Jeffersonville, NY Homes

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  /46

  $850,000

  $45K PRICE DROP

  • 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

  

  Christine Vande Vrede

  Chapin Sotheby's Intl Rlty

  99 John Deitz Rd, Jeffersonville, NY 12748
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  /7

  $1,650 Per Month

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft
  • Apartment for Rent

  4941 State Route 52 Unit 2, Jeffersonville, NY 12748

  Large 2 Bedroom 1 Full Bath with Balcony, Apt In 2 Family Home In Catskills. All Stainless Steel Appliances, Stream Front Views, Second Floor, Huge Full Attic For Storage, Private Off Street Parking, Close To Shopping, Restaurants, Entertainment. Great Location. Credit Score and Income Verification Required. 1 Month Rent, 1 Month Security, Required At Lease Signing. Pet Ok.

  Leticia Allocca Leticia J Allocca

  4941 State Route 52 Unit 2, Jeffersonville, NY 12748
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  $120,000

  Sold Mar 02, 2026

  787 Callicoon Center Rd, Jeffersonville, NY 12748

  • 1 Bed
  • 1 Bath
  • 1,023 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $117/SF
  • 87 Days On Market

  Last Listing Agent Thelonious Johnson Hart & Johnson Realty

  787 Callicoon Center Rd, Jeffersonville, NY 12748
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  Not Listed For Sale

  367 Hubert Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft
  • Built 2024

  367 Hubert Rd, Jeffersonville, NY 12748

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent William Baldwin Country House Realty Inc
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  /36

  $325,000

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

  8 Chapel St, Jeffersonville, NY 12748

  Some streets just have a feeling, and Chapel Street is one of them. Towering shade trees and classic homes line this beloved street in the Village of Jeffersonville, welcoming you to a timeless Victorian ready for its next chapter. Step inside to discover four bedrooms, two full bathrooms, and beautiful hardwood floors that speak to the craftsmanship of another era. Every room offers the

  

  Elizabeth Bernitt

  Century 21 Geba Realty

  8 Chapel St, Jeffersonville, NY 12748
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  /11

  $1,550 Per Month

  • 2 Beds
  • 2 Baths
  • 883 Sq Ft
  • Apartment for Rent

  24 Jefferson Ave, Jeffersonville, NY 12748

  Fabulously located two bedroom 2 bath, in the trendy Village of Jeffersonville. Walking distance to local store and downtown shopping district.(photos are from before current tenant moved in)

  Nancy Salvemini WOODSTOCK WAY REALTY LLC

  24 Jefferson Ave, Jeffersonville, NY 12748
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  $260,000

  Sold Jun 19, 2026

  2 County Road 164, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1900

  Last Sold Summary

  • 21% Below List Price
  • $112/SF
  • 203 Days On Market

  Current Estimated Value $258,530

  Last Listing Agent Barbara Allen HomeSmart Homes & Estates

  2 County Road 164, Jeffersonville, NY 12748
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  Est $436,923

  Not Listed For Sale

  374 E Hill Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft
  • Built 2014

  374 E Hill Rd, Jeffersonville, NY 12748

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Brian Garber Land and Water Realty LLC
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  /18

  $289,000

  • 3 Beds
  • 1.5 Baths
  • 1,492 Sq Ft

  5030 State Route 52, Jeffersonville, NY 12748

  A true Jeffersonville original, thoughtfully prepared for its next chapter. Set along the banks of the gentle brook, this 1930 Craftsman has been carefully gutted, offering a rare opportunity to restore a home with authentic character while bringing your own vision to life.Originally built by the owners of nearby Kohler Lumber, the home still showcases many of its original Craftsman details,

  

  Edward Rabon

  Compass Greater NY, LLC

  5030 State Route 52, Jeffersonville, NY 12748
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  /10

  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • 783 Sq Ft
  • Apartment for Rent

  4941 State Route 52 Unit 3, Jeffersonville, NY 12748

  2 Bedroom Stream Front Apt With Stainless Steel Appliances, Outside Waterfront Private Deck, Kitchen With Dining Area, New Bedroom Floor, New Hall Chandelier, Great Location Close Distance To Shopping, Restaurants, Natural Beauty Setting. Tenant Pays Electric Heat, Electricity. Credit Report & Income Verification Required. Pets Ok Call Broker, Additional information: Appearance :Excellent,

  Leticia Allocca Leticia J Allocca

  4941 State Route 52 Unit 3, Jeffersonville, NY 12748
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  $290,000

  Sold Oct 01, 2025

  521 Hessinger and Lare Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 3 Baths
  • 1,782 Sq Ft
  • Built 1989

  Last Sold Summary

  • 23% Below List Price
  • $163/SF
  • 146 Days On Market

  Current Estimated Value $313,630

  Last Listing Agent David Luczyski Resort Realty

  521 Hessinger and Lare Rd, Jeffersonville, NY 12748
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  Est $317,647

  Not Listed For Sale

  90 Hubert Rd Unit 13, Jeffersonville, NY 12748

  • 2 Beds
  • 1.5 Baths
  • 845 Sq Ft
  • Built 1980

  90 Hubert Rd Unit 13, Jeffersonville, NY 12748

  Last Sold Summary

  • 222 Days On Market

  Last Listing Agent Dawn Curreri Eagle Valley Realty
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  /6

  $349,900

  • Land
  • 35 Acres
  • $9,997 per Acre

  295 Jeffersonville North Branch Rd, Jeffersonville, NY 12748

  Discover the perfect setting for your dream home, country getaway, or recreational retreat on this beautiful 35± acre property in Western Sullivan County. A gentle rise in elevation creates stunning bucolic views and offers multiple ideal building sites to take advantage of the picturesque landscape. Featuring a wonderful blend of open meadows and wooded areas, the property is rich in character

  Carol Malek Malek Properties

  295 Jeffersonville North Branch Rd, Jeffersonville, NY 12748
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  /18

  $2,000 Per Month

  • 4 Beds
  • 1.5 Baths
  • 2,000 Sq Ft
  • Apartment for Rent

  4941 New York 52 Unit 1, Jeffersonville, NY 12748

  Stream Front Elegance & Spacious Natural Beauty. Yearly Rental, Unfurnished 4 Bedrooms, 1.5 Bath, Clean & Serene Home with Stream Front Deck, Natural Wildlife Setting. Vaulted Ceiling, New Kitchen, Elegantly Appointed. New Stainless Steel Appliance, Washer/Dryer, Garage, Olympic Size Pool Table. Conveniently Located in the Catskills. Close to Shopping, Restaurants. Come And Breathe Our Fresh

  Leticia Allocca Leticia J Allocca

  4941 New York 52 Unit 1, Jeffersonville, NY 12748
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  $310,000

  Sold Feb 03, 2026

  242 Callicoon Center Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft
  • Built 1988

  Last Sold Summary

  • 11% Below List Price
  • $123/SF
  • 213 Days On Market

  Current Estimated Value $320,107

  Last Listing Agent Dean Diltz Keller Williams Realty

  242 Callicoon Center Rd, Jeffersonville, NY 12748
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  /33

  Est $265,923

  Not Listed For Sale

  17 Maple Ave, Jeffersonville, NY 12748

  • 4 Beds
  • 2.5 Baths
  • 1,560 Sq Ft
  • Built 1940

  17 Maple Ave, Jeffersonville, NY 12748

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Lindsay Stevens eXp Realty
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  /39

  $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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  $208,000

  Sold May 13, 2026

  5010 State Route 52, Jeffersonville, NY 12748

  • 3 Beds
  • 1.5 Baths
  • 1,148 Sq Ft
  • Built 1920

  Last Sold Summary

  • 9% Below List Price
  • $181/SF
  • 126 Days On Market

  Current Estimated Value $212,809

  Last Listing Agent Dawn Curreri Eagle Valley Realty

  5010 State Route 52, Jeffersonville, NY 12748
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  Est $533,704

  Not Listed For Sale

  156 Sander Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft
  • Built 1973

  156 Sander Rd, Jeffersonville, NY 12748

  Last Sold Summary

  • 84 Days On Market

  Last Listing Agent William Baldwin Country House Realty Inc
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  $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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  /37

  $615,000

  Sold Nov 26, 2025

  57 Old Taylor Rd, Jeffersonville, NY 12748

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1960

  Last Sold Summary

  • 5% Below List Price
  • $244/SF
  • 44 Days On Market

  Current Estimated Value $632,988

  Last Listing Agent Kayla Camstra Anatole House LLC

  57 Old Taylor Rd, Jeffersonville, NY 12748
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  /2

  Est $259,546

  Not Listed For Sale

  14 Jefferson Ave, Jeffersonville, NY 12748

  • 3 Beds
  • 1 Bath
  • 1,387 Sq Ft
  • Built 1930

  

  14 Jefferson Ave, Jeffersonville, NY 12748

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Dara Barr Listing by Keller Williams Upstate NY Properties
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  /49

  $849,000

  $150K 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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  $960,000

  Sold Nov 10, 2025

  281 Hubert Rd, Jeffersonville, NY 12748

  • 4 Beds
  • 2 Baths
  • 2,900 Sq Ft
  • Built 1976

  Last Sold Summary

  • 2% Below List Price
  • $331/SF
  • 106 Days On Market

  Current Estimated Value $976,864

  Last Listing Agent Dominique Jenkins KW Hudson Valley United

  281 Hubert Rd, Jeffersonville, NY 12748
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  Est $182,591

  Not Listed For Sale

  50 Jefferson Ave, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1920

  50 Jefferson Ave, Jeffersonville, NY 12748

  Last Sold Summary

  • 335 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
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  /4

  $329,900

  • 5 Beds
  • 2.5 Baths
  • 2,781 Sq Ft

  4369 State Route 52, Jeffersonville, NY 12748

  Diamond in the rough. Main house has been used as a two family in years past, building at back of property has one 3 bedroom, one bath apartment and the other apartment has been started but not completed. This property consists of 15 +- acres located in the RB district in the town of Callicoon, which means several possibilities for development including gas station. The East branch of the

  Ian Blumenthal Catskill Sales Associates Inc

  4369 State Route 52, Jeffersonville, NY 12748
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  $290,000

  Sold Jan 29, 2026

  31 Erlemann Rd, Jeffersonville, NY 12748

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1975

  Last Sold Summary

  • 3% Below List Price
  • $245/SF
  • 49 Days On Market

  Current Estimated Value $307,467

  Last Listing Agent Susan Busing Matthew J Freda Real Estate

  31 Erlemann Rd, Jeffersonville, NY 12748
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  Est $393,605

  Not Listed For Sale

  679 E Hill Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft
  • Built 1931

  679 E Hill Rd, Jeffersonville, NY 12748

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Jill Halpern-Steingart Rieber Realty Inc
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  /36

  $549,000

  $20K 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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  $398,000

  Sold Mar 18, 2026

  807 Swiss Hill Rd N, Jeffersonville, NY 12748

  • 4 Beds
  • 2.5 Baths
  • 3,634 Sq Ft
  • Built 1895

  Last Sold Summary

  • 33% Below List Price
  • $110/SF
  • 572 Days On Market

  Current Estimated Value $478,124

  Last Listing Agent Dawn Curreri Eagle Valley Realty

  807 Swiss Hill Rd N, Jeffersonville, NY 12748
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  Est $430,557

  Not Listed For Sale

  18 Center St, Jeffersonville, NY 12748

  • 4 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 1910

  18 Center St, Jeffersonville, NY 12748

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
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  /27

  $389,999

  $40K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  21 County Road 164, Jeffersonville, NY 12748

  Charming Colonial on 3.73 Acres in Jeffersonville, NYWelcome to 21 County Road 164 — a spacious 2,464 sq. ft. Colonial set on 3.73 serene acres just minutes from the heart of Jeffersonville. With classic curb appeal, a covered front porch, and a paved driveway leading to a 2-car garage, this home blends privacy, comfort, and convenience.Inside, you’ll find a thoughtful open floor plan

  Maxine Schulte The Maxx Group LLC

  21 County Road 164, Jeffersonville, NY 12748
• 

  $730,000

  Sold Dec 18, 2025

  292 Sander Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $304/SF
  • 71 Days On Market

  Current Estimated Value $734,760

  Last Listing Agent Jeff Gardner Corcoran MH, LLC

  292 Sander Rd, Jeffersonville, NY 12748
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  Est $490,983

  Not Listed For Sale

  327 Jeffersonville North Branch Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 2000

  327 Jeffersonville North Branch Rd, Jeffersonville, NY 12748

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Thelonious Johnson Hart & Johnson Realty
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  /6

  $349,900

  • Land
  • 35 Acres
  • $9,997 per Acre

  TBD Jeffersonville North Branch Rd, Jeffersonville, NY 12748

  Discover the perfect setting for your dream home, country getaway, or recreational retreat on this beautiful 35± acre property in Western Sullivan County. A gentle rise in elevation creates stunning bucolic views and offers multiple ideal building sites to take advantage of the picturesque landscape. Featuring a wonderful blend of open meadows and wooded areas, the property is rich in character

  Carol Malek Malek Properties

  TBD Jeffersonville North Branch Rd, Jeffersonville, NY 12748
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  $380,000

  Sold Jun 29, 2026

  291 Behr Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 1 Bath
  • 1,513 Sq Ft
  • Built 1910

  Last Sold Summary

  • 2% Below List Price
  • $251/SF
  • 20 Days On Market

  Current Estimated Value $382,879

  Last Listing Agent Rosemarie DeCristofaro Callicoon Real Estate LLC

  291 Behr Rd, Jeffersonville, NY 12748
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  Est $426,892

  Not Listed For Sale

  179 Grebel Rd, Jeffersonville, NY 12748

  • 4 Beds
  • 3 Baths
  • 2,608 Sq Ft
  • Built 1990

  179 Grebel Rd, Jeffersonville, NY 12748

  Last Sold Summary

  • 206 Days On Market

  Last Listing Agent Thelonious Johnson Hart & Johnson Realty
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  /43

  $220,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  673 Hessinger and Lare Rd, Jeffersonville, NY 12748

  Enjoy space, scenery, and easy access to the best of the Sullivan Catskills with this well-maintained 3-bedroom, 2-bath mobile home set on 4.42 acres. The home features a large living room, comfortable layout, and plenty of room to relax indoors or out.A spacious deck accented by natural wood and stone invites you to take in the beautiful views and enjoy quiet mornings, outdoor meals, or

  Anna Milucky Century 21 Country Realty

  673 Hessinger and Lare Rd, Jeffersonville, NY 12748
• 

  $424,500

  Sold Jan 16, 2026

  209 Jim Stephenson Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 2004

  Last Sold Summary

  • $253/SF
  • 31 Days On Market

  Current Estimated Value $466,106

  Last Listing Agent Carol Malek Malek Properties

  209 Jim Stephenson Rd, Jeffersonville, NY 12748
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  Est $499,097

  Not Listed For Sale

  19 Esselman Rd, Jeffersonville, NY 12748

  • 2 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1940

  19 Esselman Rd, Jeffersonville, NY 12748

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Joe Freda Matthew J Freda Real Estate

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