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

$519,000
3 Beds 2 Baths 1004504 MLS
DRAMATIC PRICE IMPROVEMENT – Exceptional Value in the Heart of Monroe! A remarkable opportunity just became even more attractive! 45 Summit Street in the Village of Monroe is now one of the area's most exciting offerings. Set on a beautifully positioned corner lot of more than one-third acre, this Colonial combines classic character, modern updates, and an unbeatable location. Imagine being just a short walking distance from shopping, the Millponds, the public library, restaurants, and convenient NYC transportation—all while enjoying the charm and tranquility of one of Monroe's most beloved neighborhoods. Inside, you'll find 3-4 bedrooms, 1.5 baths, sun-drenched living spaces, hardwood floors, and a wood-burning fireplace. The beautifully updated custom eat-in kitchen is a standout feature, showcasing rich wood cabinetry, granite countertops, and stainless-steel appliances, seamlessly connecting to the formal dining room—perfect for everyday living and entertaining alike. Additional highlights include: • Spacious office/family room with bonus square footage • Built-in china cabinet • Walk-up attic ready for future expansion • Full basement with endless possibilities • Whole-house generator • Newly installed high-efficiency boiler • Oversized garage and expansive driveway Step outside to your private backyard retreat featuring a bluestone patio and entertainment-sized gazebo, ideal for summer gatherings, outdoor dining, and relaxing evenings with family and friends. Conveniently located just minutes from major highways, schools, hospitals, and everything that makes the Hudson Valley such a sought-after destination, this home offers the perfect blend of lifestyle, location, and value. With its dramatic price reduction and exceptional features, this is an opportunity that savvy buyers won't want to miss.

45 Summit Street, Monroe

$539,000
9 Beds 5 Baths 1003041 MLS
WOW! Prime, prime location in the heart of South Fallsburg! Situated directly on highly visible Route 42, right next to Heiden Rd and Lavista Rd, this property offers some of the best road frontage and exposure you will find in the area. Surrounded by bungalow colonies, shopping, and constant local traffic, the location alone makes this a rare and exciting opportunity for investors, business owners, or end users looking to secure a truly strategic piece of Catskills real estate. This fully legal 4-family / mixed-use property features 2 separate structures on one property, with a total of 4 apartments — currently almost fully occupied with solid year-round tenants, creating strong and stable income from day one. The property sits on beautiful grounds with plenty of flexibility and future upside. Whether you are looking for a smart investment, a property for extended family and friends to enjoy together, a central Catskills escape, or a prime location for a business opportunity, this property offers endless possibilities. There is still additional potential for the right buyer to upgrade the property, increase rents, and further maximize value over time, making this not just a stable investment, but an exciting value-add opportunity as well. The unmatched visibility and frontage on Route 42 make this an incredibly tasteful and smart investment choice. Opportunities like this — combining prime location, multiple income-producing units, mixed-use potential, strong occupancy, and future upside — are extremely hard to find, especially in one of the most desirable and rapidly growing areas of South Fallsburg. Inventory remains very limited while demand continues to grow. Priced well and expected to move fast. Whether you are an investor or an end user, opportunities like this rarely become available — Act quickly, bring your vision, and make this unique property yours!

5017 S Fallsburg Main Street Unit #5019, South Fallsburg

$599,000
3 Beds 2 Baths 1002388 MLS
Discover 515-517 East Mountain Road North—a turnkey ranch perched atop the mountain, where timeless charm meets contemporary living on over 2 acres. This exceptional home artfully blends old-world details with modern additions, creating a perfect harmony of character and comfort. The main house has been beautifully renovated and expanded, featuring a brand-new addition that transforms the living space. This sun-drenched expansion added a spacious sunroom/playroom and a pristine new full bathroom. Beautiful reclaimed wood flooring adds warmth and history throughout, while digital WiFi-enabled thermostats in every room allow you to manage comfort from anywhere. Inside, enjoy a stunning open-concept kitchen with granite countertops, a large island perfect for entertaining and everyday living, a convenient pot filler, high-end appliances, and a reverse osmosis filtration system under the sink for pure drinking water. The primary bedroom offers a private retreat with an en-suite bath featuring a walk-in shower. Peace of mind comes standard with a newly installed septic system for the main residence. Beyond the main house lies a separate 434 square foot cottage, sold as-is, that could potentially be rehabbed. Locate near multiple hiking trails and parks, this property offers a move-in ready mountain-top sanctuary with sophisticated modern upgrades and endless outdoor recreation at your doorstep.

517 E Mountain Road N Unit #515-517, Cold Spring

$599,000
4 Beds 2 Baths 1002559 MLS
Set at the end of a quiet country drive just outside Livingston Manor, 57 Sheryl Davis Road offers the kind of privacy and connection to nature that defines the best of Catskills living. Surrounded by woods and bordered by a dramatic moss-covered bluestone rock face, this contemporary take on the many historic barns that dot the country roads in the area balances thoughtful design with warmth, ease, and quiet seclusion. The four-bedroom, two-bathroom home was designed with attention to detail for both weekend escapes or full-time living, pairing sleek modern finishes with grounded, cozy details. At the center of the home, a modern kitchen with waterfall island, sculptural light fixtures, and clean-lined cabinetry flows seamlessly into the main living space, creating an effortless setting for gathering, entertaining, or curling up on the couch for a movie night in. A wood burning stove adds warmth and atmosphere during the colder months, while a generously sized first-floor bedroom and full bath offer flexibility and comfort. Upstairs, the primary bedroom features its own fireplace — equal parts practical and whimsical — alongside two additional bedrooms and a second full bath. Outdoors, the landscape unfolds as an integral part of the property’s magical landscape. Spend evenings soaking in the hot tub beneath the stars, listening to the quiet and taking in the striking natural bluestone rock face that anchors the property. Multiple outdoor spaces (fire pit anyone?) invite dining, entertaining, and long afternoons settling into the slower rhythm of upstate life. Beyond the existing home, the acreage offers future potential. A slab foundation from a former structure still remains on the property, presenting opportunities for redevelopment, whether imagined as a guest house, studio, wellness retreat, or additional creative space. Private, design-forward, and deeply connected to its surroundings, 57 Sheryl Davis Road captures a distinctly modern Catskills lifestyle just moments from Livingston Manor’s beloved restaurants, breweries, shops, and year-round charm. A short drive from the nearby towns of Roscoe, Narrowsburg, and Jeffersonville - approximately two hours from NYC. If you’re looking for a private and modern upstate escape, you’ve found it at 57 Sheryl Davis.

57 Sheryl Davis Road, Livingston Manor

$575,000
1 Beds 1 Baths 996936 MLS
Welcome to unit 62 at 160 Cabrini Boulevard --a spacious and light-filled one bedroom home nestled in the heart of Hudson Heights' Castle Village, one of Manhattan's most sought after co-op communities. Perched on the 6th floor, this exceptional residence offers breathtaking panoramic views of the Hudson River and the majestic George Washington Bridge. Watch ships glide along the water and the sunset illuminate the palisades--all from the comfort of your living room. Inside, you’ll find prewar charm at its finest: high ceilings, gorgeous floors, graceful archways, and generous closet space throughout. The large bedroom easily accommodates a king-sized bed and more, while the spacious living room provides the perfect setting for entertaining or quiet evenings at home. The windowed kitchen offers both function and potential, with the opportunity to update and customize to your taste. The windowed bathroom retains classic art deco touches that speak to the timeless beauty of the building's 1939 heritage, Castle Village is renowned for its lush private gardens, riverfront walking paths, and 5 acre landscaped grounds exclusive to residents. Amenities include a full-time doorman, fitness center, roof decks, on-site parking and more. Plus the co-op is pet friendly and offers strong financials and responsive management. Just minutes from the train, charming cafes, Fort Tyron Park, and the Cloisters, this location combines convenience, tranquility and community.

160 Cabrini Boulevard Unit #62, New York (Manhattan)

$575,000
3 Beds 3 Baths 1002927 MLS
Stunning Views!! Welcome to Beckys Hill Mountain Escape! This contemporary home located down a long private driveway, perched up on the hill, is your private oasis nestled in the stunning Sullivan Catskill Mountains! This property boasts 55.41 acres of breathtaking views and tranquil surroundings. Wake up with stunning sunrises on the expansive open porch overlooking the incredible view. With 2,092 square feet of living space, this spacious retreat offers three inviting bedrooms and two baths, including the primary suite that is conveniently located on the first floor. 2 Bedrooms and full bathroom on the top level. The full basement adds even more potential for customization and expansion. Immerse yourself in the natural beauty and endless outdoor activities that the Catskill Park has to offer. From hiking trails to pristine fishing spots, the area's recreational opportunities are at your doorstep. Sullivan Catskills is rich in culture and history. Quaint towns dot the landscape each town with its own unique charm, go explore Hurleyville, Neversink, Claryville, Livingston Manor, Roscoe, Jeffersonville, Callicoon, Bethel, offering boutique shops, art galleries, and farm-to-table dining experiences. Local festivals and events celebrate the region's heritage and vibrant community spirit for recreation, dining, and entertainment. This home is a unique opportunity to create your dream mountain retreat, with a few upgrades you can combine modern living with the serene charm of the mountains. Don't miss out on this rare gem – your ultimate escape awaits!

26 Beckys Hill Road, Hurleyville

$589,000
2 Beds 2 Baths 1000951 MLS
Elegant & spacious prewar 2 bed, 2 bath corner unit in The Colchester, one of Garth Road’s premier & only dog-friendly buildings (up to 30 lbs). Beautifully renovated & thoughtfully designed, this exceptional home blends timeless architectural character with modern sophistication & enjoys coveted western & northern exposures, filling the apartment with natural light throughout the day. A long, gracious foyer sets the tone upon entry & leads to a beautifully defined dining area, perfectly positioned for everyday dining & effortless entertaining. Elegant French doors open into the expansive living room, enhancing the home’s wonderful flow & sense of openness. Custom built-in bookcases and a marble-topped radiator cover add warmth, character, and thoughtful design, while beautiful hardwood floors run throughout. The renovated kitchen features granite countertops, stainless steel appliances, and a thoughtfully custom-designed desk positioned beneath a north-facing window. Both bathrooms have been meticulously renovated with timeless finishes. The generously sized primary & secondary bedrooms enjoy western exposures & beautiful afternoon light. Exceptional storage includes 8 closets, highlighted by two custom-fitted walk-in closets in the apartment. Residents of The Colchester enjoy an expansive private community terrace overlooking Garth Woods, offering a peaceful outdoor retreat. Perfectly situated in an unbeatable location, enjoy Garth Road’s vibrant dining scene, recently featured in the Michelin Guide, along with close proximity to Scarsdale Village and Metro-North for a convenient 33-minute commute to Grand Central Terminal. Residents receive free permit parking for Garth Road, Grayrock Road, and the nearby resident lot, and are eligible for membership at Lake Isle Country Club featuring golf, tennis, and swimming. The Bronx River Trail is just steps away for scenic walking and biking. Maintenance does not reflect STAR credit.

143 Garth Road Unit #4N, Scarsdale

$595,000
999007 MLS
Welcome to Hudson Creekside, a boutique land development in the heart of the Hudson Valley offering a rare opportunity to build your dream home in New Paltz, NY. Lot 7, located at the end of a quiet dead-end cul-de-sac, features over 4.6 acres of private, buildable land surrounded by mature trees, scenic landscape, and the natural beauty the Hudson Valley is known for. This premium New Paltz building lot offers the ideal setting for a custom home, modern retreat, weekend getaway, or full-time residence. With generous acreage and a secluded setting, there is ample space for outdoor living, gardens, a pool, guest house, or a private sanctuary immersed in nature. The dead-end location provides added privacy and minimal traffic, creating a peaceful environment while still being part of a thoughtfully planned community. Hudson Creekside is a thoughtfully designed subdivision focused on sustainability, architectural integrity, and modern Hudson Valley living. Bring your own plans and create a home that reflects your vision and lifestyle in one of the region’s most desirable emerging communities. Conveniently located just minutes from the Village of New Paltz, this property offers easy access to Mohonk Preserve, Minnewaska State Park, hiking trails, biking trails, local farms, wineries, restaurants, and shopping. Whether you are searching for land for sale in New Paltz, a Hudson Valley homesite, or a private buildable lot near outdoor recreation and vibrant village life, Lot 7 presents a unique opportunity to invest in the future of Hudson Valley living.

11 Scenic Meadow Drive, Gardiner

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.