Callicoon Center, NY Homes for Sale with Acreage

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  /36

  $429,000

  • 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
• 

  

  

  /19

  $269,000

  • Land
  • 10 Acres
  • $26,900 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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  /37

  $489,000

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

  807 Swiss Hill Rd N, Jeffersonville, NY 12748

  Beautiful circa 1895 Victorian Home! 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

  

  Dawn Curreri

  Eagle Valley Realty

  (845) 576-9694

  807 Swiss Hill Rd N, Jeffersonville, NY 12748
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  /43

  $1,400,000

  • 4 Beds
  • 2.5 Baths
  • 2,461 Sq Ft

  600 Jeffersonville North Branch Rd, North Branch, NY 12766

  Historic Farmhouse on 87+ Acres with Ponds, Outbuildings & Endless Potential.Welcome to a rare opportunity to own a piece of Sullivan County history. Set on over 87 scenic acres, this charming 1830s farmhouse blends timeless character with exceptional space and natural beauty. With two serene ponds, a picturesque water wheel, and wide open fields, the property offers the perfect backdrop for

  

  Elizabeth Bernitt

  Century 21 Geba Realty

  (845) 807-6947

  600 Jeffersonville North Branch Rd, North Branch, NY 12766
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  /8

  $180,000

  • Land
  • 10 Acres
  • $17,510 per Acre

  290 Stump Pond Rd, Livingston Manor, NY 12758

  Located on a beautiful country road in the Youngsville/ Livingston Manor area this 10+ acres offers open and level meadow as well as gently sloped wooded area. Up the hill with a few trees removed you can seemingly realize some lovely bucolic and distant mountain views. Tons of wildlife on this quiet and peaceful land. Zoning is CD – Conservation District - which allows for 3-acre minimum lot

  Carol Malek

  290 Stump Pond Rd, Livingston Manor, NY 12758
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  /12

  $99,900

  • Land
  • 10 Acres
  • $9,737 per Acre

  W Killie Rd, Fremont Center, NY 12767

  This beautiful 10 acre building lot has potential stunning views located in Fremont Center NY, Sullivan County.This lot has great potential to build your dream home overlooking serene pastures with a beautiful backdrop.Also, find its calling through abundant wildlife throughout. The lot is currently fully wooded with an upward slope. Frontage along West Killie Road is 626 feet.

  Dani Hoeverman

  W Killie Rd, Fremont Center, NY 12767
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  /61

  $649,900

  • Land
  • 59 Acres
  • $11,043 per Acre

  25 Robertson Rd, Liberty, NY 12758

  Looking for that special spot that offers the potential to build the home of your dreams? Look no further. This unique property offers a blend of open fields, lush forest, and 360-degree views. The paved road leads you into the bottom area of the parcel. This area has electricity available along the road and offers an open field with amazing views of the distant countryside along with a 320 sq

  Clint Carlson WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  25 Robertson Rd, Liberty, NY 12758
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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
• 

  

  /43

  $985,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  104 William Herbert Rd, Fremont Center, NY 12736

  Ensconced in the rolling hills of Obernburg, in the township of Fremont, this 93-acre expanse may be one of the most enchanting blends of forest and pasture to come to market in years. Once the heart of Hillside Dairy, the land carries a quiet legacy of working fields and open sky.The farmhouse dates to 1909 and is ideally situated, tucked away in its own private world at the end of a long

  Erik Freeland Country House Realty Inc

  104 William Herbert Rd, Fremont Center, NY 12736
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  /35

  $735,000 Open Sun 1PM - 3PM

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

  292 Sander Rd, Jeffersonville, NY 12748

  A rare opportunity to purchase a distinct property in Sullivan County NY has come to market just in time to enjoy the late Summer and early Autumn in the bucolic southern Catskills. 292 Sander Road is a historic, turnkey, meticulously maintained, one-of-a-kind home on a private 3.4-acre lot with picturesque views of mountains and valleys that cannot be reproduced at this price point in any

  Jeff Gardner Corcoran MH, LLC

  292 Sander Rd, Jeffersonville, NY 12748
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  /50

  $1,048,000

  • 4 Beds
  • 3.5 Baths
  • 3,750 Sq Ft

  63 Sky View Dr, Callicoon, NY 12723

  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

  Barry Becker Keller Williams Hudson Valley

  63 Sky View Dr, Callicoon, NY 12723
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  /42

  $899,000

  • 6 Beds
  • 3 Baths
  • 2,688 Sq Ft

  145 Likel Rd, Jeffersonville, NY 12748

  Ursa Manor is a charming, historic property built in 1909, originally serving as a boarding house for weary city travelers until the 1950s. The house is currently configured with six bedrooms and 3 bathrooms, plus additional rooms being used as a library, playroom, and offices, offering versatile living and working spaces. In its heyday, Sullivan County was a sought-after summer retreat from New

  Erik Freeland Country House Realty Inc

  145 Likel Rd, Jeffersonville, NY 12748
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  /21

  $719,000

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

  96 Yaun Rd, Livingston Manor, NY 12758

  Discover Yaun Road Cabin, a stunning new construction on a quiet country road near vibrant Livingston Manor, NY. This 3-bedroom, 2-bathroom home sits on nearly 5 acres of versatile land, blending open fields and secluded woodlands for a perfect balance of relaxation and recreation.The property’s expansive grounds are brimming with potential for your vision. Outside, a staircase descends

  William Baldwin Country House Realty Inc

  96 Yaun Rd, Livingston Manor, NY 12758
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  /30

  $599,000

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

  231 Boband Rd, Jeffersonville, NY 12748

  Nestled into a picturesque hillside between the sleepy hamlets of Youngsville and Jeffersonville NY, Blue Hill is a turnkey, peaceful getaway just two hours from NYC. Every room is thoughtfully designed to take advantage of natural light and beautiful surroundings. From the spacious, wraparound deck, you enter the home into the well-appointed kitchen, featuring shaker style-cabinets and

  Megan Kinealy-Hill Country House Realty, Inc.

  231 Boband Rd, Jeffersonville, NY 12748
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  /31

  $599,000

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

  231 Boband Rd, Youngsville, NY 12791

  Nestled into a picturesque hillside between the sleepy hamlets of Youngsville and Jeffersonville NY, Blue Hill is a turnkey, peaceful getaway just two hours from NYC. Every room is thoughtfully designed to take advantage of natural light and beautiful surroundings. From the spacious, wraparound deck, you enter the home into the well-appointed kitchen, featuring shaker style-cabinets and

  Megan Kinealy-Hill Country House Realty Inc

  231 Boband Rd, Youngsville, NY 12791
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  /30

  $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

  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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  /30

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft

  256 Pleasant Valley Rd, Callicoon, NY 12723

  Set well back from a picturesque country road on a wooded hillside, Pleasant Valley is a 2 bed, 2 bath, turnkey escape. Enjoy three acres of solitude, split between a level clearing of yard and mature trees for a fully ensconced feel - Pleasant Valley certainly provides the privacy you are seeking with your country home.The striking sun room is a welcome entry point to the home - full of

  Jared Gluckstern Country House Realty Inc

  256 Pleasant Valley Rd, Callicoon, NY 12723
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  /14

  $49,000

  • Land
  • 3.60 Acres
  • $13,611 per Acre

  TBD Anawanda Lake Rd, Roscoe, NY 12776

  Level 3.6 acre wooded property on a beautiful country road and property corners are marked on the road. Nice quiet location and would provide a great building site for your country home.

  Linda Mulligan Matthew J Freda Real Estate

  TBD Anawanda Lake Rd, Roscoe, NY 12776
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  /46

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,896 Sq Ft

  669 Shandelee Rd, Livingston Manor, NY 12758

  Welcome to the Shandelee Mountain House – a rare chance to claim your own slice of the Catskills on 8.25 acres, just minutes from the ever-popular hamlet of Livingston Manor. This 3-bedroom, 2.5-bath home blends solid bones with an open invitation for the next owner to bring fresh style and modern touches. Perched along a peaceful, winding mountain road, the property greets you with a gently

  James Karpowicz Listing by Coldwell Banker Timberland Properties

  

  669 Shandelee Rd, Livingston Manor, NY 12758
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  /7

  $335,000

  • Land
  • 7 Acres
  • $45,087 per Acre

  0 Beechwoods Rd Unit KEY901475, Delaware, NY 12723

  Own a stunning 7.4-acre property with panoramic views in the highly desirable Beechwoods section of Callicoon. Build your dream home and embrace the beauty of nature. Don't miss this incredible opportunity!

  Ian Blumenthal Catskill Sales Associates Inc

  0 Beechwoods Rd Unit KEY901475, Delaware, NY 12723
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  /18

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  541 Cattail Rd, Livingston Manor, NY 12758

  Quiet, Quiet, Quiet, if you are looking for that getaway like no other this is the place for you!! Can you say wild life, camp fires, yard games, trails, sun rise, sun sets, streams, hunting, and more!! Well this property has it all. Two newly not quite finished ranch style cabins joined under one roof with a large deck for the friends and family. This property is nicely located just out side the

  Gordon LeRoy Elliott & Pomeroy Inc

  541 Cattail Rd, Livingston Manor, NY 12758
• 

  

  /8

  $180,000

  • Land
  • 10 Acres
  • $17,510 per Acre

  Tbd Stump Pond Rd, Livingstn Mnr, NY 12758

  Located on a beautiful country road in the Youngsville/ Livingston Manor area this 10+ acres offers open and level meadow as well as gently sloped wooded area. Up the hill with a few trees removed you can seemingly realize some lovely bucolic and distant mountain views. Tons of wildlife on this quiet and peaceful land. Zoning is CD - Conservation District - which allows for 3-acre minimum lot

  Carol Malek Malek Properties, Inc.

  Tbd Stump Pond Rd, Livingstn Mnr, NY 12758
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  /8

  $180,000

  • Land
  • 10 Acres
  • $17,510 per Acre

  0 Stump Pond Rd Unit KEY899504, Livingstn Mnr, NY 12758

  Located on a beautiful country road in the Youngsville/ Livingston Manor area this 10+ acres offers open and level meadow as well as gently sloped wooded area. Up the hill with a few trees removed you can seemingly realize some lovely bucolic and distant mountain views. Tons of wildlife on this quiet and peaceful land. Zoning is CD – Conservation District - which allows for 3-acre minimum lot

  Carol Malek Malek Properties

  0 Stump Pond Rd Unit KEY899504, Livingstn Mnr, NY 12758
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  /49

  $474,500

  • 6 Beds
  • 2 Baths
  • 2,174 Sq Ft

  301 Stump Pond Rd, Livingston Manor, NY 12758

  Beautiful farmstead with 23+ acres of property (additional land available) has been in the same family for generations. Includes two vintage handyman farmhouses and multiple outbuildings plus a large rustic barn in need of repair. Land is gorgeous with open meadows, some woods, stone walls and a lovely pastoral view. The homes each offer 3 bedrooms; one has two enclosed porches and a walk-up

  Carol Malek Malek Properties, Inc.

  301 Stump Pond Rd, Livingston Manor, NY 12758
• 

  

  /47

  $474,500

  • 6 Beds
  • 2 Baths
  • 2,174 Sq Ft

  299 Stump Pond Rd, Livingston Manor, NY 12758

  Beautiful farmstead with 23+ acres of property (additional land available) has been in the same family for generations. Includes two vintage handyman farmhouses and multiple outbuildings plus a large rustic barn in need of repair. Land is gorgeous with open meadows, some woods, stone walls and a lovely pastoral view. The homes each offer 3 bedrooms; one has two enclosed porches and a walk-up

  Carol Malek Malek Properties

  299 Stump Pond Rd, Livingston Manor, NY 12758
• 

  

  /19

  $99,000

  • Land
  • 3.71 Acres
  • $26,685 per Acre

  0 Dutch Hill Rd, Rockland, NY 12776

  Stunning Vacant Land with Driveway, Perc Test, and Spectacular ViewsBuild Your Dream Retreat in Nature’s EmbraceDiscover a rare opportunity to own your own slice of paradise! This exceptional vacant land offers the perfect canvas for your future home or getaway, nestled in a serene and secluded setting that promises tranquility and breathtaking natural beauty.• Driveway Already

  Philip Eggleton Eagle River Realty LLC

  0 Dutch Hill Rd, Rockland, NY 12776
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  /46

  $299,999

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

  704 Cattail Rd, Livingston Manor, NY 12758

  Tucked away on 5 private acres of open space and wooded beauty, this charming 3-bedroom, 2-bath ranch offers the kind of serenity most people only dream about—without sacrificing convenience. Whether you're craving a weekend retreat or a full-time homestead, this home invites you to slow down, spread out, and truly live. Step inside to discover gleaming hardwood floors, a sun-kissed dining nook,

  Kewin Garabito eXp Realty

  704 Cattail Rd, Livingston Manor, NY 12758
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  /16

  $249,000

  • 1 Bed
  • 1 Bath
  • 932 Sq Ft

  33 Eagin Rd, Livingston Manor, NY 12758

  This property is just about as unique a structure as you can buy. This is a 1910 original hay and animal barn on Eagin Road. The barn is massive with two levels and 25 foot ceilings. The property has a well and septic, and is currently classified as a residence, because the owner has added a small efficiency apartment/living area on the first floor of the barn. The living space has a small

  John Ducey Keller Williams Hudson Valley

  33 Eagin Rd, Livingston Manor, NY 12758
• 

  

  /16

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  63 N Branch Callicoon Ctr Rd, North Branch, NY 12766

  Single family home in North Branch. Renovated 3 bedroom one bath on main floor, ready to move in. Lower level offers possible additional living space. New features include funace, driveway, how water heater,stainless steel appliances, and garage has been painted. This is an affordable home, in a beautiful area in sullivan county. Close to north branch, jeffersonville, and the delaware

  Ellie Hyde Century 21 Country Realty

  63 N Branch Callicoon Ctr Rd, North Branch, NY 12766
• 

  

  /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

  $895,000

  • 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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  /49

  $984,000

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

  99 John Deitz Rd, Jeffersonville, NY 12748

  This mountaintop 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 hidden amongst the peaks of the Sullivan County mountains. In addition, the property features two large, spring-fed ponds with a constant flow of water

  John Ducey Keller Williams Hudson Valley

  99 John Deitz Rd, Jeffersonville, NY 12748
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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
• 

  

  /34

  $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
• 

  

  /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

  William Baldwin Country House Realty Inc

  877 Shandelee Rd, Livingston Manor, NY 12758
• 

  

  /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
• 

  

  /33

  $1,195,000

  • 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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