Sleepy Hollow Real Estate Search

Sleepy Hollow Properties between $400,000 and $450,000 for Sale

Our website features the best real estate search for between $400,000 and $450,000 properties available in Sleepy Hollow and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Sleepy Hollow Properties between $400,000 and $450,000 for Sale

$400,000
3 Beds 4 Baths 1016273 MLS
A unique opportunity for builders, investors, contractors, or buyers with vision, this distinctive property offers exceptional potential. The existing 3-bedroom home had been extensively renovated and was ready for occupancy before a minor fire resulted in the interior being taken down to the framing. Importantly, the exterior of the home was not affected, providing a valuable head start for restoration and rebuilding. This rare property allows the next owner to complete the renovation and bring the home back to life while benefiting from many of the substantial improvements already made. Adding to its versatility, the property includes a second approved building site for a 1-bedroom cottage, creating flexible options for guest accommodations, a home office, rental income, or a private retreat. Beyond the improvements, the land’s natural beauty further enhances its appeal. Established fruit trees, scenic woodland trails, and striking rock outcroppings create a picturesque setting rich in character and outdoor enjoyment. Whether exploring the woods, harvesting fruit, or simply taking in the peaceful surroundings, the property offers a meaningful connection to nature. An oversized garage provides ample space for vehicles, equipment, storage, hobbies, or workshop use. Whether you’re looking to restore the existing residence, create a multi-building compound, or invest in a property with significant upside, this special parcel provides the ideal foundation to bring your plans to life. Conveniently located with easy access to the Taconic State Parkway and just minutes from the dining, shopping, arts, and cultural attractions of Red Hook, Rhinebeck, and Hudson, it offers an appealing balance of privacy and accessibility. Properties with this combination of restoration potential, additional building capacity, natural beauty, and versatile outbuildings are increasingly rare. Bring your ideas and realize the full promise of this one-of-a-kind property. Buyers to perform their own due diligence regarding approvals, permits, building requirements, and intended uses.

117 Camp Road, Red Hook

$424,900
1 Beds 2 Baths 1021918 MLS
"Spacious Tri-Level Townhome — Lives Like a 2 or 3 Bedroom!" Located in the sought-after Elm Crest community, set on a quiet cul-de-sac with a private, wooded backyard and no homes directly behind. This 1,733 sq ft home features new hardwood floors throughout the main and upper levels, an updated eat-in kitchen with new dishwasher and breakfast bar, and a spacious living/dining area with deck access for outdoor entertaining. Upstairs offers a primary suite with walk-in closet and new full bath, plus a bedroom-sized den/loft easily convertible to a second bedroom, ideal as a home office, guest space, or growing family's needs. The walk-out lower level adds a family room, workshop, and ample storage, real bonus living space beyond the main two floors. Major systems are all updated: new HVAC (central AC, furnace/heat pump), new hot water heater, newer roof, and gutters. Exterior freshly power washed and the deck newly stained (July 2026), plus fresh paint and landscaping throughout, truly move-in ready. Located in the desirable Wappingers Central School District, minutes from shopping, dining, and a nearby park with playground, pickleball, ball fields, dog park, and trails. Easy access to I-84, the Taconic State Parkway, and Metro-North rail into Grand Central via Beacon station. Low HOA ($275/month) includes a private in-ground pool, grounds maintenance, and snow/garbage removal. A rare combination of privacy, updates, and low-maintenance living in one of Fishkill's most convenient locations.

101 Elmcrest Drive, Fishkill

$424,500
3 Beds 2 Baths 1021542 MLS
Learn the history and fall in love with this charming pre-Victorian home in Cochecton's Parsonage Road Historic District. Set on a quiet country lane with no thru traffic among just six 19th-century homes, this fully updated 3-bedroom, 1.5-bath post-and-beam gem delivers timeless character without the old-house headaches. Inside, dramatic wide-plank floors and exposed beams tell the story of 1890 craftsmanship, while a brick fireplace with wood-burning stove and new chimney liner anchors the living space. The stainless steel kitchen features a European-inspired layout with in-kitchen washer and dryer, plus a custom free-standing table and workspace that stay with the home. A rare find for a home of this era: closets in all three bedrooms, including a walk-in with shelving in the primary suite. The hotel-style bath impresses with a walk-in shower beneath a skylight and a deep soaking tub. Thoughtful built-ins throughout. Outside, enjoy a 22'x 25' deck and patio combination perfect for entertaining, a fully fenced backyard with 8' privacy fence, accessible steps to the road, and a garden shed. Ample off-street parking rounds out the exterior. Easy walk to the Delaware River and Cochecton Firehouse Lounge. Minutes to Narrowsburg and Callicoon for dining, shopping, entertainment. Great investment property with a proven rental income history. Major systems have been completely refreshed for peace of mind: new boiler and gas lines, new septic tank and lines, new water filtration and aeration system, 2019 roof, and French drain. This is the historic home you've been waiting for — all the soul, none of the surprises. Schedule your private tour today. --

57 Parsonage Road, Cochecton

$420,000
2 Beds 2 Baths 1021477 MLS
Updated large two bedroom, two full bathroom, featuring vaulted ceilings and stylish, high-end finishes throughout. Dogs are allowed up to 50 lbs. As the only residence on the floor, this home offers exceptional privacy. The thoughtfully updated eat-in kitchen features a custom 5-burner gas range, stainless steel French-door refrigerator, Bosch dishwasher, designer ceramic tile flooring, and a contemporary backsplash—perfect for both everyday living and entertaining. Upgrades include refinished hardwood floors, dimmer switches in nearly every room with recessed lighting, living room with a sleek glass door wood-burning fireplace, wall-mounted smart TV recessed outlet, an updated primary bath with a marble-and-wood vanity, oversized shower with a new medicine cabinet and a secondary updated full bathroom with a tub. Both bathrooms vent out. Blinds and updated electrical outlets complete the home's extensive renovations. Pet-friendly development. Unassigned off-street parking, your own storage space! Laundry room with updated machines in the building. On-site superintendent. Commuters will appreciate the unbeatable convenience. The Bee-Line Route 65 bus to the Scarsdale Metro-North station stops right at the driveway, with less than a 10-minute trip from your door to the train platform. Residents may also apply for parking permits at both Scarsdale and Hartsdale stations. From Scarsdale, express Metro-North service reaches Grand Central Terminal in approximately 30 minutes. Ideally located close to shopping, dining, parks, and major transportation, this turnkey home offers the perfect combination of comfort, style, and convenience. You get it all in this stylish hidden gem with very little compromise!

13 Campus Place Unit #SL, Scarsdale

$438,000
1 Beds 1 Baths 1021001 MLS
Welcome to this beautifully maintained 1-bedroom, 1-bath condominium nestled in the heart of Rego Park. This bright and spacious home offers the perfect blend of comfort, convenience, and value. A welcoming entry foyer leads into an expansive living and dining area with an open, functional layout, perfect for both everyday living and entertaining. Large windows fill the home with abundant natural light, creating a warm and inviting atmosphere throughout. The generously sized bedroom easily accommodates a king-size bed with additional furniture and features ample closet space for all your storage needs. Elegant hardwood floors run throughout the home, adding timeless charm and warmth. The windowed kitchen is equipped with abundant cabinetry, generous counter space, and stainless-steel appliances, making meal preparation both practical and enjoyable. The windowed bathroom is well maintained and completes this move-in-ready residence. Located in a well-maintained condominium with low common charges and low property taxes, this home offers exceptional value. Residents enjoy unbeatable convenience with easy access to the MTA buses and subway, providing a quick commute to Manhattan. Just minutes from Queens Center Mall, Costco, supermarkets, restaurants, cafés, banks, and everyday shopping, with easy access to the Long Island Expressway (I-495) for effortless travel throughout Queens and Long Island. Whether you’re a first-time homebuyer, or searching for a smart investment opportunity, this move-in-ready condominium is one you won’t want to miss!

6385 Woodhaven Boulevard Unit #5A2, Rego Park

$415,000
2 Beds 1 Baths 1019677 MLS
**WATERFRONT RETREAT WITH PART-TIME RENTAL INCOME!** Don't miss this rare opportunity to own a beautifully restored waterfront cabin on the renowned Willowemoc creek, famous for its exceptional trout fishing. This charming property offers the best of both worlds—a peaceful Catskills getaway for your own enjoyment with the added benefit of **part-time short-term rental income when you're not using it.** Thoughtfully upgraded and modernized for comfortable year-round living while maintaining its timeless character, the home welcomes you with a covered front porch and an inviting open-concept living, dining, and kitchen area. Features include beautiful Brazilian hardwood floors, a cathedral ceiling with recessed lighting, and an energy-efficient split system providing heating and air conditioning. The home offers **two comfortable bedrooms, an updated full bathroom, and a charming loft** that provides additional sleeping or recreational space. At the rear of the home, the bright sunroom overlooks the peaceful Willowemoc Creek. French doors open to a spacious deck where you can relax around the fire pit, cast a fishing line, entertain guests, or simply enjoy the tranquil sounds of the flowing river. The property is **currently used by the sellers as a personal retreat and is also offered as a short-term rental on a part-time basis.** The home is being offered fully furnished, providing a buyer with the flexibility to continue renting it when desired while reserving time for personal use. Potential rental opportunities may include Airbnb, Vrbo, or other short-term rental platforms, subject to applicable local regulations. Additional features include **oil heat with an above-ground tank, energy-efficient split-system heating and cooling, a full basement for storage, an EV mobile charging port, and high-speed telecommunications** suitable for remote work. Ideally located in a picturesque country setting while remaining just minutes from restaurants, shopping, recreation, and local attractions. Easy access to Route 17/I-86 makes commuting convenient. **Whether you're looking for a private riverfront escape, a weekend getaway, a full-time residence, or a property that can generate rental income when you're away, this retreat offers an exceptional opportunity.

640 Debruce Road, Livingston Manor

$420,000
1 Baths 1019369 MLS
"PRICED TO SELL! Reduced the price from $459,000 to $420,000 for a quick sale!" Modern luxury Condo at H7O Condominium! High-end finishes, an open-concept layout, top-of-the-line stainless steel appliances, a convenient in-unit washer & dryer, and a private balcony with beautiful views. Situated in a premier Mid-Rise building with excellent amenities including an elevator, a fitness center, a roof deck. Located in a safe, quiet, and highly desirable neighborhood, yet just steps away from public transit, dining, and shopping. Investor-friendly with renting allowed from day one. A true turnkey gem perfect for buyers or investors alike! [ RESIDENT AMENITIES & EXPERIENCE ] Rooftop Living: Experience the stunning views from H7O 360°—an expansive rooftop deck equipped with a BBQ grill, kitchenette, picnic area, and premium lounge spaces. Unwind at the H7O Skydeck & Sky Lounge, featuring a sun deck with chaise lounges, a wet bar, and a dedicated co-working environment. Family & Play: Designed for all generations with H7O Boat Deck (an outdoor children's play space) and H7O Discovery Den (a vibrant indoor playroom). Pet-Friendly Perks: Pamper your furry friends at the private H7O Woof Deck dog run and the luxury H7O Soft Paw dog spa. Fitness & Convenience: Stay active at the H7O Flex Club fitness center. The building also features a beautifully crafted lobby with a waiting lounge, a secure Package Concierge system, a bicycle storage room, and private storage cages. [ FINANCIAL INFORMATION ] Monthly Common Charge: $306 Annual Property Tax: $4,861

618 Avenue H Unit #7G, Brooklyn

$450,000
3 Beds 3 Baths 1018305 MLS
It is a common misconception that all condos within a complex are essentially the same. This unit proves otherwise. Beautifully positioned as an end unit with sunlight from three directions, it stands out as one of the best available options in the community—especially with its prime location adjacent to the ski slope for true ski-in/ski-out convenience. The spacious open floor plan offers easy, comfortable living, with a bathroom and laundry on the main level, a welcoming front porch, and a rear deck for taking in the mountain setting. An efficient wood-burning stove adds warmth and character, while rustic wood accents create the perfect atmosphere for unforgettable après-ski moments. The second level features three bedrooms, including an ensuite primary bedroom, with a bonus sleeping loft and storage attic above. Lightly used, move-in ready, and beautifully maintained, this unit shows exceptionally well. The complex is home to many full-time, year-round residents, as well as second-home owners, some of whom offer monthly rentals to help offset ownership costs. Located adjacent to world-renowned Hunter Mountain, part of the Epic Pass network, the property benefits from strong demand for accommodations as the nearest major ski center to New York City. Beyond skiing, Hunter is surrounded by some of the best hiking and fishing on the East Coast, along with excellent restaurants and local favorites including Deer Mountain Inn and Scribner’s. Come have a look—this one is truly different.

56 Highlands Drive Unit #F1, Hunter

$450,000
3 Beds 1 Baths 1018223 MLS
Southside Poughkeepsie Colonial with Incredible Flexibility & Potential!! Charming and filled with natural light, this 3-bedroom colonial offers the perfect blend of character, comfort, and opportunity. Featuring beautiful hardwood floors throughout, a versatile bonus room ideal for a home office, den, guest room, or potential 4th bedroom, and an updated kitchen with granite countertops and stainless-steel appliances. The finished third level adds even more possibilities, offering a bonus room and partially completed bath ready for your vision—perfect for a future primary suite, guest retreat, studio, or additional living space. A separate entrance to an attached section of the home provides exceptional flexibility for extended family, guest accommodations, a home business, or potential mother-daughter setup with municipal approvals. Enjoy energy-efficient living with solar panels, ductless air conditioner heating and cooling systems, and an existing oil heating system for added convenience. Outside, you'll find a spacious yard, covered carport, and ample off-street parking. Ideally located just minutes from Vassar College, Vassar Brothers Medical Center, The Culinary Institute of America, shopping, dining, parks, and Metro-North. This is a truly exceptional opportunity offering space, versatility, energy efficiency, and room to add value in a prime Southside Poughkeepsie location. Whether you're looking for a primary residence, a multi-generational living opportunity, or an investment property with room to add value, this home delivers space, character, flexibility, energy efficiency, and incredible potential. Don't miss the opportunity to make this Southside Poughkeepsie treasure your own.

2 Wilbur Boulevard, Poughkeepsie

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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.