Chatham, NY Homes

/37
$215,000
- 2 Beds
- 1 Bath
- 736 Sq Ft
26 Houseman Ave, Chatham, NY 12037

Looking for a starter home and willing to put in some sweat equity? Or looking to downsize and have the resources to throw at a renovation? This 2 bedroom, 1 bath, 736 square foot, bungalow built in 1945 may just be what you have been waiting for. It's a project no doubt but one that is manageable. It's being sold as is, but it has strong bones and working mechanical systems. There are hardwood

Jennifer Sesma Beach & Bartolo Realtors

26 Houseman Ave, Chatham, NY 12037
$725,000

Sold Oct 30, 2025

0 Riders Mills Rd, Old Chatham, NY 12136
- Land
- 123.2 Acres
- $5,885 per Acre
Last Sold Summary
- 46% Below List Price
- 222 Days On Market
Last Listing Agent Christine Hinz Coldwell Banker Village Green

0 Riders Mills Rd, Old Chatham, NY 12136

/2
Est $803,503

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
- 209 Days On Market

/33
$2,450,000
- 3 Beds
- 2.5 Baths
- 3,100 Sq Ft
53 May Ln, Chatham, NY 12037

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the

Jeb Hart Licensed as Henry Hart Corcoran Country Living

53 May Ln, Chatham, NY 12037
/94
$2,300,000

Sold Dec 29, 2025

189 Sutherland Rd, Valatie, NY 12184
- 4 Beds
- 4.5 Baths
- 5,760 Sq Ft
- Built 2005
Last Sold Summary
- 8% Below List Price
- $399/SF
- 48 Days On Market
Current Estimated Value $2,474,912

Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.

189 Sutherland Rd, Valatie, NY 12184

/68
Est $1,449,562

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
- 122 Days On Market

/69
$1,599,000
- 6 Beds
- 5 Baths
- 5,364 Sq Ft
20 Stony Knoll, Valatie, NY 12184

Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+ square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6

Margaret Guerra Trevett Group LLC

20 Stony Knoll, 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

/33
Est $378,415

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
- 48 Days On Market

/26
$550,000

Pending
- 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 $566,735

Last Listing Agent Lenore Packet Stone House Properties, LLC

9 Jones Ave, Chatham, NY 12037

/25
Est $343,339

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
- 70 Days On Market

/45
$369,900
- 3 Beds
- 1 Bath
- 1,301 Sq Ft
331 Ashley Hill Rd, Brainard, NY 12024

Welcome to this charming 3-bedroom, 1-bath ranch nestled in the heart of Columbia County. Beautiful flower beds with winding stone pathways and a welcoming front porch create the perfect first impression. Inside, natural sunlight fills the home, highlighting the spacious dining area and inviting living room featuring a cozy wood-burning stove. The kitchen is equipped with an induction cooktop,

Mary Martin-Canova Gabler Realty, LLC

331 Ashley Hill Rd, Brainard, NY 12024
/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

/2
Est $468,983

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
- 266 Days On Market

/20
$595,000
- 5 Beds
- 2 Baths
- 1,872 Sq Ft
52 Church St, Chatham, NY 12037

Welcome to 52 Church Street, a c.1900 home set on a generously-sized quarter acre lot in the Village of Philmont. Enter through a large mudroom flanked with windows. A stylish living room flows seamlessly to a large kitchen overlooking the yard. Numerous windows and a door leading to the backyard flood the kitchen space with light. A hall leads to a second kitchen, bedroom and full bath, perfect

MATTHEW CAREY Rouse + Co Real Estate

52 Church St, Chatham, NY 12037
/28
$225,102

Sold Jun 09, 2026

3814 New York 203, Valatie, NY 12184
- 2 Beds
- 1.5 Baths
- 900 Sq Ft
- Built 1910
Last Sold Summary
- $250/SF
- 3 Days On Market
Last Listing Agent Ryan Lane Gilcrest Properties

3814 New York 203, Valatie, NY 12184

/34
Est $599,576

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
- 9 Days On Market

/61
$375,000
- 5 Beds
- 3 Baths
- 3,146 Sq Ft
22 Spring St, Chatham, NY 12037

Fully Rented Income Property in the heart of Chatham Village NY. 3 non-owner-occupied units. All photos taken pre-occupancy. 5BRS total, 3 full baths. Municipal water/sewer. Private off-street parking. Total acreage for 2 parcels (66.6-1-45 is 0.23 acre and 66.6-1-48 is 0.24 acre). Total tax figures below include both parcels. A minute drive to Main St and all shops, theater, pubs, restaurants,

Natalia de Amorim Preferred Country Properties

22 Spring 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 $336,593

Last Listing Agent Peter Forget Berkshire Hathaway Home Services Blake

3849 State Route 203, Valatie, NY 12184

Est $1,440,500

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
- 25 Days On Market

/63
$898,000

Under Contract
- 3 Beds
- 2 Baths
- 1,890 Sq Ft
996 Dugway Rd, Chatham, NY 12037

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 timber and a soaring

Peter Newman Beach & Bartolo Realtors

996 Dugway Rd, 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

/43
Est $1,270,869

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
- 23 Days On Market

/53
$599,000

$150K PRICE DROP
- 9 Beds
- 9 Baths
- 6,935 Sq Ft
1121 New York 295, East Chatham, NY 12060

2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers - properties not sold separately. Assessment/tax figures herein reflect total due for

Natalia de Amorim Preferred Country Properties

1121 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 $265,106

Last Listing Agent Michael Castellano Gilcrest Properties

1539 County Route 28, Valatie, NY 12184

/44
Est $593,740

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
- 36 Days On Market

/12
$299,000

Pending
- 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
/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 $979,194

Last Listing Agent Martin Salerno The Kinderhook Group, Inc.

4174 State Route 66, Malden Bridge, NY 12115

/35
Est $609,466

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
- 47 Days On Market

/12
$359,000

Pending
- 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. 12 miles to Hudson Amtrak, 2 hours to NYC/Manhattan. House rented. Photos pre tenant occupancy. 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,

Natalia de Amorim Preferred Country Properties

31 Thomas St, Chatham, NY 12037
$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 $3,982,223

Last Listing Agent Rachel Haley Compass Greater NY, LLC

2705 County Route 9, East Chatham, NY 12060

/16
Est $558,068

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
- 182 Days On Market

/30
$655,000
- 3 Beds
- 1 Bath
- 1,400 Sq Ft
2318 County Route 9, East Chatham, NY 12060

Tucked down a quiet country road, 2318 County Route 9 is the kind of place that feels like it's been waiting for you. Set on over five acres, this three bedroom, one bath cottage is thoughtfully designed from the inside out, every corner telling a story, every detail chosen with care.Sunlight pours through every window, framing the beauty of lush gardens and the natural world just beyond the

Shaina Marron Houlihan Lawrence Inc.

2318 County Route 9, East Chatham, NY 12060
/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 $973,902

Last Listing Agent Michael Castellano Gilcrest Properties

186 Richmond Rd, Valatie, NY 12184

/32
Est $1,215,083

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
- 5 Days On Market

/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
/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

/42
Est $1,958,788

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
- 42 Days On Market

/25
$625,000
- 5 Beds
- 3.5 Baths
- 2,982 Sq Ft
158 Hudson Ave, Chatham, NY 12037

Experience the perfect blend of 1900s farmhouse charm and contemporary comfort in the heart of Chatham. This thoughtfully updated farmhouse features an expansive open-concept kitchen and great room designed for seamless entertaining. Filled with natural light, the great room includes a wood burning stove and cozy window seat. Relax in the light-drenched enclosed front porch or enjoy dining on the

Beth Cozzolino Gabel Real Estate

158 Hudson Ave, Chatham, NY 12037

Showing Results 121 - 160, Page 4 of 18

New York Columbia County Chatham

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Chatham, NY Homes

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