Callicoon Homes under $750,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Callicoon and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Callicoon Homes under $750,000

$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

$596,500

4 Beds ⋅ 2 Baths ⋅ 1050796 MLS

A little country club, a little horse country. Set on five private acres in Callicoon’s Beechwoods, Little Holiday Farm is a beautifully updated Catskills farmhouse pairing sweeping pastoral views, a horse ready barn, and direct access to an 18-hole championship golf course. Originally built in 1948 and extensively renovated in 2015, the four-bedroom, two-bath home has the warmth and character you want in an old country house, but with modern comforts. Hardwood floors, beamed ceilings and a gas fireplace bring plenty of cozy charm, while an updated kitchen with stainless-steel appliances keeps things decidedly current. The spacious primary suite feels like a retreat of its own, with its own private screened porch overlooking the rolling hills of the Beechwoods. With a first-floor bedroom and full bath, three additional bedrooms and plenty of gathering space, there’s room to comfortably host a full house of family and friends. At the opposite end of the house, a shaded porch overlooks the grounds and pole barn, offering plenty of space for four-wheelers, motorcycles, outdoor toys - or a few four-legged friends. A full walk-out basement provides additional storage and possibilities, while five usable acres offer room to garden, roam, play and take in those big Beechwoods skies. New septic in 2025. Surrounded by rolling countryside, evenings here are measured in sunsets and stars and just how long you can stay on the porch. When civilization calls, the shops, restaurants, farmers markets of the bustling hamlets of Callicoon and Jeffersonville are both just a short drive away. Just down the road, Villa Roma serves up classic Catskills resort life - championship golf, skiing come winter, plus dining, swimming, racquet sports, bowling and plenty more. Approximately 2 hours to New York City. Little Holiday Farm is country living at its best: five beautiful acres, a barn with room for horses and farmstead dreams, all wrapped in the rolling landscape of Callicoon’s Beechwoods.

519 Route 164, Callicoon

$485,000

3 Beds ⋅ 2 Baths ⋅ 1048306 MLS

Steps from Callicoon’s charming Main Street and the Delaware River, this beautifully preserved 1900 Craftsman pairs the soul of another era with a decidedly modern point of view. Designed and built by Kohler Lumber, the local mill responsible for some of the area’s most distinctive early homes, it remains a remarkable showcase of period craftsmanship. Original Victorian 'stick and ball' millwork, carved details, paneled walls, and beautifully restored wood floors give the house a richness and sense of place that simply cannot be recreated. Thoughtfully updated while respecting its architectural history, the interiors feel warm, quiet, and refined. Original floors restored with tung oil and a subtle white-pigment finish bring a fresh, contemporary softness to the home’s extraordinary woodwork. The walls and first-floor ceilings were meticulously restored using traditional lime plaster over the home’s original wood lath. The bright, streamlined kitchen is simple and efficient, with room for a future owner to expand if desired. An adjacent powder room with laundry adds practicality, while the dining room’s carved wood details create an intimate transition to the open living and sitting rooms. The front parlor retains a particularly charming piece of the home’s history: once used as an insurance office and separated from the residence by a velvet curtain, its original iron curtain rod remains. A carved wood staircase leads to generously proportioned bedrooms, an updated bath, and a dedicated bathing and soaking suite - an unexpected and indulgent retreat. Above, the wood-paneled attic offers an atmospheric, flexible space for movie nights, a studio, home office, library, or future expansion. Behind all that history is a house thoughtfully brought into the present. Updated mechanicals, cellulose insulation installed in 2022, and a low-energy cooling system that draws naturally cool air from the stone-walled, below-grade cellar. The original 1912 cedar siding was fully stripped and restored in 2012 and repainted in 2024. Municipal water and sewer add another layer of ease. Outside, the property becomes a private little world of its own. Mature perennials, native plantings, moss-covered stone walls, and an outdoor fireplace create an enchanting backdrop for long summer dinners, cocktails by the fire, or slow mornings with coffee. Just off the kitchen, the garden makes entertaining effortless. Out front, a secluded rocking-chair porch wrapped in greenery makes it easy to forget that the heart of town is just steps away. Stroll down the hill to the Delaware River for swimming, fishing, and rafting, into town for dinner and drinks, or to the Callicoon Farmers’ Market on Sunday mornings. The new 40-acre Callicoon Riverside Park is also just a few minutes away on foot, while Grover M. Hermann Hospital is approximately two minutes away by car. Historic without feeling frozen in time and polished without losing its soul, the Callicoon Craftsman is a rare opportunity to own a beautifully preserved piece of local history in one of the Delaware River Valley’s most beloved hamlets.

22 Mill Street, 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

$749,999

7 Beds ⋅ 4 Baths ⋅ 1040279 MLS

A true Callicoon landmark, Rafters Tavern has been a staple of the community since the building's construction in 1885. Located in the heart of town, this turnkey restaurant with commercial kitchen, bar and live music venue offers a rare opportunity to acquire an established hospitality business with a loyal following. The property includes a manager's/owner's apartment and additional rentable rooms, providing multiple income streams and operational flexibility. Rich in character and history, Rafters is well-positioned for continued success as one of the area's most popular gathering places for dining, entertainment, and live performances. The property also includes an additional commercial space suitable for retail or complementary business use. Heating/Cooling system: propane upstairs, forced air and central AC, downstairs electric heating & cooling units

28 Upper Main Street, 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

$439,000

4 Beds ⋅ 2 Baths ⋅ 1010333 MLS

Historic Beechwoods Farmhouse on 14+ Acres, Major Improvements Already Made & Ready for Your Vision A rare opportunity in the highly desirable Beechwoods area of Callicoon. Set on more than 14 scenic acres between Callicoon and Jeffersonville, this historic four-bedroom, two-bath farmhouse offers the character, land, and setting you are looking for in the Sullivan Catskills. Along with an opportunity to complete the renovation to your own taste. Significant improvements are already complete, including a new roof, new porch, and partial interior renovation. The major work already started gives you a solid foundation to keep transforming the property. Bring your ideas, your style, and your vision to complete this Catskills farmhouse the way you want it. The property offers a wonderful combination of open meadows and wooded acreage, with gently rolling land and beautiful countryside. Three varieties of berry plants add to the property's agricultural character and offer the opportunity for gardening, harvesting, and enjoying the land. The farmhouse's history as both a working farm and seasonal retreat adds to its character and sense of place. Today, it offers the potential for a classic country farmhouse, Catskills retreat, hobby farm, hunting retreat, or private weekend getaway. The location is equally compelling. Approximately four miles from the Delaware River and conveniently situated between Callicoon and Jeffersonville, you'll be close to fishing, kayaking, canoeing, tubing, hiking, cycling, farmers' markets, restaurants, breweries, and the many cultural and recreational attractions of the Sullivan Catskills. The sellers are motivated. If you've been considering this property but weren't sure it was the right time to move, now is the time to take another look. This parcel has plenty of road frontage that may allow for another building site.

58 Polster 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

$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

$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

Start Your Search

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.

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.