Sleepy Hollow Real Estate Search

Sleepy Hollow 5 Bedroom Properties for Sale

Our website features the best real estate search for 5 bedroom 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 5 Bedroom Properties for Sale

$1,928,000
5 Beds 5 Baths 1008163 MLS
Thoughtfully designed with exceptional craftsmanship and today's most desirable finishes, this newly constructed Colonial offers the perfect combination of luxury, comfort, and modern living in a prime Plainview location. Featuring 5 bedrooms, 4.5 bathrooms, and a two-car garage, the home showcases a spacious open floor plan with soaring ceilings, abundant natural light, and refined architectural details throughout. At the heart of the home is a beautifully appointed chef's kitchen featuring premium appliances, gas cooking, custom cabinetry, and an oversized center island that flows seamlessly into the expansive living and entertaining areas. A desirable first-floor ensuite bedroom offers ideal flexibility for guests, extended family, or a private home office. The luxurious primary suite is a true retreat, complete with a spa-inspired bathroom and an oversized closet. Three additional bedrooms include a Jack-and-Jill bath and a separate ensuite. An expansive backyard offers the perfect setting for entertaining, recreation, or future outdoor amenities. The full unfinished basement with outside entrance presents endless possibilities. Ideally located near parks, shopping, dining, transportation, and major roadways, this exceptional new construction offers an outstanding opportunity to enjoy refined living in one of Plainview's most sought-after locations. Pictures are examples of finished homes by this esteemed builder, not exact details.

22 Northern Parkway E, Plainview

$950,000
5 Beds 3 Baths 1033771 MLS
A Car Enthusiast's Dream! Offering an extraordinary 6-car garage, including a 2-car attached garage and an impressive 4-car detached garage, this exceptional property is a rare find! Welcome to the Hudson Rivertown of Stony Point! This beautifully renovated 5 bedroom, 3 bath Colonial, in the highly sought-after Hamlet of Tomkins Cove is privately nestled on over 1.2 picturesque acres. With 2,500 square feet of thoughtfully updated living space, this exceptional property combines spacious living, modern finishes, and unparalleled privacy. A picturesque tree-lined drive welcomes you home, leading to a circular driveway that creates an impressive arrival while providing ample parking. Car enthusiasts, hobbyists, or those in need of additional storage will appreciate the attached 2-car garage as well as the impressive detached 4-car garage. From the moment you step inside, you'll notice the extensive renovations throughout. The freshly painted interior and a stunning new designer kitchen featuring quartzite countertops, stainless steel appliances, and abundant cabinetry. The first floor also offers a formal living room, formal dining room, family room, guest bedroom and full bathroom, creating a seamless blend of style and functionality. Upstairs, the spacious primary suite serves as a private retreat, complete with a beautifully en-suite bath. The additional bathrooms have also been tastefully updated, offering move-in-ready comfort throughout the home. Step outside to your own private oasis. A enclosed heated 3 season room and trex deck overlooks the expansive, park-like grounds, providing the perfect setting for entertaining or relaxing while surrounded by nature. Whether it's the vibrant colors of autumn, snow-covered mountain vistas in winter, or lush greenery in the warmer months, the scenery is truly unforgettable. Located 40 minutes from NYC, 20 minutes to NJ, nearby Bear Mountain State Park, Harriman State Park, Seven Lakes, West Point, Woodbury Commons. This exceptional Colonial is ready to welcome you home.

87 Mott Farm Road, Tomkins Cove

$2,000,000
5 Beds 5 Baths 1024657 MLS
Welcome to this 5-bedroom luxury home offering approximately 6,251 square feet of total usable living space on a beautifully landscaped, level 0.95-acre cul-de-sac property. Designed for grand entertaining and comfortable everyday living, this exceptional residence welcomes you with a sweeping paver driveway leading to a three-car garage and an impressive two-story foyer highlighted by a dramatic curved staircase with an open-to-below architectural design. The thoughtfully designed main level features elegant formal living and dining rooms, a sun-filled family room anchored by a gas fireplace, a convenient powder room just off the grand foyer, and a private guest suite complete with a radiant-heated full bathroom. At the heart of the home is a beautifully appointed chef's eat-in kitchen showcasing custom cabinetry, granite countertops, a center island, premium Sub-Zero appliances, and a spacious breakfast nook with views of the backyard. Upstairs, the tranquil primary suite offers a walk-in closet and spa-inspired bath, accompanied by three additional generously sized bedrooms and a second full bathroom, providing comfortable accommodations for family and guests. The fully finished lower level is designed for exceptional entertaining with a dedicated movie theater, expansive recreation room, custom wet bar complete with a wine cooler, and an additional powder room for added convenience. Step outside to your own private resort featuring a pristine gunite in-ground swimming pool with a separate spa, expansive paver patio, covered gazebo, inviting fire pit, sprawling park-like lawns, and mature landscaping that provides outstanding privacy. Smart home technology and a whole-house generator add modern convenience and peace of mind. Offering 5 bedrooms, 3 full bathrooms, and 2 half bathrooms across approximately 6,251 square feet of usable living space on nearly one acre, this remarkable residence delivers timeless elegance, exceptional entertaining spaces, and the convenience of an easy commute to New York City.

10 Deforest Court, West Nyack

$929,000
5 Beds 3 Baths 1034126 MLS
Welcome to this well-maintained legal 2-family home located in the desirable neighborhood of Saint Albans, Queens. Whether you're looking for a primary residence with rental income or a smart investment opportunity, this versatile property offers exceptional value. The first-floor apartment features two spacious bedrooms, a bright living area, a full kitchen, and a handicap-accessible bathroom. The property also offers wheelchair access to the backyard, providing added convenience and accessibility. Step outside to enjoy the oversized backyard, complete with an above-ground pool that can easily be removed if desired. The second-floor apartment is a beautifully updated duplex that extends into the finished attic, providing additional living space. This renovated unit features two bedrooms, updated flooring, fresh paint, and a bright, modern feel throughout. The full finished basement includes a separate outside entrance, a laundry area with washer and dryer, and two finished rooms, offering flexible space for recreation, a home office, storage, or extended living needs (subject to local regulations). Additional highlights include a private driveway, generous outdoor space, and a convenient location close to schools, shopping, restaurants, parks, and public transportation. Whether you're an investor seeking strong rental potential or a homeowner looking to offset your mortgage with rental income, this legal 2-family property presents an outstanding opportunity. Schedule your private showing today!

11535 197th Street, Saint Albans

$750,000
5 Beds 5 Baths 1033586 MLS
Escape to the peace and beauty of the Town of Neversink with this exceptional Colonial home, privately situated on 11 scenic acres along a quiet country road. Offering approximately 4,000 square feet of living space, this impressive property combines comfort, versatility, and country charm, all while benefiting from remarkably low annual property taxes of just $5,325. Designed to accommodate a variety of living arrangements, the home offers outstanding potential for a mother-daughter residence or extended family living. The finished lower level provides approximately 2,000 square feet of additional living space and features a spacious bedroom, a full bathroom, and a well-appointed butler's pantry complete with a sink, dishwasher, and ample cabinetry. The remainder of the lower level is set up for storage and a utility room. The expansive family and recreation area is enhanced by radiant heated floors, a wood or pellet stove for added warmth and ambiance, and enough room for oversized tables, making it ideal for entertaining, hobbies, or family gatherings. A walkout door leads directly to a private patio overlooking the property. The main level is equally inviting, offering five generously sized bedrooms, four full bathrooms, and one half bath. The heart of the home is the bright eat-in kitchen, complemented by a formal dining room for holiday gatherings and a second dining area surrounded by windows that overlook the beautifully landscaped backyard. The spacious living room is anchored by a classic wood-burning fireplace, creating the perfect setting for relaxing evenings with family and friends. Step outside and discover everything this remarkable property has to offer. The 11-acre parcel provides an ideal blend of open space and privacy with beautifully maintained gardens, a greenhouse for gardening enthusiasts, and three storage sheds for equipment and tools. The oversized two-car detached garage offers tremendous additional potential, with enough space on the second floor to create an apartment, guest suite, home office, or workshop. A separate carport currently serves as covered storage for tractors and outdoor equipment. Built with practicality in mind, the home is served by an oversized 1,500-gallon septic system designed to accommodate a large family and was professionally pumped just two years ago. Whether you're looking for a spacious family home, multi-generational living, or simply a private country retreat with room to grow, this outstanding Neversink property offers endless possibilities. Surrounded by the natural beauty of the Catskills yet conveniently located within easy reach of nearby towns, shopping, dining, and outdoor recreation, this is a rare opportunity to own a truly special property. This is much more than a home—it's a lifestyle. Schedule your private tour today and experience everything this exceptional property has to offer

115 Twinshaven Road, Napanoch

$774,900
5 Beds 2 Baths 1033951 MLS
Location, location! Private neighborhood with no thru-traffic features this lovely 4 to 5 bedroom, 2 bathroom, cape cod style home. This home has nice curb appeal and has been professionally landscaped and maintained and has a brand new driveway. There are hardwood floors on the first floor and the living room and den both feature newer Bay windows. The den can also be a 5th bedroom if needed because it does have a closet and a door. The kitchen was updated with custom wood cabinets, newer appliances (2013) and features a gas stove. Love that gas cooking! The dining room is a nice size and open to the living room for easy holiday entertaining. The kitchen has on outside entrance to the beautiful new paver patio in the yard. If you need a 2nd bedroom on the 1st floor your in luck! This home has it and there is also a full bath that was updated in 1998. The 2nd floor boasts 3 more bedrooms! The primary bedroom has 2 double closets and then some. The other 2 bedrooms are nice sizes and have built-ins for storage and one even has a desk! The full bath on this floor has also been updated in 1998! The basement is finished and has some space for a den or gym equipment and then there is a room that can be used as an office or a craft room. Utilities and storage are also down here. This .25 acre property has a beautiful yard. It is flat and usable. The paver patio is brand new and is accessible right off of the kitchen. Then there is plenty of lawn for activities as well as a new shed. Sprinklers (2010) in front and back with 4 to 5 zones. Front railing 2021 from Dukes of Iron. Insulated Attic in 2015. Front and storm door 2024. Side fences in front from 2023. Boiler 2018 and cleaned in 2024. Basement window replaced in 2016. Cleaned dryer vent in 2025. Garage door and motor was replaced in 2021 and has new garage door opener. Upstairs under carpet is plywod. Built-ins in bedrooms stay. Roof and Skylights 2021, Cesspool 1998, 200 Amp, Generator Outlet, New Chimney Cap. Seller looking to close around November.

43 Genesee Drive, Commack

$799,900
5 Beds 3 Baths 1033943 MLS
Escape to total privacy and rural charm at 234 Mary Taylor Rd! Nestled at the end of a quiet road on 29.6 acres with a winding stream, this spacious 5-bedroom Colonial is an absolute dream for homesteaders, outdoor enthusiasts, and multi-use property buyers alike. A major highlight of this property is the dedicated second building—a fully equipped dining hall designed for large-scale entertaining! Featuring a second kitchen complete with a custom pizza oven, an expansive dining area, and flexible open space, this impressive structure offers endless potential: - Event Venue & Hosting: Perfect for hosting weddings, retreats, holiday parties, or family reunions. - Guest Suite or Multi-Generational Living: Easy to adapt for extra guest quarters or private living quarters. - Creative Studio or Clubhouse: Ideal for a workshop, game room, home business, or art studio. - The main home boasts 5 generously sized bedrooms for flexible family living, direct attached garage access, plus an additional detached garage/workshop and a 40'x24' pole barn. The scenic acreage features a mix of tillable land for gardening or animals, and rich, wooded terrain complete with a custom deer stand for hunting. Best of all, the property is sold fully furnished and can include the tractor, excavator, and lawn equipment for a completely turnkey country setup! Enjoy total country seclusion with prime convenience: - 10 minutes to Vroman's Nose Nature Preserve - 30 minutes to Mine Kill State Park - 35 minutes to Windham Mountain & regional skiing - 45 minutes to Albany International Airport Whether you're looking to host, farm, hunt, ski, or create an income-generating retreat, this unique sanctuary has it all!

234 Mary Taylor Road, Call Listing Agent

$4,995,000
5 Beds 7 Baths 1027507 MLS
Tucked away on a tranquil cul-de-sac in the prestigious Town of Bedford, this masterfully reimagined gated home defines the next generation of Bedford luxury real estate. Just a short, convenient jaunt from the energy of Manhattan, 2 Barry Court provides a seamless transition from city living to serene countryside retreat, making it an ideal residence for those seeking fresh air, privacy, and refined relaxation. More than just a home, this is a lifestyle property located near the historic Bedford Village Green, the scenic Bedford Riding Lanes, and the vibrant Katonah boutique district. Set on four manicured acres with mature trees and open sky, the estate invites you to unwind in total tranquility—whether for weekends or for full time living. Designed by revered architect Teo Siguenza and developed by the esteemed Grasso Development Corporation, the residence blends timeless character with modern luxury. Inside, a two-story foyer opens to light-filled, 10’ high living spaces, while a custom chef’s kitchen (with Subzero and Wolf appliances) flow effortlessly into a vaulted family room with a statement stone fireplace. The primary suite offers a private oasis with dual dressing rooms, spa-like baths, and its own sitting room with a fireplace. The home's exterior truly shines: a brand new heated gunite pool with automatic cover, pool cabana with full bath and an expansive bluestone terrace transform the property into a resort-style getaway. With its unique combination of proximity to New York City and complete privacy, this move-in-ready estate is perfectly suited for buyers seeking a luxurious home without sacrificing access to the city.

2 Barry Court, Katonah

$1,099,000
5 Beds 2 Baths 1033051 MLS
Welcome to this spacious and well-maintained 5-bedroom, 2-full-bath, 1-car garage home in the highly desirable Plainview School District. Tucked away on a quiet, small residential loop, this three-level home offers a peaceful and private setting with no homes directly behind the property—a special feature that provides added privacy and an open feel. Enjoy a convenient location close to shopping, parks, restaurants, medical facilities, and houses of worship, with easy access to major roadways. New York City is also just a short distance away, offering the perfect blend of suburban convenience and city accessibility. With 1,962 square feet of living space, 800 Sq. ft finished basement and 2,762 total, this versatile home offers generous space for everyday living, entertaining, working from home, and extended family needs, along with abundant storage throughout. The main level welcomes you with a comfortable living room featuring glass sliding doors leading to a large wooden deck and spacious backyard. The backyard is fully enclosed with a white vinyl fence, creating a private outdoor setting ideal for relaxing, entertaining, gardening, or enjoying time with family and friends. The formal dining room provides an inviting space for gatherings, while the eat-in kitchen features a cozy breakfast nook and stainless-steel appliances, including a natural gas range, refrigerator, microwave, and dishwasher. A first-floor bedroom and full bathroom add exceptional flexibility to the home and can easily accommodate guests, a home office, or an extended family member seeking convenient first-floor living. The second floor offers four additional bedrooms, a full bathroom, and a versatile den. The den provides valuable additional space that can be used as a home office, reading room, play area, hobby space, or private retreat. The full height basement provides even more valuable living and storage space, with approximately three-quarters finished, heated, and air-conditioned. The finished portion includes a spacious playroom, pantry/storage area, and large cedar closet. The unfinished portion features a workshop, laundry area, additional cedar closet, and ample storage space. The home has been lovingly maintained and thoughtfully cared for over the years, with improvements including vinyl siding, an updated first-floor bathroom, central air conditioning, and conversion to natural gas for both heating and cooking. Additional desirable features include beautiful oak flooring and Andersen windows and doors. With its spacious layout, flexible bedroom configuration, finished basement, private fenced backyard, quiet setting, and highly desirable Plainview location and school district, this home offers a wonderful opportunity to create the space and lifestyle you've been looking for.

46 Margaret Drive E, Plainview

$1,150,000
5 Beds 5 Baths 1032617 MLS
Welcome to 857 Western Hwy N, a charming single-family home nestled in the picturesque town of Blauvelt, NY. This delightful property was built in 1946 and exudes timeless appeal and character. Situated on a spacious lot spanning over 78,000 sqft. this home offers plenty of room to roam and enjoy the serene surroundings. Upon entering the home, you are greeted by a warm and inviting atmosphere that is sure to make you feel right at home. The main level features a cozy living room, perfect for relaxing with loved ones or hosting gatherings. The adjacent dining area is ideal for enjoying meals with guest, while the well-appointed kitchen boasts ample cabinet and counter space for all your culinary needs. Outside, the expansive lot offers endless possibilities for outdoor enjoyment. From gardening to playing sports or simply relaxing in the fresh air, the options are endless. The lush greenery and mature trees create a peaceful and private oasis that you can enjoy year-round. The lot can be redone but at the moment houses a waterfall (small) with koi pond in season, two treehouses, and various eccentric landscaping additions. This home can truly be made your own. Located in the sought-after town of Blauvelt, this home offers the perfect blend of tranquility and convenience. With easy access to major highways, shopping, dining, and entertainment options, you'll have everything you need right at your fingertips. Plus, top-rated schools and parks are just a short distance away, making this the ideal location for households of all sizes. In summary, 857 Western Hwy N is a delightful home with a rich history and plenty of potential. Property is large and an investor or business' dream. Property is only about 35-40 minutes from Times Square depending on traffic. Property is being sold as is but open to negotiations.

857 Western Highway, Blauvelt

$2,180,000
5 Beds 5 Baths 1033593 MLS
Stunning Luxury Home with Professional Office Space on a Rare 9,672 Sq. Ft. Lot in Prime Flushing! A rare opportunity to live, work, and enjoy exceptional space all in one property! This beautifully maintained oversized residence, measuring approximately 56' × 35.5', sits on an impressive 9,672 sq. ft. lot. Public records classify the property as a 1-family residence with 1 store or office, creating a unique opportunity for buyers seeking a spacious home together with dedicated professional or business space. The residence features 5 spacious bedrooms and 4.5 bathrooms across three above-ground levels, plus a fully finished basement with a separate entrance. A beautifully finished attic crafted with rich cherry oak wood provides an impressive additional space ideal for entertainment, recreation, or other flexible uses. The inviting living room features beautiful hardwood floors and a wood-burning masonry fireplace, creating a warm and elegant atmosphere. The formal dining room flows into a gourmet eat-in kitchen featuring custom cabinetry, quartz countertops, a large marble center island, and premium stainless steel appliances. Additional highlights include a spacious family room, generous living areas, abundant natural light, quality craftsmanship throughout, and dedicated professional/office space—an exceptional feature for professionals or business owners looking for the convenience of operating close to home. Buyer should independently verify that their intended business or professional use complies with applicable zoning, licensing, and other requirements. Outside, enjoy a large private backyard with plenty of room for entertaining, gardening, and relaxation, along with a detached two-car garage. Ideally located just a short walk to the Murray Hill LIRR Station and minutes from Downtown Flushing, with convenient access to shopping, dining, parks, schools, and transportation. Oversized 9,672 sq. ft. lot, spacious residence, professional/office space, private backyard, and two-car garage—all in a prime Flushing location. A truly rare live/work opportunity and a must-see!

3011 Murray Street, Flushing

$1,200,000
5 Beds 5 Baths 1033072 MLS
This masterfully crafted, brand new colonial estate in Shoreham redefines modern elegance, offering an unparalleled fusion of sophisticated residential luxury and strategic professional utility. Spanning 4,000+ square feet of meticulously curated living space, this residence represents the pinnacle of new construction, designed for those who demand both aesthetic perfection and functional excellence. Architectural Grandeur: The experience begins in a breathtaking 22 foot foyer, where soaring ceilings and bespoke craftsmanship set an immediate tone of prestige. The open concept layout is defined by 9 foot ceilings on the main level, intricate crown molding and sophisticated coffered ceilings. The interior is anchored by premium 3 1/2” red oak hardwood flooring with elegant smoked oak borders, complemented by dual staircases adorned with custom wrought iron spindles and bathed in natural light through Andersen 400 Series windows. A Culinary Masterpiece: The heart of the home is a chef’s kitchen of rare quality, designed to host the most discerning gatherings. It features professional-grade stainless steel appliances, expansive quartz countertops, and a massive center island with dual sided cabinetry. The kitchen flows seamlessly into the family room, where a gas fireplace creates a warm, inviting atmosphere, while multiple Anderson Frenchwood sliders provide a graceful transition to the outdoor living areas. Refined Accommodations: The residence offers five generously appointed bedrooms and five full bathrooms, ensuring ultimate privacy and convenience. Every bedroom is thoughtfully designed, with each suite enjoying private access to a full bathroom. The first floor includes a versatile bonus room, ideal candidate for a private executive office, a sophisticated guest suite, or a professional consultation space further enhancing the home’s adaptability for a modern lifestyle. Uncompromising Infrastructure: Built to an exacting standard, the home is equipped with a suite of high performance systems: * Climate & Efficiency: 2 zone central air conditioning, forced hot air heating and a high efficiency Navien Energy Star system. * Garage & Utility: An oversized two car garage with a 300 amp service, featuring access to possible radiant floor heating and a central vacuum system. * Foundation: A full basement with both interior and exterior access, optimized with a premium egress window for safety and natural light. Outdoor Sanctuary: Situated on 0.78 acres of future manicured grounds, the estate makes a striking first impression with a cobblestone and blacktop driveway (coming soon) framed by custom paver walls. The outdoor entertainment experience is elevated by a mahogany wraparound porch and an expansive mahogany deck. The property will be fully serviced by an 8 zone in-ground irrigation system, with ample space to curate a private pool retreat or expand parking capacity as needed. A Strategic Investment: With its refined finishes, versatile floor plan and substantial parking capacity, this property is uniquely positioned to serve as a high end professional office or boutique practice. Whether for an attorney, accountant, or medical professional, the layout provides a professional atmosphere without compromising the warmth and exclusivity of a premier residence. Located in the prestigious Shoreham-Wading River school district, this estate offers close proximity to local vineyards and farms, with a seamless commute to the Hamptons and major expressways. This is a singular opportunity to acquire a residence of unmatched quality in the heart of Shoreham.

48 S Rt 25A E Route 25A, Shoreham

$3,999,900
5 Beds 5 Baths 1029824 MLS
SUMMERWIND – An Extraordinary Waterfront Estate on the Connetquot River. Welcome to Summerwind, one of Oakdale’s most distinguished waterfront estates. Privately set behind stone gates on 1.09 beautifully landscaped acres, this custom-built residence offers approximately 6,286 square feet of luxurious living space, 200 feet of Connetquot River frontage, and a 150-foot private deep-water dock with float and direct access to the Great South Bay, Fire Island, and the Atlantic Ocean. Built in 2004 with exceptional craftsmanship, this three-story brick Colonial showcases Brazilian cherry hardwood floors, handcrafted custom millwork including archways & crown moldings, soaring ceilings, crystal chandeliers, wall sconces and timeless architectural details throughout. The gourmet chef’s kitchen features custom cabinetry, expansive granite countertops, premium appliances, pantry with additional refrigerator, and an oversized center island that opens seamlessly to the spectacular Great Room with a coffered ceiling and fireplace. The luxurious primary suite offers a private sitting area with fireplace, spa-inspired bath, his/hers walk-in closet suite has custom dressing room and built-ins with inlaid custom doors and island with marble tops and lighting, laundry shoot from primary bedroom to laundry room and a private balcony overlooking the resort-style backyard and waterfront. Additional guest suites, a formal dining room, music room, executive office, billiards room, home theater, recreation rooms, tremendous amount of closets for storage, a finished 2000 square foot third floor, and a full finished basement with outside entrance provide exceptional space and flexibility, and the outdoor living rivals a private resort with a 48’x 28’ freeform Gunite pool featuring a natural rock waterfall and waterslide, a 10’x14’ pool cabana, expansive covered terraces, natural stone patios, fire pit, professionally landscaped gardens, and a private sports court. Western exposure provides breathtaking sunsets over the Connetquot River. Built to an exceptional standard, the home features 2x6 construction, 600-amp electrical service, 45kw whole-house diesel backup generator, security cameras and alarm, dual-fuel heating (natural gas and oil), six-zone high-efficiency air conditioning, radiant-heated bathroom floors, separate electrical subpanels throughout the home, garage, and cabana, and a 4-inch water service. Situated at an approximate elevation of 11.5 feet in an X Flood Zone, no FEMA flood insurance is currently required. Summerwind is a rare opportunity to own one of Long Island’s premier waterfront estates—where timeless architecture, exceptional engineering, world-class boating, and resort-style living come together in one extraordinary property. A legacy estate unlike any other.

608 Shore Drive, Oakdale

$535,000
5 Beds 4 Baths 1031408 MLS
Built in 1880, this brick Victorian residence seamlessly blends historic elegance, architectural detail, and modern functionality. The beautifully preserved brick main structure exudes durability and classic charm. The front porch features an ornamental pavilion crowned with a faceted pointed roof - a striking detail reflecting the artistry of Victorian design. Together, the sculptured porch and brick exterior create a warm and inviting facade. A standout feature is the 2025 Brava synthetic slate roof, accented by copper rakes, valleys, drip edges, and custom copper detailing over the bay window. Delivering the timeless appearance of natural slate with exceptional durability and minimal maintenance, it beautifully complements the original bluestone window headers. In 2024, all flat roofs were replaced, and in 2023, Leaf Gutter systems were installed for added convenience. The custom gingerbread trim, inspired by a historic home in Orleans, Cape Cod, incorporates sixteen Gothic cusps as a subtle nod to the house number. These intricate architectural details create exceptional curb appeal while honoring the home's Victorian heritage. Inside, the owner's residence is thoughtfully designed for both comfortable everyday living and entertaining. The main level features an inviting entry hall adorned with Thibaut wall coverings, a sun-filled living room showcasing original architectural details, and a formal dining room enhanced by an arched bay window, Egg & Dart crown moldings, and beautifully appointed old English Greeff (F. Schumacker & Co.) wallpaper. Off the dining room, a charming coffee conservatory with classic black-and-white checkered floors creates a delightful alcove for morning coffee, a favorite book, or evening cocktails. Bathed in natural light and perfectly suited for botanical displays, this unique space offers a rare touch of conservatory-inspired living seldom found in today's homes. The eat-in kitchen, accented with wainscoting, is rich in character and features butcher block countertops, solid wood cabinetry, stainless steel appliances, and a skylight that fills the space with natural light. A convenient mudroom and full bath add practicality to the home's historic charm. Upstairs, you'll find three bedrooms, all featuring original hardwood flooring, a dedicated home office, and a second full bath. Two bedrooms showcase beautiful stained-glass windows, while three cedar closets provide additional character and functionality. Additionally, two legal units (not pictured) offer exceptional flexibility for rental income, guest accommodations, a variety of living conditions, or a private workspace, however, can potentially be converted to a one or two family home. Outside, a private fenced garden provides a peaceful retreat with mature plantings that offer season-long color. Fig and hydrangea trees, David Austin roses, lavender, and other established perennials create a picturesque setting that enhances the home's architecture. Beyond the garden lies a portion of historic Drew Field, included as part of the property. Once owned by the Drew Methodist Church and the setting for cherished community sunrise services, this expansive green space of lawn of (an additional 0.35 acres) and mature trees provides a rare sense of openness, privacy, and connection to the area's history. Combining architectural significance, modern updates, income-producing potential, and enchanting gardens, this extraordinary Victorian offers a rare opportunity to own a truly one-of-a-kind property. Rich in history yet perfectly suited for modern living, it is a home to be cherished for generations.

16 Elizabeth Street, Port Jervis

$1,395,000
5 Beds 5 Baths 1026138 MLS
NEW CITY! Wow, what an opportunity! Offering over 6,000 square feet of living space, this spectacular home boasts stunning landscaping and truly exceptional curb appeal. Welcome home to this beautiful property, perfectly situated on a magnificent, private lot with a gorgeous pool. A grand entryway welcomes you into a sunken living room, while oversized windows, loads of skylights, and abundant natural light create a bright and inviting atmosphere throughout the home. The oversized dining room is ideal for entertaining. Enjoy cooking in the state-of-the-art eat-in kitchen featuring granite countertops, a center island, and stainless steel appliances, which opens seamlessly to a warm and inviting family room with a fireplace. The main level also showcases an extraordinary great room with soaring ceilings that is truly one of a kind, enhanced by the abundance of natural light. The main level also features one conveniently located bedroom and a full bathroom. A three-car garage completes the main level. Upstairs, the luxurious primary suite offers a beautiful bathroom, two walk-in closets, and an incredible bonus room that can serve as a home office, sitting room, gym, or whatever best suits your lifestyle. Three additional spacious bedrooms and another full bathroom complete the upper level. The finished lower level features a huge family/recreation room, an additional powder room, and a spacious cedar closet. Step outside to your own private oasis with a stunning two-tier deck, gorgeous pool, expansive lawn, and exceptional privacy. Thoughtfully maintained and enhanced over the years, this exceptional home features a finished basement (August 2016), a replaced pool heater (April 2017), a new home water heater (September 2019), a new pool liner (July 2020), rebuilt backyard woodwork and retaining walls (May 2022), and two new A/C units (October 2025). This remarkable home truly has it all and won’t last!

17 Snowdrop Drive, New City

$699,000
5 Beds 3 Baths 1025456 MLS
Welcome home to this spacious 5-bedroom, 2.5-bath Colonial, perfectly situated on a fully fenced one-third acre property. Freshly painted throughout with new flooring on both levels, new carpet on stairs. This home is ready for its next chapter. Step inside the welcoming entry foyer, which leads to a bright and inviting living room, formal dining room, and a comfortable family room featuring a cozy wood-burning fireplace—the perfect gathering place for relaxing evenings. A convenient first-floor powder room adds to the home's thoughtful layout. The updated eat-in kitchen is designed for both everyday living and entertaining, showcasing beautiful stone countertops, stainless steel appliances, and two Lazy Susan cabinets that maximize storage and functionality. Upstairs, you'll find all five generously sized bedrooms, including a spacious primary suite complete with a walk-in closet, an additional closet, and a private en-suite bathroom. Four additional bedrooms and a full hall bathroom provide plenty of room for guests, or a home office. Step outside to the expansive, fully fenced backyard where you'll find plenty of space for entertaining, gardening, pets, or play. Two storage sheds provide ample room for outdoor equipment, tools, and seasonal items, making organization a breeze. Additional highlights include the washer and dryer, which are included with the home, adding extra convenience for the next owner. Offering space, comfort, thoughtful updates, and exceptional functionality, this Colonial is move-in ready and waiting for its next owner to make it their own. Don't miss your opportunity to call this wonderful property home! Sold As Is.

10 Summercress Lane, Coram

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.