Callicoon Homes with Driveway Parking features

Welcome to Callicoon, New York—a hidden gem nestled in the heart of Sullivan County, where the charm of small-town living meets the beauty of nature. This picturesque town is a haven for those seeking a peaceful retreat, surrounded by the stunning landscapes of the Catskill Mountains and the serene Delaware River. With its rich history, vibrant arts scene, and an array of outdoor activities, Callicoon is the perfect place to call home.

One of the standout features of the homes in Callicoon is the convenience of driveway parking. Imagine coming home after a long day, pulling into your own private driveway, and stepping into your sanctuary. Driveway parking not only offers ease and accessibility but also adds a layer of comfort and security to your daily routine. Whether you’re unloading groceries or welcoming friends, having dedicated parking space right at your doorstep simplifies life in this charming town.

Callicoon boasts a variety of homes that cater to diverse tastes and lifestyles, from quaint cottages to spacious family residences. Each property is uniquely designed, often featuring beautiful gardens and outdoor spaces that invite you to enjoy the fresh air and stunning views.

Living in Callicoon means embracing a lifestyle that balances tranquility with community spirit. With local shops, farmers' markets, and seasonal festivals, you'll find plenty of opportunities to connect with neighbors and enjoy the vibrant local culture. Discover the beauty and charm of Callicoon, where your dream home awaits with the convenience of driveway parking to enhance your living experience.

Newest Callicoon Homes with Driveway Parking features

$1,299,999

4 Beds ⋅ 4 Baths ⋅ 1031174 MLS

A private gated community surrounded by nature. This exceptional retreat offers the perfect blend of privacy, luxury, and tranquility. Enter to a spacious great room featuring a stunning stone fireplace, creating a warm and inviting gathering space. The chef’s kitchen is thoughtfully designed for both everyday living and entertaining and flows seamlessly into a beautiful sunroom overlooking the pond. Decking surrounds the home, providing the perfect setting to enjoy the peaceful outdoors. The main level includes an additional bedroom and a full bathroom. Upstairs, the private suite features an en suite bathroom, with an outside balcony offering a relaxing retreat. The finished lower level boasts two additional bedrooms, a laundry room, a spacious entertaining room, providing ample space for guests. Outside, you’ll find a luxurious stone patio complete with a spa, Jacuzzi, and a high-end outdoor kitchen, all overlooking a picturesque pond. A separate guest house offers even more flexibility, featuring a welcoming front deck, its own laundry room, and an attached two-car garage, making it perfect for visitors, or a private home office. There is an additional 3 Car detached garage and generator. This remarkable property combines charm with modern amenities in one of the area’s most peaceful and private settings. Close to trendy restaurants, quaint towns, farmers markets, fishing, hiking, casino, Holiday Mountain Ski area and Bethel Woods Center for the arts and the Callicoon movie theatre.

140 Kenoza Trail, Callicoon

$989,000

4 Beds ⋅ 4 Baths ⋅ 1030710 MLS

Welcome to “Long Farm”. Begging to be the backdrop of your most memorable moments, this newly constructed custom designed home is your country house dream come true. Perfectly set back off a quiet country road and perched on a knoll on 5+ acres with fabulous meadow and mountain views from nearly every room, this one checks all the boxes. 4 BR’s 3.5 BA’s, primary bedroom with gorgeous bath and walk in closet and sliders to outdoor deck is on main level and a second suite plus two more bedrooms occupy the upstairs. Lots of glass lets in an abundance of natural light, while soaring cedar-lined ceilings, wide plank white oak flooring and a really cool suspended Aurora Aether wood burning fireplace set the tone with a cozy and classy vibe. The amazing open plan with island kitchen is perfectly appointed for entertaining friends and family. Sliders off the dining area give way to an outdoor space that will never disappoint. Taking advantage of the gorgeous view and glorious sunsets, there is an outdoor kitchen, fire pit and shower which are just a few of the extras this talented developer has added to this home. Full basement offers an additional 1200 SF with 10’ ceilings. Long Farm is a new development of specially curated homes with fresh clean lines, warm wood accents, locally sourced materials and quality workmanship. Amenities are yours to choose and may include a clubhouse, gym, walking trails, pool, tennis and more. Near to area attractions including the Delaware River, Bethel Woods, breweries, cideries, dining, skiing, lakes, hiking trails, and everything the Sullivan County Catskills has to offer. More Amazing lots and plans available to suit your personality and needs. Additional Information: Amenities:Guest Quarters,Storage,

32 Long Farm Way, Callicoon

$315,000

3 Beds ⋅ 2 Baths ⋅ 1024336 MLS

We are proud to present this wonderful home in the highly sought-after Beechwoods area, renowned for its breathtaking countryside views and peaceful rural setting. This well-maintained residence features three bedrooms and one-and-a-half bathrooms, including a primary bedroom with its own private half-bath ensuite. The home also offers an attached two-car garage and a spacious basement, providing ample storage and flexibility for a variety of uses. Step outside onto the rear deck and enjoy the stunning Beechwoods views while taking in the beauty of the surrounding landscape. The property is enhanced by mature apple trees, established grapevines, and a large backyard—perfect for entertaining, gardening, or simply enjoying the outdoors. Conveniently located just minutes from the vibrant hamlets of Callicoon, Jeffersonville, Narrowsburg, Roscoe, and Livingston Manor, you’ll enjoy easy access to boutique shopping, dining, golf courses, outdoor recreation, and year-round entertainment. Whether you’re seeking a full-time residence, weekend retreat, or investment opportunity, this Beechwoods property offers the perfect blend of country charm, privacy, and convenience.

22 Kratz Road, 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

$465,000

4 Beds ⋅ 2 Baths ⋅ 1010333 MLS

Historic Beechwoods Farmhouse on 14+ Acres in the Sullivan Catskills Set on more than 14 scenic acres in the highly desirable Beechwoods area of Callicoon, this four-bedroom, two-bath farmhouse offers a rare opportunity to own a piece of Catskills history. Ideally located between the hamlets of Callicoon and Jeffersonville, the property combines country charm, privacy, and beautiful views in one of Sullivan County's most sought-after locations. Originally operated as both a working farm and a seasonal retreat, this property reflects the rich agricultural and vacation heritage that helped shape the Sullivan Catskills. The land gently slopes across the landscape, creating views of the surrounding countryside. A mix of open meadows and wooded areas offers a balance of sunlight, shade, and natural beauty throughout the seasons. For those who appreciate the rewards of country living, the property features three varieties of berry plants, providing opportunities to harvest fresh berries for homemade jams, pies, and seasonal treats. The acreage invites gardening, recreation, nature observation, and simply enjoying the outdoors from your own private retreat. Located approximately four miles from the Delaware River, the area offers year-round outdoor recreation. Fishing, kayaking, canoeing, tubing, hiking, cycling, and exploring the region's farmers markets, restaurants, breweries, and arts venues are all part of the Catskills lifestyle. One of the most exciting features of this property is that renovations have already begun, offering the next owner the opportunity to continue the transformation. Whether your vision is a classic farmhouse, a modern country retreat, a hobby farm, or a weekend getaway, the foundation has been laid for you to create a home that reflects your style and goals. Rich in history, surrounded by natural beauty, and filled with potential, this Beechwoods farmhouse is ready for its next chapter. Bring your vision, complete the renovations, and create the country property you've been dreaming about in the heart of the Sullivan Catskills. Call for a tour right now.

58 Polster Road, 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

$995,000

3 Beds ⋅ 3 Baths ⋅ 1006876 MLS

Modern luxury and serenity await you, perched high above the Hamlet of Callicoon and within 5 minutes to the center of town. Whether you are seeking a peaceful full-time residence or an elegant weekend escape, this custom-designed modern country retreat perfectly blends refined architecture with expansive indoor-outdoor living. The residence, set on 8.02 acres, features 3 bedrooms and 2.5 baths, highlighted by soaring cathedral ceilings and a seamless open floor plan. The dining area is anchored by a stunning wall of windows, offering panoramic mountain and valley views of the surrounding natural landscape. Practical amenities include a two-car detached garage with ample storage and a convenient covered walkway. The outdoor living space is designed for entertaining, featuring a bluestone patio surrounding an inground fiberglass saltwater pool and an outdoor dining lanai - all located just minutes from downtown Callicoon. The property is ideally situated near local farmers' markets, breweries, outstanding restaurants, and hiking trails. With easy access to kayaking and the vibrant Main Street of Callicoon, this home offers the perfect balance of secluded privacy and community charm. Located 2 hours from NYC.

118 Froehlich Drive, 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

$685,000

3 Beds ⋅ 3 Baths ⋅ 1003008 MLS

Set on 10 breathtaking acres with sweeping panoramic views, this exceptional property offers the perfect blend of comfort, privacy, and Catskills charm. The beautifully maintained home features 3 bedrooms and 3 bathrooms, thoughtfully designed living spaces, and expansive decks that showcase the stunning natural surroundings from nearly every angle. At the heart of the home is a spacious thought out kitchen complete with skylights, abundant storage, and generous counter space—an inviting space any home chef will appreciate. Sun-filled living areas feature oversized windows that frame the landscape and create a seamless connection to the outdoors. The finished lower level is designed for entertaining, featuring a full wet bar, full-size pool table, and direct access to an inviting patio and outdoor firepit area—perfect for relaxing evenings under the stars while taking in the peaceful scenery. Additional highlights include a fantastic detached two-car garage and beautifully usable acreage ideal for recreation, gardening, or simply enjoying the tranquility of nature. Conveniently located just minutes from the charming hamlet of Callicoon, and a short drive to Narrowsburg, Livingston Manor, Jeffersonville, and Roscoe, this property offers easy access to some of the region’s best shopping, dining, farmers markets, and outdoor recreation.

340 Hospital Road, Callicoon

$599,000

4 Beds ⋅ 2 Baths ⋅ 999372 MLS

A rare opportunity in the heart of the Catskills — this stunning 5-acre property offers a true million-dollar view, unmatched privacy, and direct access to a championship 18-hole golf course. Whether you’re dreaming of a peaceful country home, a high-earning VRBO retreat, or a charming bed-and-breakfast, this property delivers location, scenery, and potential that simply can’t be replicated. The home exudes warmth and charm. The house was gutted 11 years ago and walls were moved. so you are not buying that old house in the country, but an up to date version of it. Septic was replaced in 2025. Inside you will find a living room with a gas fireplace, an up to date kitchen with dining area and a main bedroom suite you always dreamed about. You are surrounded by Callicoon's magnificent Beechwoods. The views are spectacular. No light pollution here! Life in the country does not get any better.

519 County Route 164, Callicoon

$1,048,000

4 Beds ⋅ 4 Baths ⋅ 993379 MLS

Step into serene sophistication with this immaculate custom contemporary Gambrel-style country home, a true architectural showpiece blending rustic charm with modern design. The expansive open-concept living space stuns with soaring 30-foot Hemlock wood ceilings, dramatic exposed beams, and a floor-to-ceiling stone fireplace. Gleaming hardwood floors and panoramic windows flood the home with natural light, perfectly framing sweeping views of Pennsylvania and New York’s rolling countryside. Awarded Sullivan County’s 2007 Home of the Year, this 3,750 sq ft residence sits gracefully on 7.32 stone-walled private acres. The thoughtfully designed floor plan features four bedrooms and 3.5 baths, including two luxurious primary ensuites. Custom touches are everywhere: radiant heat with central A/C, a chef’s kitchen with bluestone island counters, Wolf six-burner stove, SubZero refrigerator, and Miele appliances, plus wine fridges to complete the picture. Remote Nest controls, a steam room, hot tub, and outdoor shower add everyday luxury. The lifestyle continues outdoors with terraces, open sky, half basketball/pickleball court, garden and your own private retreat. A two-story 2,000 sq ft barn-door garage provides space for cars, recreational gear, or even creative projects. There’s also a 2nd floor space to expand your imagination! Whether it’s entertaining around the fire, soaking in the hot tub, or simply enjoying quiet mornings with sunlight pouring in, this home is built for comfort and unforgettable moments. All just two hours from NYC, minutes to Callicoon and the Delaware River with its fine dining, shops, and cultural life. This Catskills treasure offers the best of both worlds—modern elegance set against timeless country beauty.

63 Sky View Drive, Callicoon

$444,000

2 Beds ⋅ 2 Baths ⋅ 983165 MLS

Price reduction and offer of $20k credit plus new furnace! This 26.43 acre parcel of land features a home with 2 bedrooms, 2 full baths, and a spacious loft area that serves as the 3rd bedroom. The sunny, bright great room has a cathedral ceiling. There is a full basement and a one car garage underneath. You will also find a shed and a lovely pond where only the ducks are missing! House and deck will need some TLC, and the seller is offering a $20,000 credit at closing. Seller will also replace the furnace before closing. Come and take a look and present all offers! This could be your ideal get-away from city stress if you apply some elbow grease. This is a delightful rural location for kids to ride bikes or for you to jog or walk. Pack a picnic and hike down to the creek to enjoy a dip in the water and a luncheon al fresco. There is a second clearing along W Simmon, together with substantial road frontage to subdivide or build another home. It is 10 minutes to downtown Callicoon with its eateries, shopping, entertainment, Delaware River activities and Sunday Farmers Market. Or 10 minutes to Roscoe to fly fish in your favorite streams!

10 W Simmon, Callicoon

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