Pine Plains, NY Homes

/5
$140,000
- Land
- 1.5 Acres
- $93,333 per Acre
25 Five Roses E, Ancram, NY 12502

Ready to build, this 1.5-acre parcel is located on a peaceful country road in the scenic town of Ancram, Columbia County, New York. Board of Health approval is already in place for a four-bedroom residence, saving valuable time in the building process. The property is well-prepared with an installed septic system, existing well, driveway, and underground electric service run from the road to a

Richard Brenner RICH BRENNER REALTY LLC

25 Five Roses E, Ancram, NY 12502
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$520,000 Sold Dec 30, 2025

30 N Main St, Pine Plains, NY 12567
- 4 Beds
- 2.5 Baths
- 3,180 Sq Ft
- Built 1880
Last Sold Summary
- 13% Below List Price
- $164/SF
- 99 Days On Market
Current Estimated Value $545,062

Last Listing Agent Arleen Shepley Elyse Harney Real Estate

30 N Main St, Pine Plains, NY 12567

Est $2,139,487 Not Listed For Sale

729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
- 4 Beds
- 3 Baths
- 4,361 Sq Ft
- Built 1798
729 Cold Spring Rd Unit 731, Stanfordville, NY 12581

Last Sold Summary
- 32% Above List Price
- $373/SF
- 50 Days On Market
Last Sold Price $1,625,000

Last Listing Agent OLIVER BROWN Houlihan Lawrence Inc.

/18
$239,900
- 3 Beds
- 2 Baths
- 1,820 Sq Ft
16 Ryan Rd, Pine Plains, NY 12567

Adorable 3-bedroom ranch ready for you to move in. Ideal for First-time home buyers or anyone tired of paying rent. Bright eat in kitchen, living room with fireplace. door that leads out to large back yard. Close to schools, Village of Pine Plains and TSP. County living at its best. Additional Information: HeatingFuel:Oil Above Ground,

Joseph Lukic Compass Greater NY, LLC

16 Ryan Rd, Pine Plains, NY 12567
$250,000 Sold Apr 01, 2025

97 North Rd, Red Hook, NY 12571
- 2 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1951
Last Sold Summary
- 2% Below List Price
- $200/SF
- 77 Days On Market
Current Estimated Value $262,232

Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

97 North Rd, Red Hook, NY 12571

/3
Est $362,362 Not Listed For Sale

599 Bean River Rd, Millerton, NY 12546
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
- Built 1950
599 Bean River Rd, Millerton, NY 12546

Last Sold Summary
- 8% Above List Price
- $258/SF
- 53 Days On Market
Last Sold Price $335,000

Last Listing Agent Christopher Virtuoso Keller Williams Realty HV Nort

/20
$410,000
- 3 Beds
- 2.5 Baths
- 2,688 Sq Ft
73 Meusel Rd, Pine Plains, NY 12567

A large and roomy home is for sale in the charming Village of Pine Plains, NY. Situated in a residential neighborhood with views of the surrounding hills, the home sits well back from the road on a corner lot. On the first floor are two living rooms, a dining room, an eat-in kitchen, a powder room and a mudroom. Off the kitchen is a partially finished three season room and a deck. Upstairs is the

David Norman Hall Houlihan Lawrence, Inc

73 Meusel Rd, Pine Plains, NY 12567
$1,975,000 Sold Mar 17, 2025

0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503
- 4 Beds
- 3 Baths
- 4,144 Sq Ft
- Built 2000
Last Sold Summary
- 21% Below List Price
- $477/SF
- 428 Days On Market
Last Listing Agent Neil Charles Neil Charles Real Estate, LLC

0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

Est $487,251 Not Listed For Sale

3469 Route 199, Pine Plains, NY 12567
- 3 Beds
- 2.5 Baths
- 2,272 Sq Ft
- Built 1983
3469 Route 199, Pine Plains, NY 12567

Last Sold Summary
- 39% Above List Price
- $154/SF
- 146 Days On Market
Last Sold Price $350,000

Last Listing Agent Daniel Balassone VYLLA Home

/31
$549,000
- Land
- 43.69 Acres
- $12,566 per Acre
Tbd Hicks Hill Rd, Pine Plains, NY 12567

Enjoy nature on your own 43 scenic acres located on Hicks Hill Road and additional access from Knob Hill Road, which is across from apprx 600 acres of protected land that can not be developed offering exceptional long term privacy. A versatile existing barn provides potential for a variety of uses. With over 1,400 feet of road frontage on Hicks Hill Road and electric available on the property,

Jeannine Simmons Corcoran Country Living

Tbd Hicks Hill Rd, Pine Plains, NY 12567
$2,510,460 Sold Aug 06, 2025

53 Brooks Rd, Pine Plains, NY 12567
- 6 Beds
- 5.5 Baths
- 4,000 Sq Ft
- Built 1850
Last Sold Summary
- 16% Below List Price
- $628/SF
- 300 Days On Market
Last Listing Agent Anthony D'Argenzio Houlihan Lawrence, Inc

53 Brooks Rd, Pine Plains, NY 12567

/43
Est $722,297 Not Listed For Sale

3327 Route 199, Pine Plains, NY 12567
- 4 Beds
- 3 Baths
- 3,000 Sq Ft
- Built 1787
3327 Route 199, Pine Plains, NY 12567

Last Sold Summary
- 9% Above List Price
- $220/SF
- 49 Days On Market
Last Sold Price $660,000

Last Listing Agent Audrey Winslow Houlihan Lawrence, Inc.

/35
$18,750,000 Pending
- 11 Beds
- 7.5 Baths
- 7,500 Sq Ft
461 Silvernails Rd, Pine Plains, NY 12567

Ingadi, the Zulu word for garden, is a true legacy compound all set within 127 acres of pristine land with a total of 11 bedrooms across four distinct residential structures. A magical journey of the senses where the Roeliff Jansen Kill and the Shekomeko Creek merge, ensuring sustainability while creating one of the most spiritually powerful and visually stunning experiences in the Hudson Valley.

Byron Anderson Compass Greater NY, LLC

461 Silvernails Rd, Pine Plains, NY 12567
$515,000 Sold Oct 27, 2025

43 Stissing Mountain Dr, Pine Plains, NY 12567
- 3 Beds
- 1.5 Baths
- 1,862 Sq Ft
- Built 1983
Last Sold Summary
- 21% Below List Price
- $277/SF
- 93 Days On Market
Current Estimated Value $535,173

Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

43 Stissing Mountain Dr, Pine Plains, NY 12567

/2
Est $466,605 Not Listed For Sale

6 Sheldon Dr, Pine Plains, NY 12567
- 3 Beds
- 2 Baths
- 1,310 Sq Ft
- Built 2006
6 Sheldon Dr, Pine Plains, NY 12567

Last Sold Summary
- 30% Below List Price
- $275/SF
Last Sold Price $360,000

Last Listing Agent Larry Havens Havens Real Estate

/50
$8,475,000
- 6 Beds
- 7.5 Baths
- 12,418 Sq Ft
367 Prospect Hill Rd, Ancramdale, NY 12503

First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation,

George Langa Houlihan Lawrence Inc.

367 Prospect Hill Rd, Ancramdale, NY 12503
$595,000 Sold Feb 19, 2026

100 Knob Hill Rd, Stanfordville, NY 12581
- 3 Beds
- 1.5 Baths
- 1,725 Sq Ft
- Built 1965
Last Sold Summary
- 3% Above List Price
- $345/SF
- 27 Days On Market
Current Estimated Value $584,535

Last Listing Agent Kimberly Wickes R. Ferris Real Estate, LLC

100 Knob Hill Rd, Stanfordville, NY 12581

Est $667,234 Not Listed For Sale

2067 Route 83, Pine Plains, NY 12567
- 3 Beds
- 2 Baths
- 1,640 Sq Ft
- Built 1810
2067 Route 83, Pine Plains, NY 12567

Last Sold Summary
- 16% Above List Price
- $351/SF
- 53 Days On Market
Last Sold Price $575,000

Last Listing Agent Kornelia Tamm BHHS Hudson Valley Properties

/6
$139,000
- Land
- 4.6 Acres
- $30,217 per Acre
620 Bean River Rd, Pine Plains, NY 12567

Great opportunity for 1 residence (property in Hamlet Zone, possibley subdividable) Approved septice design and existing shared driveway. Newly renovated home on adjoining lot. 8 acre lot on the other side also available for purchase. Owner will consider 3 year financing with substantial downpayment.

David Birch Barns and Farms Realty LLC

620 Bean River Rd, Pine Plains, NY 12567
$350,000 Sold Dec 31, 2025

0 New York 82 Unit KEYM420064, Stanfordville, NY 12581
- Land
- 5.02 Acres
- $69,721 per Acre
Last Sold Summary
- 7% Below List Price
- 725 Days On Market
Last Listing Agent Steve Bruman Corcoran Country Living

0 New York 82 Unit KEYM420064, Stanfordville, NY 12581

/16
Est $264,763 Not Listed For Sale

3066 Church St, Pine Plains, NY 12567
- 3 Beds
- 2 Baths
- 1,416 Sq Ft
- Built 1870
3066 Church St, Pine Plains, NY 12567

Last Sold Summary
- 39% Below List Price
- $134/SF
- 52 Days On Market
Last Sold Price $190,000

Last Listing Agent Brad Rebillard Dutchess Country Realty, Inc.

/21
$255,000 Pending
- 3 Beds
- 2 Baths
- 1,037 Sq Ft
22-28 Ryan Rd, Pine Plains, NY 12567

Looking for a piece of property for a great low price? Looking for two homes for the price of one? Looking for a good-sized plot of land? Here is a great opportunity for you to acquire one manufactured home, and one mobile home, both on the same plot of land with 2.30 acres! Investors will consider this property for rental income or tear-down and rebuild. Currently, the main manufactured home has

Jorge Lugo Real Broker NY LLC

22-28 Ryan Rd, Pine Plains, NY 12567
$307,500 Sold Mar 20, 2025

3088 Church St, Pine Plains, NY 12567
- 3 Beds
- 2 Baths
- 2,328 Sq Ft
- Built 1872
Last Sold Summary
- 10% Below List Price
- $132/SF
- 43 Days On Market
Current Estimated Value $334,544

Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

3088 Church St, Pine Plains, NY 12567

Est $400,433 Not Listed For Sale

3018 Church St, Pine Plains, NY 12567
- 3 Beds
- 2 Baths
- 1,703 Sq Ft
- Built 1875
3018 Church St, Pine Plains, NY 12567

Last Sold Summary
- 27% Above List Price
- $185/SF
- 27 Days On Market
Last Sold Price $315,000

Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

/38
$489,000
- 4 Beds
- 2.5 Baths
- 2,040 Sq Ft
82 Lake Rd, Pine Plains, NY 12567

A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite

MICHELLE FRANCESE Corcoran Country Living

82 Lake Rd, Pine Plains, NY 12567
$135,000 Sold Jan 23, 2026

58 Britton St, Pine Plains, NY 12567
- Land
- 0.93 Acre
- $145,161 per Acre
Last Sold Summary
- 10% Below List Price
- 94 Days On Market
Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

58 Britton St, Pine Plains, NY 12567

Est $488,284 Not Listed For Sale

17 Smith St, Pine Plains, NY 12567
- 6 Beds
- 2,550 Sq Ft
- Built 1952
17 Smith St, Pine Plains, NY 12567

Last Sold Summary
- 15% Above List Price
- $167/SF
- 88 Days On Market
Last Sold Price $425,000

Last Listing Agent Thomas Zengen Thomas Zengen

/15
$1,995,000
- Land
- 150.48 Acres
- $13,258 per Acre
1533-1539 Route 83, Pine Plains, NY 12567

Discover a rare 150-acre estate in one of the Hudson Valley’s most coveted farmland corridors. This property offers a private building site accessed by a scenic driveway and showcases the best of Hudson Valley living where nature meets luxury. Enjoy panoramic views of protected farmland, Shekomeko Creek, and wooded mountains. Surrounded by conservation land, this estate ensures lasting privacy

John Panzer Elyse Harney Real Estate

1533-1539 Route 83, Pine Plains, NY 12567
/38
$390,000 Sold Apr 04, 2025

717 County Route 7, Pine Plains, NY 12567
- 3 Beds
- 2.5 Baths
- 1,850 Sq Ft
- Built 1870
Last Sold Summary
- 2% Below List Price
- $211/SF
- 49 Days On Market
Current Estimated Value $836,629

Last Listing Agent Brad Rebillard Dutchess Country Realty, Inc.

717 County Route 7, Pine Plains, NY 12567

Est $564,658 Not Listed For Sale

7760 S Main St, Pine Plains, NY 12567
- 3 Beds
- 2 Baths
- 1,643 Sq Ft
- Built 1960
7760 S Main St, Pine Plains, NY 12567

Last Sold Summary
- 4% Below List Price
- $359/SF
- 19 Days On Market
Last Sold Price $590,000

Last Listing Agent CHRISTINE BATES William Pitt

/3
$104,000
- Land
- 4 Acres
- $26,000 per Acre
Knob Hill Rd N Knob Hill Rd, Stanfordville, NY 12581

Beautiful Lot. Located in an established residential area in the town of Milan. Surrounded by well maintained homes. Minutes to Taconic State Parkway for easy commute. Terrain is partially cleared and partially wooded.Topography is level with some sloping. There is a driveway roughed in.

Peggy Santamorena Houlihan Lawrence Inc.

Knob Hill Rd N Knob Hill Rd, Stanfordville, NY 12581
/32
$280,000 Sold Aug 01, 2025

1283 County Route 7, Ancram, NY 12502
- 3 Beds
- 1.5 Baths
- 1,368 Sq Ft
- Built 1880
Last Sold Summary
- 6% Below List Price
- $205/SF
- 73 Days On Market
Current Estimated Value $299,776

Last Listing Agent Margaret Clarke Corcoran Country Living

1283 County Route 7, Ancram, NY 12502

Est $434,738 Not Listed For Sale

17 Farview Ave, Pine Plains, NY 12567
- 4 Beds
- 1.5 Baths
- 2,165 Sq Ft
- Built 1948
17 Farview Ave, Pine Plains, NY 12567

Last Sold Summary
- 26% Above List Price
- $159/SF
- 10 Days On Market
Last Sold Price $345,000

Last Listing Agent Brad Rebillard DUTCHESS COUNTRY REALTY INC. M

/20
$1,250,000
- 4 Beds
- 2.5 Baths
- 3,360 Sq Ft
216 North Rd, Red Hook, NY 12571

?? 216 North Rd, Red Hook, NY 12571 Offered on 119 Acres – A Rare Hudson Valley Retreat Experience the best of country living on this stunning 119-acre estate bordering a state park, offering endless opportunities for outdoor recreation and peaceful privacy. This completely renovated 4-bedroom, 2-bath home combines modern comfort with the beauty of nature. Every detail has been updated — move-in

Bill Flood Houlihan Lawrence Inc.

216 North Rd, Red Hook, NY 12571
$370,000 Sold Apr 07, 2025

0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502
- Land
- 36.66 Acres
- $10,093 per Acre
Last Sold Summary
- 6% Below List Price
- 85 Days On Market
Last Listing Agent Andrew Gates Houlihan Lawrence Inc.

0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502

Est $476,137 Not Listed For Sale

35 Pine St, Pine Plains, NY 12567
- 4 Beds
- 2 Baths
- 2,884 Sq Ft
- Built 1890
35 Pine St, Pine Plains, NY 12567

Last Sold Summary
- 33% Above List Price
- $124/SF
- 46 Days On Market
Last Sold Price $357,000

Last Listing Agent Sean Eidle BHHS Hudson Valley Properties

/25
$869,900 Pending
- 5 Beds
- 3.5 Baths
- 5,650 Sq Ft
19 Friendship Ln, Red Hook, NY 12571

Welcome to your private oasis and come enjoy this 3 bedroom 2.5 bath Colonial situated on 5 plus acres. The home also features an in law unit above the garage which has 2 additional bedrooms, a full bathroom, a galley kitchen and open living room. The home is very close to the Taconic State Parkway and US Rte 199 making it an easy drive to anywhere. The town of Red Hook boasts vibrant shops and

Jeffery Dolfinger Century 21 Hudson Valley Rlty.

19 Friendship Ln, Red Hook, NY 12571
$100,000 Sold Sep 10, 2025

1691 Jackson Corners Rd, Red Hook, NY 12571
- 2 Beds
- 1.5 Baths
- 984 Sq Ft
- Built 1970
Last Sold Summary
- 47% Below List Price
- $102/SF
- 79 Days On Market
Last Listing Agent Catherine Mondello Mondello Upstate Properties

1691 Jackson Corners Rd, Red Hook, NY 12571

Est $361,501 Not Listed For Sale

3 Carla Terrace, Pine Plains, NY 12567
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
- Built 1968
3 Carla Terrace, Pine Plains, NY 12567

Last Sold Summary
- 5% Above List Price
- $302/SF
- 89 Days On Market
Last Sold Price $345,000

Last Listing Agent Andrea Replansky BHHS Hudson Valley Properties

/27
$213,750
- 3,444 Sq Ft
245 Hicks Hill Rd, Stanfordville, NY 12581

Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

Ernie Acampora River Realty Services, Inc.

245 Hicks Hill Rd, Stanfordville, NY 12581

Showing Results 41 - 80, Page 2 of 18

New York Dutchess County Pine Plains

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