Jeffersonville, NY Homes

/25
$350,000
- 7 Beds
- 4 Baths
- 3,376 Sq Ft
5041 New York 52, Jeffersonville, NY 12748

Just outside of the quaint hamlet of Jeffersonville in the heart of Sullivan County is this 7- bedroom farmhouse on a .46 cleared and level lot just waiting for someone to add their finishing touches.Home features hard wood flooring through out the main floor. Open concept kitchen, living/dining area. First floor suite with en suite full bathrooms, second full bathrooms on main level along with

Jason Grossman

Keller Williams Hudson Valley

(845) 668-6136

5041 New York 52, Jeffersonville, NY 12748
$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

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
- $372/SF
- 48 Days On Market
Last Sold Price $735,000

Last Listing Agent William Baldwin Country House Realty Inc

/28
$224,000 Pending
- 3 Beds
- 1.5 Baths
- 1,148 Sq Ft
5010 State Route 52, Jeffersonville, NY 12748

1920s Two story farmhouse! This home welcomes you with it's rocking chair front porch which leads to the open dining and kitchen area with an extra space that could be a mud/laundry room or a big pantry, living room with a lot of windows and a half bath, high ceilings. The second level boasts 3 bedrooms and a full tiled bath with a tub. There is an attic and a basement. Nice back yard! ***New

Dawn Curreri

Eagle Valley Realty

(845) 409-8770

5010 State Route 52, Jeffersonville, NY 12748
$240,000 Sold Jul 11, 2025

5044 State Route 52, Jeffersonville, NY 12748
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Built 1951
Last Sold Summary
- 15% Below List Price
- $240/SF
- 34 Days On Market
Current Estimated Value $242,269

Last Listing Agent David Elder Carole Edwards Realty

5044 State Route 52, Jeffersonville, NY 12748

Est $420,343 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
- 11% Above List Price
- $198/SF
- 40 Days On Market
Last Sold Price $380,000

Last Listing Agent Brian Garber Land and Water Realty LLC

/28
$625,000
- 2 Beds
- 2 Baths
- 1,560 Sq Ft
47 Hemmer Rd, Jeffersonville, NY 12748

Set against a backdrop of sweeping pastoral and mountain views, this thoughtfully renovated rustic barn blends timeless character with modern comfort in all the right ways. With its striking silhouette, hand-hewn beams, and sliding doors that frame the landscape like a living painting, the home captures the romance of its agricultural past while offering a turnkey retreat designed for effortless

Catherine Quintard

Compass Greater NY, LLC

(845) 605-7846

47 Hemmer Rd, Jeffersonville, NY 12748
$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 $312,243

Last Listing Agent David Luczyski Resort Realty

521 Hessinger and Lare Rd, Jeffersonville, NY 12748

/33
Est $306,550 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
- 36% Above List Price
- $144/SF
- 43 Days On Market
Last Sold Price $225,000

Last Listing Agent Lindsay Stevens eXp Realty

/42
$568,888
- 4 Beds
- 3 Baths
- 1,663 Sq Ft
4741 State Route 52, Jeffersonville, NY 12748

Paradise Found!! Walk into this newly renovated home and fall in love. Experience the ultimate lakeside living in this beautifully renovated home, boasting breathtaking lake views and watching the sunset right from your newly constructed back deck. Unwind after a long day enjoying the serene and peaceful unobstructed lake views. With four spacious bedrooms and three modern bathrooms, this

Carol Malek Malek Properties

4741 State Route 52, Jeffersonville, NY 12748
$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 $329,675

Last Listing Agent Dean Diltz Keller Williams Realty

242 Callicoon Center Rd, Jeffersonville, NY 12748

Est $533,378 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
- 6% Above List Price
- $208/SF
- 84 Days On Market
Last Sold Price $505,000

Last Listing Agent William Baldwin Country House Realty Inc

/29
$699,999
- 10 Beds
- 4 Baths
- 3,431 Sq Ft
495 Swiss Hill Rd N, Jeffersonville, NY 12748

Dreaming f the past? Want to find your way back home? Here it is! One old style boarding house and former evergreen tree farm with plenty of room to create a life "Inn".This one of a kind older style home is a rare find! Driving into this stunner, through the elegant evergreens sits a piece of history. Fully loaded with old time woodwork an amazing post and beam barn and THREE green houses.

Diane Butler Diane C. Butler

495 Swiss Hill Rd N, Jeffersonville, NY 12748
/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 $597,304

Last Listing Agent Kayla Camstra Anatole House LLC

57 Old Taylor Rd, Jeffersonville, NY 12748

Est $324,028 Not Listed For Sale

24 Terrace Ave, Jeffersonville, NY 12748
- 4 Beds
- 1 Bath
- 1,754 Sq Ft
- Built 1935
24 Terrace Ave, Jeffersonville, NY 12748

Last Sold Summary
- 8% Above List Price
- $171/SF
- 41 Days On Market
Last Sold Price $299,900

Last Listing Agent Harley Hendrix Coldwell Banker Timberland

/37
$525,000
- 4 Beds
- 2 Baths
- 4,000 Sq Ft
301 & 305 Hust, Jeffersonville, NY 12748

Remarkable! 12 plus acres. Step into history with this extraordinary 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 include rolling

Diane Butler Diane C. Butler

301 & 305 Hust, Jeffersonville, NY 12748
$419,760 Sold Apr 09, 2025

90 Hubert Rd Unit 13, Jeffersonville, NY 12748
- 2 Beds
- 1.5 Baths
- 845 Sq Ft
- Built 1980
Last Sold Summary
- $497/SF
- 222 Days On Market
Current Estimated Value $323,367

Last Listing Agent Dawn Curreri Eagle Valley Realty

90 Hubert Rd Unit 13, Jeffersonville, NY 12748

Est $597,810 Not Listed For Sale

284 Hust Rd, Jeffersonville, NY 12748
- 3 Beds
- 2 Baths
- 1,378 Sq Ft
- Built 1992
284 Hust Rd, Jeffersonville, NY 12748

Last Sold Summary
- 16% Below List Price
- $515/SF
- 35 Days On Market
Last Sold Price $710,000

Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc

/19
$500,000 Pending
- 3 Beds
- 2 Baths
- 2,690 Sq Ft
24 Birch Ridge Rd, Jeffersonville, NY 12748

.

Desiree Beecham River Realty Services, Inc.

24 Birch Ridge Rd, Jeffersonville, NY 12748
$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 $924,127

Last Listing Agent Dominique Jenkins Keller Williams Hudson Valley

281 Hubert Rd, Jeffersonville, NY 12748

Est $256,000 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
- 11% Above List Price
- $166/SF
- 58 Days On Market
Last Sold Price $230,000

Last Listing Agent Dara Barr Keller Williams Upstate NYProp

/35
$264,900 Pending
- 3 Beds
- 2 Baths
- 2,320 Sq Ft
2 County Road 164, Jeffersonville, NY 12748

Single-family home with legal accessory apartment. Live in one and rent the other. Large spacious two-family home with in-ground pool and sauna, tons of potential, and a giant detached 2/3 car garage. Just a short stroll from the charm of downtown Jeffersonville and minutes from the world-renowned Bethel Woods Center for the Arts, this beautifully appointed Colonial home artfully balances

Barbara Allen HomeSmart Homes & Estates

2 County Road 164, Jeffersonville, NY 12748
$599,000 Sold Jul 29, 2025

157 Sander Rd, Jeffersonville, NY 12748
- 3 Beds
- 2 Baths
- 1,216 Sq Ft
- Built 1987
Last Sold Summary
- $493/SF
- 15 Days On Market
Current Estimated Value $621,208

Last Listing Agent Jill Borenstein Anatole House LLC

157 Sander Rd, Jeffersonville, NY 12748

Est $260,936 Not Listed For Sale

34 Mill St, Jeffersonville, NY 12748
- 6 Beds
- 2.5 Baths
- 2,660 Sq Ft
- Built 1900
34 Mill St, Jeffersonville, NY 12748

Last Sold Summary
- 18% Above List Price
- $83/SF
- 71 Days On Market
Last Sold Price $221,000

Last Listing Agent Dominique Jenkins Keller Williams Hudson Valley

/49
$899,000
- 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
$485,000 Sold May 02, 2025

327 Jeffersonville North Branch Rd, Jeffersonville, NY 12748
- 3 Beds
- 3 Baths
- 3,000 Sq Ft
- Built 2000
Last Sold Summary
- 3% Below List Price
- $162/SF
- 57 Days On Market
Current Estimated Value $505,018

Last Listing Agent Thelonious Johnson Hart & Johnson Realty

327 Jeffersonville North Branch Rd, Jeffersonville, NY 12748

Est $392,361 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
- 3% Above List Price
- $235/SF
- 18 Days On Market
Last Sold Price $380,000

Last Listing Agent Jill Halpern-Steingart Rieber Realty Inc

/27
$389,999
- 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
$162,000 Sold Jun 27, 2025

50 Jefferson Ave, Jeffersonville, NY 12748
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1920
Last Sold Summary
- 29% Below List Price
- $141/SF
- 335 Days On Market
Current Estimated Value $172,807

Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc

50 Jefferson Ave, Jeffersonville, NY 12748

Est $429,604 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
- 5% Below List Price
- $200/SF
- 12 Days On Market
Last Sold Price $450,000

Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc

/30
$985,000
- 3 Beds
- 2.5 Baths
- 2,700 Sq Ft
233 Goldsmith Rd, Jeffersonville, NY 12748

Alive with style and attitude, The Smithwood House redefines modern retreat living. This brand-new construction blends cutting-edge architecture with a cool, sophisticated vibe, offering an alternative to bland contractor grade shoeboxes. Clean architectural lines, light wells, an open stairwell and loft, and expansive windows, elevate the home’s stunning, one-of-a-kind design. Every detail has

Jonathan Minerick HomeCoin.com

233 Goldsmith Rd, Jeffersonville, NY 12748
$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 $294,377

Last Listing Agent Susan Busing Matthew J Freda Real Estate

31 Erlemann Rd, Jeffersonville, NY 12748

Est $231,979 Not Listed For Sale

5030 State Route 52, Jeffersonville, NY 12748
- 3 Beds
- 1.5 Baths
- 1,492 Sq Ft
- Built 1930
5030 State Route 52, Jeffersonville, NY 12748

Last Sold Summary
- 185% Above List Price
- $55/SF
- 509 Days On Market
Last Sold Price $81,500

Last Listing Agent Christopher Rose REALHome Services & Solutions

/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
$395,000 Sold May 20, 2025

119 Behr Rd Unit TR17, Jeffersonville, NY 12748
- 3 Beds
- 2.5 Baths
- 2,016 Sq Ft
- Built 2005
Last Sold Summary
- 12% Below List Price
- $196/SF
- 260 Days On Market
Current Estimated Value $421,839

Last Listing Agent Jean Dermer Barbanti Group

119 Behr Rd Unit TR17, Jeffersonville, NY 12748

Est $427,495 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
- 7% Above List Price
- $153/SF
- 206 Days On Market
Last Sold Price $400,000

Last Listing Agent Thelonious Johnson Hart & Johnson Realty

/5
$249,000
- Land
- 31 Acres
- $8,032 per Acre
4861 Swiss Hill, Jeffersonville, NY 12748

Private and Pristine! 31.68 acres of mature evergreen tree's will welcome you home. Build your future dream in the heart of the country. Close to the beautiful villiage of Jeffersonville and only a stones thow to the Delaware River National Park!

Diane Butler Diane C. Butler

4861 Swiss Hill, Jeffersonville, NY 12748
$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 $524,155

Last Listing Agent Dawn Curreri Eagle Valley Realty

807 Swiss Hill Rd N, Jeffersonville, NY 12748

Est $391,656 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
- $227/SF
- 40 Days On Market
Last Sold Price $391,500

Last Listing Agent Joe Freda Matthew J Freda Real Estate

/26
$225,000
- 4 Beds
- 1 Bath
- 1,740 Sq Ft
7 Old Route 52, Jeffersonville, NY 12748

4 Bedroom Cape. Fantastic Location in Jeffersonville, right on the creek! Fish in your back yard! It doesn't get any better than this. This Sullivan Co. property consists of 2 lots (1.93 Ac & .34 Ac.) Total 2.27 Acs. Bordering 500 ft of the East Branch of Callicoon Creek -one of the best trout streams In NYS. Old Rte 52 is Your Driveway & is maintained by the Town! Located at the corner of Rt 52

Siobhan Scanlan Win Morrison Realty-K

7 Old Route 52, Jeffersonville, NY 12748

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New York Sullivan County Jeffersonville

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