Chatham, NY Homes

/28
$225,000
- 2 Beds
- 1.5 Baths
- 900 Sq Ft
3814 New York 203, Valatie, NY 12184

Tucked away in a peaceful, picturesque setting, this charming two-bedroom, 1.5-bath cottage offers the perfect blend of comfort and natural beauty. Perched to capture a gorgeous lake view, the home provides a true hideaway feel while still offering easy, everyday living.Inside, you'll find a cozy and inviting layout designed for relaxation, while outside, the property truly shines. Enjoy your

Ryan Lane Gilcrest Properties

3814 New York 203, Valatie, NY 12184
/17
$460,000 Sold Oct 24, 2025

16 Middlebrook Ln, Chatham, NY 12037
- 3 Beds
- 2 Baths
- 1,308 Sq Ft
- Built 1968
Last Sold Summary
- 4% Below List Price
- $352/SF
- 38 Days On Market
Last Listing Agent Tracy Tassinari Gabel Real Estate

16 Middlebrook Ln, Chatham, NY 12037

/2
Est $888,710 Not Listed For Sale

142 Riders Mills Rd, Old Chatham, NY 12136
- 3 Beds
- 2 Baths
- 2,807 Sq Ft
- Built 1840
142 Riders Mills Rd, Old Chatham, NY 12136

Last Sold Summary
- 6% Below List Price
- $338/SF
- 209 Days On Market
Last Sold Price $950,000

Last Listing Agent Rochelle Bartolo Beach & Bartolo Realtors

/26
$550,000
- 4 Beds
- 4 Baths
- 4,008 Sq Ft
2948 Cty Rt 9, Chatham, NY 12060

4,008+/- sqft 1850 Greek Revival in excellent condition w/large, open, bright rooms on first level including wood-burning fireplace and eat-in Cherry kitchen w/Shaker cabinetry - updated/bright lighting throughout- second floor offers 4 large bedrooms - 2 full / 2 half baths - period hardwood floors throughout - private rear deck... Period 2,000+ sqft POST & BEAM BARN - large driveway/parking

Natalia de Amorim PREFERRED COUNTRY PROPERTIES

2948 Cty Rt 9, Chatham, NY 12060
/33
$587,250 Sold Nov 19, 2025

9 Jones Ave, Chatham, NY 12037
- 4 Beds
- 1.5 Baths
- 1,968 Sq Ft
- Built 1880
Last Sold Summary
- 10% Below List Price
- $298/SF
- 98 Days On Market
Current Estimated Value $570,317

Last Listing Agent Lenore Packet Stone House Properties, LLC

9 Jones Ave, Chatham, NY 12037

/68
Est $1,368,464 Not Listed For Sale

540 County Route 17, Valatie, NY 12184
- 5 Beds
- 6 Baths
- 5,655 Sq Ft
- Built 1994
540 County Route 17, Valatie, NY 12184

Last Sold Summary
- 50% Below List Price
- $482/SF
- 122 Days On Market
Last Sold Price $2,725,000

Last Listing Agent Anthony D'Argenzio Houlihan Lawrence

/59
$898,000 Open Sat 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,890 Sq Ft
996 Dugway Rd, Chatham, NY 12037

OPEN HOUSE SATURDAY 11AM to 1PM. Sophistication meets rustic charm in this custom-built country retreat, perched in the hills of Spencertown on coveted Dugway Road. Set on 8.2 picturesque acres, this estate offers a rare blend of distant views, sunny meadows, and a private stream with waterfalls. The home's soul is found in its organic details: wide-plank flooring milled from the property's own

Peter Newman Beach & Bartolo Realtors

996 Dugway Rd, Chatham, NY 12037
/45
$655,000 Sold Jun 30, 2025

53 10 Broeck Rd, Chatham, NY 12037
- 2 Beds
- 2 Baths
- 1,600 Sq Ft
- Built 2006
Last Sold Summary
- 5% Above List Price
- $409/SF
- 16 Days On Market
Last Listing Agent Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

53 10 Broeck Rd, Chatham, NY 12037

/33
Est $350,060 Not Listed For Sale

50 Kinderhook St, Chatham, NY 12037
- 5 Beds
- 4 Baths
- 3,492 Sq Ft
- Built 1850
50 Kinderhook St, Chatham, NY 12037

Last Sold Summary
- 25% Above List Price
- $80/SF
- 48 Days On Market
Last Sold Price $280,000

Last Listing Agent Dennilu Sosa de La Fuente Monticello

/12
$299,000
- 3 Beds
- 2 Baths
- 1,634 Sq Ft
44 Kinderhook St, Chatham, NY 12037

Charming Village home off Kinderhook St. Big yard, big rooms and walking distance to the schools and Main St. A big living room, a big den kitchen and dining room downstairs. Three bedrooms and two full baths upstairs.

Tim McEachern Gabel Real Estate

44 Kinderhook St, Chatham, NY 12037
/38
$292,500 Sold Oct 20, 2025

3849 State Route 203, Valatie, NY 12184
- 2 Beds
- 2.5 Baths
- 1,846 Sq Ft
- Built 1920
Last Sold Summary
- 10% Below List Price
- $158/SF
- 17 Days On Market
Current Estimated Value $309,063

Last Listing Agent Peter Forget Berkshire Hathaway Home Services Blake

3849 State Route 203, Valatie, NY 12184

/25
Est $311,959 Not Listed For Sale

83 Center St, Chatham, NY 12037
- 3 Beds
- 1 Bath
- 1,496 Sq Ft
- Built 1930
83 Center St, Chatham, NY 12037

Last Sold Summary
- 30% Above List Price
- $160/SF
- 70 Days On Market
Last Sold Price $240,000

Last Listing Agent Kathryn Gerstman Empire Real Estate Firm LLC

/12
$359,000
- 3 Beds
- 1.5 Baths
- 1,280 Sq Ft
31 Thomas St, Chatham, NY 12037

c1900's Colonial w/ detached garage located off a quiet side street in the center of coveted Chatham Village NY a mere 12 miles to Hudson Amtrak and 2 hours to NYC/Manhattan. Leave your car at home as you're a short walk to Main St, schools, library, shopping and a delectable variety of eateries, from fine to relaxed dining including Yianni's Chatham House, Bimi's Canteen, Chatham Brewing, Fiesta

Natalia de Amorim Preferred Country Properties

31 Thomas St, Chatham, NY 12037
/96
$315,000 Sold Nov 04, 2025

4520 New York 66, Malden Bridge, NY 12115
- 3 Beds
- 2 Baths
- 1,648 Sq Ft
- Built 1970
Last Sold Summary
- 21% Below List Price
- $191/SF
- 74 Days On Market
Last Listing Agent Ted Banta RVW Select Properties

4520 New York 66, Malden Bridge, NY 12115

/2
Est $450,852 Not Listed For Sale

7 Harmon Heights Rd, Chatham, NY 12037
- 4 Beds
- 2 Baths
- 2,100 Sq Ft
- Built 1950
7 Harmon Heights Rd, Chatham, NY 12037

Last Sold Summary
- 37% Above List Price
- $157/SF
- 266 Days On Market
Last Sold Price $330,000

Last Listing Agent Tracy Tassinari Gabel Real Estate

/24
$325,000
- 3 Beds
- 2 Baths
- 3,000 Sq Ft
1135 New York 295, East Chatham, NY 12060

1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High

Natalia de Amorim Preferred Country Properties

1135 New York 295, East Chatham, NY 12060
/17
$220,000 Sold Jan 27, 2026

1539 County Route 28, Valatie, NY 12184
- 2 Beds
- 1 Bath
- 1,328 Sq Ft
- Built 1938
Last Sold Summary
- 12% Below List Price
- $166/SF
- 69 Days On Market
Current Estimated Value $278,307

Last Listing Agent Michael Castellano Gilcrest Properties

1539 County Route 28, Valatie, NY 12184

/34
Est $636,212 Not Listed For Sale

65 Austerlitz St, Chatham, NY 12037
- 4 Beds
- 3 Baths
- 3,200 Sq Ft
- Built 1930
65 Austerlitz St, Chatham, NY 12037

Last Sold Summary
- 59% Above List Price
- $125/SF
- 9 Days On Market
Last Sold Price $400,000

Last Listing Agent Karen Van Buren Berkshire Hathaway HomeService

/33
$525,000 Open Sat 12PM - 2PM
- 3 Beds
- 3 Baths
- 2,768 Sq Ft
524 Angel Hill Rd, Chatham, NY 12037

Welcome to your own peaceful escape, tucked away on nearly five wooded acres with sweeping hilltop views--yet just minutes from Ghent and Chatham. This spacious contemporary home offers both privacy and a strong connection to the surrounding natural beauty. Set at the end of a long driveway on 4.8 wooded acres, coming home feels like a retreat into peace and stillness. The well-maintained home

Darcey Volans The Kinderhook Group, Inc.

524 Angel Hill Rd, Chatham, NY 12037
/41
$998,000 Sold Mar 09, 2026

4174 State Route 66, Malden Bridge, NY 12115
- 3 Beds
- 2.5 Baths
- 2,986 Sq Ft
- Built 1986
Last Sold Summary
- $334/SF
- 107 Days On Market
Current Estimated Value $999,072

Last Listing Agent Martin Salerno The Kinderhook Group, Inc.

4174 State Route 66, Malden Bridge, NY 12115

Est $1,384,500 Not Listed For Sale

801 Dugway Rd, Chatham, NY 12037
- 4 Beds
- 2.5 Baths
- 2,688 Sq Ft
- Built 2001
801 Dugway Rd, Chatham, NY 12037

Last Sold Summary
- 9% Above List Price
- $475/SF
- 25 Days On Market
Last Sold Price $1,275,801

Last Listing Agent Dina Palin Houlihan Lawrence, Inc

/37
$785,000 Pending
- 4 Beds
- 4 Baths
- 2,400 Sq Ft
40 Engel Rd, Old Chatham, NY 12136

Willow Pond Retreat — 12 Acres of Serenity and Soul Welcome to Willow Pond Retreat, a soulful, private 12-acre country sanctuary where life is meant to be lived, not merely observed. Here, whispering willows frame a tranquil pond, daffodils bloom in abundance, and meandering garden paths invite you to wander among mature trees and timeless beauty. The four bedroom, four bath main home exudes

Nancy Felcetto Brown Harris Stevens Hudson

40 Engel Rd, Old Chatham, NY 12136
$3,750,000 Sold Nov 04, 2025

2705 County Route 9, East Chatham, NY 12060
- 5 Beds
- 3.5 Baths
- 4,100 Sq Ft
- Built 1793
Last Sold Summary
- 6% Below List Price
- $915/SF
- 154 Days On Market
Current Estimated Value $3,658,987

Last Listing Agent Rachel Haley Houlihan Lawrence, Inc

2705 County Route 9, East Chatham, NY 12060

/43
Est $1,322,686 Not Listed For Sale

801 Dugway Rd Unit 50, Chatham, NY 12037
- 4 Beds
- 2.5 Baths
- 2,688 Sq Ft
- Built 2001
801 Dugway Rd Unit 50, Chatham, NY 12037

Last Sold Summary
- 4% Above List Price
- $475/SF
- 23 Days On Market
Last Sold Price $1,275,801

Last Listing Agent Dina Palin Houlihan Lawrence Inc.

/51
$2,895,000
- 7 Beds
- 4 Baths
- 5,188 Sq Ft
311 County Route 13, Old Chatham, NY 12136

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

Nikki Carchedi Stone House Properties, LLC

311 County Route 13, Old Chatham, NY 12136
/65
$899,000 Sold Jul 01, 2025

186 Richmond Rd, Valatie, NY 12184
- 6 Beds
- 6 Baths
- 4,602 Sq Ft
- Built 1999
Last Sold Summary
- 8% Below List Price
- $195/SF
- 246 Days On Market
Current Estimated Value $969,347

Last Listing Agent Michael Castellano Gilcrest Properties

186 Richmond Rd, Valatie, NY 12184

/44
Est $583,314 Not Listed For Sale

944 Dugway Rd, Chatham, NY 12037
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 1972
944 Dugway Rd, Chatham, NY 12037

Last Sold Summary
- 6% Above List Price
- $304/SF
- 36 Days On Market
Last Sold Price $548,000

Last Listing Agent Peter Newman Beach & Bartolo Realtors

/16
$169,000 Pending
- 2 Beds
- 1 Bath
- 940 Sq Ft
45 Houseman Ave, Chatham, NY 12037

The sweetest little 2-bedroom, 1-bath home! Offering 940 square feet of comfortable living space with a functional layout and great natural light throughout. The home features a bright living area, cozy kitchen, and two nicely sized bedrooms, making it ideal for simple, low-maintenance living. Conveniently located in the Village of Chatham with easy access to local shops, dining, and major

Rebecca Sullivan KW Platform

45 Houseman Ave, Chatham, NY 12037
/27
$725,000 Sold Oct 30, 2025

00 Riders Mills Rd, Chatham, NY 12037
- Land
- 123.2 Acres
- $5,885 per Acre
Last Sold Summary
- 46% Below List Price
- 231 Days On Market
Last Listing Agent Laurie Ylvisaker Coldwell Banker Village Green

00 Riders Mills Rd, Chatham, NY 12037

/35
Est $620,336 Not Listed For Sale

563 Pratt Hill Rd, Chatham, NY 12037
- 3 Beds
- 2 Baths
- 1,701 Sq Ft
- Built 1830
563 Pratt Hill Rd, Chatham, NY 12037

Last Sold Summary
- 7% Above List Price
- $341/SF
- 47 Days On Market
Last Sold Price $580,000

Last Listing Agent Kirsten Stoltmann Past Member

/11
$390,000 Pending
- Land
- 45 Acres
- $8,667 per Acre
0 County Route 28-A Unit 20251992, Chatham Center, NY 12184

Commanding panoramic views in the heart of Chatham Center span the Helderbergs, Jiminy Peak and the Berkshires, and into Village of Chatham — all visible from the top of this dramatic hilltop parcel. With 5-acre zoning, the property has potential for subdivision, or the perfect opportunity to build a striking home on the hill, surrounded by sweeping, bucolic landscapes. A rare and spectacular

Scott Paladino Chatham Properties

0 County Route 28-A Unit 20251992, Chatham Center, NY 12184
/91
$1,300,000 Sold Aug 22, 2025

3 Pratt Rd, Nassau, NY 12123
- 4 Beds
- 2.5 Baths
- 3,940 Sq Ft
- Built 1800
Last Sold Summary
- 32% Below List Price
- $330/SF
- 46 Days On Market
Last Listing Agent Richard Byrne Four Seasons Sotheby's Int.

3 Pratt Rd, Nassau, NY 12123

/16
Est $551,154 Not Listed For Sale

170 Macedonia Rd, Chatham, NY 12037
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
- Built 2006
170 Macedonia Rd, Chatham, NY 12037

Last Sold Summary
- 14% Above List Price
- $242/SF
- 182 Days On Market
Last Sold Price $485,000

Last Listing Agent Natalia de Amorim Preferred Country Properties

/51
$2,750,000
- 6 Beds
- 5 Baths
- 6,000 Sq Ft
356 Slate Hill Rd, Chatham, NY 12037

A rare opportunity to own a masterfully reimagined circa-1861 post-and-beam barn, transformedinto a one-of-a-kind luxury estate set on 89 pristine acres in the heart of Columbia County. Surrounded by sweeping pastoral views, open fields, and tranquil natural beauty, this exceptional property offers privacy, scale, and timeless craftsmanship. The residence spans approximately 6,000 square feet

Anne Harrison Country Life Real Estate, LLC

356 Slate Hill Rd, Chatham, NY 12037
/26
$2,450,000 Sold Dec 03, 2025

190 Mallory Rd, Chatham, NY 12037
- Land
- 90 Acres
- $27,222 per Acre
Last Sold Summary
- 91% Below List Price
- 132 Days On Market
Last Listing Agent Anne Harrison Country Life Real Estate, LLC

190 Mallory Rd, Chatham, NY 12037

/32
Est $1,245,305 Not Listed For Sale

86 Stonewall Rd, Chatham, NY 12037
- 4 Beds
- 5 Baths
- 3,296 Sq Ft
- Built 1850
86 Stonewall Rd, Chatham, NY 12037

Last Sold Summary
- 12% Above List Price
- $338/SF
- 5 Days On Market
Last Sold Price $1,115,000

Last Listing Agent Joseph Briggs William Pitt Sothebys Intn'l

/27
$379,000 Under Contract
- 2 Beds
- 1 Bath
- 1,040 Sq Ft
336 Ashley Hill Rd, Brainard, NY 12024

Hidden Gem~This well-maintained, two- bedroom ranch-style home has so much to offer. It features a spacious living room with a wood burning fireplace and a large picture window, a light filled dining room and a well appointed kitchen.Outdoor living too with a charming front porch, a back deck perfect for dining and a hill top gazebo for quiet time. Over ten acres of wooded wonderland

Lenore Packet Stone House Properties, LLC

336 Ashley Hill Rd, Brainard, NY 12024
/27
$340,000 Sold Dec 05, 2025

4269 State Route 203, North Chatham, NY 12132
- 5 Beds
- 3 Baths
- 2,740 Sq Ft
- Built 1904
Last Sold Summary
- 29% Below List Price
- $124/SF
- 87 Days On Market
Current Estimated Value $380,882

Last Listing Agent Jack Van Buren Berkshire Hathaway Home Services Blake

4269 State Route 203, North Chatham, NY 12132

/42
Est $2,299,415 Not Listed For Sale

284 Reed Rd, Chatham, NY 12037
- 5 Beds
- 3.5 Baths
- 4,350 Sq Ft
- Built 1985
284 Reed Rd, Chatham, NY 12037

Last Sold Summary
- 31% Above List Price
- $405/SF
- 42 Days On Market
Last Sold Price $1,762,000

Last Listing Agent Anjali Arora Corcoran Country Living - Hud

/42
$850,000
- 3 Beds
- 2.5 Baths
- 2,395 Sq Ft
10 7 Bridges Rd, Old Chatham, NY 12136

Nestled on 12 private acres in the serene hamlet of Old Chatham, New York, this charming log cabin offers the perfect blend of rustic appeal and modern comfort, with breathtaking panoramic views of the Catskill Mountains that change with the seasons from vibrant autumn foliage to snow capped peaks in winter. The warm, inviting main home features 3 spacious bedrooms and 2 full baths, highlighted

Tyler Bervy Stone House Properties, LLC

10 7 Bridges Rd, Old Chatham, NY 12136

Showing Results 121 - 160, Page 4 of 18

New York Columbia County Chatham

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