Callicoon Center, NY Homes for Sale

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  /50

  $624,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  519 County Route 164, Callicoon, NY 12723

  Welcome to Doc Holiday's Little Farm in Callicoon's Beechwoods hills! Coming to this warm and cozy house is like meeting your soulmate and falling head over heels ... in love! It is obvious that sellers of this little farm are animal lovers. Horse and donkey will greet you by the barn; the chickens are happy in their little houses; in the basement for now are cages with little rabbits patiently

  

  Rosemarie DeCristofaro

  Callicoon Real Estate LLC

  (845) 498-0861

  519 County Route 164, Callicoon, NY 12723
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  /29

  $699,000

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  57 Sheryl Davis Rd, Livingston Manor, NY 12758

  Set at the end of a quiet country drive just outside Livingston Manor, 57 Sheryl Davis Road offers the kind of privacy and connection to nature that defines the best of Catskills living. Surrounded by woods and bordered by a dramatic moss-covered bluestone rock face, this contemporary take on the many historic barns that dot the country roads in the area balances thoughtful design with warmth,

  

  Edward Rabon

  Compass Greater NY, LLC

  (845) 409-0770

  57 Sheryl Davis Rd, Livingston Manor, NY 12758
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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

  (845) 443-4418

  63 Sky View Dr, Callicoon, NY 12723
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  /11

  $450,000

  $50K PRICE DROP

  • Land
  • 5.12 Acres
  • $87,891 per Acre

  LOT 9 Wood Lake Trail, Roscoe, NY 12736

  Lot 9 at Florence Lake Estates is a premier direct waterfront homesite, offering rare, unobstructed access to the tranquil shores of Lake Florence. This spacious lot is ideal for a custom lakefront home, with gentle topography that lends itself to expansive decks, outdoor living spaces, and panoramic water views. Owners will enjoy access to the private community boat house, making it easy to

  

  Alicia Goldman

  Christie's Int. Real Estate

  (845) 299-2065

  LOT 9 Wood Lake Trail, Roscoe, NY 12736
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  /11

  $350,000

  • Land
  • 5.01 Acres
  • $69,860 per Acre

  LOT 10 Wood Lake Trail, Roscoe, NY 12736

  Lot 10 at Florence Lake Estates is a beautiful homesite offering the potential for seasonal views of both the golf course and Lake Florence, blending wooded privacy with glimpses of fairways and water as the seasons change. This lot provides a flexible canvas for a custom lodge-style, farmhouse, or contemporary home within a thoughtfully planned luxury community. Owners also enjoy access to the

  

  Alicia Goldman

  Christie's Int. Real Estate

  (845) 614-9678

  LOT 10 Wood Lake Trail, Roscoe, NY 12736
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  /43

  $1,230,000

  $170K PRICE DROP

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

  600 Jeffersonville North Branch Rd, North Branch, NY 12766

  87+ Acres, Farmhouse with 2 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 waterwheel, and wide open fields, the property offers the perfect backdrop for peaceful

  

  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
  • 10.28 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 Malek Properties

  290 Stump Pond Rd, Livingston Manor, NY 12758
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  /50

  $464,500

  • 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
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  /70

  $649,900

  • Land
  • 58.85 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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  /11

  $300,000

  • Land
  • 31.53 Acres
  • $9,515 per Acre

  0 Beechwoods Rd Unit KEY977156, Delaware, NY 12723

  Build your dream home on this beautiful slice of paradise in Callicoon! Surround yourself with 31.53 acres of rolling fields and private woods. Close to the Villa Roma and amenities. Bring your imagination and your construction plans today!

  Steven Beeson Diane C. Butler

  0 Beechwoods Rd Unit KEY977156, Delaware, NY 12723
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  /19

  $275,000

  $40K PRICE DROP

  • Land
  • 25 Acres
  • $11,000 per Acre

  295 Pleasant Valley Rd, North Branch, NY 12766

  Beautifully Wooded 25; Acre Parcel in Callicoon, NY Nestled 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 farm. Enjoy the

  Diane Butler Diane C. Butler

  295 Pleasant Valley Rd, North Branch, NY 12766
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  /44

  $545,000

  • 3 Beds
  • 1.5 Baths
  • 2,805 Sq Ft

  4700 State Route 52, Jeffersonville, NY 12748

  Love grand old homes, privacy and large airy rooms with lots of natural light? Have porch goals? Then this is the home for you. The home has been lovingly undergoing a restoration. Wood floors have been brought back to life in most of the home reflecting the care that was taken with them. The bathrooms have stayed true to the original time period with fully functioning sinks, toilets and clawfoot

  Penni-Jo Buchal Callicoon Real Estate LLC

  4700 State Route 52, Jeffersonville, NY 12748
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  /7

  $190,000

  • Land
  • 5.99 Acres
  • $31,720 per Acre

  TBD Meadow Ln, Fremont, NY 12766

  This is a wonderful opportunity to build a dream waterfront home, situated in a cozy corner of the Sullivan Catskills, amongst the rolling hills and pastures. The 5.99 acres slope gently down towards Reichmann Pond, which feels more like a small lake. There is over 200 feet of waterfront and an easily buildable site. The water is clear, fresh, and known locally for great fishing. Build out a dock

  Erik Freeland Country House Realty Inc

  TBD Meadow Ln, Fremont, NY 12766
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  /32

  $389,000

  • 3 Beds
  • 1.5 Baths
  • 1,856 Sq Ft

  5026 State Route 52, Jeffersonville, NY 12748

  Kohler Craftsman is a charming 105-year-old storybook home located in the vibrant Village of Jeffersonville. Rich in character and history, this well-maintained residence offers 3 bedrooms, 1 full bathroom, and 1 half bathroom on a beautifully landscaped and private 0.38-acre lot. The fenced yard features a heated above-ground pool, grassy lawn, and a spacious two-car garage. Originally built by

  William Baldwin Country House Realty Inc

  5026 State Route 52, Jeffersonville, NY 12748
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  /46

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  99 John Deitz Rd, Jeffersonville, NY 12748

  Perched atop a scenic mountain setting on 15.5 secluded acres, this contemporary country home offers sweeping panoramic views of the western Catskills, overlooking endless rolling hills, valleys, and open countryside. Surrounded by expansive lawns, professional landscaping, and mature woods, the property provides exceptional privacy and a peaceful setting in the heart of Sullivan County. A

  Eileen Jasper Chapin Sotheby's Intl Rlty

  99 John Deitz Rd, Jeffersonville, NY 12748
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  /49

  $899,000

  $100K PRICE DROP

  • 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
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  /45

  $899,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,875 Sq Ft

  1680 Gulf Rd, Callicoon Center, NY 12724

  Overbrook House is a design-forward Catskills retreat on nearly an acre that lives much larger thanks to multiple eye-popping indoor/outdoor spaces including a dreamy separate Guest Studio (not included in square footage). The meticulously styled main house features a den paneled with reclaimed barnwood, while the more formal living room's gas fireplace is great for ease of use and tidiness. A

  Jennifer Grimes Country House Realty Inc

  1680 Gulf Rd, Callicoon Center, NY 12724
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  /49

  $464,500

  • 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
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  /20

  $119,000

  • Land
  • 5.8 Acres
  • $20,517 per Acre

  0 Blackberry Lake Rd Unit KEY932984, Callicoon, NY 12748

  Beautiful building parcel located in Blackberry Lake Estates and offering distant views plus lake frontage! There is an existing grass driveway through the woods which opens onto a cleared meadow. A cleared path leads to 75 feet of scenic lake frontage. This diverse property would make a great homesite with so much to offer!

  Linda Mulligan Matthew J Freda Real Estate

  0 Blackberry Lake Rd Unit KEY932984, Callicoon, NY 12748
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  /18

  $199,999

  $130K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,582 Sq Ft

  5033 State Route 52, Jeffersonville, NY 12748

  Charming Tudor-style home on a spacious lot in the heart of Sullivan County. The main level features a living room, dining room, kitchen with outdoor porch, and a large flexible room ideal as a third bedroom or home office, while two bedrooms are located upstairs. Set on a large, usable yard with room to expand or create outdoor living. Strong value-add potential in a growing market, minutes to

  Louis Naccarato Corcoran Country Living

  5033 State Route 52, Jeffersonville, NY 12748
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  /40

  $299,900

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft

  4188 State Route 52, Youngsville, NY 12791

  Mobile-home in very good condition set on one acre just outside Youngsville NY. Many amenities and quality upgrades went into this 4 bedroom 2 full bath home. There are stainless kitchen appliances and a large kitchen island with plenty of cabinetry. Laundry room with washer and dryer. It has is central air and heat (propane), an alarm system, camera system for security, new septic system,

  Steven Beeson Diane C. Butler

  4188 State Route 52, Youngsville, NY 12791
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  /7

  $275,000

  $60K PRICE DROP

  • Land
  • 7.43 Acres
  • $37,012 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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  $524,900

  $44K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,663 Sq Ft

  4741 State Route 52, Jeffersonville, NY 12748

  Enjoy unforgettable sunsets from this beautifully renovated 4 bedroom, 3 bath home set on 1.5 acres. Designed for both comfort and entertaining, the home features oversized double back decks that seamlessly extend your living space outdoors. Inside, warm wood floors, recessed lighting, and spacious rooms create a bright and inviting atmosphere, complemented by large walk in closets and a

  Tammy Ierardi Modern Solutions Realty, LLC

  4741 State Route 52, Jeffersonville, NY 12748
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  /28

  $279,900

  • 2 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  10 Fred Hessinger Rd, Callicoon Center, NY 12724

  Sunny and Charming Home with a Great Price and Location! This bright and charming Arts & Crafts–style Cape has a cheerful and comfortable feeling throughout with great natural light and mountain views. A large picture window flanked by shelves is both fun and practical, adding character to the open and spacious kitchen and living area. Upstairs are two bedrooms, a full bath, and a bright office

  Jessica Maloney Compass Greater NY, LLC

  10 Fred Hessinger Rd, Callicoon Center, NY 12724
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  /35

  $292,000

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  4088 State Route 52, Youngsville, NY 12791

  Set on a full acre in the heart of Youngsville, this well-built and lovingly updated home offers comfort, charm, and true move-in-ready ease. Ideally located just minutes from the historic Village of Jeffersonville, you'll enjoy convenient access to unique shops, restaurants, grocery stores, boutiques, parks, and numerous amenities all while savoring a peaceful country setting. Inside, the home

  Deborah Gorenflo Land and Water Realty LLC

  4088 State Route 52, Youngsville, NY 12791
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  /20

  $175,000

  • Land
  • 15.16 Acres
  • $11,544 per Acre

  52 E Hill Rd, Jeffersonville, NY 12748

  This exceptional parcel with great views offers a rare combination of location, accessibility, and homesite potential. Situated in a desirable and growing area, the expansive property features optimal topography, excellent road frontage, and convenient access to many local towns including Jeffersonville, Callicoon, LIberty and Roscoe where you'll find many of the areas restaurants and shopping.

  Steven Beeson Diane C. Butler

  52 E Hill Rd, Jeffersonville, NY 12748
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  /10

  $415,000

  • 2 Beds
  • 1.5 Baths
  • 1,781 Sq Ft

  1751 Shandelee Rd, Livingston Manor, NY 12758

  Fully Remodeled Ranch in the Heart of Youngsville. Welcome to this beautifully updated 3-bedroom, 2-bath ranch-style home situated on 1.56 peaceful acres in the heart of Youngsville! This move-in ready property offers the perfect blend of comfort, space, and outdoor living. Inside, you’ll find a fully remodeled interior with a bright and inviting layout, including a spacious sunroom, gorgeous

  Jonathan Minerick HomeCoin.com

  1751 Shandelee Rd, Livingston Manor, NY 12758
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  /35

  $299,000

  • Land
  • 32.47 Acres
  • $9,209 per Acre

  0 Menges Rd Unit KEY976899, Callicoon, NY 12791

  32 acres-wooded with stream. Drive up to the property off a quiet paved road and walk into it through a pristine meadow that is dotted with wild blueberry bushes. Walking further into a mature stand of maple, birch, cherry and other assorted trees, you will find cairns and stone walls that are along the edges and interior of the land. There is a small stream that runs through the back of the

  Tom Freda Matthew J Freda Real Estate

  0 Menges Rd Unit KEY976899, Callicoon, NY 12791
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  /50

  $399,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  292 County Road 93, Roscoe, NY 12776

  Versatile 9.2 acre compound featuring a 3-bedroom, 2-bath ranch with spacious front and back decks. The full walkout basement provides livable space, plus room for storage. Two detached garages-one with an apartment above-plus a large shed, small barn and chicken coop provide additional storage and multi-use options. The apartment needs some finishing and includes a kitchen with stove and

  Linda Mulligan Matthew J Freda Real Estate

  292 County Road 93, Roscoe, NY 12776
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  /20

  $399,900

  • Land
  • 70 Acres
  • $5,713 per Acre

  301 & 305 Hust Road Hust Rd, Jeffersonville, NY 12748

  stunning building lot with plenty of room to grow. Long distance views, fields meadows and starry night skys. Unimproved raw land on the edge of a farm.

  Diane Butler Diane C. Butler

  301 & 305 Hust Road Hust Rd, Jeffersonville, NY 12748
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  /23

  $330,000

  • 3 Beds
  • 1.5 Baths
  • 1,378 Sq Ft

  40 Jefferson Ave, Jeffersonville, NY 12748

  Enjoy the convenience of in-town living at this newly gut renovated brick ranch in Jeffersonville, NY. Bright, airy, easy single floor living with modern upgrades make this a great family home, or potential investment as a rental property. Fully renovated in 2023, the home features a brand new kitchen, bathroom, windows, hot water heater, and back deck. There are three ground floor bedrooms and

  Jared Gluckstern Country House Realty Inc

  40 Jefferson Ave, Jeffersonville, NY 12748
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  /47

  $849,900

  New Construction

  • 3 Beds
  • 3 Baths
  • 3,720 Sq Ft

  1227 Gulf Rd, Callicoon Center, NY 12724

  Welcome to Stonegate House. Set back from the road at the end of a strikingly gated driveway, this delightful home is perched on a knoll overlooking its own private pond. The spacious interior offers that sought-after chalet vibe with a modern flair. Open and airy, with expansive windows that showcase the surrounding scenery, this property certainly checks all the boxes for the discerning buyer.

  Carol Malek Malek Properties, Inc.

  1227 Gulf Rd, Callicoon Center, NY 12724
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  /54

  $599,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  49 Yaun Rd, Livingston Manor, NY 12758

  Hollyhock sits a long way back from a quiet country road on 10.13 acres of meadow, woods, and historic stone walls. The house is properly private and still only a few minutes from Livingston Manor's main street, which is the increasingly rare combination people drive up here to find. The interiors are where it gets interesting: someone has been making confident, pattern-loving, vintage-respecting

  Arlena Armstrong Anatole House LLC

  49 Yaun Rd, Livingston Manor, NY 12758
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  /31

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  1779 Shandelee Rd, Livingston Manor, NY 12758

  You'll be wowed by the classic character of this Arts and Crafts home with so many original details! This 3 bedroom, 2 bath home is solid, and you'll find so many extras! (A couple of nice bonus rooms!) The covered front porch welcomes you in to a time gone by. Check out the gleaming original wood floors, built in the 30's, when craftsmen really cared about quality and exceptional detail! There

  Lynne Freda Matthew J Freda Real Estate

  1779 Shandelee Rd, Livingston Manor, NY 12758
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  /30

  $130,000

  • 5 Beds
  • 1 Bath
  • 1,274 Sq Ft

  28 Banuat Rd, North Branch, NY 12766

  Farmhouse with 5 bedrooms on 1.47 acres in country setting in "handy-man-fixer upper" condition. Property consists of level yard with large 2-story barn, 1-car garage and shed. Water source is a shared spring with deeded rights. This home has been in same family for many years. Set on a private road, enjoy pastoral views of horses, wildlife, yet just a few minutes away from the small hamlet of

  Susan Busing Matthew J Freda Real Estate

  28 Banuat Rd, North Branch, NY 12766
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  /32

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  8 Chapel St, Jeffersonville, NY 12748

  Your Quaint Upstate Retreat tucked away just off of Main St awaits you. This Victorian home has only been home to 4 special owners in its lifetime and offers a warmth to its Victorian Charm. Nestled in the up and coming Jeffersonville sits this large 4 Bedroom, 2 Full Bath home. The large rooms are so true to the design of the 1800's Victorians built. High ceilings, picture molding, multiple Bay

  Michele Rios BHHS Hudson Valley Properties

  8 Chapel St, Jeffersonville, NY 12748
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  /30

  $875,000

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

  227 Anawanda Lake Rd, Roscoe, NY 12776

  An idyllic c1875 farmhouse set across 21.76 acres of rolling fields, wooded trails, and curated gardens. Featured on the Magnolia Network, this charming property has been reimagined with a refined modern English farmhouse aesthetic that balances historic character with timeless comfort. Winding trails lined with blueberry bushes meander through the property, leading to hidden moments tucked into

  Annabel Taylor Four Seasons Sotheby's Int.

  227 Anawanda Lake Rd, Roscoe, NY 12776
• 

  

  /14

  $276,000

  $24K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,380 Sq Ft

  257 Cr 134, Fremont Center, NY 12736

  Presenting a ranch-style residence situated on an expansive 10-acre parcel, this property offers abundant opportunities for outdoor recreation, gardening, and nature-inspired pursuits. Featuring two bedrooms and a full bath, the home provides a comfortable foundation for those seeking to tailor their living space to reflect personal preferences. Although some renovation is required, the recently

  Anna Milucky Century 21 Country Realty

  257 Cr 134, Fremont Center, NY 12736
• 

  

  /13

  $179,000

  • 3 Beds
  • 1 Bath
  • 728 Sq Ft

  4178 State Route 52, Youngsville, NY 12791

  Nestled in the peaceful countryside just seconds from the charming town of Youngsville, this cozy bungalow offers endless potential. Whether you're seeking a full-time residence or a relaxing weekend getaway, this home is the perfect opportunity to create your own retreat in the heart of Sullivan County. Step inside and imagine the possibilities — with a little TLC and vision, you can transform

  Eugene Doyle Carole Edwards Realty

  4178 State Route 52, Youngsville, NY 12791
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  /30

  $525,000

  Open Sat 10:30AM - 12:30PM

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  37 Dewitts Flats Rd, Jeffersonville, NY 12748

  Welcome to Flats Modern — a beautifully reimagined home on a quiet country road where modern design meets relaxed Catskills living. Finished in striking black and situated on a half-acre of lawn, lush gardens and mature landscaping, this bright, fully renovated home blends thoughtful contemporary design with warmth and comfort throughout. Inside, vaulted ceilings and oversized windows fill the

  Heather Quaintance Country House Realty Inc

  37 Dewitts Flats Rd, Jeffersonville, NY 12748

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