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. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Sleepy Hollow real estate market? Sign up for a  Sleepy Hollow Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

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

$449,888
3 Beds 2 Baths 1045349 MLS
Welcome to this spacious, move-in-ready single-story ranch nestled in desirable Colburn Estates! This well-maintained home offers numerous updates, comfortable living spaces, and excellent flexibility for today’s lifestyle. The main level features beautifully refinished hardwood floors throughout, a welcoming living room with a wood-burning fireplace, and California-style floor-to-ceiling windows with an exterior walk-out door providing an abundance of natural light and easy access to the yard. The sunken dining room addition is a wonderful gathering space, featuring newly installed 30"x 54" skylight with copper flashing and a new wall A/C unit installed in 2026. The kitchen offers quartz countertops and a gas cooktop, while both bathrooms were tastefully remodeled in 2018. Replacement windows on the main level are approximately 20 years old. Numerous improvements provide added peace of mind, including new vinyl siding installed in 2024, a recently power-washed exterior, architectural roof shingles installed in 2014, and new 5" gutters with stainless-steel mesh gutter guards. The home also benefits from additional insulation, including 3/4" foam board added with the siding installation and R-30 attic insulation. Four brand-new basement windows have recently been installed, and the main level and garage have been freshly painted. The lower level offers tremendous potential with a separate side entrance and a large unfinished area that can be customized to suit your needs. Create a home office, potential fourth bedroom, guest space, or explore a potential mother-daughter setup, subject to necessary approvals. There is also ample room to add another bathroom. Home is serviced with 200-amp electrical service adds further convenience. The oversized two-car garage addition features a side entrance and additional attic storage with a new metal attic door. The basement provides abundant storage, with the freezer included in the sale. A 7' x 10.6' storage shed provides even more outdoor storage. The Burnham furnace was installed in 2009 and converted from oil to natural gas in 2013; the oil tank was removed at that time. Municipal water and sewer and natural gas heat add to the convenience. Appliances include refrigerator (2008), wall oven (2009), washer and dryer (2018), and dishwasher (2020). Freezer stays, Ideally located with easy access to Route 9, shopping, supermarkets, and commuting options. The Poughkeepsie Metro-North station is approximately 5.9 miles away. With its generous spaces, extensive updates, flexible lower level, and convenient location, this home truly spells Home Sweet Home!

80 Colburn Drive, Poughkeepsie

$450,000
1045255 MLS
This exceptional property offers a unique opportunity to own a waterfront restaurant property at 281 Woodcleft Avenue in Freeport, NY, positioned in one of Long Island’s well-known waterfront destinations. The property combines waterfront appeal, commercial visibility, and a highly desirable location, making it an attractive acquisition for an investor, owner-user, restaurateur, or developer seeking a property with character and long-term potential. The waterfront setting creates an exceptional atmosphere for dining, entertainment, hospitality, and other permitted commercial uses. Located along Woodcleft Avenue, the property benefits from its proximity to Freeport’s vibrant waterfront district, restaurants, entertainment, boating activity, and local attractions. The location provides an opportunity to capitalize on the steady foot traffic and destination-driven nature of the area. For an investor, this property offers the opportunity to acquire waterfront real estate in an established Long Island market. For an owner-user, it provides the chance to operate and control a property in a highly sought-after waterfront setting. With its waterfront location, commercial potential, and prime Freeport setting, 281 Woodcleft Avenue presents a compelling opportunity to acquire a distinctive piece of waterfront real estate. WATERFRONT LOCATION • PRIME FREEPORT LOCATION • COMMERCIAL REAL ESTATE • OWNER-USER/INVESTMENT OPPORTUNITY • EXCEPTIONAL VISIBILITY

281 Woodcleft Avenue Unit #2, Freeport

$400,000
2 Beds 2 Baths 1045053 MLS
Some homes just feel good the moment you enter and 1317 Saratoga Lane is one of them. Nestled in the sought-after Van Wyck Mews community, this charming 2-bedroom, 2-bath home combines warm finishes, thoughtful upgrades, and an oversized balcony perfect for taking in the surrounding views. Rich hardwood floors run throughout the home, catching the light from a classic chandelier above and the oversized balcony beyond. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, and a 5-burner KitchenAid stove. Whether you're preparing a quiet weeknight dinner or hosting friends and family on the weekend, this is the kind of kitchen that makes cooking feel effortless and enjoyable. One of the home’s standout features is the oversized balcony with expansive views, a rare bonus that extends your living space outdoors. It’s the perfect spot to start the day with coffee, enjoy fresh air in the afternoon, or unwind as the evening settles in. The primary suite offers a peaceful retreat at the end of the day, complete with a spacious walk-in closet and an ensuite bathroom featuring a double vanity, soaking tub, and separate standing shower. Thoughtful upgrades like a Culligan water system with filtered showerheads add an extra layer of comfort to everyday living. Beyond your front door, Van Wyck Mews delivers a lifestyle worth coming home to. The community offers a welcoming clubhouse, an in-ground pool for warm summer days, an outdoor grilling area, and a shared fire pit that turns ordinary evenings into something social and memorable. It’s the kind of setting that encourages you to be outside, connect with neighbors, and truly enjoy where you live. The location adds even more to love. Just minutes from Route 9 shopping, Metro-North stations in Beacon and New Hamburg, and some of the Hudson Valley’s most scenic outdoor destinations, this home offers a lifestyle that blends convenience with nature and recreation. With assigned parking, visitor parking, and additional basement storage, this thoughtfully maintained home offers easy living in one of Fishkill’s most desirable communities.

1317 Saratoga Lane, Fishkill

$400,000
3 Beds 2 Baths 1044925 MLS
Move-in ready and well located in Beacon, this 3-bedroom, 2-bath home offers 1,481 square feet of comfortable living space with easy access to everything that makes the Hudson Valley such a desirable place to call home. The main level features an eat-in kitchen and an easy, functional layout for everyday living. Step outside to a welcoming back porch and private yard, offering space to relax, garden, entertain, or simply enjoy being outdoors. Two dedicated parking spaces add everyday convenience, a valuable feature in Beacon. The exterior gutters have gutter guards to help keep leaves and debri out of your downspouts. The location puts you close to Main Street’s restaurants, shops, galleries, cafes, and community life, while also keeping you near Hudson River waterfront access, hiking, parks, and the outdoor recreation the Hudson Valley is known for. Whether you are heading into town for dinner, spending the afternoon on a trail, or enjoying a day along the river, everything is within easy reach. For buyers looking for a way to own a move-in ready home in Beacon, this property offers a compelling combination of location, space, and convenience. Leased solar panels carry a low monthly payment and help significantly reduce electric costs, adding another layer of value and efficiency. A great opportunity to enjoy Beacon living with outdoor space, dedicated parking, proximity to Main Street, and access to some of the best recreation and culture in the Hudson Valley.

4 Sycamore Drive, Beacon

$449,000
3 Beds 2 Baths 1042028 MLS
Welcome to 570 Lakes Road, a beautiful lakefront property in Monroe, NY offering stunning year-round views of Walton Lake and a lifestyle you’ll love coming home to! This charming home features 3 bedrooms and 2 full bathrooms, with a thoughtfully designed layout and plenty of space to enjoy both everyday living and entertaining. The first floor features durable, pet-friendly laminate flooring, two generously sized bedrooms, including one with a huge picture window overlooking the lake, and a beautifully renovated kitchen complete with butcher block countertops, newer appliances, and attractive tilework. A private laundry room adds convenience, while the spectacular two-story living room serves as the heart of the home, featuring a wood-burning fireplace and beautiful lake views. Upstairs, you’ll find a spacious primary suite filled with natural light, including skylights that provide breathtaking views of the night sky, along with a private ensuite full bathroom. The second-floor loft overlooks the living room and offers gorgeous lake views, making it an ideal space for a home office, reading nook, or additional sitting area. Step outside onto the amazing wraparound front deck, which extends around approximately half of the home and provides the perfect place to relax, entertain, enjoy your morning coffee, or take in the beautiful Walton Lake views throughout the seasons. But the lake lifestyle doesn’t stop at the front door! The property includes two additional lakefront parcels and a dock, providing exceptional access to the water and endless opportunities for boating, fishing, kayaking, swimming, or simply enjoying everything lake living has to offer.

570 Lakes Road, Monroe

$449,000
2 Beds 2 Baths 1044779 MLS
Welcome to The Creek House at Pepacton Hollow, a beautifully maintained Catskills cabin set across two separate lots totaling 6.19 private acres. Warm knotty pine, exposed beams and cathedral ceilings create an inviting interior, while a pellet-stove insert set within a hand-built stone fireplace and chimney makes the home especially welcoming on cool mountain evenings. Offering two bedrooms and two full baths, the home features a spacious open kitchen and dining area with an easy, comfortable flow for everyday living and entertaining. Step outside to a covered front porch accompanied by the sound of the babbling creek, with approximately 600 feet of creek frontage gently flowing along the front of the property. A large detached garage accessed via a paved driveway / parking area offers exceptional practicality, including a partial second floor for additional storage, studio space or future possibilities. The clean, dry basement houses the laundry and updated mechanicals, and a newly installed septic system was designed and approved in consultation with the DEP and CWC. Located in the sought-after Tri-Valley School District and close to Rondout Reservoir, the property offers convenient access to fishing and other designated watershed recreation, with Neversink Reservoir’s seasonal kayaking and canoeing opportunities also within easy reach.Just over two hours from New York City, this well-loved and turnkey retreat offers the rare combination of privacy, natural beauty and effortless Catskills living—a quiet place to recharge and create an entirely new rhythm of life. Come experience the sound of the creek, the warmth of the cabin and the quiet of Pepacton Hollow for yourself—schedule your private showing today. *Please note that this property is being offered fully furnished with only personal property removed.*

283 Pepacton Hollow Road, Grahamsville

$429,000
2 Beds 2 Baths 1042924 MLS
Welcome to Crystal Hill! Enjoy maintenance free living without sacrificing space with four floors of finished living space. Bring ALL your furniture but leave behind the snowblower this winter. Tucked away in the far corner of the complex, this home offers the utmost privacy and maximum tranquility. Feel right at home in this living room featuring gleaming hardwood floors, recessed lighting and sliders to your private patio where you can enjoy an evening cocktail admiring the upcoming foliage. When its getting chilly come inside and cozy up near your own fireplace. The kitchen has a second set of sliders leading to more outdoor sitting space. The second floor has two bedrooms, a walk in closet, hallway bath and a laundry room conveniently located near the bedrooms. No more carrying your laundry up from the basement! But wait, there’s more! The finished loft makes a great third bedroom or home office and the lower level offers another versatile rec-room with new flooring just installed. All of this under a two year old roof for peace of mind. Crystal Hill showcases resort style amenities including a large outdoor swimming pool with grilling area. Celebrate your next party in the pristine clubhouse, available to rent, featuring a kitchen and pool table. Additional amenities include indoor and outdoor basketball courts and a playground. Enjoy all that Haverstraw has to offer. Spend weekends exploring the scenic Hudson River waterfront. Go fishing or picnic at Bowline Park and stay for the community events. Take your loved ones for a night at the ballpark and become a fan of the Rockland Boulders baseball team. Fun for all ages! Plus Nearby golfing at the 18-hole Rotella Golf Course. Great commuter location: easy access to Palisades parkway (exit 13) and Route 202 shopping right outside the complex. Or set sail on the Hudson with close proximity to the Haverstraw–Ossining ferry. Call Crystal Hill your next home, a convenient location offering the perfect blend of suburban living, recreation, and Hudson Valley lifestyle.

122 Crystal Hill Drive, Pomona

$445,000
3 Beds 2 Baths 1044284 MLS
Welcome to 4 Seneca Drive in Milton, New York, a spacious Hudson Valley ranch offering approximately 1,912 square feet of flexible, mostly single-level living near the Hudson River. This legal three-bedroom home lives like a five-bedroom and offers 1.5 baths, a first-floor primary suite, additional first-floor bedrooms and versatile finished rooms for guests, home offices, a playroom, fitness space or multigenerational living. The spacious living room features a vaulted ceiling and oversized windows, while the kitchen offers rich wood cabinetry, generous counter space and an open connection to the adjoining living areas. A bright walk-out sunroom overlooks the private backyard and provides an inviting space for relaxing or entertaining throughout the year. One of the property’s most memorable features is its beautiful Hudson River view. From the grounds, enjoy a peaceful glimpse of the river framed by mature trees and rolling Hudson Valley scenery. Whether relaxing with morning coffee, unwinding at sunset or entertaining outdoors, the river view adds a rare sense of tranquility and connection to the surrounding landscape. Outside, enjoy expansive lawn areas, mature plantings, a rear patio, an extended driveway and a detached two-car garage with excellent parking and storage. Scenic aerial views further highlight the property’s setting above the Hudson River and the wooded hills of Milton. Convenient to Route 9W, Marlboro, Highland, Newburgh and Poughkeepsie, this Hudson Valley home is also close to wineries, farms, restaurants, shopping and outdoor recreation. First-floor living, flexible bedroom space, a detached two-car garage and Hudson River views make 4 Seneca Drive a distinctive opportunity in Milton.

4 Seneca Lane, Milton

$450,000
3 Beds 3 Baths 1043477 MLS
Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhouse style condominium offering approximately 2,000 square feet of comfortable living space in the intimate Winhaven Park Condominiums, a community of approximately 20 residences. The main level features a spacious open floor plan designed for easy everyday living and entertaining. A bright and inviting den filled with natural light provides flexible space for a home office, sitting room, or reading area. The living room features sliding glass doors leading to the deck, creating a seamless connection to the outdoors. Upstairs, you'll find two generously sized bedrooms, including a spacious primary suite with its own private en-suite full bathroom. An additional full bathroom and conveniently located second-floor washer and dryer complete this level. Pull-down attic access provides even more storage space. The finished walk-out basement adds valuable additional living space with a comfortable family room featuring a Murphy bed, making it ideal for overnight guests or flexible multi-purpose use. A mudroom provides interior access to the one-car garage, and throughout the home you'll find an impressive amount of storage. Ideally located near West Point Military Academy, Highland Falls Preserve, and Bear Mountain State Park, this home offers convenient access to recreation, hiking, scenic destinations, and the surrounding Hudson Valley. Meticulously cared for and offering plenty of space across three finished levels, this home is ready for its next owner to move in and enjoy. Community pet policy: No dogs permitted; up to two cats allowed.

26 Winhaven Court Unit #19, Highland Falls

$435,000
2 Beds 1 Baths 1042705 MLS
WELCOME TO HIGHLY SOUGHT AFTER WARWICK, NEW YORK! This beautifully maintained ranch on 0.95 acre of completely FLAT property is nestled on a quiet street in the GREENWOOD LAKE SCHOOL DISTRICT. This home offers comfort, functionality, and thoughtful upgrades. Boasting 2-bedrooms AND 2 BONUS rooms, an eat-in kitchen with quartzite countertops, solid wood Starmark cabinetry, and direct access to the backyard. Engineered hardwood floors enhance the living spaces, while Anderson 400 Series windows provide quality and efficiency. The home also includes a 1-car garage, FULL basement, and approximately 800 sq. ft. of back patio space—perfect for entertaining. Outdoor living shines with Wi-Fi-enabled speakers, permanent app/Wi-Fi-controlled eave LED lighting with customizable colors and patterns, and a raised-bed enclosed garden equipped with water and misters. The patio is hard-wired for a hot tub, and electricity extends to the shed. Major updates include siding, seamless gutters and soffits (2020); Navien 98% efficient natural-gas boiler for heat and on-demand hot water (2020); well pressure tank (2022); Central air (2023) and driveway resurfacing (2023) following the 2022 driveway installation. The 200-amp electrical panel is generator-ready with an additional panel and transfer switches (generator not included). Kitchen appliances were purchased in 2016, with a Bosch dishwasher added in 2019. Cast-iron baseboard heat keeps the home comfortable, while its location near a commuter route adds everyday convenience. Enjoy all that the area has to offer such as - year round activities, lakes, ski resorts, wineries, hiking/biking, boating and SO much more!

499 Old Dutch Hollow Road, Monroe

Start Your Search

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.