuary in the prestigious Emerald Green community. This stunning newly-constructed bi-level home (built in 2024) blends modern luxury with a tranquil Catskills setting, offering over 2,304 square feet of meticulously finished living space on a quiet cul-de-sac. Interior Highlights: Open-Concept Living: The upper level features sprawling hardwood floors and airy 9-foot cathedral ceilings that lead into a sun-drenched living and dining area. Chef’s Kitchen: Experience high-end culinary design with gleaming granite countertops, an open kitchen layout, and a spacious pantry. Primary Suite: A large, private retreat complete with a full ensuite bathroom and a generous walk-in closet. Versatile Living: The lower level offers a fully finished basement, perfect for a family room, home office, or guest quarters. Massive Garage: Storage is never an issue with the 600+ sq. ft. dual-climate, 2-car attached garage. Outdoor & Community Living: Step out onto your private deck to enjoy the peaceful neighborhood or take advantage of the premium amenities offered by the Emerald Green Property Owners Association: Lake Privileges: Access to Lake Louise Marie for boating, fishing, and lakeside beach relaxation. Resort Amenities: Enjoy a newly renovated in-ground pool, tennis and pickleball courts, a fitness center, and a modern clubhouse. Location & Convenience: Situated less than 0.5 miles from State Route 17, this home is a perfect year-round residence or weekend getaway, You are just a short drive from world-class entertainment at Resorts World Catskills, the Kartrite Indoor Waterpark, and Bethel Woods Center for the Arts.

68 Picadilly Circle, Rock Hill

$549,000
2 Beds 2 Baths 991672 MLS
Situated on beautiful spring-fed Lake Muskoday, this dreamy lakefront home is the perfect getaway with stunning views, great proximity to fun towns, and convenient upgrades - hello mini-splits! With nearly panoramic views, the sparkling water is never out of sight and is the perfect backdrop for everything there is to love about lake life. Bright and airy with tons of natural sunlight, the main level of this home has well appointed spaces for living and lounging, and a charming built in banquet. As you head upstairs you’ll find a cute loft perfectly set up for napping, reading, or quietly enjoying views of the water. Each of the spacious bedrooms features extra high ceilings, warm wood paneling and tons of oversized windows and natural sunlight. The primary has sliding glass doors that lead out to a private and peaceful deck overlooking the lake. The second bedroom has 4 full size beds (2 bunks!) and allows for larger groups to stay the night. A second full bath completes this floor. Outside you’ll love the newly upgraded dock for enjoying your morning coffee, lounging on the water, and taking in the sunset. Easy access to the water makes launching a canoe, paddle board or kayak to explore this gorgeous lake a breeze. The HOA includes access to 250 acres of trails and other community amenities. It also oversees maintaining the pristine quality of beautiful Lake Muskoday. Lake Muskoday only allows electric motors to ensure a serene setting. Ten Minutes to the bustling Main Street of Roscoe - and 20-25 to Livingston Manor and Callicoon - means you have got a myriad of choices for dining, farmers markets, shopping and more! Spend your weekends exploring favorites like Grizzly Bagels, The Junction, Taylor & Ace + Material Index, Hound Books, Upstream Wines, Sunshine Colony, The Walk In, Callicoon Pantry, Callicoon Theatre - and truly so many more great spots! The beauty of this corner of the Catskills abounds with nearby hiking trails, waterfalls, state parks, and so many fishing spots - all while being just 2 hours to NYC!

212 Trout Brook Road, Roscoe

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