Monticello Real Estate

Welcome to Monticello, New York—a charming village nestled in the heart of Sullivan County. Known for its rich history and vibrant community, Monticello is not just a place to live, but a place to thrive, particularly for families seeking a nurturing environment for their children’s education.

The Monticello Central School District is a cornerstone of this welcoming community, dedicated to providing an exceptional educational experience for its students. With a commitment to academic excellence, the district boasts a range of programs tailored to meet diverse learning needs, ensuring that every child has the opportunity to succeed. From early childhood education to advanced placement courses in high school, Monticello’s schools strive to foster a love for learning and personal growth.

Parents will appreciate the small class sizes that allow for personalized attention, as well as the dedicated faculty who are passionate about cultivating each student’s potential. Beyond academics, Monticello Central School District offers a variety of extracurricular activities, including sports, arts, and clubs, encouraging students to explore their interests and develop valuable life skills.

The district is also known for its strong community involvement, with numerous events and initiatives designed to engage families and promote collaboration between schools and local organizations. This sense of community creates a supportive atmosphere where students can flourish both in and out of the classroom.

Choosing Monticello means choosing a vibrant community with a commitment to quality education. Discover the perfect home for your family in this picturesque village, where educational opportunities and a strong sense of belonging await!

Newest Listings in Monticello

$524,000

4 Beds ⋅ 3 Baths ⋅ 1049763 MLS

Experience the best of both worlds with this furnished 2500 sq ft country home. You'll wake up in the mornings with deer in the backyard, yet you're only 15 minute drive from grocery stores and attractions. In the Rec Room, you'll find ballet barres and mirrors for a variety of home fitness activities. After your workout the sauna and hot tub will be your favorite place to recover. The wood burning fireplace is wonderful for those cold Catskills nights. Two decks and a patio to enjoy the mountain breezes, sunsets, and stars here in the Catskills. This home has a seven year track record as a successful short term rental. The existing management team is excited and willing to work with a new owner, and will convey with hundreds of positive reviews. Home can be purchased furnished if you desire to continue it as a STR/second home. For those wishing to purchase the home as primary residence, the home can be delivered empty and unencumbered by rentals. Full financials are available. Main Level Rooms: Open concept living area with large kitchen, bar seating, dining area and wood burning fireplace. The principal bedroom accommodates a king bed and has an ensuite full bathroom with shower. Bedroom 2 is queen size, and bedroom three will accommodate a full bed. There is an additional full bath on the main level with a shower/tub combo. Lower Level Rooms: The massive recreation room has ballet barres and a wall of mirrors. The media room opens out to a covered patio. The flex room is currently set up as bedroom four that accommodates a queen bed. The full bath with shower also includes an indoor infrared sauna. A full laundry room and multiple storage closets provide plenty of room for all your belongings or supplies for your short term rental. Outdoors: You will find multiple decks and a patio at the home. There is a fire pit in the backyard.

140 Starlight Drive, Monticello

$100,000

1050431 MLS

Some properties give you a place to build. This one gives you an entire lifestyle to build around it. Set within the sought-after Wolf Lake community, this homesite offers the opportunity to start with the land and create a home around the way you actually want to live. No inherited floor plan. No renovations to undo someone else's choices. Start fresh with the architecture, finishes and outdoor spaces that make sense for you, whether that means a modern farmhouse, contemporary design, wooded retreat or a home with room for multiple generations. And what surrounds your future home is just as important as what you build. Ownership in Wolf Lake provides access to an approximately 1,800-acre recreational area, creating an extraordinary backdrop for exploring the outdoors throughout the seasons. Lake access at 186–188 Canal Road adds another dimension to life here. Summer mornings can begin on the water, afternoons can be spent paddling or enjoying the shoreline, and evenings bring you back home beneath the trees. Beyond Wolf Lake, the surrounding Catskills and Hudson Valley put hiking trails, wetlands, farmers markets, vineyards, live music, local restaurants and small-town destinations within easy reach. There is always somewhere new to explore, yet some of the best weekends may be the ones when you never leave the lake. And when the city calls, NYC is still within reach, making this an opportunity to create a very different kind of home base without giving up access to it. Walk the property before deciding what belongs here. Find the spot where the house could sit. Picture the windows facing the trees, the deck or patio outside, the garden, the firepit and the places where summer days will eventually stretch into evening. Right now, it is land. What comes next is entirely yours.

169 Canal Road, Wurtsboro

$550,000

1048196 MLS

Exceptional opportunity to own approximately 48.06 acres of vacant land in the Town of Thompson, Sullivan County. Offering substantial acreage and road frontage along Gregory Road, this property presents an exciting opportunity for a private estate, recreational retreat, investment, or potential future development. The parcel is identified as Tax ID 56.-1-10.5 and is currently classified as rural vacant land. An existing survey depicts the property as Lot 2 containing approximately 48.06 acres, providing valuable information regarding the property’s boundaries and configuration. Located in the Monticello area with convenient access to the surrounding Catskills, shopping, dining, recreation and major roadways. The property’s size and setting provide the privacy and flexibility that are increasingly difficult to find. Buyers and buyers’ agents should perform their own due diligence regarding zoning, subdivision potential, permitted uses, utilities, wetlands, septic, well, access and all required municipal approvals.

Gregory Road, Monticello

$130,000

1050203 MLS

Distinctly positioned just below the spring-fed source of Black Lake, this iconic woodland homesite stretches along roughly six hundred feet of crystal-clear water. A true four-season stream-side sanctuary, Black Lake Creek is a coveted brook-trout habitat. The property features heritage stone formations, towering oaks, and private woodland seclusion. Set at the headwaters of the Toronto Reservoir and tucked behind the gates of The Chapin Estate, this fully buildable lot is ready for immediate construction. The Chapin Estate encompasses over 2,500 acres of preserved wilderness surrounding approximately 1,750 acres of freshwater lakes. This gated, year-round residential community is renowned for luxury second homes and its close proximity to New York City. Membership to the private, residents-only Lake Club is optional for this homesite. Within the gates, The Chatwal Lodge is located just one mile away, offering dining now and spa services forthcoming. Owners may also obtain a boat slip at the Lake Club, granting access to both Toronto Reservoir and Swinging Bridge Reservoir. Photos and lot lines are provided for marketing purposes only. Buyer to verify all information prior to sale.

Lot 3 Chapin Trail, White Lake

$60,000

1049713 MLS

SMALLWOOD, NY - BUILDING LOT IN THE DESIRABLE MOUNTAIN LAKE COMMUNITY - The sale includes three parcels totaling 1.62 acres within walking distance to a private lake. The parcels are located on a quiet dead-end road offering a beautiful, peaceful setting for a new home. Smallwood is.a unique place to live, you’ll be enchanted by its beauty and welcomed by the warm and inviting community. This hidden gem offers you an incredible outdoor experience all out your front door. The jewel is the pristine 65 acre Mountain Lake that allows for kayaking, fishing, swimming at the beach with a life guard on duty, activities, the best 2 mile walk around the lake, all while being captivated by nature in this very special setting. While there is no HOA, joining the Civic Association is optional for members and their guests to be able to use this private/members only lake. This also allows for the use of the tennis/pickleball courts and the Clubhouse. Separately with membership, is the Smallwood Club for seasonal use of the olympic size in-ground heated pool, weekly events/activities at the Clubhouse where you can catch up with your neighbors in a great way. Smallwood also features a 100 acre Reserve with marked hiking trails, a state-of-the-art dog park, an outdoor playground that also has exercise equipment or you can just sit by the brook. Approximately 2+ hrs from GWB/NYC, makes this location a very easy commute. Close by you'll find many quaint towns for dining/shopping, the Delaware River for rafting/fishing, Bethel Woods Preforming Arts Center for amazing concerts under the stars, Kartrite Indoor Water Park, Resorts World Casino, skiing at Holiday Mountain/Big Bear at Masthope Mountain, many hiking/biking trails and absolutely the best farmers markets you'll find anywhere, all for a very beautiful life in the country.

Orange Avenue, Smallwood

$2,495,000

5 Beds ⋅ 5 Baths ⋅ 1049043 MLS

Welcome to 129 Starlight Road - a new 5,500-square-foot modern lake home combining breathtaking views, architectural design, and the grandeur of true lakefront living. Anchored by 78 feet of private, pristine beach and your own dock, the estate commands unobstructed west-facing views across miles of shimmering water to a forever-protected, rugged forest shoreline. All year long, your day ends with marbled sunsets over the water. Three thirty-foot glass atriums capture the golden-hour light, framing panoramic sunsets. Spanning 4,000 square feet across two main levels - complemented by a 1,500-square-foot windowed recreational attic - the layout balances grand open-concept gathering with serene retreats. Five generously proportioned bedrooms include two dedicated primary suites and three en-suite baths. In total, four full bathrooms and one powder room are meticulously appointed. At the heart of the main floor, the expansive great room anchors the residence, framed by a 55-inch Superior linear gas fireplace and a soaring glass facade. European tilt-turn windows capture the vistas, while massive lift-and-slide glass doors extend living onto the outdoor deck. Extra-long engineered white-oak flooring stretches in 7.7-inch-wide planks across social areas, transitioning to 5-inch planks in bedrooms. The chef’s kitchen includes a windowed breakfast nook and an 8.5-by-4.5-foot island with honed quartz countertops with waterfall edges. Custom solid-wood cabinetry in a pencil-trim shaker profile pairs with a full-height quartz backsplash and integrated display shelf. A double-sized pantry, wet bar, white fireclay sink with black Kohler faucet, and integrated recycling make this space both functional and refined. The 48-inch induction range with exterior-vented hood, counter-depth smart refrigerator, Emerald Series dishwasher, Sharp microwave drawer, and dedicated Summit wine refrigerator provide power, precision, and style. Bathrooms are crafted as spa retreats. Both primary baths feature double-head Lentz thermostatic showers in brushed gold (the upper primary suite also includes a luxurious 69-inch freestanding soaking tub) and 60-inch double vanities. The detached 825 sq ft garage is built to custom marine specs: 28 feet deep with 10-foot ceilings and twin 12-by-10-foot doors to accommodate trailered boats with swim platforms attached and towers raised. Life on the water unfolds across 78 feet of private beachfront, a dock, and a dedicated boat ramp. Steps from the shore, three lake-level bays provide dry, climate-ready storage for skis, surfboards, kayaks, canoes, and life jackets. Spanning 889 acres, nine miles in length, Swinging Bridge Reservoir is an uncrowded haven for waterskiing, wakeboarding, surfing, and jet skiing. Two full-service marinas provide dock maintenance, fuel, and storage. At dawn and dusk, glass-like waters invite paddleboarding and kayaking into secluded coves. Prime fishing awaits offering exceptional seasonal angling and fine ice fishing. Outdoor living spaces include four balconies, two bluestone decks with glass railings, stone-capped foundation walls, a hot tub, outdoor hot-and-cold shower, kitchen hookups, a circular driveway, and landscaped grounds. Engineered for efficiency, radiant heating warms the entire ground-floor slab, backed by dual-fuel, dual-zone furnaces and heat-pump air conditioning. Dual ERV systems circulate filtered fresh air. The exterior pairs thermally modified pine and custom steel-panel cladding beneath a Budmat Iron Click steel roof. Equipped with 300-amp electrical service, Starlink internet, smart-home wiring, five security cameras, biometric Wi-Fi entry, and EV-charger readiness. Just 90 miles from the George Washington Bridge, this estate offers immediate proximity to Bethel Woods Center for the Arts, Resorts World Catskills, The Eldred Preserve, and much more.

129 Starlight Road, Monticello

$425,000

3 Beds ⋅ 2 Baths ⋅ 1049558 MLS

Three bedrooms two Baths with one having stall shower and washer/ dryer. White oak floors refinished. All windows replaced and have been tinted allowing you to see out and nobody see in. All new shades most are remote. Front door has three panel each is motorized. Custom crown moldings in living and dining area. Two driveways with lots of room for cars. All appliances are included. Kitchen cabinets with pull-out doors for double storage and ceiling done to match cabinets. Generator with cross over panel. The home has 200- amp electric service. Home converted from electric to oil heat. Trek decking front and back. Full dry basement with storm drain. Low Taxes

142 N Emerald Drive, Rock Hill

$2,200,000

1049341 MLS

SALE IS FOR BUILDING ONLY - BUSINESS IS RELOCATING LOCALLY Excellent opportunity to own a substantial, well-built commercial property located directly on Broadway in the heart of the Village of Monticello. Offering approximately 21,000 sq. ft. of versatile commercial space on 2.23 acres, this property is currently utilized as an office supply business, warehouse and offers tremendous potential for a variety of commercial uses. The building features extensive warehouse space with high ceilings, concrete floors, and several overhead doors providing convenient access for deliveries, loading, and distribution. In addition to the warehouse areas, the property includes approximately six to eight private offices, three bathrooms, and ample space that can be configured to accommodate a wide range of business operations. Served by municipal water and sewer, the property also offers a large parking area with plenty of on-site parking for employees, customers, and commercial vehicles. Its combination of office, warehouse, and storage space makes it well suited for distribution, light manufacturing, wholesale operations, contractors, service businesses, retail, storage, or an owner-user looking for a substantial commercial facility. Centrally located on Broadway, the property is within walking distance of restaurants, shopping, public transportation, Village Hall, and other local businesses and services. With approximately 21,000 sq. ft., 2.23 acres, excellent access, and a highly visible Monticello location, this is a unique opportunity for an investor or business owner seeking a large and adaptable commercial property in Sullivan County.

369 E Broadway, Monticello

$229,000

2 Beds ⋅ 1 Baths ⋅ 1049660 MLS

Very nice starter ranch home on just over half acre of land on southwoods drive in town of Thompson. Kitchen features newer stainless appliances, along with new cabinets still in the box waiting to be installed by new owner. Living room off of the kitchen with new carpets, 2 bedrooms with hardwood flooring and a full bathroom all on main level. Screened in porch off of kitchen nice for three season outdoor dining. Oil baseboard heat with updated boiler in basement. Large paved driveway for ample parking. Conveniently located near 17 for commuters along with under 5 miles to holiday mountain ski hill, along with indoor water park.

432 Southwoods Drive, Monticello

$749,000

5 Beds ⋅ 3 Baths ⋅ 1049202 MLS

LAKEFRONT LIVING AT IT'S BEST - Come home to exquisite lakefront living in this spacious contemporary retreat in the exclusive Emerald Green community. Designed to showcase its spectacular private lake views, this three-story, 5-bedroom, 3-full-bath home offers an inviting open-concept layout, soaring cathedral ceilings, multiple outdoor spaces, and a generous backyard leading directly to the lakefront. The main level features a bright, open floor plan encompassing the kitchen, dining area, and living room, all oriented toward the breathtaking lake view. The living room features a beautiful stone propane fireplace, creating a warm and inviting gathering space. A bedroom and full bath complete the main level. Upstairs offers two rustic bedrooms and a full bath, all opening onto a beautiful lake-facing landing. The walkout lower level opens directly to the backyard and lakefront and features gorgeous bluestone tile flooring, a spacious game room/family room, a second stone fireplace, two additional bedrooms, a recently renovated full bath, and a convenient laundry/mudroom. The outdoor living area is exceptional, with renovated front and rear decks ideal for entertaining, relaxing, and enjoying the spectacular setting. A recently built large storage shed provides space for all your lake and outdoor gear. Parking is plentiful, with a two-car driveway in front plus a separate side driveway accommodating 6+ additional cars. With lake views from virtually every level and direct access to the peaceful private lakefront, this is a home built for relaxing, entertaining, and creating memories with family and friends. The Emerald Green amenities include a full access fitness center, with indoor and outdoor basketball, tennis, and pickle ball courts, dog park, several pools, community beach front, and much more – providing a premium vacation experience to all community members. Embrace Lakefront Living at its Best. As for some features of the home: 1. New Roof (2022) 2. Rebuilt chimney (2020) (see photo of top) 3. New Shed (2021) 4. New Front deck (2021), new back deck (2018) 5. New basement bathroom (2026) 6. New driveway on side of house (2021) can fit up to 6 cars 7. Stripped and shined bluestone basement level (2026)

74 Lake Shore Drive S, Rock Hill

$249,900

2 Beds ⋅ 2 Baths ⋅ 1049377 MLS

Welcome to your private retreat in the Town of Mamakating! Set on a beautiful 1.25-acre parcel, this charming 2-bedroom, 1.5-bath home offers the perfect blend of privacy, comfort, and convenience. Enjoy peaceful mornings or relaxing evenings from the inviting wrap-around porch while taking in the natural beauty surrounding the property. Inside, the home offers a comfortable layout with plenty of potential to make it your own. Two sheds provide tons of additional storage for tools, toys, outdoor equipment, and more. Conveniently located with easy access on and off Route 17 and the future I-86 corridor, commuting and exploring all that the Catskills and surrounding area have to offer is a breeze. If you're looking for a private setting without sacrificing accessibility, this Mamakating gem is one you won't want to miss!

27 Little Road, Wurtsboro

$299,999

3 Beds ⋅ 3 Baths ⋅ 1049204 MLS

This inviting 3-bedroom, 2-bathroom home is a great fit for an end user looking for comfort, space, and opportunity. Situated on a generous 100 x 95 lot, the property offers a spacious feel both inside and out. It features a garage, along with well-maintained grass in the front and back yard, creating a pleasant and welcoming curb appeal. The home also includes a basement with strong potential to be nicely finished, offering extra living space, a recreation area, home office, or storage options. With its solid layout and desirable lot size, this property presents an excellent opportunity to make it your own. The basement offers exciting possibilities, with plumbing already in place for an additional bathroom and space for another legal bedroom, making it ideal for future expansion. Whether you’re looking to finish the basement for extra living space, a recreation area, or added functionality, this home provides a strong foundation to build on.

6 Thomas Street, Monticello

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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.