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

$539,000
3 Beds 3 Baths 1032637 MLS
Welcome home to this beautifully maintained custom ranch, ideally situated on a peaceful corner lot at the end of a cul-de-sac in the Town of Shawangunk. Nestled on approximately 0.84 acres within the Pine Bush School District, this spacious 3-bedroom, 3-bath home offers over 2,000 square feet of comfortable living space designed for today’s lifestyle. Step inside to discover an inviting open-concept layout featuring hardwood floors, a bright and spacious living area, and a large kitchen with abundant cabinetry that flows seamlessly into the heart of the home. The expansive family room showcases a beautiful brick fireplace with a cozy wood stove, along with dedicated space that’s perfect for a home office, hobby area, or additional gathering room. The private primary suite includes its own full bath, while the home’s versatile floor plan offers flexibility for multigenerational living, extended family, or guests. A full basement, attic, crawl space, and attached garage provide exceptional storage and endless possibilities for future expansion. Outdoor living is just as impressive. Enjoy morning coffee or evening entertaining under the covered rear porch overlooking the level backyard. Gardening enthusiasts will appreciate the fenced garden with water access, while the detached shed with electric, water, and a concrete floor makes an ideal workshop or storage space. An installed generator transfer switch adds peace of mind year-round. Conveniently located just minutes from schools, parks, shopping, restaurants, and major commuter routes including Route 17 and I-84, this property offers the perfect balance of privacy, functionality, and accessibility. If you’ve been searching for a home with generous living space, quality craftsmanship, and room to grow, this Pine Bush gem is one you won’t want to miss. Schedule your private tour today!

2 Schrempp Lane, Pine Bush

$590,000
1031950 MLS
Welcome to The Virginia Queen Inn, an 1860 Italianate set directly on the village green in Jefferson, within the town's recently designated National Register Historic District. The two-story, four-bay wood-frame house spans roughly 2,756 square feet across a cross-gabled main block and rear wing, trimmed in deep Italianate friezes, paired scrolled brackets, and modillion blocks. Behind that facade sit nine guest suites and eight and a half baths, recently renovated. With a current legal non-conforming Operating Permit as a boutique hotel, with no short-term rental restrictions. A separate street-level commercial storefront adds a second use to this rare offering on one of the Catskills' beautifully preserved historic villages. Inside, wide-plank hardwood floors run beneath arched doorways, high ceilings, original pocket doors, and a turned-baluster staircase rises from an entry hall lit by a diamond-paned pendant fixture. The facade's Italianate entrance retains its paired doors with glazed upper panels, opening onto a foyer that sets the tone for a house built on careful, tactile detail. Two guest suites are arranged across the first floor, with the remaining seven bedrooms located on the second floor, most with private or ensuite baths. The second-floor signature suite opens onto a private balcony overlooking the green, and several suites can combine or share adjoining baths, giving a new owner flexibility for a full house of overnight guests, a large gathering, or a quieter stay. Outside, the one-story wrap-around porch spanning the facade and east elevation retains its original squared posts and corner braces with punchwork detailing; the east elevation section was enclosed in glass around 1920 and today serves as a sun porch overlooking the green. A separate street-level commercial storefront, with its own private entrance onto the green, is ready for a café, bakery, gift shop, or gallery, giving a new owner the option to run a business alongside the residence, or lease the space independently. The Virginia Queen Inn occupies one of Jefferson's most visible corners, neighboring the historic Maple Museum and the new Middlebrook Café & Bakery. The current owners have invested in the systems that support the house today: a new Navien propane hot water system, a Generac generator, updated plumbing, dedicated main-floor laundry with half bath, and a newer metal roof over a dry, well-kept attic. Jefferson itself is one of the region's least-altered nineteenth-century villages. From the porch, it's a short walk to the Jefferson General Store, the Mill Pond Inn & Restaurant, and Heartbreak Hotel. Stamford is six miles away, Cooperstown twenty-four, and Albany forty-five, with Amtrak service from Albany-Rensselaer and ski country at Hunter, Windham, Belleayre, and Plattekill all within reach. Offered fully furnished, The Virginia Queen Inn is ideal for a buyer drawn to hospitality, large-scale entertaining, or simply stewarding one of Jefferson's most storied addresses.

138 Main Street, Jefferson

$549,900
4 Beds 3 Baths 1032584 MLS
EXCEPTIONAL NEW CONSTRUCTION VALUE! A rare opportunity to own a beautifully crafted new home at an exceptionally attractive price. Thoughtfully designed with quality, comfort, and modern living in mind, this home offers the benefits of new contraction with outstanding value. This contemporary colonial home features, 8 rooms, 4 bedroom, 3 full baths, walkout bonus space, and sits on 2.3 picturesque, private acres. It has everything, beauty & style, and is loaded with upgrades, high end finishes, smart energy efficient features .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 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, quartz counters dual vanities and also 2 additional bedrooms with great main bath with tub & linen closet. It has central air & heat & comfort height toilets and much more. No carbon footprint. Basement has an additional, huge finished bonus room w walkout door with beautiful tile floors and separate entrance and 2 car garage Relax, entertain, experience nature, serenity and the sounds of birds or bbque on your 13x13’ back deck. All this tranquility, yet it’s less than 10 minutes to I 84 and ten minutes to train station in Port Jervis to commute to NYC and 10 minutes to Port Jervis, a quaint Renaissance city complete with upscale shops and trendy gourmet dining , near 3 rivers and cultural events. Start loving where you live.

804 Peenpack Trail, Sparrowbush

$575,000
6 Beds 2 Baths 1030768 MLS
Step into the rich history of this circa 1865 home, located in the City of Poughkeepsie's Historic District. Offering approximately 3,876 square feet across three finished levels, this residence showcases a distinctive Mansard roof, pocket doors, original millwork, bay windows, extensive built-ins, decorative fretwork, and other preserved architectural details that reflect its history and craftsmanship, such as plaster ceilings and walls throughout. A grand staircase with ornate woodwork and a built-in hall settle welcomes you upon entry, while hardwood floors, high ceilings, and ornate cast-iron radiators continue throughout much of the home. Spacious rooms provide flexibility for everyday living, entertaining, home office space, or creative pursuits. The kitchen complements the home's period appeal with custom wood cabinetry, built-in hutches, exposed brick, granite countertops, a movable center island, and a bright bay-window dining area. A freestanding wood stove set on a decorative mosaic tile hearth adds warmth and architectural interest. Additional features include a covered front porch, three finished levels, a full unfinished basement, municipal water and sewer, oil heat, and mature landscaping. Conveniently located near Route 9, Metro-North, the Mid-Hudson Bridge, the Poughkeepsie waterfront, restaurants, shopping, parks, Vassar Brothers Medical Center, Marist University, Vassar College, and other Hudson Valley amenities. A rare opportunity to own a substantial historic home in the City of Poughkeepsie's Historic District, offering preserved architectural details, generous living space, and a convenient Hudson Valley location. Don't miss out! **Some photos have been virtually staged**

129 Academy Street, Poughkeepsie

$549,000
2 Beds 1 Baths 1031870 MLS
Welcome to the Carlton House, a beautifully maintained prewar cooperative nestled in the heart of the Jackson Heights Historic District. This sunny two-bedroom, one-bath home sits on the top floor with open eastern and southern exposures over the neighborhood's landmarked English garden homes. Hardwood floors run throughout, radiators provide heat, and window air conditioning units keep things comfortable in the warmer months. A large foyer welcomes you in, anchored by a decorative chandelier and flanked by two closets. A Comelit video intercom connects over WiFi and works with Alexa and Google Home for easy building access. From the foyer, the living room opens up with a picture window framing long views of the garden homes below, plus a deep sill perfect for plants to soak up the sun — and plenty of room to configure the furniture layout to your taste. A wrought-iron railing adds architectural character on the way to the dining area, which has its own ceiling fan and light fixture. The windowed, galley-style kitchen retains its original charm, with a gas range, deep basin sink, white cabinetry, and track lighting overhead. There's space beside the refrigerator for a small table or added counter space — a great opportunity to put your own stamp on it. The primary bedroom easily fits a king-sized bed and is filled with light from three windows, with two closets and an ornate ceiling fan overhead. The second bedroom is generously sized as well, with two windows and a closet. Between the two bedrooms, a hallway with room for a console table and mirror leads to the windowed bathroom, finished in classic black-and-white tile with a soaking tub and a separate stall shower. Building amenities further enhance the appeal, offering a part-time doorman, a well-equipped gym, a private garden, laundry facilities, and a garage with a short waiting list. Located just steps from tree-lined streets, Paseo and Travers parks, a vibrant Sunday green market, and a thriving culinary scene featuring Zagat-rated restaurants, this residence offers the best of Jackson Heights living. This is your chance to create the New York City home of your dreams.

34-41 85th Street Unit #6L, Jackson Heights

$569,000
3 Beds 3 Baths 1032282 MLS
Just constructed in 2026, 375 Breezy Hill Rd is waiting for you to come make it your own. No detail has been overlooked in this private country retreat where modern design meets the beauty and privacy of 2 picturesque acres. Thoughtfully designed with a striking black exterior and warm wood accents, this exceptional new home offers a timeless look that complements its natural surroundings. Inside, abundant natural light and peaceful views create a seamless connection to the landscape, with tranquility waiting outside every window. With the benefits of new construction and plenty of room to spread out, this is your opportunity to enjoy a fresh start in a beautiful setting. This new build is situated in a bucolic setting just a few miles from modern comforts. The wooded backdrop is the perfect setting for a cozy fire pit, evening gatherings, or quiet moments under the stars. Inside, thoughtful craftsmanship is evident throughout - from the unexpected coffered ceiling in the primary bedroom to the bright, open-concept floor plan designed for effortless entertaining. Custom touches, including a built-in microwave seamlessly integrated into the oversized island, Energy Star kitchen appliances, and beautifully designed shelving in the primary closet add both style and functionality. The mudroom features a sink and washer/dryer hookups - making the transition from work effortless and streamlined as you pass into your home. Just over two hours from New York City, this brand-new home offers the rare combination of new construction, privacy, and convenience. Move right in and make this thoughtfully designed new build your own, with a fresh, modern foundation ready for your personal style. Set in a peaceful private setting such that every day feels like a getaway—without giving up easy access to the city. Schedule your private showing today!

375 Breezy Hill Road, Parksville

$550,000
3 Beds 3 Baths 1030912 MLS
Welcome to **98 Black Creek Road**—a beautifully maintained split-level home offering the perfect blend of privacy, space, and convenience in the heart of Esopus. Nestled on approximately **2 acres** of peaceful, tree-lined property, this move-in ready residence features **3 spacious bedrooms, 2.5 bathrooms, and over 2,200 square feet** of comfortable living space. Sunlight fills the open living and dining areas, creating a warm and inviting atmosphere that's perfect for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry and counter space, making meal preparation a pleasure. Upstairs, the spacious primary suite provides a private retreat complete with its own en-suite bath, while two additional bedrooms and a versatile den/home office offer flexibility for today's lifestyle. The lower level provides generous storage space with endless possibilities for a home gym, recreation room, workshop, or additional finished living area. An attached two-car garage adds convenience and extra storage. Step outside onto the rear deck and enjoy the serenity of your private backyard, surrounded by mature trees and nature. Whether you're hosting summer barbecues, enjoying your morning coffee, or simply unwinding after a long day, this property offers the peaceful setting you've been searching for. Ideally located just minutes from Route 9W, you'll enjoy easy access to **Kingston, Highland, New Paltz, Rosendale, Marlboro, and Poughkeepsie**, making commuting, shopping, dining, and recreation exceptionally convenient. If you've been looking for a home that combines country tranquility with everyday accessibility, **98 Black Creek Road** is an opportunity you won't want to miss. Schedule your private showing today and experience all this exceptional property has to offer.

98 Black Creek Road, Esopus

$574,900
4 Beds 2 Baths 1031630 MLS
Endless Possibilities Await! Bring your imagination and unlock the incredible potential of this one-of-a-kind contemporary home nestled on a .29-acre lot in desirable Congers within the award-winning Clarkstown School District. Offering nearly 2,900 square feet of living space, this distinctive residence is filled with architectural character just waiting to be restored to its full glory. Step inside and discover soaring vaulted ceilings, dramatic exposed wood beams, oversized windows that fill the home with natural light, and two inviting wood-burning fireplaces—including a striking cultured stone fireplace that anchors the dining room and a cozy wood-burning stove that adds warmth and charm. A spiral staircase leads to a loft-style bedroom, while skylights and open living spaces create an airy, chalet-inspired feel throughout. The home's unique design offers an exceptional canvas for those looking to renovate and create something truly special. While the property does require updating—including new flooring, as carpeting is being removed due to pet odors—the opportunity to transform this home into a stunning custom residence is undeniable. Whether you're an investor, contractor, or buyer with a vision, you'll appreciate the home's generous proportions, distinctive architectural details, and desirable location close to parks, shopping, restaurants, commuter routes, and everything Clarkstown has to offer. If you've been searching for a home with character, space, and the chance to make it your own, this is the opportunity you've been waiting for. Bring your creativity and breathe new life into this hidden gem.

59 Jolliffe Avenue, Congers

$539,000
2 Beds 2 Baths 1031882 MLS
Welcome to this beautifully renovated 2-bedroom, 2-bathroom cooperative residence in the heart of Oakland Gardens. Thoughtfully redesigned with high-end finishes and modern upgrades throughout, this exceptional home offers the perfect blend of style, comfort, and functionality. The spacious layout features custom-designed closets that provide abundant storage, including a generously sized primary bedroom closet with an organized shelving system. The renovated kitchen is equipped with stainless steel appliances, including a refrigerator, stove, and dishwasher, along with ample cabinetry and counter space, making it ideal for both everyday living and entertaining. The sun-filled living room flows seamlessly into a formal dining area, creating an inviting space for relaxing or hosting family and friends. Both bathrooms have been tastefully updated with contemporary finishes, while beautifully refinished original hardwood floors add warmth and character throughout the home. Additional improvements include updated electrical wiring for added convenience and peace of mind. Residents enjoy an outstanding selection of resort-style amenities, including an Olympic-sized swimming pool, tennis complex, a 6,000-square-foot fitness center with group classes, multiple playgrounds, resident storage facilities, and both indoor and outdoor parking options. The community also features 24/7 on-site security and video surveillance, offering comfort, convenience, and peace of mind in one of Queens' most desirable cooperative communities.

75-26 Bell Boulevard Unit #LD, Oakland Gardens

$575,000
3 Beds 3 Baths 1031234 MLS
Tucked along a quiet, tree-lined drive overlooking the first fairway of Red Hook Golf Club, this beautifully maintained townhome offers a peaceful setting where nature, recreation, and convenience come together. Just 7 minutes to the Village of Rhinebeck and 10 minutes to Red Hook, you'll enjoy easy access to shopping, acclaimed restaurants, farmers markets, theaters, hiking trails, and everything the Hudson Valley has to offer, while coming home to a setting that feels like a private park. Wake to sweeping views of lush green fairways, specimen trees, and an abundance of birds, including hummingbirds that frequent the expansive rear deck throughout the day. Whether you're an avid golfer or simply appreciate the beauty and tranquility of the landscape, this home offers an exceptional lifestyle. A new remote-controlled retractable awning (2024) creates the perfect shaded retreat for outdoor dining or relaxing while overlooking the course. Freshly painted and filled with natural light, the home features 3 bedrooms, 2.5 baths, beautiful new wood floors, and a spacious primary suite with soaring ceilings, a large walk-in closet, and an en-suite bath. The eat-in kitchen is equipped with stainless steel appliances and opens through sliding glass doors to the oversized deck, while the formal dining room and inviting living room provide comfortable spaces for entertaining and everyday living. A full dry basement offers abundant storage or future finishing potential, and the attached one-car garage is complemented by a generous driveway plus additional guest parking directly across from the home. Recent updates include a newer roof, central air conditioning, hot water heater, beautiful new wood flooring, and the 2024 retractable awning, offering peace of mind for years to come. Low HOA fees include lawn care, snow removal, garbage service, and driveway sealing, allowing for truly low-maintenance living. Enjoy dinner just a short stroll away at The Grove restaurant, spend weekends at the nearby Dutchess County Fairgrounds or Old Rhinebeck Aerodrome, or explore the charming villages of Rhinebeck, Red Hook, and Tivoli with their renowned dining, boutiques, and cultural attractions. With municipal water and sewer, an unbeatable location, and one of the most serene settings in the area, this is Hudson Valley living at its best.

66 Tee Lane, Red Hook

$529,999
3 Beds 2 Baths 1031608 MLS
Price Improvement! SELLERS ARE READY TO MOVE! Schedule a showing and bring an offer! Situated on its own road in the sought after Minisink Valley School District, this 3 edroom, 2 full bath Cape Cod home sits on almost an acre of fllat, professionally landscaped land, offers over 2000 square foot of finished living space plus additional versatile areas designed for both everyday comfort and entertaining with family and friends. Buyers searching for a home with an open concept layout will love and appreciate the spacious living and family rooms complete with cathedral ceilings, red maple flooring and high custom arched windows that will make conversation flow seaminglessly between the kitchen and the living room areas. Picture yourself in the Four Season room area relaxing with friends, playing games, enjoying a cocktail, or just watching nature unfold. Or on a chilly night, sitting around the propane stove and solving all the world problems. Or go outside and ice skate on the pond with some hot chocolate in hand! (Road and pond is maintained by the Town of Wallkill). The quaint kitchen area also opens up to these areas allowing the bridge of entertaining guests while preparing meals. The homes layout includes three spacious bedrooms. The primary bedroom and primary bathroom can be found on the first floor. Another recently renovated bathroom (2025) can also be found on this floor. In 2003, when the addition was added onto the home, new "Shaker" vinyl siding was added, as well as shingles and new windows. All new Bluestone concrete steps were added in August of 2024. Life is easy with Leaf Filter which was installed in 2021. Water softener is owned. New septic installed in 2020 and a new above ground oil tank was installed in 2025. Conveniently located just 70 minutes from New York City and close to I-84, Route 17, and 17M, the New York Thruway, nearby Metro-North Railroad Stations, shopping (Middletown Galleria), walking trails, restaurants, wineries, apple and pumpkin picking, and so much more! Buyers looking for a practical choice for commuting to and from NYC, with Metro North, buses and other trains, will find this home a practical choice for accessibility in Orange County. Come and take a look! You will want to stay! Schedule your appointment today!

31 Bendlin Lane, Howells

$537,500
3 Beds 3 Baths 1030461 MLS
Welcome to 38 West Taconic Drive, a rare brick corner lot charmer in the desirable Hillside Lake neighborhood of Wappingers Falls, offering its next owner the best of both worlds: quiet country living with less than a five minute drive to the Taconic State Parkway. Impeccably maintained by its current owners, the home offers three bedrooms and baths, a formal dining room and multiple living areas, including a bonus room that opens to the yard. Two fireplaces, one on each level, add to further warmth and charm. The home features a modern kitchen, updated baths, yet retains its rustic charm throughout, paying homage to its country roots. The home boasts new central air with a heat pump, offering electric or oil heating options, quality designer lighting throughout the home. which will transfer with the sale, newer, updated windows & septic system. Outside, the backyard is an entertainers'paradise: the fenced in back yard is divided into multiple outdoor entertaining spaces and comes complete with an outdoor fireplace and raised deck to be converted to accommodate the many visitors who will flock to your home. The recently paved driveway has been widened allowing parking for 8 cars, in addition to the oversized garage two car garage. The side yard is approximately 3,000 sq/ft and features a highly sought-after wrought-iron courtyard gazebo. The yard is 3/4 fenced in. This space can easily become he wildflower garden of your dreams, the largest vegetable garden in town, or a place to park your RV or boat. Pictures do not do this property justice. Book your appointment today.

38 W Taconic Road, Wappingers Falls

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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.