Sleepy Hollow Real Estate Search

Sleepy Hollow Properties between $450,000 and $500,000 for Sale

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Newest Sleepy Hollow Properties between $450,000 and $500,000 for Sale

$495,000
1040152 MLS
An Extraordinary Opportunity to Shape the Future of Rhinebeck Village LOT 5 -on South Street 98 ft x 95 ft There are very few moments when history and possibility intersect. After an extensive five-year planning and approval process, 6 Mulberry Street—one of Rhinebeck Village's most storied properties—is entering its next chapter. For the first time, four exceptional residential homesites are being offered for sale, representing what may be the last significant opportunity to build a custom luxury residence within the Village's coveted Historic District. Approved by both the Village of Rhinebeck and the Dutchess County Board of Health, each parcel is ready for construction of a bespoke home of up to approximately 3,000 square feet, thoughtfully designed for modern living with approvals for three bedrooms, a dedicated home office, and a den. These are not simply vacant lots—they are fully entitled opportunities to create homes that will define the next generation of Rhinebeck architecture. Imagine a timeless farmhouse, a refined modern interpretation of a village classic, or an architect-designed estate that seamlessly blends historic character with contemporary luxury. Here, every home becomes part of the fabric of one of America's most beloved small towns. Located just moments from Rhinebeck's celebrated Main Street, residents will enjoy effortless access to award-winning restaurants, independent boutiques, art galleries, cafe & #233;s, the renowned farmers market, and cultural destinations, while remaining surrounded by the natural beauty of the Hudson Valley. Weekend escapes become unnecessary when every day begins in one of New York's most desirable destinations. With luxury homes in Rhinebeck Village commanding prices well into the multi-million-dollar range and opportunities to build virtually nonexistent, these approved homesites offer a remarkable chance to create a residence tailored precisely to your vision—without the uncertainty, time, and complexity of the entitlement process. Whether you're building your forever home, a weekend retreat from Manhattan, or a lasting legacy, this is an offering of exceptional rarity. A once-in-a-generation opportunity to build something truly extraordinary in the heart of Rhinebeck Village. This was one tax lot that has been divided into 5 separate tax lots and the updated property tax amounts per lot are not accurately updated in this listing.

6 Mulberry Street, Lot #5, Rhinebeck

$488,888
4 Beds 2 Baths 1041418 MLS
YES! I got it Back, Priced More Aggressively to Sell! This is the largest living space and only Flexible 4 Bedroom(TRUE 3 Bedroom) in the area of Kew Garden/ Briarwood area with over 1,550 square feet of living space with one of the largest private terraces(72 Square Feet!). This apartment, on the 12th floor has unobstructed views from all the windows to the beautiful natural sunlight than many other apartments can’t enjoy without being at this height/ floor. Recently renovated and freshly painted - all 3 large bedrooms fits King Size Beds (plus a flexible dining room space can legally be converted to 4th bedroom), 2 full bathrooms, floor-to-ceiling glass doors to the terrace, and huge picturesque windows in the living room and other rooms too. Enjoy plenty of storage with abundant closets including 2 deep walk-ins with floor-to-ceiling doors entries in all. For the best peace and quiet, this apartment features thick (up to 8 Inches) concrete ceilings/floors(unlike other places, you must walk on eggshells, lol), double pane windows, as well as 5 zones of central air conditioning/Heat you control individually. The 24-hour doorman which holds your packages, new virtual intercom ensure security and screening of your guests from the convenience your phone. Just seconds from the fully renovated E & F express subway station and in front of the express buses to Flushing, The Bronx and Manhattan. The Greenbriar Building is across from Hoover Park, a playground, 2 sitting parks, public library, shoppes, house of worships and restaurants. Close to Van Wyck and Grand Central highways, schools, JFK, and LaGuardia airports! The Maintenance includes real estate tax and all utilities (cooking gas, electricity, central air/heat, only extra cost is Internet!)). A very Pet friendly building with 2 main large elevator with separate service elevator and entrance. Come see what few have witnessed, an apartment with more square footage than some homes in the area! Garage is NOW OPEN, ask about special rate for residents!

85-15 Main Street Unit #12J, Briarwood

$499,000
3 Beds 3 Baths 1041000 MLS
Welcome to 3 Allerton Ave, a charming and well-maintained Ranch-style home nestled in one of Middletown’s sought-after neighborhoods. Set on a private 0.20-acre lot, this inviting property offers a peaceful suburban setting with shopping, dining, public transportation, and commuter routes just minutes away. A welcoming front porch leads into a bright foyer and semi-open living space connecting the living room, dining room, and sunroom/ office space. Hardwood floors throughout the main level add warmth and character, while abundant windows fill the home with natural light. The well-appointed kitchen features granite countertops, tile flooring, and a coordinating tile backsplash. The main level offers two bedrooms, including a primary bedroom with an ensuite half bath, plus an additional full bathroom, and sunroom/ office provides flexible space for work or relaxation and opens directly to a spacious back deck overlooking the fenced backyard—ideal for entertaining, barbecues, or enjoying your own private outdoor retreat. The recently finished lower level expands the living space with a large recreation area, third bedroom, and full bathroom, offering excellent flexibility for guests, a home office, gym, media room, or additional living space. With approximately 2,248 square feet of total living space. 1,328 square feet on the main level and 920 square feet on the lower level! A one-car attached garage, paved driveway, municipal water and sewer, and natural gas. Conveniently located near Route 17, with the train and bus stations approximately 10 minutes away, this home offers an excellent combination of comfort, privacy, and commuter convenience. Don't miss the opportunity to make this inviting Middletown home your own!

3 Allerton Avenue, Middletown

$495,000
3 Beds 2 Baths 1040646 MLS
Spanning 1,109 square feet, Residence #3 at 247 Mount Hope Place offers a blend of modern design, natural light, and intuitive layout-perfect for effortless everyday living. Enter into a sun-soaked living and dining area framed by oversized windows that overlook a tree-lined street. The open-concept layout provides seamless flow between lounging, dining, and entertaining, while warm hardwood floors and recessed lighting enhance the airy ambiance. The chef's kitchen pairs clean lines with striking finishes: a glossy glass-tile backsplash, quartz countertops, and sleek two-tone cabinetry complemented by a full suite of stainless-steel appliances and a peninsula with breakfast bar seating. Tucked quietly away from the social spaces, the bedroom wing hosts three bright rooms-including a king-sized primary suite with a walk-in closet and private Juliet balcony. The two secondary bedrooms offer flexibility for guests, office, or a studio. Each bathroom offers its own distinctive spa-like experience-one featuring a deep soaking tub framed by designer tile accents, the other showcasing a sleek glass-enclosed rain shower and modern vanity-providing thoughtfully varied layouts to suit different moods and moments. Additional highlights include: - In-unit washer/dryer - Split-system heating + cooling for year-round comfort - Excellent closet space throughout - Thoughtful layout with privacy between living and sleeping areas - Set on a quiet block in Mount Hope, you're moments from local parks, neighborhood cafés, and convenient subway access via the B/D lines-connecting you to Manhattan in minutes. THE COMPLETE OFFERING TERMS ARE IN AN OFFERING PLAN AVAILABLE FROM THE SPONSOR 17402 HOLDINGS, LLC AT 1822 FULTON STREET BROOKLYN, NY 11233. FILE NO.CD21-0214

247 Mount Hope Place Unit #3, Bronx

$464,000
4 Beds 2 Baths 1040884 MLS
Nestled in a peaceful neighborhood, this charming fully furnished home offers an incredible opportunity for both personal enjoyment and investment. Conveniently located just minutes from Route 17, the property provides easy access to major transportation routes and is approximately 1.5 hours from NYC. Thoughtfully remodeled nine years ago with custom touches throughout, this home has been successfully operated as a short-term rental, making it an attractive turnkey investment for those looking to continue its rental potential. The home is being offered fully furnished, allowing a new owner to seamlessly continue hosting guests from day one. The home features four spacious bedrooms, including a private primary suite located on the second floor with generous closet space and its own full bathroom. The inviting living room features a propane fireplace, creating a warm and cozy gathering space. An open and effortless flow connects the dining area, living room, and kitchen, making entertaining easy and enjoyable. Step outside to the expansive deck, complete with a built-in bar—perfect for entertaining and enjoying the outdoors. The backyard offers an above-ground pool and a fire pit, creating an ideal setting for relaxing, hosting guests, and making the most of every season. The unfinished basement provides abundant storage space and offers the potential to create a workshop, recreation area, or additional finished living space. Ideally situated just minutes from Bethel Woods Center for the Arts, Resorts World Catskills, the Kartrite Resort & Indoor Waterpark, and countless restaurants, shops, outdoor activities, and attractions, this property offers the perfect combination of comfort, convenience, and proven short-term rental potential. Fully furnished. Successful short-term rental history. Turnkey and ready to enjoy or continue as an income-producing property!

158 Harris Road, Harris

$485,000
3 Beds 3 Baths 1040236 MLS
Welcome Home to Brighton Green! Beautifully maintained and thoughtfully designed, this stunning Aylesford model townhouse offers over 1,700 square feet of comfortable living space, along with a beautifully finished basement with additional storage. From the moment you enter, you'll appreciate the warm elegance of the hardwood flooring, custom crown and boxed molding, and spacious open-concept feel. The inviting living room features a striking gas fireplace, while the formal dining room offers an ideal space for entertaining family and friends. This home has everything you've been looking for. The spacious eat-in kitchen features white cabinetry, stainless steel appliances, tiled backsplash, and a convenient full pantry. Just off the kitchen, step through the back door onto your private patio and backyard—ideal for relaxing or enjoying outdoor gatherings. Upstairs, the generously sized primary suite offers a walk-in closet, an additional wall closet, and a luxurious spa-like bathroom perfect for relaxation. Two additional bedrooms, a hall bathroom, and a convenient second-floor laundry room complete the level. The home also includes an attached garage and a finished basement offering flexible space for storage, hobbies, or additional living needs. Residents of Brighton Green enjoy wonderful community amenities, including a clubhouse with fitness room and billiards, an outdoor heated pool, and a playground. Ideally situated near I-87 and I-84, shopping, public transportation, bus and train service, and just approximately one hour from NYC, this townhouse offers the perfect combination of comfort, convenience, and community living.

12 Brighton Drive Unit #1404, Newburgh

$479,900
3 Beds 2 Baths 1040462 MLS
A Hudson Valley Lifestyle with Room to Live, Work & Play Just one block from the Hudson River, this beautifully maintained Marlboro ranch offers the kind of space and flexibility that's increasingly hard to find. Set on approximately 1.19 acres in a quiet neighborhood, this 2 to 3-bedroom, 2-bath home combines comfortable living with an expansive finished lower level, a spectacular sunroom, and an incredible detached garage setup. Inside, the main level welcomes you with gleaming hardwood floors and an abundance of natural light. The renovated kitchen is designed for both everyday living and entertaining, featuring granite countertops, a tiled backsplash, abundant cabinetry, and a center island. The spacious living room offers a large bay window, while the home's 300-square-foot heated sunroom is a true highlight. With walls of windows and vaulted ceilings, this versatile space brings the outdoors in and can serve as a family room, home office, studio, or simply your favorite place to relax while taking in the seasonal river and mountain views. The finished lower level adds another dimension to the home, with generous ceiling height, a second full bath with jetted tub, and a walkout leading directly to the patio and backyard. Whether you need a recreation room, guest area, home gym, workshop, or additional living space, there is room here to make it your own. And then there's the garage. The oversized 36' x 30' detached three-car garage provides an exceptional amount of room for vehicles, hobbies, equipment, or a serious workshop. Combined with the additional car/boat port, this property is particularly well suited to car enthusiasts, boaters, outdoor recreation lovers, or anyone who simply needs substantial storage and workspace. Outside, the large, open property provides plenty of room to garden, entertain, play, or enjoy the peace and privacy of your own Hudson Valley retreat. And with the Hudson River just a block away, you'll have easy access to the beauty and recreation that make this part of the Valley so special. Conveniently located near the area's wineries, orchards, farm stands, restaurants, and major commuter routes, this is more than a ranch home—it's an opportunity to enjoy space, flexibility, and a Hudson River lifestyle in one of the Hudson Valley's most desirable settings. Bring your cars. Bring your boat. Bring your hobbies. Bring your vision. There's room for all of it here.

35 Hillside Drive, Marlboro

$465,000
2 Beds 2 Baths 1038761 MLS
Welcome to effortless, one-level living in the highly sought-after 55+ community of Jefferson Village. This beautifully maintained Cambridge model—one of the community’s most sought-after floor plans—is a desirable first-floor end unit with no one above you and no one below you, and only three steps to entry. Offering an exceptional combination of privacy, space, natural light, and convenience, this is truly a special opportunity within Jefferson Village. Bright, sunny, and beautifully inviting, the home features two spacious bedrooms and two full bathrooms, including a generous primary suite with a private en-suite bath. The thoughtfully designed floor plan includes a spacious living room, formal dining room, and modern kitchen upgrades. Step outside onto your beautiful private balcony overlooking the Jefferson Village neighborhood—an ideal setting for morning coffee, relaxing with a book, or enjoying the peaceful surroundings. Additional highlights include abundant closet space, an in-unit washer and dryer, a one-car garage conveniently located right next to the condominium, and a large private storage room—all adding to the exceptional convenience of this home. Jefferson Village is truly an exciting lifestyle, offering a welcoming and active community with many trips, classes, your own personal garden, and plenty of opportunities to make new friends. Residents also enjoy a community center, swimming pool, tennis courts, state-of-the-art fitness center, clubs, social events, movies, dances, guest speakers, and an impressive variety of activities. Say goodbye to the upkeep of a large home and enjoy a carefree lifestyle without the worry of snow removal or landscaping. Ideally located close to Jefferson Valley Mall, shops, public transportation, and the Taconic Parkway, with convenient access to dining, golf, medical offices, and everything the surrounding area has to offer. Move-in ready, exceptionally bright, and wonderfully private, this sought-after Cambridge model at 43 Unit A Jefferson Oval is a special opportunity to enjoy the very best of Jefferson Village living. Offered at $465,000. On market this Friday, August 21st!

43 Jefferson Oval Unit #A, Yorktown Heights

$499,000
3 Beds 2 Baths 1040402 MLS
Renovated 3BR / 2BA Co-Op on the Grand Concourse Corridor Step inside 675 Walton and the pre-war character announces itself: a sunken living room with original wrought iron railings, an arched built-in niche, and herringbone parquet floors that simply aren't built into modern apartments anymore. Three true bedrooms, two full baths, generous pre-war proportions, and charming original touches like a porthole window in the interior hall. The renovation is firmly 2026. A light-oak shaker kitchen with quartz counters, matte black hardware, and a full stainless appliance package with gas cooking. Both bathrooms rebuilt to hotel standards — large-format white tile, slate-look floors, floating vanities, matte black fixtures. Refinished dark hardwoods, fresh white walls, and leafy tree-lined views from every bedroom. The building itself sets the tone before you arrive: stately pre-war brick, a marble-clad lobby, and original Art Deco elevator doors. Location built for how you actually live. Minutes from the 4, B, and D at 161st Street–Yankee Stadium — Midtown and FiDi a direct ride away for Manhattan commuters and hybrid workers. A short walk to the Bronx County Courthouse and Hall of Justice. Yankee Stadium, Bronx Terminal Market, Mullaly Park, Macombs Dam Park, and Joyce Kilmer Park are all right outside your door. The numbers work. Offered at $499,000 with a buyer-friendly 10% minimum down payment — genuine three-bedroom, two-bath ownership at a price that doesn't exist across the Harlem River. For the professional or growing family who won't trade space, light, and character for a Manhattan ZIP code. Private showings by appointment.

675 Walton Avenue Unit #2B, Bronx

$489,000
2 Beds 3 Baths 1039925 MLS
Welcome to effortless, resort-style living in one of the most desirable gated communities in the Hudson Valley! Welcome to Hudson Pointe! This beautifully designed townhouse offers spacious, light-filled living across multiple levels, featuring two generously sized bedrooms, two-and-a-half bathrooms, and a versatile open loft—perfect for a home office, den, guest space, or reading retreat. The finished lower-level flex space provides even more room for a family room, media room, playroom, or entertaining area. Enjoy the privacy and security of a gated setting along with exceptional community amenities, including a private in-ground pool with cabana, beautifully appointed clubhouse, and fully equipped fitness center. The location is equally impressive—within walking distance of Vassar Brothers Medical Center and just minutes from Metro-North, shopping, dining, colleges, and everyday conveniences. Explore everything the Hudson Valley has to offer, including the Poughkeepsie waterfront, Walkway Over the Hudson, scenic parks, hiking and biking trails, wineries, breweries, historic destinations, acclaimed restaurants and all that the Hudson Valley has to offer! With generous living space, a flexible layout, maintenance-free convenience, and an outstanding commuter location, this exceptional home combines the comfort of a private residence with the amenities of a year-round retreat. This is more than a townhouse—it’s a lifestyle! Stop clicking and start dialing!

308 Bridgeview Drive, Poughkeepsie

$495,000
2 Beds 3 Baths 1039199 MLS
Welcome to this beautifully maintained lakeside home, a cozy, charming retreat where peaceful water views shape the rhythm of everyday living. Nestled directly across from the shimmering lake, this inviting residence offers a bright, sun-filled bonus room, perfect as a private office, creative studio, serene reading nook, or bedroom, framed by tranquil scenery that inspires and soothes. Set within a vibrant and welcoming community, you’ll enjoy access to multiple picturesque beaches, scenic walking paths, nearby cafes, restaurants, and local shops that make daily living feel effortless and enjoyable. Renovated in 2019 and lovingly cared for, the home blends warmth and functionality with fresh paint, a newly paved driveway, and a fully fenced backyard and patio ideal for outdoor gatherings or quiet moments of retreat. The flexible mother-daughter layout with its own private entrance provides wonderful versatility for extended family, guests, or multi-generational living. The upstairs was previously enjoyed as a 3-bedroom layout, and the finished basement offers excellent potential as a comfortable 1-bedroom for extended family or guests, adding even more adaptability to the home’s design. Located in the highly sought-after Carmel School District and just over an hour from NYC, with quick access to I-84 and Metro-North, this home offers the perfect balance of vacation-style serenity and commuter convenience. Come experience this charming lakeside gem, it will not last.

222 N Terry Hill Road, Carmel

$499,999
3 Beds 3 Baths 1039462 MLS
Welcome to The Tides, one of Rocky Point’s most desirable communities. This three-bedroom, three-bath L-ranch is set on a .35-acre corner lot at the entrance to a cul-de-sac, surrounded by the subdivision’s attractive mix of architectural home styles, broad curb-lined roads, and gently rolling blocks. The home’s classic L-shaped layout provides excellent separation of space, with the bedrooms—including the primary suite with private bath—positioned along the south side of the home. A generous entry foyer with coat closet creates a natural transition into the formal living and dining areas, while the inviting den features a wood-burning fireplace and opens to the large eat-in kitchen with breakfast bar. At the rear of the home, find an in-line laundry area, third full bath with shower, and direct access to the oversized two-car garage with additional attic storage. The full basement with outside entrance, multiple windows and high ceilings make for a great space to create an at-home gym, work space or play room. Additional features include central air conditioning, an updated oil burner, single-layer architectural roof, cedar walk-in closet, full attic with pull-down staircase, covered front porch, and rear porch accessed through sliding glass doors. Please note there is plywood beneath the carpeting. Lovingly maintained in largely original condition since its 1968 construction, this home offers a rare opportunity to preserve its substantial character or reimagine it into the open, modern ranch so many buyers seek today. Its proven construction, generous footprint, and highly functional layout provide an exceptional canvas for the next owner. Residents of The Tides enjoy private deeded access to Tide Beach through electronically gated entry, with seasonal security, bathrooms, a barbecue and seating area, private playground, and access to Long Island Sound. Conveniently located moments from Rocky Point’s business district, shopping, grocery stores, restaurants, and everyday conveniences. A tax grievance has been filed.

1 Briar Court, Rocky Point

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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.