Callicoon Center, NY Homes for Sale

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  /30

  $485,000

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  581 Hessinger and Lare Rd, Jeffersonville, NY 12748

  This Home Has A Tiled Entryway, An Open Kitchen And Dining Area With A Large Island, And Ample Cabinetry. The Living Room Features A Stone Fireplace, There Is An Office, A Sunny Family Room (Potential Fourth Bedroom), Laundry Facilities, And A Half Bath. The Second Floor Has A Spacious Primary Bedroom With A Walk-In Closet, A Generous Bath With A Jacuzzi Tub, Double Sinks, And A Glass-Enclosed

  

  Dawn Curreri

  EAGLE VALLEY REALTY

  (845) 366-2889

  581 Hessinger and Lare Rd, Jeffersonville, NY 12748
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  /14

  $133,000

  • Land
  • 10 Acres
  • $13,300 per Acre

  Lot 7.4 Hankins Rd, Fremont Center, NY 12736

  10+/- Country Acres! Nestled in the Town of Fremont, Sullivan County, NY, this lovely 10 Acre property boasts approximately 2 acres of cleared land with 367'+/- of road frontage and stone walls. Come and experience this one-of-a-kind property that offers you an opportunity to own a beautiful piece of the countryside, surrounded by open skies, countryside views and clean fresh air. The rolling

  

  Dawn Curreri

  Eagle Valley Realty

  (845) 599-8189

  Lot 7.4 Hankins Rd, Fremont Center, NY 12736
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  /19

  $285,000

  • Land
  • 10 Acres
  • $28,500 per Acre

  922 Hankins Rd, Fremont, NY

  Was your 2025 resolution to build your dream home? Welcome to a one-of-a-kind 10-acre retreat designed as your future home or hidden getaway site. This stunning parcel features an acre of a serene pond up to 16 feet in depth – ideal for swimming, rowing, or fishing once stocked. Meander along scenic trails, enjoy fresh blueberries from the bushes, and savor the apples from your trees. The

  

  Elizabeth Bernitt

  Century 21 Geba Realty

  (845) 807-6947

  922 Hankins Rd, Fremont, NY
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  /36

  $489,000

  • 4 Beds
  • 2.5 Baths
  • 3,634 Sq Ft

  807 Swiss Hill Rd N, Jeffersonville, NY 12748

  Let the large double front doors welcome you into this 3 story home featuring a lovely front foyer, main level, high ceilings, wood floors throughout, a living room, library w/ plenty of book shelves, pocket doors, formal dining room w/ built-in cabinets, kitchen w/ an island, a half bath & a wonderful sunroom. Charming wide staircase leads to the 2nd floor that hosts a primary bedroom w/ a full

  

  Dawn Curreri

  EAGLE VALLEY REALTY

  (845) 576-9694

  807 Swiss Hill Rd N, Jeffersonville, NY 12748
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  /36

  $449,000

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  165 Boband Rd, Jeffersonville, NY 12748

  Welcome to the Boband Bungalow! This charming two bedroom, one bath house boasts some of the most epic views you can imagine! Nestled on just over 21 acres, Boband Bungalow offers the perfect blend of privacy, comfort, and charm. Enjoy the views of the sweeping rolling hills from the living room & master bedroom and the wrap around deck. It's a front row seat to all of nature's wonders.

  

  Edward Rabon

  Century 21 Geba Realty

  (845) 713-8341

  165 Boband Rd, Jeffersonville, NY 12748
• 

  

  /22

  $729,000

  • 3 Beds
  • 3 Baths
  • 2,345 Sq Ft

  1211 Gulf Rd, Roscoe, NY 12776

  Newly constructed, gated luxury chalet with a pond. (The photos are of a model home--This home will have light color hardwood bamboo floors and off-white kitchen cabinets). Nestled on 3 acres this home boasts 2,345 sq. ft. of elegant living space complemented by a generous 1,375 sq. ft. semi-finished walk-out basement. Interior includes 3 Bed/3 Baths with 2 master suites with en-suite bathrooms.

  

  Joy Romano

  Joy Romano Realty

  (607) 536-9813

  1211 Gulf Rd, Roscoe, NY 12776
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  /9

  $949,000

  • 4 Beds
  • 1.5 Baths
  • 2,344 Sq Ft

  187 Hahn Rd, Livingston Manor, NY 12758

  This mountain top farm has a long history of agriculture. The 1800's farmhouse is full of historic charm with wide plank floors and wood burning cookstove all set alongside a babbling brook. The entire property exudes pastoral beauty and charm. Roughly half the property is open hay field and pasture and half a mix of hardwood and hemlock forest. The barns are old and sound and aching for some new

  Travis O'Dell Land and Water Realty LLC

  187 Hahn Rd, Livingston Manor, NY 12758
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  /29

  $562,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  853 Shandelee Rd, Livingston Manor, NY 12758

  Welcome to this stylish, turnkey home perched atop Shandelee Mountain. Just minutes from the welcoming Western Catskills town of Livingston Manor, NY, this 3-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. Set on 2.5 acres, the property boasts a brand-new, steaming hot tub—ideal for cooler, starlit nights in the mountains. Step out your back door and discover direct

  Heather Quaintance Country House Realty Inc

  853 Shandelee Rd, Livingston Manor, NY 12758
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  /28

  $619,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  612 Beechwoods Rd, Callicoon, NY 12723

  Discover Beechwoods Cottage, an efficient newly constructed home built on 2.75 acres of serene country meadow. Located less than 15 minutes from Jeffersonville and Callicoon, and just over 2 hours from New York City, this 3-bedroom, 2-bathroom retreat offers sweeping mountain views and serves as an ideal primary residence or weekend getaway.Inside, the home features high ceilings and expansive

  William Baldwin Country House Realty Inc

  612 Beechwoods Rd, Callicoon, NY 12723
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  /26

  $689,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  377 Hubert Rd, Jeffersonville, NY 12748

  In a quiet corner of the Western Catskills, sits Woodsview Hideaway, a stylish modern retreat. Designed with an eye towards maximizing the enjoyment of the surrounding landscape, this beautiful home in Jeffersonville, NY is brand new and move-in ready for its first owners. The entranceway offers a convenient coat closet and guides you into the sleek and spacious kitchen. Modern flat front black

  Megan Kinealy-Hill Country House Realty Inc

  377 Hubert Rd, Jeffersonville, NY 12748
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  /41

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 2,161 Sq Ft

  649 County Road 95, Obernburg, NY 12767

  “Meadow Lodge” is a unique private retreat on a scenic rise with stunning Western Catskills and meadow views. The dramatic Adirondack-style, authentic log cabin features massive timbers, a soaring Great Room with stone fireplace, huge windows and glass doors opening to a wraparound deck, all set amidst 44 magical acres of rolling fields and woodland. The open-concept layout includes a renovated

  Jennifer Grimes Country House Realty Inc

  649 County Road 95, Obernburg, NY 12767
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  /40

  $717,000

  • 4 Beds
  • 3 Baths
  • 2,903 Sq Ft

  605 Dutch Hill Rd, Roscoe, NY 12776

  Drive down the winding lane through lush greenery and experience the joy as the view opens to your own secluded compound: an immaculate contemporary home, a 36'x32' horse barn, run-in stable, workshop/studio, multiple-use buildings, fenced paddocks, and mowed paths throughout the almost 20 pastoral acres of your private sanctuary. This gorgeous property is located just minutes from the popular

  Joe Freda Matthew J Freda Real Estate

  605 Dutch Hill Rd, Roscoe, NY 12776
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  /45

  $984,000

  • 3 Beds
  • 2.5 Baths
  • 2,416 Sq Ft

  99 John Deitz Rd, Jeffersonville, NY 12748

  This immaculate contemporary sits on 15 private acres with unparalleled views of the western Catskills, miles of hills and valleys, and an expansive, rolling lawn.Backed up by woods, residents enjoy all the privacy and solitude of a house on a mountaintop. In addition, the property features two large, spring-fed ponds with a constant flow of water that keeps both ponds fed with clean and clear

  John Ducey Keller Williams Hudson Valley

  99 John Deitz Rd, Jeffersonville, NY 12748
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  /33

  $649,000

  • 4 Beds
  • 3.5 Baths
  • 2,754 Sq Ft

  39 Cr96, Fremont, NY 12736

  Just in time for summer! From the North end of Tennanah Lake you have the view and the lake frontage facing due south the entire length of the lake. Tennanah is one of the only, and arguably the most pure mountain lake that is completely private with motorboats allowed. The house is upgraded throughout with a brand new septic system installed in 2022. Currently a short term rental, it is a very

  Travis O'Dell Land and Water Realty LLC

  39 Cr96, Fremont, NY 12736
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  /18

  $299,999

  • Land
  • 49 Acres
  • $6,111 per Acre

  0 Hessinger and Lare Rd, Youngsville, NY 12791

  55 Acres in Youngsville, Sullivan County – Two Deeded Parcels! A rare opportunity to own 55 acres of natural beauty in the heart of Sullivan County. This unique property consists of two separately deeded parcels (49.9 acres + 5 acres), offering flexibility for building, investment, or recreation. Engineering has been completed on the 49.9 acre parcel. Features include mature woods, scenic trails,

  Susan Giordano John J Lease REALTORS Inc

  0 Hessinger and Lare Rd, Youngsville, NY 12791
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  /41

  $1,250,000

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  1556 Gulf Rd, Callicoon Center, NY 12724

  Tucked into a hidden hillside meadow of wild apple trees, this 1880s Catskills farmhouse feels like a well-kept secret. Set on nearly 11 acres of cultivated wilderness, the home is both private and conveniently located—just over two hours from NYC and minutes to dining and essentials.Inside, a mudroom leads to an open-concept kitchen, dining, and living space. Designed by the restaurateur-owner,

  Robin Jones Anatole House LLC

  1556 Gulf Rd, Callicoon Center, NY 12724
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  /50

  $979,000

  • 4 Beds
  • 2 Baths
  • 2,900 Sq Ft

  281 Hubert Rd, Jeffersonville, NY 12748

  This is the one you've been waiting for—a true private luxury retreat nestled on 6.89 acres of pristine, sweeping mountain-view land in the heart of the Catskills. Designed for both relaxation and grand entertaining, this stately 4-bedroom, 2-bathroom home spans 2,900 square feet of light-filled, open-concept living space.Step into the newly designed chef’s kitchen—an entertainer’s

  Dominique Jenkins Keller Williams Hudson Valley

  281 Hubert Rd, Jeffersonville, NY 12748
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  /31

  $329,000

  • Land
  • 32 Acres
  • $10,428 per Acre

  0 Menges Rd Unit KEY867163, Callicoon, NY 12791

  31 acres with beautiful views, ancient stone walls, fertile maintained meadows blending into a pristine forest. Perfect for a small farm or estate to build your dream house on, as the land is perfect for farming, gardening, hunting, ATV riding, and all of the outdoor sports. Prime subdivision potential here because the overall parcel is 31 acres and it consists of 3 tax parcels; two-6.38 acre

  Tom Freda Matthew J Freda Real Estate

  0 Menges Rd Unit KEY867163, Callicoon, NY 12791
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  /20

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft

  877 Shandelee Rd, Livingston Manor, NY 12758

  Shandelee Skyview, a breathtaking mountain retreat atop Shandelee Mountain in Livingston Manor, NY, offers a spacious 4-bedroom, 3-bathroom country home on 7 level acres with sweeping mountain views. Its versatile design and scenic surroundings make it ideal as a full-time family residence, a short- or long-term rental, or a seasonal vacation home.Inside, the home features a thoughtful layout

  William Baldwin Country House Realty Inc

  877 Shandelee Rd, Livingston Manor, NY 12758
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  /31

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,162 Sq Ft

  117 Buddenhagen Rd, Callicoon, NY 12723

  This charming country home in Callicoon’s beautiful Beechwoods area is privately set off a quiet road. The serenity of bird song fills the air. The well-maintained Cape Cod style house is nestled nicely on a lush lawn. The vibe is completely pastoral: Surrounded by stone walls, the yard has a fenced garden area, several perennial gardens, apple trees and a mix of open and wooded areas. There’s

  Joe Freda Matthew J Freda Real Estate

  117 Buddenhagen Rd, Callicoon, NY 12723
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  /17

  $60,000

  • Land
  • 1.47 Acres
  • $40,816 per Acre

  53 Menges Rd, Callicoon, NY 12758

  Discover the potential of this 1.47-acre parcel in the picturesque Town of Callicoon! Nestled in a peaceful setting with a charming small pond, this property offers a great opportunity to build your dream home or explore various development possibilities. Zoned Settlement District (SD), the lot allows for a wide range of permitted uses—see the permitted uses list for full details. Whether you're

  Cesar Landestoy Keller Williams Hudson Valley

  53 Menges Rd, Callicoon, NY 12758
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  /44

  $339,000

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft

  242 Callicoon Center Rd, Jeffersonville, NY 12748

  WOW! Where else are you going to find this type of property in the majestic Catskills for this price?! Unique & eclectic chalet/cape style home with 3 bedrooms, 2 1/2 bathrooms, a huge & usable walkout basement/lower level, a 600 square foot detached garage/workshop built in 2021, lots of decks, patios & balconies, a hot tub, AND a relaxation shed! NEW upgrades include main floor full bathroom

  Dean Diltz Keller Williams Realty

  242 Callicoon Center Rd, Jeffersonville, NY 12748
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  /23

  $229,000

  • 3 Beds
  • 1 Bath
  • 1,872 Sq Ft

  934 County Road 93, Roscoe, NY 12776

  LOCATION! Fixer upper. Good bones on this home looking for a new chapter. 2 lots included 934 and 932 County Rd. #93.Are you handy? Looking to get into the market? Come take a look.

  Philip Eggleton Eagle River Realty LLC

  934 County Road 93, Roscoe, NY 12776
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  /33

  $1,295,000

  • 3 Beds
  • 3 Baths
  • 2,958 Sq Ft

  150 Bethlehem Rd, Callicoon Center, NY 12724

  Nestled where eagles glide, this beautiful and tranquil hilltop retreat is located less than two hours from NYC/GWB. Ascending the private driveway winding through forested hillside, you’ll experience a shift in pace as this stunning custom-built home comes into view. Sited thoughtfully, the home affords commanding views of the surrounding countryside, and benefits from the integration of passive

  John Roynon Land and Water Realty LLC

  150 Bethlehem Rd, Callicoon Center, NY 12724
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  /18

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,688 Sq Ft

  57 Menges Rd, Youngsville, NY 12791

  Beautiful farmhouse recently renovated with a lot to offer! The roof and deck are just 8 years old. The exterior is re-painted. Windows are new. New flooring throughout the home. Brand new refrigerator, microwave, vent fan. New center island installed in kitchen. New cabinets in kitchen and bathroom. New recessed lighting throughout. Updated electrical. Located in a quiet hamlet. All furniture is

  Sean Walker Keller Williams Realty

  57 Menges Rd, Youngsville, NY 12791
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  /29

  $710,000

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft

  168 Meyer Rd, Livingston Manor, NY 12758

  Looking for the right log home in the Catskills? This spacious chalet sits above both the very desired Livingston Manor and Youngsville. An open floor plan with a large, dining room and living room area with the center piece the large stone fireplace. Step out through either of the large glass doors leading to a large rear deck to enjoy nature. The kitchen consists of beautiful hickory cabinets

  Ryan Edwards Carole Edwards Realty

  168 Meyer Rd, Livingston Manor, NY 12758
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  /19

  $315,000

  • Land
  • 25 Acres
  • $12,600 per Acre

  295 Pleasant Valley Rd, North Branch, NY 12766

  Beautifully Wooded 25; Acre Parcel in Callicoon, NYNestled in the heart of New York’s farming community, this lovely 25 acre parcel in the Town of Callicoon offers a perfect blend of privacy, nature, and rural charm. With abundant wildlife, serene mountain views, and endless opportunities to explore the countryside, this is an ideal spot to build your dream home or start a small

  Diane Butler Diane C. Butler

  295 Pleasant Valley Rd, North Branch, NY 12766
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  /20

  $177,000

  • 2 Beds
  • 1 Bath
  • 560 Sq Ft

  24 Lovett Ln, Jeffersonville, NY 12748

  Charming 2 bedroom new listing, thoughtfully built from the ground up with attention to every detail. This home boasts a range of updated features, including brand-new appliances, modern bathroom, new siding, fresh flooring, updated paint, and stylish wood cedar roof and lighting decor with tons more. Additionally, a newly constructed wood porch graces both the front and rear, adding to the

  Sean Walker Keller Williams Realty

  24 Lovett Ln, Jeffersonville, NY 12748
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  /7

  $799,000

  • Land
  • 88 Acres
  • $9,080 per Acre

  0 Stump Pond Rd, Callicoon, NY 12724

  Nestled near the charming towns of Jeffersonville, Livingston Manor, Callicoon, and the Delaware National River Basin in western Sullivan County, this stunning 88-acre property in Shandelee offers a unique blend of natural beauty and potential — all for an amazing price of just $799,000!The land features 10.8 acres of open meadow with breathtaking southeastern views, ideal for building your dream

  Diane Butler Diane C. Butler

  0 Stump Pond Rd, Callicoon, NY 12724
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  /48

  $349,900

  • 3 Beds
  • 3 Baths
  • 1,782 Sq Ft

  521 Hessinger and Lare Rd, Jeffersonville, NY 12748

  3 bed 3 bath ranch style home for sale that offers a perfect blend of modern updates and rural charm. Situated on a peaceful 3.19-acre lot in Jeffersonville, New York, near Livingston Manor and Callicoon. This property provides ample space for relaxation, entertainment, and outdoor activities. With over 1,782 square feet of beautifully maintained living space, this home is designed for comfort

  David Luczyski Resort Realty

  521 Hessinger and Lare Rd, Jeffersonville, NY 12748
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  /48

  $485,000

  • 3 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  581 Hessinger Lare Rd, Jeffersonville, NY 12748

  Great Location! This Unique Stone-Sided Contemporary Home Has A Tiled Entryway, An Open Kitchen And Dining Area With A Large Island, And Ample Cabinetry. The Living Room Features A Stone Fireplace, There Is An Office, A Sunny Family Room (Potential Fourth Bedroom), Laundry Facilities, And A Half Bath. The Second Floor Has A Spacious Primary Bedroom With A Walk-In Closet, A Generous Bath With A

  Maria Wagner Eagle Valley Realty

  581 Hessinger Lare Rd, Jeffersonville, NY 12748
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  /33

  $375,000

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft

  359 County Road 95, Obernburg, NY 12767

  Step back in time with this 1909 farmhouse, nestled in the heart of the Catskills in the town of Fremont, NY. This spacious 5-bedroom, 2-bath home has lots of character with its original built-ins, hardwood floors and charm. Plenty of space for family, guests, or even a potential bed & breakfast. The property includes a leased US Post Office, offering a unique investment opportunity (currently 1

  Fleur Bailey Carole Edwards Realty

  359 County Road 95, Obernburg, NY 12767
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  /37

  $324,500

  • Land
  • 14 Acres
  • $23,686 per Acre

  Dyker Road Dyker Rd, Callicoon, NY 12766

  10+ acres of gently sloping open meadow with southern exposure and stunning views. Ideal building site located in Western Sullivan County, just a short distance from the Delaware River National Park. Enjoy easy living in a country setting nestled amidst farmland, yet still close to town. Local attractions include the Bethel Woods Performing Arts Center, the Kartrite Water Park, and excellent

  Diane Butler Diane C. Butler

  Dyker Road Dyker Rd, Callicoon, NY 12766
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  /37

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  704 Cattail Rd, Livingston Manor, NY 12758

  Nestled on a serene 5-acre lot, this home offers the perfect blend of tranquility and convenience. This charming 3-bedroom, 2-bathroom ranch-style home boasts 1,350 square feet of beautifully maintained living space. Step inside to find gleaming hardwood floors, a cozy dining area, and a spacious first-floor master bedroom. The full, unfinished basement provides ample storage or the potential for

  Kewin Garabito eXp Realty

  704 Cattail Rd, Livingston Manor, NY 12758
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  /49

  $999,000

  • 7 Beds
  • 6 Baths

  354 E Hill Rd, Jeffersonville, NY 12748

  Majestic Grand Lady from days gone past. Started life as a 20 room boarding house, 1 bdrm guest house & dairy farm & in the 1960's the main building was turned into 5 apartments, 1-2 bdrm, 1 studio, 1 efficiency & 2- 1 bdrm. Also 9 bedrooms on the third floor but there is no heat or plumbing on that floor. Scenic views abound on the 47+ acre farm with over 30 acres of fertile pasture land, apple

  Darlene O'Dell Resort Realty

  354 E Hill Rd, Jeffersonville, NY 12748
• 

  

  /23

  $299,000

  • Land
  • 48 Acres
  • $6,216 per Acre

  0 Shandelee Rd, Youngsville, NY 12791

  Gorgeous acreage in Youngsville! Bring your ideas to life on this scenic 48 acre lot with direct street access to Shandelee Rd/CR-149. Enjoy a prime location, only 25 minutes from the Monticello Casino, 20 minutes from Bethel Woods, and a 15 minute drive to Route 17 (I-86). This lot has amazing potential to create a breathtaking primary residence, campground, potential subdivision, or nature

  Victoria Wander Divine Realty NY, LLC

  0 Shandelee Rd, Youngsville, NY 12791
• 

  

  /11

  $465,000

  • Land
  • 54 Acres
  • $8,674 per Acre

  0 Shandelee Rd Unit KEY804620, Callicoon, NY 12758

  Gorgeous property in Livingston Manor! Look no further for privacy and serenity, this property is about a half mile from the county road and is the ultimate nature lover's paradise. Upon entering the property you will find approximately half an acre of cleared land, perfect to build your dream home! The rest of the 50+ acres are a wonderful combination of level ground, slopes and curves, as well

  Victoria Wander Divine Realty NY, LLC

  0 Shandelee Rd Unit KEY804620, Callicoon, NY 12758
• 

  

  /33

  $449,900

  • 4 Beds
  • 3 Baths
  • 1,680 Sq Ft

  206 Yaun Rd, Livingston Manor, NY 12758

  Million Dollar View for half the price! This 4 BR, 3 bath home is ready for the next chapter. Needs updating and some work to make it beautiful, but this gorgeous location makes it worth all the effort. Absolutely stunning views will greet you every day from the home’s main attraction, which is the sunroom with walls of windows taking in the glorious scenery. Every day offers a different vista

  Carol Malek Malek Properties

  206 Yaun Rd, Livingston Manor, NY 12758
• 

  

  /17

  $999,000

  • Land
  • 145 Acres
  • $6,867 per Acre

  344 Midway Rd, Livingstn Mnr, NY 12758

  SPECTACULAR PANORAMIC MOUNTAINTOP VIEWS ON 145+ ACRES IN THE SOUGHT AFTER TOWN OF LIVINGSTON MANOR, NY located in the famous Sullivan Catskills. This parcel is tucked away on a remote and quiet road with a discrete entry point. Once you're on the roads that meander within this parcel you'll ride though a beautiful lush forest that offers a mix of mature trees, stone walls and interesting

  Caroline Akt Caroline Akt Realty LLC

  344 Midway Rd, Livingstn Mnr, NY 12758
• 

  

  /37

  $995,000

  • 4 Beds
  • 2 Baths
  • 4,000 Sq Ft

  301 & 305 Hust, Jeffersonville, NY 12748

  Remarkable 84-Acre Historic Estate Step into history with this extraordinary 84-acre estate, featuring an authentic 19th-century stagecoach depot and a beautifully preserved period barn with a charming guest cottage or rental opportunity.The main building showcases stunning timber frame construction, original wide-plank floors, and timeless craftsmanship. The sprawling grounds

  Diane Butler Diane C. Butler

  301 & 305 Hust, Jeffersonville, NY 12748

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