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

$589,999
4 Beds 2 Baths 1037720 MLS
Welcome to 5 Columbia Circle, a turn-key raised ranch tucked inside the gated Highland Lake Estates community in Highland Mills. From the moment you arrive, this home delivers what most listings only promise: modern updates, real peace of mind, and a backyard that earns its keep. Four bedrooms plus an office/den give you room to live and work without compromise. Two full bathrooms, California Closets in every upstairs bedroom, Pella doors, and Andersen 400 Series windows reflect a home maintained with discipline, not shortcuts. The mechanicals back it up: hot water heater (2021), whole-house water softener and filtration system (2023), and an upgraded back deck (2019) built for those gorgeous Hudson Valley sunsets. Comfort and security are handled. A heated garage with its own thermostat means projects don't stop in January. A central-station monitoring system covers fire, burglary, low-temperature, and carbon monoxide, plus camera coverage for complete confidence. The fenced backyard and lawn sprinkler system round out a property that's genuinely move-in ready. Location is the quiet advantage here. The Metro-North Harriman station sits under 10 minutes away, with NYC roughly 50 miles and about an hour out via I-87 and Route 17. Woodbury Common Premium Outlets, grocery, and everyday essentials are a short drive down Route 32. Weekends open up fast: Harriman State Park and Bear Mountain for hiking, nearby golf, and local wineries and farms that make Orange County living what it is. Enjoy local access to the John P. Burk Memorial Pool, Earl Resevoir and Brickley Field as well for all your athletic enjoyment. This is the rare home where the big ticket items are already done and done right. All that's left is to move in, relax and watch the sun go down right off your back deck.

5 Columbia Circle, Highland Mills

$549,999
4 Beds 3 Baths 1037800 MLS
PINE BUSH SCHOOLS – 2022 Modern Chalet Just Minutes from Orange County. Skip the 12-month wait and tens of thousands in post-closing upgrades. This 2022-built chalet already includes a heated pool, oversized outdoor entertainment area, privacy fencing, and premium appliances. Perfectly positioned against the scenic Wurtsboro Ridge State Forest with direct access to the renowned Long Path Trail, this home is a true haven for outdoor enthusiasts—blending nature, luxury, and modern design. Just 75 minutes to the GWB, and just 15 minutes to Middletown NY where access to NYC (via the Metro North as well as Greyhound/Trailways) along with an abundance variety of shopping, dining, and everyday amenities awaits. Explore the charm of historic Wurtsboro and Bashakill Wildlife Management Area right down the road, filled with locally owned shops, restaurants, and Bashakill Winery. For more adventure, you're just a short drive to Bethel Woods Center for the Arts, Resorts World Casino, Kartrite Indoor Waterpark, and Legoland. Step inside to soaring cathedral ceilings and a dramatic two-story fireplace that anchors the open-concept living space. Rich hardwood floors flow throughout, leading into a beautifully designed kitchen featuring granite countertops, tiled backsplash, high-end appliances and a sleek oven with range hood—perfect for entertaining or everyday living. The first-floor primary suite offers a private retreat with tray ceilings, spacious walk-in closets, and a spa-like ensuite bath complete with double vanity, custom tiled shower, and frameless glass doors. Upstairs, you’ll find a versatile loft space, an additional full bath, and a fourth bedroom—ideal for guests, a home office, or flex space. Outdoor living shines with a deck with seasonal mountain views, oversized patio, and a fully fenced backyard with convenient access points on both sides. Enjoy summer days in your heated above-ground pool, all set against a peaceful natural backdrop.

164 Shawanga Lodge Road, Bloomingburg

$550,000
2 Beds 1 Baths 1037210 MLS
FIX & FLIP • FIX & HOLD • INVESTMENT OPPORTUNITY • FUTURE DEVELOPMENT Rare opportunity for investors, flippers, and owner-builders in the desirable Riverside Manor neighborhood of Elmsford, within the Town of Greenburgh. Built in 1937, this single-family home presents a unique opportunity to renovate, reposition, and create significant value. Whether your strategy is Fix & Flip, Fix & Hold, or creating your dream home, this property offers an exciting path for an investor looking for a project with substantial potential. A major advantage is that the property is enrolled in a federally funded elevation project through FEMA’s Hazard Mitigation Grant Program (HMGP Project #4480-0076). $197,000 Federal funding has been approved to raise the structure and elevate the home two feet above the Base Flood Elevation (BFE). The project is expected to be managed through the Town of Greenburgh, with licensed design professionals and contractors overseeing the engineering and construction process. The existing home features a one-story frame design with crawlspace construction, making it well suited for the planned elevation project. An active National Flood Insurance Program (NFIP) policy with $250,000 in building coverage is currently in place and may be eligible for transfer, subject to applicable requirements. INVESTOR HIGHLIGHTS * Fix & Flip potential * Fix & Hold / rental investment opportunity * Opportunity to renovate and substantially improve the property * FEMA-funded elevation project already approved * Planned elevation 2 feet above BFE * Town of Greenburgh involvement in the elevation process * Licensed professionals and contractors to oversee engineering/construction * Existing $250,000 NFIP building coverage, potentially transferable * One-story frame construction with crawlspace * Opportunity to create a modern, future-ready home * Desirable Riverside Manor location PRIME LOCATION Conveniently located near major transportation routes, including I-287, I-87, and the Saw Mill River Parkway, providing convenient access throughout Westchester and the surrounding region. The property is also near the Metro-North Harlem Line, offering access to New York City. Outdoor recreation is close by, including the Saw Mill River Greenway and Greenburgh Nature Center. Whether you’re an experienced flipper looking for your next project, an investor seeking a long-term hold, or a buyer looking to build and create a customized future-ready home, this is an opportunity worth exploring. Bring your vision, renovation strategy, and investment plan — the possibilities are significant.

9 Babbitt Court, Elmsford

$575,000
1037657 MLS
TO- BE- BUILT! A Rare, High-Upside Redevelopment Opportunity: Unlock the Full Potential of 18 Dorland Avenue. is unequivocally one of the most compelling redevelopment parcels to hit the Dutchess County market in years. This 1.65-acre site, strategically zoned Residential Multi-Family (RM), offers a unique blend of scale, flexibility, and location that is virtually unmatched in the current market. Whether you are a seasoned developer, institutional investor, or visionary owner-user, this property is engineered for value creation and rapid appreciation in a region where demand for quality housing and specialized facilities continues to outpace supply. Property Overview: Lot Size: 1.65 acres (approx. 70,567 sq. ft.) Zoning: Residential Multi-Family (RM) Permitted Yield: Up to 10 units by right; potential for more with variance Building Height: Up to 40–45 feet Sewer Access: Available from Durocher Terrace and Dorland Avenue School District: Arlington Central Existing Structure: Condemned 3-bed, 2-bath home with indoor pool (not accessible) Other Permitted Uses: Childing or Adults day care, hospitals, nursing homes, alternate care housing, public utility structures Utilities: Public water, electric, trash collection available Taxes (2025): $6,008.00 Highlights: Prime infill location in a high-demand, supply-constrained corridor Flexible RM zoning supports multifamily, healthcare, and institutional uses Level, easily buildable site with dual sewer access—minimizing infrastructure costs Immediate access to major retail and transit. Strong demographic and rental fundamentals in Dutchess County’s most resilient submarket. Zoning & Permitted Uses: Residential Multi-Family (RM) District The RM zoning designation at 18 Dorland Avenue is a developer’s dream, offering both density and flexibility. By right, the parcel supports the construction of up to 10 residential units, with a maximum building height of approximately 40–45 feet—ideal for a boutique apartment building, townhome cluster, or stacked flats. Permitted Uses Include: Multifamily dwellings (up to 10 units; potential for more with variance) Family day care homes (subject to §210-65) Hospitals, nursing homes, and alternate care housing (subject to §210-91) Public utility structures (subject to §210-96) Key Zoning Advantages: Density: 10 units on 1.65 acres equates to ~6 units/acre—well-suited for mid-density multifamily or specialized residential Height: 40–45 feet allows for three to four stories, maximizing rentable square footage and design flexibility Alternative Uses: Healthcare, day care, and utility infrastructure permitted, expanding the buyer pool and exit strategies Variance Potential: Developers seeking higher density may pursue a variance for up to 20 or even 30 units, subject to municipal approval and parking requirements. Recent precedent in the area suggests that well-conceived projects with strong community benefit have a favorable path through the entitlement process.

18 Dorland Avenue, Poughkeepsie

$529,000
2 Beds 1 Baths 1037420 MLS
Set on approximately 6.7 acres with a natural running stream, this spacious property offers a rare combination of land, privacy, and opportunity. Whether you're looking for a private Hudson Valley retreat or envisioning the opportunity to build your dream home, the possibilities here are truly exciting. For the buyer who can see beyond the existing structure and recognize the value of the land, the setting, and the property's potential, 35 School House Lane offers an exceptional opportunity to create something truly special. The existing dwelling provides the unique advantage of being able to live on the property while you plan and build your dream home. In the meantime, enjoy everything this beautiful setting has to offer. The real standout is the land—6.7 acres of natural beauty with a running stream, offering space to explore, garden, entertain, recreate, or simply enjoy the peace and privacy of your own piece of the Hudson Valley. Imagine creating your own private retreat surrounded by nature, with room for gardens, outdoor living, recreation, or simply a quiet place to escape and recharge. The possibilities are limited only by your imagination. The location makes this property even more appealing. Situated in sought-after Rosendale and conveniently located near Kingston, New Paltz, and Rhinebeck, you'll have easy access to some of the Hudson Valley's finest restaurants, shopping, galleries, farms, and cultural attractions. Outdoor enthusiasts will find some of the region's best hiking, biking, climbing, and recreational opportunities right at your fingertips. This is the Hudson Valley lifestyle at its best—space, nature, privacy, recreation, and the freedom to create something uniquely your own. Properties offering this much land, natural beauty, and potential are becoming increasingly difficult to find. If you're looking for a property where you can put your ideas into action and create something truly exceptional, 35 School House Lane is a rare opportunity worth discovering. The land is here. The vision is yours. The possibilities are waiting.

35 School House Lane, Rosendale

$529,900
4 Beds 4 Baths 1034457 MLS
Dead-End Privacy, Legal Accessory Apartment, Close to Shops & Taconic Parkway This Lagrangeville mother-daughter offers true multigenerational flexibility: a legal accessory apartment (1BR, 1BA) with its own separate entrance, ideal for extended family, rental income, or guests. Rent for the accessory apartment was $1,400/month plus $75 for garbage and wifi, with electric and heat included. Tucked at the end of a private dead-end street with only four homes total, the property pairs seclusion with everyday convenience — just minutes from the Taconic State Parkway and close to two shopping plazas featuring ShopRite, Dunkin', a pet store, preschool, and a beloved family-owned Italian bakery. Inside, the main kitchen impresses with generous counter and cabinet space, Italian tile backsplash, and granite countertops. A sun-drenched sunroom off the primary bedroom offers year-round flexibility, while the primary bath is a private retreat with a jacuzzi tub and separate shower. Brand new central air (installed July 2026) keeps the whole home comfortable. The grounds are a gardener's dream, with mature flowering trees and perennials including dogwood, magnolia, red bud, and azalea, alongside hostas, lilies, daffodils, climbing roses, and more — a landscape that blooms in waves from spring through summer. Entertain effortlessly on the large back deck with gazebo and stone patio, perfect for summer gatherings. A door at the top of the stairs also opens up further possibilities — home office or Airbnb potential — beyond the accessory apartment itself. Privacy, gardens, updates, and income potential — this is a home that offers something for everyone. Sale is AS IS. Washer does not convey. The 1BR/1BA accessory apartment is included in the total square footage and bedroom/bathroom count. Recently appraised at $560,000.

7 Lyceum Road, Lagrangeville

$525,000
3 Beds 2 Baths 1035806 MLS
This is your dream fully renovated one-level home in the heart of Red Hook, tucked away in a quiet neighborhood while keeping you close to shops, restaurants, parks and easy access to Taconic State Park. Thoughtfully renovated from top to bottom, this home blends modern comfort, elevated finishes, and effortless one-level living. Step inside to a bright, beautifully finished interior where wide-board pine flooring brings warmth and character throughout the main level. At the heart of the home, the brand-new custom kitchen features beautifully crafted cabinetry, quartz countertops, a tiled backsplash, and a full suite of new appliances, including refrigerator, range, microwave, and dishwasher. The bathrooms continue the refined aesthetic with quartz surfaces and fresh, modern finishes. Nearly every major component of the home has been updated, giving you the luxury of simply moving in and enjoying it. Improvements include a brand new 30-year asphalt shingle roof, new 200-amp electrical service, new vinyl siding with a stone façade accenting the front porch, new Andersen windows, new front entry door and rear slider, and new interior doors throughout. A new high-efficiency two-zone heat pump system provides heating and cooling throughout the home, complemented by a new water heater. The lower level offers even more beautifully finished living space with new engineered flooring and plenty of flexibility for a family room, home office, gym, media room, or guest space. Outside, a newly built wood deck extends the living space into the backyard, creating the perfect setting for morning coffee, summer dinners, and entertaining. Completely refreshed inside and out, this is a rare opportunity to own a truly move-in-ready home in the heart of Red Hook—don't miss your chance to call this your home!

15 Amherst Road, Red Hook

$568,500
2 Beds 1036836 MLS
Investors and owner-occupants alike, take note: this Nyack multi-family gem delivers the kind of income potential that makes weekend math genuinely fun. With separate gas and electric meters serving each unit, tenants handle their own utilities while you enjoy the perks of smart, hands-off ownership. Inside, you will find vinyl flooring & hardwood floors that lend warmth and enduring character throughout. Each unit offers 1 Bedroom, Living Room, Bath & Eat in Kitchen. You can choose to occupy one unit and lease the other or rent both for maximum return. A basement adds valuable storage, workshop space, laundry and mechanicals, keeping everything tidy and out of sight. Parking, that elusive treasure in a bustling river village, is a genuine bonus here, this property offers parking for 2 cars for each unit, sparing you the daily hunt for a spot along the street. Speaking of the village, the location is downright enviable. Montefiore Nyack Hospital sits practically around the corner, a huge draw for those seeking a short commute. Old World Food Market handles grocery runs with ease, while a nearby bus stop keeps transit options open. When you crave fresh air, Village of Nyack Memorial Park offers scenic riverside views just minutes away, and downtown Nyack's celebrated boutiques, cafes, and art galleries are always within reach. Opportunities to own a versatile, income-producing property in such a coveted, accessible community are rare and rarely linger long. Schedule your private showing today and see the possibilities for yourself.

92 N Highland Avenue, Nyack

$590,000
2 Beds 1 Baths 1034778 MLS
A spacious approximately 1,000-square-foot two-bedroom, one-bath co-op located in the heart of historic Jackson Heights. This well-proportioned home offers classic pre-war character, generous room sizes, high ceilings, hardwood floors, ample closet storage, and abundant natural light. Offered in original condition, the apartment presents an opportunity to bring your own vision to a generously sized two-bedroom layout while retaining the character and scale of a classic Jackson Heights residence. The building also features a landscaped rear garden, providing a shared outdoor setting within the community. Garage parking is available by waitlist, subject to building policies and availability. Ideally situated near the 74th Street/Jackson Heights transportation hub, with convenient access to multiple subway and bus lines, the location provides excellent connectivity throughout Queens and to Manhattan. Residents are also close to Flushing Meadows Corona Park, neighborhood shopping, restaurants, everyday services, and a variety of schools and community amenities. A distinctive opportunity to own in one of Queens' renowned historic neighborhoods, with approximately 1,000 square feet of space, classic architectural character, and the flexibility to create a home tailored to your own preferences. Co-op board approval is required. Property is being offered in as-is condition. All information is deemed reliable but is subject to verification.

37-22 85th Street Unit #31, Jackson Heights

$525,000
3 Beds 3 Baths 1033232 MLS
Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

66 Reservoir Road, Pawling

$525,000
2 Beds 2 Baths 1036503 MLS
Welcome to Woodcrest Village, a sought-after 55+ community offering the perfect combination of comfort, convenience, and low-maintenance living. This beautifully maintained and freshly painted second-floor corner unit is move-in ready and filled with natural light. Its desirable end-unit location provides added privacy and quiet, with the added benefit of no neighbors above. Step inside to a bright and inviting open-concept living and dining area designed for both comfortable everyday living and easy entertaining. Beautiful laminate flooring and neutral finishes create a warm, welcoming backdrop ready to complement any style. The spacious living area flows seamlessly into the dining space, while a French slider opens to a large private balcony overlooking the community pool and pool house. Whether enjoying your morning coffee, reading a book, or unwinding at the end of the day, this private outdoor space is a wonderful extension of the home. The adjoining kitchen offers ample cabinetry and counter space along with a convenient breakfast bar that keeps the kitchen connected to the main living area. The kitchen appliances are less than two years old, adding to the home's move-in-ready appeal. A newer washer and dryer, also less than two years old, provide additional convenience. The home features two generously sized bedrooms and two full baths, offering flexibility for overnight guests, a home office, or additional living space. The spacious primary bedroom is a peaceful retreat with plenty of natural light, while custom blinds throughout add both style and functionality. Woodcrest Village offers residents an array of amenities designed to enhance an active and enjoyable lifestyle, including an outdoor swimming pool and pool house, a fully equipped fitness center, and beautifully landscaped grounds. The community's convenient location puts shopping, restaurants, medical care, and the hospital within easy reach, while nearby parks within walking distance provide additional opportunities to enjoy the outdoors.

100 Woodcrest Lane Unit #124, Mount Kisco

$599,900
3 Beds 2 Baths 1032890 MLS
Set above Wolf Lake on a wooded hillside, 109 Canal Road offers something increasingly difficult to find: a home with genuine character, beautiful lake views, remarkable outdoor spaces, and an unusually substantial connection to the water. Across the road, 85 feet of deeded lake access is shared with the immediate neighbors and includes a beach, sun deck, dock, seating area, and storage racks for canoes and kayaks. The longtime home of a respected local contractor and craftsman, the property has been refined over decades with an unmistakably personal hand. Knotty pine walls and ceilings, skylights, cherry-toned hardwood floors, arched openings, and lake-facing bay windows in both the dining area and living room give the interior the warmth of a true woodland retreat. Two full baths, including a soaking tub, add comfort without losing the home's rustic character. The grounds may be the property's most memorable feature. Just over half an acre has been shaped into a series of intimate outdoor spaces with dry-stacked stone walls, bluestone steps and patios, mature plantings, a waterfall pond, a second lily pond, landscape lighting, and paths winding through the wooded hillside. Water moves through a small brook created by the seller, where birds gather to bathe and the sound of running water turns an ordinary afternoon into something special. It is the kind of place where you can lose the stress of the week and, perhaps, find a little of yourself again. This is not a conventional lake house, nor is it direct waterfront, yet it offers many of the experiences people seek in one. It is something more individual: a home shaped and refined over decades with a craftsman's skill and an artist's eye, overlooking Wolf Lake, with an exceptional place at the water and grounds that would take years to imagine, let alone recreate. Located within Wolf Lake, one of Sullivan County's most sought-after private lake communities, the property offers access to approximately 1,800 acres of member-owned protected forestland, three spring-fed lakes, a community beach, clubhouse, basketball court, playground, and additional recreational facilities. All approximately 90 minutes from the George Washington Bridge. Annual association dues are $1,350, with a one-time new-member fee of $5,250.

109 Canal Road, Wurtsboro

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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.