Smallwood Homes with Monticello School district

Welcome to Smallwood, New York—a hidden gem nestled in the heart of Sullivan County. Known for its tranquil atmosphere and breathtaking natural beauty, Smallwood offers a unique blend of rustic charm and modern conveniences, making it an ideal place for families, retirees, and nature enthusiasts alike. With its lush landscapes, serene lakes, and vibrant community spirit, Smallwood is the perfect escape from the hustle and bustle of city life.

One of the standout features of this quaint community is its inclusion in the Monticello School District. Renowned for its commitment to educational excellence, the Monticello School District provides a nurturing environment where children can thrive academically and socially. Families residing in Smallwood can take pride in knowing that their children have access to quality education, innovative programs, and dedicated teachers who are invested in their success.

The housing market in Smallwood is diverse, offering a range of options from charming cabins and cozy bungalows to spacious family homes. Whether you're seeking a weekend retreat or a permanent residence, you'll find properties that cater to every lifestyle and budget. Many homes boast stunning views of the surrounding mountains and easy access to outdoor activities such as hiking, fishing, and boating.

In Smallwood, you’ll discover a close-knit community where neighbors become friends, and every day feels like a vacation. With its picturesque setting, excellent schools, and welcoming atmosphere, Smallwood is not just a place to live—it's a place to call home. Come explore the possibilities and experience the magic of Smallwood for yourself!

Newest Smallwood Homes with Monticello School district

$239,000

2 Beds ⋅ 2 Baths ⋅ 1025829 MLS

NEW LISTING IN SMALLWOOD NY SUNNY, BRIGHT AND METICULOUSLY MAINTAINED SEASONAL COTTAGE - Welcome to this beautiful updated home where the owners spared no expense making sure this home had everything they wanted in it over the years. Upgrades include a new roof/gutters, mini split, composite decking, new asphalt, carport, shed, new kitchen/bathrooms, appliances, flooring and a beautiful outdoor three season room with storm windows. This home is outfitted perfectly and essentially like new. Inside you’ll find a perfect little kitchen that is extremely functional, with a built in hutch for additional storage, a large living room, two nice size bedrooms and a large full bathroom, the 1/2 bath features a new stacking washer/dryer combo. The parcel is a nice size with a large front/back yard, new composite decks are maintenance free and with two sheds you have lots of storage. The outdoor three season building features lots of windows and will probably be the favorite place for everyone to spend time. Smallwood is a hidden gem that offers you an incredible outdoor experience all out your front door. The jewel is a the pristine 65 acre Mountain Lake that allows for kayaking, fishing, swimming at the beach with a life guard on duty, annual actives, the best walk around the lake, all while being captivated by nature and wildlife in this very special setting. While there is no HOA joining the Civic Association is optional to use this private lake is for members only. This also allows for the use of the tennis/pickle ball 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. Life is pretty special in Smallwood. Approximately 2+ hrs from GWB/NYC, makes this special home 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 amazing hiking/biking trails and absolutely the best farmers markets you'll find anywhere, all for a very beautiful life in the country.

5 Liberty Place N, Smallwood

$329,000

3 Beds ⋅ 1 Baths ⋅ 1020052 MLS

Set on a fully fenced half-acre in the Mountain Lake community, this thoughtfully renovated 1935 cottage pairs classic cabin character with bright, comfortable interiors and a series of recent updates. Mature trees and established landscaping create a sense of privacy while remaining just moments from Mountain Lake, local dining, and the area's many recreational attractions. The traditional cabin exterior retains its timeless charm, while inside, bright and comfortable interiors have been updated throughout. A fully insulated front porch wrapped in windows serves as a welcoming introduction to the home and provides additional year-round living space. Beyond, the open living and dining area features vaulted wood ceilings, hardwood floors, and a striking stone fireplace. The beautifully updated kitchen retains its original built-in hutch, a nod to the home's 1935 origins. A renovated bathroom and heated floors throughout add comfort and functionality to the interior. Three bedrooms, together with insulated front and rear porches, offer flexibility for guests, a home office, or additional living space. Outside, a spacious deck overlooks the backyard, creating an inviting setting for morning coffee, outdoor dining, or evenings under the stars. Wildlife, hiking trails, and the natural beauty of Sullivan County are all close at hand, while Bethel Woods Center for the Arts is less than 10 minutes away, offering world-class concerts and cultural events throughout the season. Owners have the option to purchase annual lake rights, providing access to boating, fishing, kayaking, and the Smallwood Beach Club, along with optional membership to the community clubhouse, pool, and year-round events. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this move-in-ready home offers comfort, character, and an easy connection to lake life in Smallwood.

18 W Mitchell Street, Smallwood

$248,500

2 Beds ⋅ 1 Baths ⋅ 1018533 MLS

Smallwood Summer Sale! Location, Location! Year-round 2 bedroom, 1 bath cottage is 2 blocks from Mountain Lake and Smallwood's Civic Park. Gorgeous Smallwood stone fireplace with glass doors, hardwood floors, knotty pine ceilings, skylights, ceiling fan, large eat-in-kitchen with propane stove, electric heat, huge enclosed porch with added dining/lounging space. Many possibilities that check a lot of boxes. Drilled well, metal roof, front deck, large back yard as property expands 2 roads for added privacy. Perfect for firepit, yard games, gardening, barbeques and the pups. Smallwood offers Civic Park Membership with pickleball, tennis, basketball, children's playground and events clubhouse. Lake membership includes use of beautiful Mountain lake for birdwatching, kayaking, swimming from sandy beach w/ lifeguard and fishing. Visit the Forest Reserve, waterfall, hiking trails and dog park. Join the Club at Smallwood for heated pool, clubhouse and daily/nightly activities. Nearby Bethel Woods Center for the Arts, festivals, farmers markets, Delaware river, antique shops and waterfront dining. Visit Resorts World Catskill Casino, Kartrite Water Park and an abundance of mountains, lakes and rivers. So much to explore, call to take the tour!

24 Eldridge Street S, Smallwood

$199,999

2 Beds ⋅ 1 Baths ⋅ 1018951 MLS

Charming Updated Seasonal Smallwood Cottage Near Bethel Woods – Rare Basement & Spacious Deck! Escape to the Catskills and enjoy the perfect blend of vintage charm and modern updates in this beautifully maintained seasonal cottage in the sought-after Smallwood community. Built in 1940, this 2-bedroom, 1-bath retreat offers approximately 988 square feet of space including a large basement—an uncommon and highly desirable feature in Smallwood. Inside, you'll find a thoughtfully updated open-concept kitchen featuring a new island, new electric stove, and stunning Brazilian granite countertops accented with dramatic black quartz veining. The home has been extensively upgraded with new electrical wiring, a new hot water heater, a newly remodeled bathroom, and a new wood-burning stove with a new chimney liner, providing comfort, efficiency, and cozy Catskills charm. Ideally located just minutes from Bethel Woods Center for the Arts, this property offers easy access to world-class concerts, cultural events, and outdoor recreation. Enjoy nearby community amenities including the local lake beach, dog park, hiking trails, and all that the Smallwood lifestyle has to offer. Property Highlights: • 2 bedrooms, 1 newly remodeled bathroom • Approximately 988 sq. ft., including a rare basement • Spacious outdoor deck for relaxing and entertaining • Open-concept kitchen with new island • New electric stove • Brazilian granite countertops with black quartz veining • New electrical wiring throughout • New hot water heater • New wood-burning stove and new chimney liner • Minutes from Bethel Woods Center for the Arts • Close to the lake beach, dog park, and outdoor recreation • Move-in ready with numerous recent upgrades Whether you're seeking a seasonal getaway, weekend retreat, or investment property, this charming Smallwood cottage offers modern updates, unique features, and an unbeatable location in one of the Catskills' most beloved communities.

118 E Thompson Place, Smallwood

$125,000

2 Beds ⋅ 1 Baths ⋅ 1017632 MLS

Tucked away on a picturesque, tree-lined block in the heart of Smallwood, this seasonal cabin proves that design and cozy charm can live hand in hand. Perfect for spring-through-autumn escapes, this property delivers a spacious feel that defies its footprint. The interior features a thoughtfully arranged layout that includes two comfortable bedrooms and a full bath. The 112-square-foot screened-in porch is utilized as a light-filled bedroom, effectively transforming the cabin into a three-bedroom retreat. It is the perfect spot to wake up to the sound of rustling leaves or to wind down with a good book, completely immersed in the fresh mountain air. The seamless transition from indoor comfort to outdoor living makes this property an absolute haven for warm-weather relaxation and entertaining. Step outside onto the expansive back deck, perfectly scaled for hosting great summer parties, weekend barbecues, or quiet morning coffees under a canopy of mature trees. Just beyond the deck, the property opens up to a wonderful, fully fenced-in backyard area. This space is an incredible asset, offering total peace of mind, ideal , especially if you have a dog who loves to run and explore. Whether you are searching for your own serene weekend getaway or a quintessential Catskills vacation property, this Smallwood gem offers the ultimate seasonal escape with all the warmth, character, and functionality you could ever dream of. Close to Bethel Woods , lakeside dining, antiquing and fabulous farmer's markets. This one is not to be missed.

55 E Reindeer Trail, Smallwood

$340,000

4 Beds ⋅ 3 Baths ⋅ 1014498 MLS

Escape to your perfect upstate retreat or income-producing getaway! This rustic, spacious log-sided home is ideally located in the sought-after Bethel area within the charming hamlet of Smallwood—an ideal destination for vacationers year-round. Enjoy exclusive access to Mountain Lake, complete with a beach, boating, kayaking, fishing, and scenic hiking trails—making this property a dream location for Airbnb guests and weekend escapes. This 4-bedroom, 3-bath home offers a highly desirable layout, including a first-floor primary suite with en-suite bath, perfect for convenience and guest flexibility. The inviting country kitchen, dining area, and oversized living room with a cozy Avalon woodstove create the perfect setting for relaxing after a day of outdoor adventure. Designed with comfort and entertainment in mind, the home features multiple outdoor spaces including two decks, a large screened-in porch, and a dedicated barbecue area—ideal for hosting guests or enjoying peaceful summer evenings. Additional highlights include a laundry room, ample storage, and a 4-car driveway for convenient guest parking—an added bonus for short-term rental use. Located on a quiet dead-end road yet just minutes from Bethel Woods Performing Arts Center, White Lake, local dining, shopping, and Sullivan County attractions, this property checks every box as a turnkey vacation home, second residence, or high-demand Airbnb investment.

22 Ballard Street, Smallwood

$424,900

3 Beds ⋅ 2 Baths ⋅ 1003006 MLS

Welcome to the quintessential lake house in the storybook community of Smallwood. This charming four-season home immediately captivates with its outdoor setting; relax on your private deck to enjoy beautiful views of Mountain Lake while listening to the soothing sounds of White Lake Creek close by. It is an idyllic backdrop for morning coffee or evening relaxation. Inside, this three-bedroom, one-and-a-half-bath retreat perfectly captures the nostalgia of a classic getaway while offering rare, year-round comfort. The well-sized, light-filled rooms showcase beautiful vintage details, highlighted by a cozy working fireplace and classic hardwood floors that run throughout. Unlike many traditional cottages in the area, this layout features a formal, full-size dining room made for hosting gatherings, as well as a significantly sized mudroom—a premium and highly unusual luxury for a Smallwood property that provides the perfect transition space for gear in any season. Adding to the incredible value, the back of the property includes an extra lot complete with fire pit, offering a private outdoor oasis with plenty of room for your imagination to run wild. Offering the perfect blend of unique water features, rare architectural space, and timeless character, this home is the ultimate Sullivan County escape for all four seasons. Optional Pool and Lake Club memberships available which would include tennis and pickleball courts and numerous other activities. Bethel Woods,lakeside dining and antiquing are nearby. Come take a look...

628 Lake Shore Drive, Smallwood

$289,000

3 Beds ⋅ 2 Baths ⋅ 1004410 MLS

Charming Smallwood cabin offering lake rights and rare extra land—three additional lots included for a total of .85 acres. Tucked away on a quiet dead-end road, this semi private property blends original character with thoughtful updates and modern comfort. A privacy fence encloses the backyard, where a screened-in deck overlooks the peaceful, wooded setting—perfect for morning coffee,summer evenings outdoors around the firepit. Inside, you’ll find hardwood floors throughout, a classic brick fireplace, and many original details that give the home its warm, timeless feel. In 2018, a substantial addition created two extra bedrooms and an additional full bath, expanding the layout while maintaining the cabin’s charm. All bathrooms have been tastefully updated, offering a fresh, move-in-ready interior. Located in the desirable Smallwood community, residents enjoy lake rights, a beautiful non-motorboat lake, beach area, playground, and dog park—a true Catskills lifestyle package, for a small annual fee. Just minutes to Bethel Woods Center for the Arts, lakeside dining in Kauneonga Lake, the weekly farmers market, hiking, breweries, and all the best Sullivan County amenities. A serene and peaceful retreat with space, character, and an unbeatable location.

26 Ballard Street, Smallwood

$194,500

2 Beds ⋅ 2 Baths ⋅ 1003927 MLS

Tucked away on a beautiful corner lot in the sought after Hamlet of Smallwood, this warm and inviting log sided 3 season (May-October) home is the perfect escape to the mountains. Just minutes from Minnie Falls and Mountain Lake, you'll enjoy the beauty of nature while relaxing in a home with rustic charm and thoughtful craftsmanship. Step inside this life size dollhouse with cathedral ceilings and skylights letting in natural light, handcrafted wood cabinetry, rich wood floors and moldings that gives the home a cozy lodge feel. A built in hutch adds timeless character, while thermostats in every room and an in wall air conditioner provide comfort on those hot summer days and chilly fall nights. This move in ready retreat offers two bedrooms and two full baths, including a spacious primary bedroom with its own private en suite bath. Appreciate the abundance of storage throughout the home. Enjoy morning coffee in the enclosed porch, entertain on the wrap around deck surrounded by nature creating a storybook setting that feels peaceful, private and unforgettable. Join the Civic Association and enjoy Mountain Lake for non-motor boating, swimming, fishing and tennis for a fee or join the Club at Smallwood (membership required) and enjoy the heated pool. Smallwood offers Minnie Falls, hiking trails in the Forest Reserve, playground, outdoor work out equipment and a dog park. Near to Bethelwoods Performing Arts Center, Kauneonga Lake for lakeside dining, motor boating and local farmers markets. Close to Resorts World Casino, Kartrite Indoor Water Park and Holiday Mountain for winter and summer activities.

38 W Adirondack Trail, Smallwood

$289,000

3 Beds ⋅ 2 Baths ⋅ 997620 MLS

SMALLWOOD YEAR ROUND HOME SET ON A NICELY WOODED LOT WITH OPTIONAL LAKE PRIVILEGES - Home features an open floor plan with a first floor bedroom and full bath. Kitchen has granite countertops, stainless steel appliances with an island for seating. Living area has a wood stove for extra heat that will warm the entire house, main level has in-floor radiant heat. With three bedrooms and two full baths this home will accommodate all. The yard is large with a garden, storage shed and room for additional outdoor living designs. Smallwood is a hidden gem that offers you an incredible outdoor experience all out your front door. The jewel is a the pristine 65 acre Mountain Lake that allows for kayaking, fishing, swimming at the beach with a life guard on duty, annual actives, the best walk around the lake, all while being captivated by nature and wildlife in this very special setting. While there is no HOA joining the Civic Association is optional to use this private lake is for members only. This also allows for the use of the tennis/pickle ball 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. Life is pretty special in Smallwood. Approximately 2+ hrs from GWB/NYC, makes this special home 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 amazing hiking/biking trails and absolutely the best farmers markets you'll find anywhere, all for a very beautiful life in the country.

23 Woodland Way, Smallwood

$124,900

2 Beds ⋅ 1 Baths ⋅ 996891 MLS

Motivated seller!! Sweet Smallwood 3 season cottage is now on the market. Considerable eat in kitchen has plenty of cabinets, gas stove and ample countertop space for large family meals. Plenty of social gathering space in the living room and a newly added spectacular family room perfect for movie nights with gorgeous, warming, propane fireplace. Step out onto wrap around deck for sunrise coffee or sunset cocktails. Grassy knoll can be fenced to create a private outdoor firepit lounge. Newer windows, wood floors and roof that is 8 years old. Be part of the Smallwood lake community with a sandy beach, non-motor boating, fishing, outdoor sports court, walking trails near the waterfall, outdoor exercise equipment and dog park. The Club at Smallwood has heated pool with daily and nightly activities. The amenities and adventures are abundant. Nearby Bethel Woods, Resorts World Catskill Casino, Kartrite Waterpark, lakefront dining, festivals and farmers markets. Visit the lakes, mountains and rivers. Own a piece of the Catskills. Call to take the tour!

74 E Thompson Place, Smallwood

$54,000

995785 MLS

Exceptional opportunity to own 2.47 +/- acres comprised of 3 private lots. Ideally located a short distance from Mountain Lake in sought after Smallwood. This engineered property offers a rare blend of privacy and natural beauty creating the perfect setting to build your dream home. Surrounded by peaceful scenery while remaining close to recreation and all that Smallwood has to offer. Two additional lots included in the sale. Lot 44.-15-4 is approximately 1.72+/- acres. Lot 44.-15-3 is approximately .39+/- acres & 44.-15-8 is approximately .34+/- acres. Three contiguous lots totaling approximately 2.47 +/- acres. Taxes are inclusive of all 3 lots. Don't miss this rare opportunity to create your own oasis on this exceptional property!

Glenwild Drive, Smallwood

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