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Southern Catskills Homes for Sale

Welcome to the stunning landscapes only found within the Southern Catskills. Here you can enjoy the charm of multiple towns and villages including Roscoe, Livingston Manor, Liberty, Bethel, Monticello, and Narrowsburg, all of which are a part of Sullivan County. While each of these charming towns has its own sense of community and boasts its own quaint offerings, the Southern Catskills are often known best for the towns of Monticello and Roscoe.

Surprisingly, Roscoe is a very small area compared to other towns and villages in the Southern Catskills, however, Roscoe is often known best by both locals and tourists alike by the name, “Trout Town, USA” thanks to its prominent options for fishing within and surrounding the heart of this small hamlet. While Roscoe is often thought of as its own town, it is a southwestern hamlet of a larger city, Rockland. Roscoe is small, and offers a community where neighbors wave to each other, and smiles are always in style, often transporting you back to a simpler time when neighborly chatter was common.

Much like Roscoe, small-town charm is in no short supply when calling Monticello home. Compared to many of the other towns and villages in the Southern Catskills, Monticello is much larger, seeing higher levels of tourism thanks to the Resorts World Catskills, one of the Catskills newest and most luxurious casinos. While the casino provides ample dining and entertainment options, Monticello is also home to an assortment of outdoor recreational activities, from thrill-seeking off roading adventures to nature walks, expert hiking trails and more, the area is a hot spot for those looking to settle down in their own mountain retreat while still enjoying ample entertainment options as well as those looking for the ideal vacation spot in the Southern Catskills.

The Catskills are home to a multitude of different ski destinations, casinos, resorts, and small-town charms, ensuring that whether you’re in search of an adrenaline-pumping adventure, a quiet place to slow down and unwind, or are hoping to hit the jackpots, when choosing to call the Southern Catskills home, you can enjoy a plethora of offerings within the multiple towns and villages in the region. One of the most common offerings within the Catskills is an abundance of outdoor recreation and the Southern Catskills are no exception. Miles of hiking trails, biking trails, kayak drop in points, fishing, hunting, golfing, skiing, and more are in no short supply, ensuring that regardless of the type of outdoor recreation you’re searching for, you can easily enjoy it all within the Southern Catskills. With the Southern Catskills being a hot spot for tourism and travel, it’s easy to see why so many people choose to call these quaint villages and towns home, living as if they were on vacation all year long.

Search all Southern Catskills Real Estate

3 Beds ⋅ 1 Baths ⋅ 154677 MLS

Wow! Amazing ranch with spectacular new kitchen, stone countertops, gorgeous new full bathroom, gleaming hardwood floors, walk out basement, new roof, windows, electrical service. What an amazing space , walk to stream ! This is a Fannie Mae Homepath property!

2 Barbara Road, Wawarsing

This building lot consists of 1.6 acres and is located in Wallkill NY, Ulster County.The lot is situated in a quiet development and awaits its forever home. Electricity is available at the road.This property is in close proximity to all the area has to offer in Newburgh, Poughkeepsie, Gardiner, and New Paltz. It is located just minutes to the NYS Thruway, and just under 1.5 hours to New York City.

58 Church Street, Plattekill

10 Beds ⋅ 8 Baths ⋅ 154617 MLS

Rising above the landscape at the summit of a quiet dead-end road, Painter Hill Castle offers unparalleled seclusion and sweeping panoramic views. This 300-acre compound includes three distinct homes: an Old World-inspired castle, a guesthouse, and a vintage stone cottage. With miles of hiking and riding trails, three horse stables, an in-ground pool, and a charming creek with its own picturesque bridge, this extraordinary property is designed for those who value elegance and privacy.The main residence is custom-built with incredible attention to detail. Handcrafted built-ins, custom red oak doors, soaring ceilings and a Vermont slate roof all contribute to the grandeur. Enjoy views of the Shawangunk Mountain foothills through leaded glass windows, and unwind by the stately stacked-stone fireplace. The bright, graceful foyer sets a sophisticated tone for the rest of the house, while the Chef's Kitchen, complete with a cozy dining nook, a spacious walk-in pantry, and top-of-the-line appliances, makes every meal feel special. Each of the four bedrooms comes with its own luxurious en suite, offering privacy and convenience for guests and family members alike. The grand living room opens to an exquisite stone courtyardan idyllic space for entertaining-and a three-bay garage provides ample room for vehicles, ATVs, and equipment, making it easy to store and access everything you need for your next adventure.At the entrance to the estate, the vintage stone cottage radiates fairy-tale charm. This enchanting three-bedroom, two-bath retreat, complete with its own garage, provides a private and cozy getaway for family and friends. Near the heated, gunite pool, a two-bedroom, one-bath guesthouse offers flexible options for rental or guest quarters. This unparalleled property offers elegance and nature's beauty in equal measure, creating the perfect setting for an exceptional lifestyle. A rare find less than 100 miles from Manhattan, Painter Hill Castle redefines luxury living.

414 Painter Hill Road, Wawarsing

4 Beds ⋅ 2 Baths ⋅ 154595 MLS

This split level home sits on almost an acre can be your new starter home. This home needs TLC and is being sold AS IS Call listing agent for more information and to schedule an appointment

10 Elizabeth Drive, Plattekill

4 Beds ⋅ 3 Baths ⋅ 154449 MLS

Welcome home to this stunning 1850s colonial on over an acre in the heart of Ulster County tucked between Wallkill and Gardiner in the desirable Wallkill School District. As you enter through the oversized rocking chair front porch into the more then 2900 sq ft 4 bed / 2.5 bath home you immediately notice its grander and original characteristics throughout - An oversized den with fireplace off the front hall and a grand dining room with built in cabinets with direct access to kitchen that's ready for all those holiday gatherings with family and friends. Head into the chef's kitchen, with tons of counter space that has all newer appliances including double wall oven, large gas cooktop and butcher block island ready to enjoy! The first floor also boasts an updated powder room, a living room with gas fireplace set in stone with original barnwood mantel and an amazing, oversized sun filled family room with French doors into the living room and direct access to the kitchen and backyard. The first floor is truly setup for entertaining with a great flow from one room to another. Head upstairs and you are greeted with an updated full bath, 3 large sized bedrooms and a master suite that includes wood burning fireplace and multiple large closets plus an oversized full bathroom with beautiful, tiled shower. STUNNING Exposed original beams and original wide plank hardwood floors, some over 2 feet in width, throughout add charm and character that cannot be recreated! Head outside and you will find the updated rear composite deck directly off the kitchen, with a BBQ area that overlooks the large fenced in back yard with inground pool with slide, two sheds, and tons of additional patio space poolside with a built-in fire pit! The oversized garage can easily fit 4 cars plus more with lots of shelving for storage. MANY updates throughout including automatic whole house generator, new water heater, new roof and new heat pump and new central AC system. Minutes to route 300 and 87 and under 70 miles to NYC, this home is a true commuters dream!

1199 State Route 208, Shawangunk

7 Beds ⋅ 3 Baths ⋅ 154180 MLS

Welcome to Gardiner! This charming owner-occupied property is nestled on a quiet dead-end road on 1.7 acres. This property has 2 units with 2 bedrooms & 1 bathroom & In-law suite with 3 bedrooms & 1 bathroom. Unit 1 & 2 are freshly painted and have new flooring. Updates include: New roof, boiler, oil tank. You have ample parking with a long driveway to accommodate everyone vehicles without issue. You'll love exploring all the Hudson Valley and all it has to offer. Discover the beauty of the River to Ridge Trail, wineries, breweries, Mohonk Preserve, or take a quick 20-minute drive to Metro North in Poughkeepsie for easy commuting options. The Mid Hudson Civic Center in Poughkeepsie is also just a stone's throw away! Don't miss out on this fantastic opportunity to own a piece of tranquility close to all the action.

15 Cook Lane, Gardiner

4 Beds ⋅ 5 Baths ⋅ 152405 MLS

Welcome to the pinnacle of architectural brilliance, contemporary luxury & total privacy that is A House in the Woods. A captivating fusion of cutting-edge design & unrivaled sophistication, this architectural marvel redefines the boundaries of modern country living, seamlessly blending sleek aesthetics with advanced technological integration that allows form to meet function & innovation to intertwine with elegance.Sited on 8.49 boulder-strewn acres, with no neighbors in sight, this home abuts the 2,500-acre Awosting Reserve, which virtually assures that nature will be at your doorstep for decades to come. The home is reached from a dead-end street & a stone-filled drive that winds pass a 25-ft-high, show-stopping, undulating Cor-Ten steel wall.Step inside & be greeted by natural light streaming through 15-ft floor-to-ceiling windows. Designed by award-winning architect William Reue to the exacting specifications of the current owner, every aspect of this home has been meticulously crafted.This net-zero, LEED Silver-certified, all-electric home features quadruple-pane windows & 74 roof-mounted solar panels with microinverters. There is radiant-heat flooring throughout, an Aprilaire 8100 energy recovery ventilator, & a direct-exchange geothermal heating & cooling system. Smart-home automations include wi-fi connected thermostats & Nest security cameras.An expansive & open-concept gourmet kitchen, living & dining areas, custom-designed cabinetry & top-grade appliances, honed Caesarstone countertops, a Scandanavian-style sauna, a two-car garage (with a 40-amp ChargePoint EV charger) & a basement exercise room complete the picture.The guest wing contains all three guest bedrooms, each of which features an en suite bathroom. The main guest bathroom features a bathtub that faces a floor-ceiling-window. There is also a sitting room with a queen-sized Murphy bed & kitchenette containing a refrigerator, sink, & electric cooktop. Finally, there is a walk-in closet containing a large-capacity LG washer & dryer set, as well as storage space for linens.A mere 2 hours from Midtown Manhattan, 20 minutes from Minnewaska State Park Preserve & the famed Gunks, 30 minutes to New Paltz & bus service to Manhattan, & 40 minutes to Poughkeepsie & the Metro-North/Amtrak station, this home represents the epitome of contemporary luxury that effortlessly combines unparalleled style, technological innovation, & architectural excellence.

121 Sheldon Road, Gardiner

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