Callicoon Homes under $400,000

Welcome to Callicoon, New York – a delightful gem nestled in the heart of Sullivan County! Known for its picturesque landscapes, charming small-town vibe, and rich history, Callicoon offers a unique blend of rural tranquility and vibrant community spirit. As you stroll along the banks of the Delaware River or wander through the quaint streets lined with historic buildings, you’ll quickly understand why so many are drawn to this enchanting region.

Callicoon is not only a haven for nature lovers and outdoor enthusiasts, but it also boasts a thriving arts scene, delicious local dining options, and a warm, welcoming community. With its proximity to the Catskill Mountains, residents can easily indulge in hiking, fishing, and skiing, making it an ideal location for those who appreciate the great outdoors.

For those seeking a home in this idyllic setting, Callicoon offers a variety of charming properties under $400,000. Whether you’re looking for a cozy cottage, a spacious family home, or a quaint retreat, there’s something for everyone in this affordable market. With its appealing architecture and scenic surroundings, these homes provide an excellent opportunity for first-time buyers, families, or anyone looking to escape the hustle and bustle of city life.

Embrace the peaceful lifestyle Callicoon has to offer, where community and nature intertwine seamlessly. Explore the possibility of making this charming town your new home, and discover the perfect property that fits your budget and dreams. Your new life in Callicoon awaits!

Newest Callicoon Homes under $400,000

$199,000

2 Beds ⋅ 2 Baths ⋅ 1056117 MLS

This move-in-ready and relatively maintenance free 2-bedroom, 2-bathroom condo at Villa Roma Resorts features an updated kitchen with new appliances, new flooring, updated bathrooms, and a new furnace making the transition to Catskills living that much easier. Enjoy four-season recreation nearby, with golf, pools, tennis, pickleball, dining, live entertainment, skiing, and snow tubing at the Villa Roma. Just minutes from Callicoon’s shops, restaurants, farmers market, and the Delaware River, this condo is an inviting weekend escape or year-round home over looking the 10th hole of the Villa Roma Golf Course. Own the getaway. Enjoy the resort. Live the Catskills lifestyle.

432 Villa Roma Road Unit #2A, Callicoon

$339,000

5 Beds ⋅ 2 Baths ⋅ 1055547 MLS

Endless possibilities meet location! Zoned for both commercial and residential use, this unique property offers incredible flexibility for savvy buyers, investors, or entrepreneurs. Situated right on Route 17B at the crossroads of Callicoon, North Branch, and Hortonville, the building is currently configured as two separate living spaces, each featuring its own kitchen and bathroom. Space & Layout Flexibility * Ground Floor (3-Bedroom Unit): A highly visible space perfect for a boutique retail shop, creative studio, or professional offices. It can also remain a spacious 3-bedroom apartment featuring a large eat-in kitchen. * Upper Floor (2-Bedroom Unit): Highlights include a loft-style attic and a large deck looking out over Callicoon Creek. It is the ultimate spot for relaxing. Endless Potential Whether you want to convert the building into a live/work setup, run a storefront downstairs, manage two profitable rental units, or live in one while renting out the other—the options are yours. The Location You are right in the thick of it. The property is just minutes away from downtown Callicoon, the Delaware River, and world-class concerts at Bethel Woods Center for the Arts. Opportunities with this much versatility and waterfront charm don’t pop up often. Come take a look and imagine the possibilities!

6 County Route 121, Callicoon

$179,900

2 Beds ⋅ 2 Baths ⋅ 1045360 MLS

Your Catskills escape awaits! This inviting 2-bedroom, 2-bathroom condo at Villa Roma offers the perfect blend of comfort, recreation and resort-style living. Enjoy access to an incredible range of amenities and activities, including indoor and outdoor pools, golf, tennis, pickleball, hot tubs, dining, live entertainment, skiing, snowboarding, snow tubing and more. Whether you're looking for a weekend getaway, vacation home or investment opportunity, this property puts four-season Catskills recreation right at your fingertips. Just minutes from Callicoon's shops, restaurants, farmers markets and the Delaware River, you'll have everything you love about the Catskills close by. Own the getaway. Enjoy the resort. Live the Catskills lifestyle.

4 Joe D Drive Unit #4C, Callicoon

$40,000

1014395 MLS

This 0.82 acre property has Beechwoods Rd address, however, access is through ROW. Trailer has been removed and old barn and storage building remain. Both are filled with wood, metal, doors, etc. Mobile home was removed some years back but another mobile home could be placed here again. There is shallow well and there was septic. No representations made as to condition of well or septic. Cash sale only, in "as is" condition.

16 Beechwoods Road, Callicoon

7 Villa Vista Drive Unit #702, Callicoon

$349,000

3 Beds ⋅ 3 Baths ⋅ 1010833 MLS

Welcome to this immaculate Beechwood Estates II condominium townhouse in Callicoon's Beechwoods hills. Pride of ownership is visible throughout. A 3 bedroom, living/dining room, eat-in kitchen, 2 full baths, and a covered porch with an open deck offer lots of space for the weekend warriors or full time residents. The attached garage and the fully finished basement with a half bath complete the picture. There is an LP operated full house generator; an alarm system; an alarm for the hot water heater, and a built-in dehumidifier in the finished basement. Enjoy golf at the Villa Roma Resort's 18 hole golf course and shop and dine at the wonderful shops and eateries you will find in Callicoon, Jeffersonville and Livingston Manor. This is a 4-season home in New York's Catskills which allows many city dwellers to cope with another busy city week. Come and take a look!

7 Villa Vista Drive Unit #702, Callicoon

$355,000

3 Beds ⋅ 2 Baths ⋅ 1005698 MLS

Peaceful Country Retreat on Over 5 Acres Welcome to 12 Mesmer Road — a charming country home set on more than 5 scenic acres, offering privacy, tranquility, and plenty of space to enjoy the outdoors. Whether you’re searching for a full-time residence, weekend escape, or investment opportunity, this property delivers the perfect blend of comfort and countryside charm. The home features three bedrooms and two full bathrooms, along with a spacious eat-in kitchen and separate dining area ideal for family gatherings and entertaining. The oversized living room is filled with natural light thanks to a skylight and large sliding glass doors that open to the backyard patio — perfect for outdoor dining and relaxing summer evenings. Step outside to take in beautiful country views, mature trees, classic stone walls, and peaceful creeks that run throughout the property. On warm days, enjoy your own private heated in-ground pool, creating the ultimate setting for summer fun, barbecues, and quiet relaxation. Conveniently located just minutes from Callicoon, Narrowsburg, Jeffersonville, and Bethel Woods Center for the Arts, this property offers the serenity of country living while remaining close to local shops, dining, and entertainment. If you’re looking for space, privacy, and a true escape to the countryside, 12 Mesmer Road is a must-see. Schedule your private showing today!

12 Mesmer, Callicoon

$379,000

5 Beds ⋅ 2 Baths ⋅ 982483 MLS

Three story Victorian 5-BR home located on the end of a quiet cul-de-sac overlooking the bustling village of Callicoon, the Callicoon Creek and the Delaware River. In-town living doesn't get better than this. Enter on a large wrap-around porch and into a well-built home. You are greeted by an expanse of gleaming wood floors and a large living room and dining room. The updated eat- in kitchen has oak cabinets and granite counter tops. French doors lead into a quiet family room. Upstairs on the 2nd level find 3 bedrooms and a full bath. The 3rd level has 2 bedrooms with an additional bonus room. In the basement you will find the oil furnace, 200-amp electric panel and plenty of room for storage or workshop. This grand home has many original features such as beautiful wood floors, wood trim, 2- story staircase, stained glass windows, and more. Updated features include replacement windows, vinyl siding and a mini-split unit on first floor for heat and AC and fully insulated. Need storage and parking? Outside find a large detached 1-car garage plus a fenced in garden. In-town living is easy, because Callicoon is a fun town with activities including: The Farmers Market, movie theater, a community center offering tennis, swimming pool and pickleball, the Delaware River, great restaurants and shops.

11 Highview Avenue, Callicoon

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