Sleepy Hollow Real Estate Search

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

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

$435,000
2 Beds 2 Baths 1038744 MLS
Welcome to 69 Montgomery Street, a beautifully maintained circa 1849 Colonial Victorian set in the heart of Poughkeepsie’s historic district, where original character and thoughtful modern updates come together. Step inside to soaring ceilings, gleaming red oak floors, and oversized, sun-filled rooms that immediately showcase the scale and craftsmanship of this historic home. The main level offers a spacious living room that flows naturally into the grand dining room—an inviting setting for everything from quiet dinners to holiday gatherings. The well-appointed kitchen features an induction cooktop and Sub-Zero refrigerator, combining modern function with the home’s timeless surroundings. One of the most special spaces is the screened-in porch, accessible from both the kitchen and dining room. Tucked away from the street and overlooking the private backyard toward Garfield Place, it’s the kind of space made for morning coffee, summer dinners, and slow evenings at home. Upstairs, beautiful wide-plank pine floors continue throughout two generously sized bedrooms and a flexible third room that can easily serve as a home office, den, nursery, or additional bedroom. A full bathroom completes this level. The walk-up attic offers even more possibilities. With impressive ceiling height and generous space, it provides an opportunity to create a dramatic primary suite, studio, or additional living area while preserving the architectural character of the home. The lower level adds another layer of flexibility, featuring a newly renovated full bathroom, separate entrance, and space perfectly suited for guests, a recreation room, home office, or private retreat. Rich in 19th-century character yet thoughtfully updated for modern living, 69 Montgomery Street offers the space, history, and architectural details that simply cannot be replicated today—all within convenient reach of shopping, transportation, universities, medical centers, and everything Poughkeepsie and the Hudson Valley have to offer.

69 Montgomery Street, Poughkeepsie

$425,000
3 Beds 2 Baths 1039491 MLS
Your lake getaway awaits—less than two hours from New York City! Welcome to this charming 3-bedroom ranch in the sought-after Lake Louise Marie community, where comfortable one level living meets beautiful natural surroundings and an active recreational lifestyle. One of the home's most impressive features is the unobstructed lake view, offering a beautiful backdrop from the property and a peaceful atmosphere that makes every day feel like a getaway. Inside, the home offers a warm and inviting layout with beautiful wood flooring, abundant natural light, large windows, and sliding glass doors overlooking the backyard. Central air conditioning keeps the home comfortable during the warmer months. Step outside into your own private outdoor retreat. The beautiful patio features a charming waterfall, creating a peaceful and inviting setting for morning coffee, outdoor dining, entertaining guests, or simply relaxing at the end of the day. Mature trees and established landscaping add privacy and character, while the waterfront setting provides endless opportunities to enjoy the outdoors. Lake Louise Marie is a wonderful destination for recreational lake living, and electric-powered boats are permitted, making it possible to enjoy boating and time on the water while preserving the peaceful character of the lake. Community Amenities Just ¼ Mile Away The community clubhouse and recreation facilities are approximately ¼ mile from the home, offering: Swimming pool, Tennis courts, Basketball court, Playground and Clubhouse. Whether you're looking for an active environment or a relaxing weekend escape, there's plenty to enjoy close to home. Come experience the tranquility of the lake, the beauty of the waterfall patio, and the convenience of nearby community amenities. Whether you're looking for a full-time residence, weekend retreat, or summer escape, this Lake Louise Marie ranch offers a wonderful opportunity to enjoy the best of lakeside living.

210 Lake Shore Drive E, Rock Hill

$425,000
3 Beds 2 Baths 1038615 MLS
From the moment you enter this rare three-bedroom unit at Sadore Lane Gardens, it’s clear this turnkey apartment is something special. Thoughtfully designed and exceptionally well cared for, every room reflects the attention to detail essential in creating a home that feels both sophisticated and welcoming. The cohesive design carries seamlessly throughout with hardwood floors enhancing the continuity while maximizing natural light and everyday functionality. The inviting living room serves as the centerpiece with an adjacent dining area, ideal for entertaining. The updated kitchen boasts quartz countertops, custom cabinetry, a stylish mirrored backsplash, and stainless-steel appliances. Space abounds here, allowing for a convenient office nook off the kitchen. The primary bedroom suite which includes a walk-in mosaic tile shower is the standout retreat, offering the kind of elevated, tranquil atmosphere you would expect from a luxury hotel suite. Additionally, there is an updated hall bathroom for guests and two more generously-sized bedrooms with ample closet space offering exceptional flexibility, providing comfortable quarters for guests, a home office, or unique spaces tailored to your lifestyle. Community amenities include an Olympic-sized swimming pool and three playgrounds. Conveniently located with quick access to major highways, parkways, and public transportation. Local bus service provides access toward the #4 subway, while the BxM4C express bus offers direct service toward Manhattan. Tuckahoe Metro-North is also nearby, providing another convenient option for commuting into NYC and throughout Westchester. Close proximity to an array of shopping, dining, parks, and everyday services makes errands and outings easy to incorporate into your daily routine.

4 Sadore Lane Unit #3B, Yonkers

$418,500
3 Beds 1 Baths 1028937 MLS
Welcome to this charming Cape-style home, tucked away in a quiet neighborhood and thoughtfully cared for by its current owners. With recent updates throughout, this move-in-ready home offers the perfect combination of comfort, character, and potential. Step inside to find beautifully refinished hardwood floors and a newly updated kitchen featuring brand-new cabinets and flooring. The home also features central air for year-round comfort, along with the convenience of municipal utilities. A new roof with a transferable warranty offers added peace of mind for the next homeowner. One of the highlights of this property is the outdoor living space. The fenced-in yard offers plenty of room to relax, entertain, or simply enjoy time outdoors. A beautiful deck with a retractable awning and outdoor TV creates a true extension of the home's living space and the perfect setting for everything from morning coffee to summer gatherings. A hot tub, detached garage, and storage shed complete the backyard. The home also offers plenty of possibilities for the future. A full basement provides additional space and storage, while the partially finished attic offers great potential to create additional living space, a home office, or simply even more storage. Meticulously maintained and thoughtfully updated, this home is an excellent opportunity for a first-time buyer, someone looking to downsize, or anyone who appreciates a turnkey home with the flexibility to grow into additional space. Move right in and make it your own.

6 Broad Street, New Windsor

$440,000
3 Beds 2 Baths 1036770 MLS
Historic Colonial Era Home in the Heart of Sugar Loaf, NY. Located just 60 minutes from NYC. Zoned Residential/Commercial. Step into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Built in 1770, this unique property features:• One of a kind Colonial era home, featuring original exposed hand-hewn beams, barn siding walls, and a fireplace• Two spacious workshops/studios – ideal for artists, entrepreneurs, or makers – currently a woodcarvers workshop. • A must-see, living piece of history full of soul and story• Stunning view of Sugar Loaf Mountain right out your front door. Zoned commercial/residential, this home offers the perfect blend of live-work potential — ideal for a workshop, gallery, studio, or cozy retreat. Just steps away:• 2 popular restaurants• A vibrant performing arts center• Local breweries with live music• Coffee shop/ Roaster & Brunch House• Year-round craft markets & community events. Sugar Loaf is a renowned creative hub, and this home is at the very center of it all. Nestled in the heart of Sugar Loaf’s artisan community, this unique home and shop was long owned by a cultural mainstay — a woodcarver, painter, entertainer, and local luminary whose influence helped shape Sugar Loaf’s identity as an artists’ village back in the mid 1960’s.  This property offers more than walls and beams. Full of character and creative potential, this property is perfect for artists, craftsmen, woodworkers or anyone drawn to a vibrant, storied community. It offers a living canvas for makers and dreamers to carry forward a tradition of creativity. Don't miss your chance to own a timeless treasure in one of the Hudson Valley’s most beloved villages.

1367 Kings Highway, Chester

$449,500
4 Beds 2 Baths 1037125 MLS
Welcome to 170 Hooker Avenue! A charming 1930s Colonial offering tasteful updates preserving the timeless character in the heart of the Southside of Poughkeepsie. Step inside to discover beautiful gleaming hardwood floors throughout, classic architectural details, arched openings, built-in shelving, and a welcoming living room surrounding a wood burning fireplace. The spacious formal dining room is a standout, featuring a striking decorative ceiling and French doors that lead to the enclosed three-season room that is an inviting space surrounded by windows, perfect for relaxing, reading, or enjoying your morning coffee. (not included in the finished sq ft) The kitchen blends classic charm with modern convenience, featuring rich wood cabinetry, granite countertops, newer stainless steel appliances, a tiled backsplash, and generous storage. A convenient half bath and additional flex space complete the main level. Upstairs you'll find four bedrooms and a full bath, including a generously sized primary bedroom. The home also offers a full basement for additional storage and utility space and 1 car garage under. Outside, mature landscaping, a stone retaining wall, and classic Colonial curb appeal create a welcoming first impression. Additional features include a brand new roof with transferable warranty, sleek black gutters, private driveway, municipal water, sewer and access to natural gas on the street. With just over 1,800 square feet of finished living space, plus the three-season room, this home offers a wonderful combination of character, functionality, and opportunity. 170 Hooker Avenue is ready for its next chapter, come experience the warmth and character of this classic Poughkeepsie home. Excellent location, minutes to Route 9, the Walkway over the Hudson, Marist University, Culinary Institute of America, great restaurants, shopping, schools and more! Come see all that the beautiful Hudson Valley has to offer!

170 Hooker Avenue, Poughkeepsie

$429,000
1 Beds 1 Baths 1038226 MLS
Welcome to Residence 3B at 403 East 87th Street, a distinctive multi-level one-bedroom offering a sense of space and separation rarely found at this price point on the Upper East Side. This thoughtfully designed home features three distinct living areas. The main level includes a spacious eat-in kitchen and an updated bathroom. Upstairs, the private bedroom comfortably accommodates a king-sized bed and offers generous closet space, abundant natural light, and peaceful tree-lined views. The bright and versatile lower level provides plenty of room to relax, entertain, and create a dedicated work-from-home area. This pet-friendly cooperative features an elevator and on-site laundry. Guarantors and co-purchasing are permitted. The building also offers exceptional flexibility for a Manhattan co-op: shareholders may sublet after two years of primary residence, with no limit on future subletting. Ideally located near Whole Foods, Fairway, the Q and 4/5/6 subway lines, Central Park, and Carl Schurz Park, with some of the neighborhood’s best dining, shopping, and conveniences just outside your door. Residence 3B is not your typical one-bedroom. Its unique multi-level layout, generous proportions, and flexible ownership policies make it a rare Upper East Side opportunity. Schedule your private showing today! Please note: Images have been digitally edited to remove existing furnishings and virtually staged in multiple styles to illustrate the residence’s potential.

403 E 87th Street Unit #3B, New York (Manhattan)

$450,000
2 Beds 2 Baths 1036322 MLS
Welcome to this exceptional two-bedroom, two-bath home with a private balcony in a sought-after doorman building on Garth Road! The spacious living room flows seamlessly into the dining foyer and opens to your private balcony overlooking tree-lined Garth Road—the perfect spot for morning coffee, al fresco dining, relaxing with friends, or simply enjoying the outdoors. The oversized primary bedroom comfortably accommodates a king-size bedroom set plus a cozy reading chair. The corner second bedroom offers incredible flexibility as a bedroom, home office, den, or guest room and features a walk-in closet. The eat-in kitchen is ready for everyday living and entertaining with new quartz countertops, stainless steel appliances, and abundant cabinetry. With six closets, including three walk-ins, storage will never be an issue. Laundry is on every floor. Directly across the street, Garth Road’s playground and ball field provide convenient recreation, while Scarsdale Village and the Metro-North station are just a short distance away. Residents enjoy free permit parking on Garth Road, Grayrock Road, and the resident lot. You’ll also have the opportunity to join Lake Isle Country Club, featuring an 18-hole golf course, eight tennis courts, and five swimming pools, including a 50-meter Olympic pool. The Bronx River Trail is just steps away for walking, jogging, and biking. This is more than a home—it’s the perfect blend of space, convenience, recreation, and lifestyle in one of Scarsdale’s most desirable locations. NO PETS. Credit score of 700+, DTI below 35%, liquid assets after closing of 6 months maintenance and mortgage.

281 Garth Road Unit #B1G, Scarsdale

$435,000
2 Beds 1 Baths 1036599 MLS
Privacy seekers, this one is for you! Never before offered for sale...until now!! Tucked away on 3.4 wooded acres and completely hidden from the road, this Warwick property offers a peaceful retreat surrounded by a canopy of nature. Located in the Greenwood Lake School District and approximately one hour from New York City, it delivers exceptional privacy without sacrificing convenience. Built by the original owner with care and craftsmanship, this contemporary ranch offers comfortable one-level living and distinctive architectural details, including a skylight. A vaulted living room ceiling offers an open, airy feel, while the eat-in kitchen window frames views of a beautiful stone wall, mature greenery, and the private property beyond... The attached carport has been screened in for seasonal use as a three-season room, creating an inviting place to relax, entertain, and enjoy the woodland surroundings. The space can also be returned to carport use during the cooler months. Freshly painted and professionally cleaned, this home is ready for its next owner to move in, personalize, and build equity through future cosmetic improvements. Conveniently located near the Villages of Warwick and Greenwood Lake, with easy access to NJ Transit and the Tuxedo train station, this private retreat brings together location, lifestyle, privacy, and value. The property is being offered in its current as-is condition. Showings are by confirmed appointment only. ***Please do not enter the property without an appointment.

368 Old Dutch Hollow Road, Greenwood Lake

$410,000
4 Beds 2 Baths 1036827 MLS
This spacious one-and-a-half-story Cape Cod home is attractively situated on a knoll along Route 42, just a few miles from the Village of Woodbourne. Set on one acre of property, the home offers a versatile layout with five bedrooms, 1.5 bathrooms, and plenty of room for a growing household, weekend retreat, or anyone looking for additional space. The property also features a detached one-car garage and offers excellent potential for the new owner to complete several improvements already underway. Included with the sale are 36 boxes of new flooring, ready for installation, as well as a number of new replacement windows that have not yet been installed—giving the next owner a valuable head start on future renovations. The home is serviced by a drilled well and also has municipal water available, providing additional convenience and flexibility. Another unique feature is a second driveway with a granted easement providing additional access to the home. This additional access adds convenience and may be especially useful for deliveries, contractors, or future improvements to the property. Located only minutes from the Village of Woodbourne and within easy reach of shopping, restaurants, services, and the many recreational attractions of the Catskills, this property combines a convenient location with considerable potential. With five bedrooms, an acre of land, a detached garage, two means of access, and flooring and replacement windows included in the sale, this property presents an excellent opportunity for a buyer ready to add their own finishing touches. Motivated seller—come take a look and see the possibilities this property has to offer

6310 State Route 42, Woodbourne

$425,000
3 Beds 1 Baths 1037275 MLS
Welcome to this affordable ranch-style home in the Washingtonville Central School District, offering comfortable one-level living in a convenient location. Less than a 5-minute drive from the center of town, the home provides easy access to restaurants, banks, schools, local businesses, offices, the library, and the historic Brotherhood Winery, the oldest winery in the country. Inside, the home is updated, cozy, and move-in ready, with fresh paint, newer kitchen cabinetry, appliances, and flooring. Additional features include new ductless A/C for warm summer days, hot water baseboard heating with on-demand hot water, a newer bathroom with marble flooring and ceramic-tiled walls, hardwood flooring throughout the living space, and ceiling fans with lights in all three bedrooms. The unfinished walk-out basement is already piped for a bathroom, offering excellent future potential. The home also features 200 AMP electric service, a newer septic and well, and a well-maintained furnace. Outside, the property offers a lovely setting on a low-traffic street with a newer paved municipal road, level green front, side, and back yards, a newer paved driveway, a one-car garage, and abundant storage space in the walk-out basement. The spacious private backyard includes a freestanding covered patio and a separate fenced area ideal for gardening. Positioned near the center of the lot, the home provides privacy and allows for excellent use of the entire property. The location also offers easy access to surrounding towns, the train station, major roadways, Stewart International Airport, and West Point. For reference, the current average electric bill is approximately $125; propane is used only for cooking, and oil is used for heat and hot water.

20 Meadow Avenue, Washingtonville

$450,000
5 Beds 3 Baths 1037491 MLS
Mountain Living Meets Catskills Adventure! Discover the perfect Catskills getaway in this spacious 2,256 sq. ft. mountain-top home, offering 5 bedrooms and 2½ baths on approximately 1.9 acres in the Town of Hunter. Ideally positioned for those who love the outdoors, this property puts some of the region's most spectacular destinations right at your doorstep. Enjoy easy access to North-South Lake, Kaaterskill Falls, and Hunter Mountain Ski Resort, with endless opportunities for hiking, skiing, kayaking, fishing, and exploring the beauty of the Catskills. After a day of adventure, come home and relax or entertain on the large deck overlooking the generous yard--perfect for gatherings, summer barbecues, or simply enjoying the peaceful mountain setting. Inside, the generous floor plan provides plenty of room for gathering and entertaining guests, with five bedrooms and ample living space designed for comfortable year-round living or a Catskills retreat. And when you're ready to explore beyond the mountain, it's just a quick trip to the Village of Catskill, Village of Saugerties, and Village of Woodstock, where you'll find restaurants, shops, galleries, entertainment, and the unique charm of the Hudson Valley. Whether you're looking for a full-time residence, weekend escape, or investment opportunity, this Hunter Mountain-area property offers the space, setting, and location to embrace the best of Catskills living.

398 Lake Road, Hunter

$425,000
3 Beds 3 Baths 1031656 MLS
Some homes check the boxes. This one makes you want to stay a while. Tucked away on a quiet dead-end street in Unionville, 30 High Street offers something increasingly hard to find: privacy, peace, and room to breathe. No through traffic. No constant hum of cars. Just a beautifully maintained newer home in a setting that feels a little removed from it all. Built within the last decade, this 3-bedroom, 3-bath home offers 1,860 square feet of finished living space, beautiful hardwood floors, and a thoughtfully designed kitchen featuring granite countertops, a gas range, convection oven, and a walk-in pantry that may quickly become your favorite room in the house. The primary suite features three closets and a private bath, while two additional bedrooms offer flexibility for family, guests, or a home office. And then there’s the 900+ square-foot full walk-out basement, unfinished, but full of potential. Gym? Media room? Workshop? Recreation space? You decide. Step onto the elevated deck and enjoy the peaceful backyard, whether you’re hosting friends, sipping your morning coffee, or proudly doing absolutely nothing. Located in the Minisink Valley Central School District, with easy access to Warwick, Middletown, I-84, Route 6, and Route 17M, you get a quiet, country-like setting without giving up convenience. The Appalachian Trail is also approximately 8.8 miles away. For buyers ready to trade traffic and noise for space and breathing room, 30 High Street isn’t just a change of address; it’s a change of pace. See it for yourself. Just don’t be surprised if you find yourself wanting to stay.

30 High Street, Unionville

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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.