Introducing one of Highland Mills’ most impressive estates—an architectural statement set on 6.5 private acres in the Monroe–Woodbury School District. Built by a seasoned general contractor for his own family, this 5,140+ sq ft residence pairs exceptional craftsmanship with the scale and sophistication of a true luxury home.

A sun-filled two-story foyer welcomes you with a sweeping handcrafted staircase and a dramatic Palladian window that frames the outdoors. The great room rises with towering ceilings and centers on a striking floor-to-ceiling stone fireplace, surrounded by oversized windows and multiple sets of Andersen doors that bathe the space in natural light.

The kitchen is a standout—a 12' marble island, full-size Sub-Zero refrigerator and freezer, 8-burner Wolf range, beverage station, and custom cabinetry combine to create a space built for serious cooking and effortless entertaining. It flows seamlessly into the dining and living areas, creating an ideal environment for gatherings of any size.

A first-floor flex space is conveniently located adjacent to a full bath and den with its own fireplace. This offers versatility for guests, multi-generational living, or a private office. Additional conveniences include a mudroom off the three-car garage and a stylish powder room.

Upstairs, the primary suite provides a true retreat with tray ceilings, hardwood floors, and a spa bathroom featuring travertine tile, a jacuzzi tub, rain shower, and marble finishes. Three additional bedrooms, two well-appointed full baths, and a second-floor laundry complete the level.

The home’s construction reflects quality at every turn: 2x6 Douglas fir framing, 12 concrete foundation, spray foam insulation, Buderus boiler, 300-amp underground electric, owned propane tank, central vacuum, built-in speakers, and automatic lighting throughout. Designed for efficiency, comfort, and longevity, this is a home engineered to outperform others in its class.

Outside, a 20' x 25' bluestone patio overlooks two cleared acres with wooded surroundings—offering privacy, space for recreation, and the potential for future enhancements such as a pool or guest cottage.

Located minutes from highways, trains, and Woodbury’s private lake, pool, and recreation complex, this property offers a rare blend of convenience, seclusion, and true custom construction.

A standout luxury offering rarely available at this level in Orange County

INCREDIBLE VALUE IN THE GREENS OF WOODBURY! This is your opportunity to own a spacious Colonial in one of the Hudson Valley's most sought-after neighborhoods at an exceptional new price. Offering over 3,400 square feet of living space, this 5-bedroom, 4-full-bath home is ideal for buyers looking to build equity while creating their dream home. Situated in the highly desirable town of Woodbury, this home features a dramatic two-story foyer, soaring ceilings, hardwood floors, skylights, and an open floor plan designed for comfortable everyday living and entertaining. The eat-in kitchen offers granite countertops, stainless steel appliances, abundant cabinetry, and overlooks the inviting family room with a cozy wood-burning fireplace.
The spacious primary suite includes a walk-in closet and private en-suite bath, while four additional bedrooms provide flexibility for guests, home offices, multigenerational living, or room to grow and adapt over time. The real showstopper is the backyard, featuring an in-ground pool, expansive paver patio, and a private full-size basketball court—an ideal setting for entertaining, recreation, and making lasting memories. A full walkout basement offers tremendous potential for additional finished living space, a recreation room, home gym, media room, or possible extended living area with the proper approvals.
This home has been priced to reflect the cosmetic updates and TLC a new owner may wish to make, presenting an outstanding opportunity to personalize a home in an established neighborhood where values continue to remain strong.
Conveniently located just minutes from Woodbury Common Premium Outlets, parks, hiking trails, golf courses, restaurants, shopping, and major commuter routes including I-87, Route 17, and public transportation to New York City. Residents also enjoy access to Woodbury Parks & Recreation, offering year-round activities and amenities. If you've been searching for space, location, and unlimited potential, this is the opportunity you've been waiting for. Bring your vision and make this exceptional property your forever home. Schedule your private showing today!

Welcome to this beautiful, bright, spacious and cheery home in Briarcliff Estates, one of the most highly-desired communities in Southern Orange County. This house offers so much from its open, architectural layout with archways and soaring ceilings to its updates and pristine condition. Enjoy hardwood floors throughout both levels, updated stainless steel appliances, gas fireplace, sliding doors to deck upstairs and also to patio downstairs. The primary suite is spacious with high ceilings, walk-in closet and a large bathroom with a shower and tub. The laundry, two additional bedrooms and a full bathroom are at the other end of the home on the same main floor. Downstairs features a spacious bedroom, family room and full bathroom with a tub and shower. From downstairs, walk out to a spacious, paved patio and fenced-in area to keep the 4-legged family members safe! The property goes pretty far back into the wooded area so it can be cleared even further if the new owner wishes to do so. Other features include a new HVAC system, whole house generator, 2-car garage and so much more. Close to the NYC trains and buses with major shopping, the village, schools and restaurants nearby. Don't miss it. Won't last!

Bright, sunny, and spacious, this beautifully maintained home offers an open, airy feel with updated kitchen and bathrooms, soaring cathedral ceilings and a clean, cared-for interior throughout. Designed for both comfort and functionality, this home features a formal dining area, wood-burning fireplace, and a desirable primary suite complete with a full bath, walk-in closet and peaceful water views.
With four bedrooms and 2.5 baths, there’s plenty of space to live your best quality of life. Enjoy a fully-finished walkout basement and a walkout mudroom/laundry room, adding the luxury of convenience . The two-car garage and level property make everyday living easy and accessible.
You’ll love the beautiful stone patio at the front of the house enhancing the home’s curb appeal. The back yard is sprawling and spacious and boasts a gorgeous patio great for entertaining and relaxing. Perfectly located, this home is close to major shopping and restaurants, and is within walking distance to Mombasha Park. NYC Commuters will appreciate being just 14 minutes to the Tuxedo train station and 12 minutes to the Harriman train station. The first batch of photos had virtual staging. Carpet replaced with wood floors, and rooms were painted. Otherwise, the rest is the same with staged furniture. Original photos at the end.

Built with architecturally refreshing, solid construction, this home combines charm, practicality, and a prime location. Don’t miss it. Won’t last!

Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances, Recessed lighting & durable Vinyl plank floors -low maintenance & stylish for a busy lifestyle. Enjoy everyday living & entertaining with a formal dining room that opens to a sliding door to the back deck with a view. Sunny Living room with Bay window, cozy gas fireplace with a striking surround tile & vinyl plank floors perfect for relaxing evenings at home. . Down the hallway to a Primary suite with Full Private Primary bath, 2 additional bedrooms & second Full bath serves the remaining bedrooms. The finished lower level offers flexibility with a private full bath and family room with vinyl flooring and an additional room for an office, guest room or playroom. Laundry room. Practical conveniences include a spacious 2 car garage with Mechanicals and storage. Blacktop driveway with room for 4 cars. Public Water & Sewer is included in the taxes. In 2020 a new gas heating system was installed and updated Air conditioning in 2018. Set on .26 acre landscaped lot with road frontage in a quiet residential neighborhood. A generous back yard with a view of the Village Park. This home offers the perfect balance of comfort and convenient living in a sought-after village location. This is an excellent home for buyers seeking convenience, updates and flexible living. Includes a Shed. Solar Panels are leased. Close to major highways and shopping.

Lovely and classic ranch perfectly perched up high with beautiful, peaceful views of the mountains. This home is bright and airy featuring three bedrooms, two full bathrooms, large formal dining room, sun-filled living room and a kitchen that walks out onto a deck overlooking the quiet back yard. You'll love the rich oak floors throughout. Delivered freshly painted and deep cleaned, this house is a clean slate for any additional updates the buyer may want to do. Wonderful location right in the village of Monroe under 5 miles to the NYC train and under a mile to the bus. Short bike ride to the village restaurants, shopping and the bike path around the beautiful lakes of Monroe. Quality of life is superb! Close to major shopping and Woodbury Commons Shopping outlets. Don't miss it. won't last!

Country living meets today's life style in this farm-like, partially renovated home featuring new kitchen in 2013, newer wide-plank wood floors, newer windows throughout, new boiler 2025, and new hot water heater 2025! Spread out nice and big in this sprawling ranch with large, spacious rooms and lots of character and light streaming through. A good clean-up, a little love and paint job will do the trick! You will LOVE Ranch living and the feeling of freedom and privacy at the end of the road. This property even has zoning for commercial use! Bring the trucks and the trailers. The property is an acre and has plenty of space for the big toys a garden, storage and more. There is an above ground pool in very good condition. Seller didn't open it this year because of the sale but it's in good working order. Located SO close to major shopping, highways, commuter busses and train. Enjoy easy living, convenience, affordability and flexibility all in one. Rare find. Don't miss it. Won't last. Goshen School District.