Sleepy Hollow Real Estate Search

Sleepy Hollow Properties for Sale

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Sleepy Hollow Properties for Sale

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Newest Sleepy Hollow Properties for Sale

$689,999
2 Beds 3 Baths 1047459 MLS
Welcome to Willow Wood at Smithtown, a remarkable townhouse and condominium development featuring the stunning Apple Wood model with 1,900 interior square feet. As you enter, you’re greeted by a spacious foyer bathed in natural light from a skylight, leading to an open staircase that ascends to the second floor. Upstairs, you’ll find a well-designed layout that includes a primary en suite with two walk-in closets and a double vanity featuring both a tub and shower, alongside a second bedroom, also with a walk-in closet. Conveniently located off the bedroom is a laundry room for easy access. Returning to the main level, the cozy living and dining room combination showcases engineered hardwood floors and a gas fireplace, with sliding doors that open to a private patio—ideal for outdoor relaxation. The spacious eat-in kitchen is perfect for gatherings, while a conveniently located powder room and ample closet space throughout ensure both comfort and functionality. The home also includes a one-car garage with an electric opener, offering additional parking and storage solutions. For added security, the property is fully alarmed with Ring cameras at the front door and garage door. Monthly common charges of $500.00 includes landscaping and maintenance, access to the inground saltwater pool, clubhouse, and fitness center, snow removal, and water, along with discounts on Optimum TV and Internet services. Community amenities further enhance the living experience with an inground pool, clubhouse, fitness center, and a relaxing gazebo, all in a pet-friendly environment. Don’t miss out on this exceptional chance to live in a vibrant community at Willow Wood in Smithtown!

5 Monitor Road, Smithtown

$539,000
3 Beds 2 Baths 1050159 MLS
New Construction in the Heart of the Village of Saugerties Welcome to your opportunity to own a stunning brand-new construction home in the charming Village of Saugerties--where contemporary design meets the natural beauty of the Hudson Valley. This thoughtfully designed resident offers 3 bedrooms, 2 full bathrooms, and a versatile loft, complemented by over 800 square feet of finished lower-level living space, that includes a third bedroom. The bright, open-concept kitchen and living area is filled with abundant natural light and seamlessly connects to expansive outdoor decking, creating the perfect setting for entertaining or everyday living. Enjoy picturesque views of the scenic Hudson River and seasonal views of the Esopus Creek providing a beautiful and ever-changing natural backdrop throughout the year. *Property Highlights *Brand-new construction and appliances *3 spacious bedrooms plus a unique loft area *2 full ceramic-tiled bathrooms *Open-concept kitchen flowing into a bright and inviting living room *Engineered wood flooring throughout the main living areas *Natural gas mini-split heating and cooling systems *Italian radiators providing efficient heat on the main floor *Pella windows and sliding glass doors *Expansive 600-square-foot deck for seamless indoor-outdoor living *Loft space ideal for a reading nook, home office, or private retreat *Over 800 square feet of finished lower-level living space featuring a spacious media room/recreation room *Private third bedroom on the lower level *Radiant heated floors throughout the lower level *Utility room and laundry with washer and dryer *Architectural spiral staircase *Engineered wood siding *Standing seam metal roof *Spray foam insulation for enhanced energy efficiency *Off-street parking area Ideally located just minutes from the Village of Saugerties' vibrant shops, restaurants, galleries, and waterfront attractions, this exceptional home offers the perfect combination of modern comfort, quality craftsmanship, and convenience. Secure your new home today and enjoy the best of village living with beautiful creek views, seasonal Hudson River Vistas and thoghtfully designed spaces for work, relaxation and entertaining.

33 Valley Street, Saugerties

$679,900
3 Beds 3 Baths 1050106 MLS
Come fall in love with this stunning 3-bedroom plus office Contemporary Colonial, beautifully set on just under an acre in one of Monroe’s most sought-after neighborhoods. Originally a ranch, the home was thoughtfully expanded approximately 20 years ago and transformed into a spacious, light-filled home with dramatic architectural details and a wonderful open layout. The heart of the home is the impressive two-story great room with soaring vaulted ceilings, a dramatic wall of windows, a fireplace and plenty of recessed lighting. The kitchen offers abundant cabinetry, granite countertops, stainless steel appliances and a glass mosaic tile backsplash, and opens beautifully to the main living spaces. Two bedrooms are conveniently located on the main level, offering flexibility for family, guests or one-level living. Upstairs, the primary suite feels like a true retreat. Double doors lead into the spacious bedroom, complete with gorgeous mountain views and a large walk-in closet. The oversized primary bath features a Jacuzzi tub, double sinks, a makeup area and a beautiful bay of windows. Just outside the primary suite is a separate office, perfect for working from home; the owners have also used this space as a fourth bedroom. The finished lower level adds tremendous additional living space with dimmable recessed lighting, built-in bookshelves and plenty of room to make the space your own. Use it as a family room, home bar, playroom, study, library or a combination of spaces. There is also an additional home gym. There truly is plenty of room for everyone. Additional features include central air on all three levels, two-zone central air with the upstairs system replaced, gorgeous hardwood flooring, a new hot water heater installed in August 2024, Pella windows, newer carpeting on the main level, upgraded electric, a one-car attached garage, and a second refrigerator and freezer that will remain. All COs are in place. Outside, the property is just as special. The park-like grounds surround a gorgeous in-ground pool, creating a spectacular private backyard retreat perfect for relaxing, entertaining and enjoying the warmer months. This is the kind of backyard everyone will want to gather in—an entertainer’s dream and your own private summer oasis. Located just moments from Berry Road Park, formerly Faber Farm, with access to hiking trails leading to Mombasha Lake, and offering deeded lake rights to Balder Lake, a private freshwater lake ideal for swimming, kayaking, non-motor boating and peaceful winter days of skating, this is more than a house—it is a property and lifestyle that are hard to duplicate. All of this is just minutes from shopping, dining, entertainment, schools, major roadways and the Harriman train station, while still feeling tucked away in a beautiful country setting. Located within the highly sought-after Monroe-Woodbury School District, with Pine Tree and Sapphire Elementary Schools nearby, this truly is one of those special Monroe properties that offers space, character, recreation, convenience and an incredible setting all in one.

27 Margaret Road, Monroe

$469,900
2 Beds 2 Baths 1049340 MLS
Welcome to this chic, beautifully renovated 2-bedroom, 2-bathroom condominium in Ossining's iconic 1820 schoolhouse conversion. Originally built as a schoolhouse and thoughtfully converted in 2007 into an intimate 12-unit condominium, this one-of-a-kind residence seamlessly blends a Soho-inspired aesthetic with the warmth, character and charm of the Hudson Valley. Step inside to a spacious, open-concept interior featuring soaring ceilings and a huge sun-filled living room. The elevated kitchen offers granite countertops and new stainless steel appliances (2025). The open-layout allows the kitchen, dining and living areas to flow effortlessly together, creating a sophisticated yet comfortable sense of space. The private bedroom area offers two beautiful bedrooms, including a large primary ensuite designed as a serene retreat. The primary bedroom is filled with natural light through large windows, complemented by automated window treatments for effortless comfort and privacy. A fews steps down lead to tastefully renovated primary bathroom, featuring a sophisticated, modern design complete with radiant heated floors. A walk-in custom organized closet completes this exceptional primary suite. The generously sized second bedroom is ideal for guests or a home office. Just beyond is the distinctive, updated second bathroom that adds another layer of style and sophistication to this home. The unit also comes with an assigned parking spot(#11) and private laundry. Fabulous location with easy access to the scenic Croton Aqueduct trail and all that Ossining has to offer. This vibrant, welcoming community has a cool vibe, with a Recreation Center offering something for everyone, from adult basketball to children's programs, as well as a stunning riverfront and close proximity to the Metro North Train station. Enjoy delicious local restaurants, an amazing famers market, lively street fairs, outdoor summer concerts and so much more-all adding to the energy that makes Ossining such a special place to call home.

88 Broadway Unit #2B, Ossining

$299,000
4 Beds 2 Baths 1049419 MLS
Nestled along the banks of the famed Willowemoc Creek in the heart of Roscoe, New York—widely known as “Trout Town USA”—this charming American Foursquare home offers the perfect blend of historic character and exceptional riverfront living. With 4 bedrooms, 2 bathrooms, and approximately 1,524 square feet, this beautifully maintained property sits on a peaceful stretch of the creek with private river frontage and direct access to some of the region’s most celebrated trout waters. Inside, the home was painted within the last 2.5 years, both bathrooms are updated, most of the house has new flooring, while the kitchen/dining area and downstairs bathroom feature radiant heated floors for year-round comfort. The living room includes preparation and venting for a pellet stove, offering an easy option for additional warmth and cozy ambiance. Both the front and back porches have been rebuilt, one finished with durable Trex decking, creating ideal spaces to relax while overlooking the property and listening to the river. Downstairs, a restaurant-grade water filtration system enhances water quality throughout the home. The water heater and boiler are both under 10 years old, and a new furnace was installed in 2017. Additional improvements include replacement windows, a roof installed in 2010, and professional excavation around the home 2.5 years ago to optimize drainage. A full walk-up attic provides exciting possibilities—perfect for creating a third-floor guest suite, studio, or private retreat. Outside, the property feels like a small riverside sanctuary. Concord grapes and rhubarb grow naturally on the land, complemented by fruit trees, flower gardens, and a lush lawn stretching toward the river beneath the sweeping branches of mature willows. Set on a quiet private dead-end road that is paved and maintained by the town, the home offers both privacy and convenience. Beyond the property, Roscoe and the surrounding Catskills provide endless recreation. Spend your nights at Catskill Resort Casino and your days fly fishing on Willowemoc Creek and the nearby Beaver Kill, hiking in Catskill Park, exploring local breweries, or skiing at Holiday Mountain Ski and Fun Park. With charming shops, farm markets, and restaurants, Roscoe perfectly balances small-town charm with world-class outdoor adventure. Rich with character, this classic American Foursquare riverfront home offers Catskills living at its finest—historic charm, thoughtful improvements, and legendary trout fishing right outside your door. Tax Map #36.A-1-11.2

53 Yorktown Road, Roscoe

$885,000
4 Beds 2 Baths 1050105 MLS
LEGAL 2-FAMILY DUPLEX | SOUTH ORANGETOWN SCHOOLS | 3-CAR GARAGE | VACANT | LOW TAXES. Rare opportunity to own a legal side-by-side 2-family duplex offering exceptional flexibility for both owner-occupants and investors. Each unit features 2 bedrooms and 1 full bath, with one residence significantly larger than the other. Ideal for an owner who wants to enjoy a more spacious home while generating rental income from the second unit. Prefer an investment property? Rent both units and take advantage of the strong income potential. Both apartments offer their own private basements for storage, separate utilities including gas, electric and water, and individual washer/dryer. Recent and desirable improvements include newer furnaces (2026 and 2017), updated electric (2012), and roof, siding and windows (2012). Beautiful wood floors, high ceilings and classic architectural character add warmth and charm, while updated kitchens and bathrooms provide modern comfort. A 3 car garage adds tremendous value and convenience, with additional driveway and off-street parking. Both units will be delivered vacant, providing an incredible opportunity for the new owner to choose their own tenants, live in one unit, or customize to your needs. Located in the desirable South Orangetown School District and conveniently close to town, the historic Old 76 House, shopping, dining and transportation, including bus service to NYC. Whether you're looking for a smart investment, a multi-generational living arrangement, or the opportunity to offset your mortgage by living in one unit and renting the other, this versatile property is one you won't want to miss! Professional photos to come 9/26.

5 Central Avenue, Tappan

$625,000
4 Beds 2 Baths 1050119 MLS
Incredible location just a third of a mile to the Peekskill Metro-North station, the Peekskill Riverfront Green Park, and the beautiful walking trails along the Hudson River!Catch the train in a flash and enjoy everything this vibrant city has to offer. The second-floor unit was completely renovated in 2021 with new flooring, a modern kitchen, and an updated bath. Each apartment features its own dedicated washer and dryer, alongside high-efficiency, wall-mounted heating systems (ENERGY STAR Qualified Equipment) that provide instant hot water. An enclosed front porch currently serves as a functional mudroom and storage space. The level backyard offers abundant parking accessed via a wide driveway, easily accommodating up to 6 cars. A convenient exterior basement entrance opens directly to the yard, perfect for outdoor projects. The full basement also provides excellent potential for future finished living space (subject to proper city permits).Enjoy city sewer, town water, and low taxes in a thriving community known for its outstanding dining, theaters, live concerts, and local arts scene. Fully rented with fantastic income and a survey is readily available. Both units are occupied and require advance notice for all showings—please plan accordingly!The City of Peekskill, New York, is widely celebrated as one of the Hudson Valley's most dynamic and accessible cultural hubs. Perfectly positioning a mix of scenic natural beauty and a bustling urban center, it provides an exceptional quality of life for residents and a magnetic destination for visitors. $625,000 price is for fully occupied. Can be delivered vacant at $650,000 with an extended closing date.

113 Old Bay, Peekskill

$1,250,000
1049539 MLS
PRIME ROUTE 9 COMMERCIAL OPPORTUNITY — Exceptional visibility, access and redevelopment potential in the heart of Dutchess County’s dominant commercial corridor. Situated on 2.95 acres at 1630 Route 9 in the Town of Wappingers this highly visible property offers approximately 195 feet of frontage along U.S. Route 9, with traffic counts historically exceeding 40,000 vehicles per day, PLUS additional access from New Hackensack Road. This rare through-lot configuration provides outstanding exposure and convenient access from two roads. The property is improved with an existing 8,100 Sqft commercial building featuring approximately 14-foot ceilings and 95 existing on-site parking spaces. The combination of generous acreage, existing commercial improvements and excellent access creates tremendous flexibility for an owner-user, investor or developer seeking immediate occupancy, adaptive reuse, expansion or future redevelopment. LOCATION IS THE STORY. Positioned within one of the Hudson Valley’s strongest and most established commercial corridors, the property is surrounded by a significant concentration of national retailers, restaurants, shopping centers and entertainment destinations. Nearby businesses and destinations include Lowe’s, Hannaford, Imperial Plaza Shopping Center, Double O Grill, Perkins Restaurant & Bakery and Spins Bowl. Just north along the Route 9 corridor is Poughkeepsie Galleria, featuring Target, Macy’s, DICK’S Sporting Goods, Best Buy, Sephora, H&M, Old Navy, Regal Cinemas and more than 100 additional shopping, dining and entertainment destinations. Located within the Town of Wappinger’s HD (Highway Design) zoning district, the property offers exceptional commercial flexibility. Potential uses include retail, restaurant, professional and business offices, medical and health-care offices, banking, personal services, veterinary uses, pet grooming, day care, educational and training uses, together with additional uses permitted under the Town zoning code, subject to applicable municipal approvals. Town sewer serves the property, with municipal/Village water reported as available. Few Route 9 properties combine this many critical commercial fundamentals in one offering: 2.95 acres, parking for 95 ,195 feet of Route 9 frontage, high daily traffic exposure, two-road access, an existing 8,100 sqft commercial building, ±14-foot ceilings, established commercial infrastructure and flexible HD zoning. An outstanding opportunity for retail, restaurant, medical, professional, veterinary, service-oriented or other commercial users—or for a developer seeking a prominent redevelopment site in the center of an established regional trade area. Survey and existing floor plans available. All uses and redevelopment possibilities to be independently verified.

1630 Route 9, Wappingers Falls

$479,000
3 Beds 2 Baths 1050085 MLS
Welcome to Village Life! Location, lifestyle, and a home you can enjoy immediately! At 30 Glenmere Avenue, you’re just a short walk from the restaurants, bars, shops, library, farmers market, pickleball, and everyday conveniences that make village living so appealing. The middle school and high school are also within easy walking distance. Love the outdoors? Enjoy the most beautiful sunsets from the front porch and morning coffee on the back deck. Glenmere Lake is about a mile away, where you can kayak, fish, hike, picnic, or simply enjoy some time by the water. Whether it’s grabbing dinner with friends, heading out for a walk, or spending a summer afternoon outside, so much of what you enjoy is close to home. Inside, the home has been thoughtfully updated with the big-ticket items already addressed. A whole-floor addition was completed in 2015, along with updates to the plumbing and electrical systems. The heating system, water heater, roof, and central air have also been replaced. The kitchen offers freshly painted cabinets and newer appliances, creating a comfortable and functional space while leaving room to add your own personal style. The property offers a deck overlooking the backyard with a fire pit, room to garden, entertain, relax, or enjoy time outdoors—without the maintenance of a large property. With 1,590 square feet, there’s plenty of room for everyday living, working from home, hosting friends, and settling into your next chapter. Come for the walkability. Stay for the lifestyle.

30 Glenmere Avenue, Florida

$1,550,000
4 Beds 2 Baths 1050014 MLS
Completely renovated from top to bottom, this exceptional Port Washington residence has been thoughtfully reimagined with sophisticated modern finishes, timeless design, and quality craftsmanship throughout. Every detail has been carefully considered, from the brand-new siding, roof, windows, gutters, and high-efficiency central heating and air conditioning to the beautifully renovated kitchen, designer bathrooms, and new wood flooring, creating a truly turnkey home. The inviting open-concept first floor offers an effortless flow between the spacious living room, dining area, and stunning new kitchen, featuring an oversized quartz island that serves as the perfect centerpiece for both everyday living and entertaining. A first-floor bedroom and full bathroom provide exceptional versatility, ideal for guests, a home office, or convenient one-level living. Upstairs, the generously proportioned primary suite provides a private and luxurious retreat, complete with two beautiful skylights that fill the space with natural light, a beautifully appointed ensuite bathroom with elegant marble floors and a custom walk-in closet. Two additional bedrooms, a second full bathroom, and a convenient laundry room complete the second level. A sliding glass door off the kitchen opens directly to the patio, creating a seamless connection between the indoor and outdoor living spaces. The patio leads to the newly finished garage, complete with a new garage door, offering a beautifully appointed setting for entertaining, al fresco dining, or relaxing with family and friends. This exceptional home combines the ease of turnkey living with stylish design, modern amenities, and thoughtful functionality throughout.

6 Slocum Avenue, Port Washington

$2,575,000
4 Beds 4 Baths 1050115 MLS
An impeccable one of a kind East Hampton retreat with its own full recreational amenity package of a TENNIS COURT and POOL. This well-maintained four bedroom contemporary has been recently renovated and is situated on 1.6 acres of bountiful nature, with tall trees and privacy. Located a short distance from East Hampton Village and Sag Harbor, this retreat is centrally located for the Hampton life-style. The open floor plan has a large renovated kitchen (2021) with a stone top island and a sun-lit view of the tennis court and pool. The pool has an oversized deck area and the gazebo is the transition /entertainment center point leading from the pool to the tennis court. Inside, the kitchen leads to the entertaining area adorned with high ceilings and a wall of glass sliders with transoms above. The entertaining area contains a fireplace and is complimented by a large deck that runs sixty feet, exposing one to breathtaking natural setting surrounding the tennis court and pool. The first floor has four oversized bedrooms and renovated bathrooms (2024). The lower level has a sauna to unwind in and a large unfinished full level to complete as your heart desires for a gym, media room or game room. The home has a two car attached garage . Appointments are appreciated with 24 hour notice. Field measurements of GLA are different from Town Record (2,100 sqft.) Information has been provided by the Seller and has not been independently verified by the Broker. Information is deemed reliable but not guaranteed.

2 Little Court, East Hampton

$1,999,000
4 Beds 4 Baths 1050111 MLS
Nestled at the end of a tranquil cul-de-sac (dead end street) and bordered by the scenic Staten Island neighborhood Lighthouse Hill, this custom Center Hall Colonial estate delivers unmatched privacy, architectural grandeur, and resort-style living. Spanning 4,760 square feet of primary living space—plus an additional 1,500 square feet in the finished lower level—this home rests on a 13,000-square-foot lot designed for seamless indoor-outdoor entertaining. Architectural Highlights & Interiors • Grand Entrance: A dramatic two-story foyer featuring exquisite custom crown molding, double coat closets, and fine chandeliers sets an elegant tone. • Formal Reception: Expansive formal living and dining rooms designed with intricate trim work and custom paint finishes. • Chef's Kitchen & Living: Premium gourmet kitchen with professional Viking appliances, custom cabinetry, dining area, and sliders to the resort-style grounds. Adjacent family room features a classic wood-burning fireplace and direct yard access. • Primary Retreat: 4-spacious bedrooms located on top floor, a sprawling primary suite with a dedicated dressing room, custom walk-in closet, and a spa-inspired 4-piece bathroom. Three additional oversized bedrooms and a full bath. • Refined Details: Radiant heated floors, custom window treatments, fine crown moldings, and pull-down attic storage, high end finished throughout. Lower Level & Outdoor Oasis • Finished Lower Level: 1,500 sq. ft. of fully tiled living space featuring a massive recreation room and a 3/4 bath. • Parklike Grounds: Custom paver patio framing a fully equipped outdoor kitchen, surrounded by lush greenbelt views. Includes a two-car attached garage and generous driveway parking.

78 Eleanor Street, Staten Island

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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.