Pine Plains Homes for Sale

/50
$3,995,000
- 4 Beds
- 4 Baths
- 4,103 Sq Ft
476 Carpenter Hill Rd, Pine Plains, NY 12567

Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a

Rebecca Doh

William Raveis Lifestyles Rlty

(518) 594-8655

476 Carpenter Hill Rd, Pine Plains, NY 12567
/50
$729,000
- 3 Beds
- 2.5 Baths
- 2,971 Sq Ft
546 Hicks Hill Rd, Stanfordville, NY 12581

Beautiful Colonial lives like a 4-bedroom featuring a covered porch with wooden rocking bench. Enjoy the beauty of over 5 acres of nature. Long driveway leads to 2 car garage set back off the road. Privacy with convenience and a short ride to the Taconic State Parkway. Inside, enjoy the fantastic layout of a perfectly designed colonial with maximum space and superior design including a spacious

Joseph Iannibelli

Keller Williams NY Realty

(845) 444-3630

546 Hicks Hill Rd, Stanfordville, NY 12581
/4
$145,000
- Land
- 5 Acres
- $28,884 per Acre
0 Mount Ross Rd, Pine Plains, NY 12567

Every once in a while, an exceptional opportunity like this turns up. Located in rural Pine Plains this 5.02-acres is a pair of vacant building lots that offers privacy and serenity. These two contiguous parcels are completely wooded and accessed via a shared driveway. Your dream home is only limited by your imagination these parcels will invigorate that imagination. The Town center and the

Larry Havens

Havens Real Estate

(518) 672-6676

0 Mount Ross Rd, Pine Plains, NY 12567
/24
$3,600,000
- Land
- 229 Acres
- $15,727 per Acre
0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546

Sensational vistas of the stunning and unspoiled countryside extending to the Taconic's to the East and from a hidden knoll with an elevation of 1,250' there is a magnificent private setting with incredible Catskill views. The main parcel of 157 acres is offered for the first time in generations and that parcel adjoins a 71.5-acre parcel, this was a family owned and operated farm. Both properties

Larry Havens

Havens Real Estate

(518) 676-2868

0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546
/14
$285,000
- Land
- 9 Acres
- $32,872 per Acre
3362 New York 199, Pine Plains, NY 12567

Here is an opportunity for you to build your dream home.8.67 acres of land in Pine Plain in Dutchess County, New York is for sale. This exceptional property is situated behind a 70-foot road frontage on Route 199.Key Features:Location: Pine Plains in Dutchess County, New YorkLand Size: 8.67 acresAccess: 70 feet of road frontage on Route 199Amenities: Cleared

Community Lands

3362 New York 199, Pine Plains, NY 12567
/21
$749,000
- 2 Beds
- 2 Baths
- 1,624 Sq Ft
37 Stissing Mountain Dr, Pine Plains, NY 12567

Welcome to 37 Stissing Mountain Drive. Perfectly nestled on 6.9 acres of peaceful woodland, this newly built 2-bedroom, 2-bath home is a modern sanctuary that beautifully balances simplicity, sustainability, and style—just minutes from the heart of Pine Plains NY.Inside you will find a sun-filled, open-concept living space with soaring 22-foot vaulted ceilings that frame sweeping views of the

Jason Nadeau Compass Greater NY, LLC

37 Stissing Mountain Dr, Pine Plains, NY 12567
/38
$875,000
- 4 Beds
- 1.5 Baths
- 2,709 Sq Ft
7668 Route 82, Pine Plains, NY 12567

Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an

Susan Whalen George T Whalen Real Estate

7668 Route 82, Pine Plains, NY 12567
/11
$900,000
- 5 Beds
- 2.5 Baths
- 2,413 Sq Ft
2365 Route 83, Pine Plains, NY 12567

Rare opportunity to own 160 breathtaking acres in the heart of Pine Plains, featuring rolling fields, wooded terrain, and scenic wetlands. Anchoring the property is an antique farmhouse awaiting restoration, set within a 7 plus acre residential area offering privacy and pastoral charm. Most of the property is protected under a conservation easement, preserving the natural landscape while allowing

Richard Brenner Rich Brenner Realty, LLC

2365 Route 83, Pine Plains, NY 12567
/43
$1,175,000
- 5 Beds
- 3 Baths
- 2,482 Sq Ft
303 Hicks Hill Rd, Stanfordville, NY 12581

Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming

HOMER STALEY JR. Staley Real Estate, LLC

303 Hicks Hill Rd, Stanfordville, NY 12581
/17
$345,000
- 2 Beds
- 3 Baths
- 1,728 Sq Ft
46 Myrtle Ave, Pine Plains, NY 12567

Check out this charming two family home in the Town of Pine Plains. Live in one unit and keep the other unit rented OR rent out the entire building. One unit was recently updated. Separate utilities and each unit has its own driveway and storage shed. Covered porch, screened-in porch, large backyard. Convenient location, walk to shops & local attractions.

Susan Whalen George T Whalen Real Estate

46 Myrtle Ave, Pine Plains, NY 12567
/38
$579,000
- 3 Beds
- 2.5 Baths
- 2,269 Sq Ft
540 Hicks Hill Rd, Stanfordville, NY 12581

Charming 3-bedroom, 2.5-bathroom Colonial nestled on 5.58 private acres. Enjoy quiet moments on your wrap-around rocking chair front porch and take in picturesque views of Stissing Mountain. This inviting home features a spacious living room, formal dining room and an eat-in kitchen that flows into a comfortable family room perfect for gatherings. Step out from the family room onto a patio ideal

Rita Longo Howard Hanna Rand Realty

540 Hicks Hill Rd, Stanfordville, NY 12581
/13
$230,000
- Land
- 19 Acres
- $11,856 per Acre
A Skunks Misery Rd, Millerton, NY 12546

Stunning 19.4 Acres – Estate Setting on a Premier Country RoadDiscover the perfect blend of natural beauty and refined location with this 19.4-acre parcel situated on a picturesque country road, renowned for its stately homes and rural charm.With multiple elevated building sites, long road frontage, and sweeping view potential, this property offers endless opportunities. Explore

Robert Dunlop Havens Real Estate

A Skunks Misery Rd, Millerton, NY 12546
/30
$595,000
- 4 Beds
- 2.5 Baths
- 3,180 Sq Ft
30 N Main St, Pine Plains, NY 12567

Grand 1880 Colonial Estate Sale - Historic Fixer-Upper with Original Features and Garden Oasis Near Town CenterThis rare 1880 Grand Colonial is a dream opportunity for restoration enthusiasts and anyone searching for a historic fixer-upper near the heart of town. Situated on a flat, tree-lined lot, this estate sale is being sold as is and is filled with authentic charm—from original

Arleen Shepley Elyse Harney Real Estate

30 N Main St, Pine Plains, NY 12567
/13
$4,950,000
- 3 Beds
- 2 Baths
- 5,000 Sq Ft
3362 New York 199, Pine Plains, NY 12567

To-Be-Built Luxury Estate with Infinity Pool & Panoramic Catskill Views – Pine Plains, NY. Elevated high above the valley floor with sweeping, unobstructed Catskill Mountain views, this to-be-built custom estate is a rare opportunity in the heart of the Hudson Valley. Set on an extraordinary piece of land—offering total privacy and dramatic natural beauty—this 5,000+ square foot

Michael Lund Corcoran Country Living

3362 New York 199, Pine Plains, NY 12567
/33
$2,495,000
- 3 Beds
- 3 Baths
- 4,648 Sq Ft
387 Skunks Misery Rd, Millerton, NY 12546

Perched high above Millerton in the Hudson Valley, this exceptional 2020-built contemporary farmhouse estate commands 53± private acres with panoramic western views spanning the Catskills and Berkshire Mountain Range, including Mount Kaaterskill. Wide red oak hardwood floors unite the main level, where abundant natural light floods through expansive windows, creating an atmosphere of

Elyse Morris Elyse Harney Real Estate

387 Skunks Misery Rd, Millerton, NY 12546
/7
$145,000
- Land
- 3.45 Acres
- $42,029 per Acre
66 Ryan Rd, Pine Plains, NY 12567

Build your dream home in the heart of Pine Plains, surrounded by nature, history, and vibrant Hudson Valley living, on this exceptional 3.45 Acre elevated homesite, Board of Health approved for a 4-bedroom residence, with sweeping views of majestic Stissing Mountain. This remarkable parcel offers the perfect blend of tranquility, natural beauty, and convenience, presenting a rare opportunity to

Vida Odescalchi Legacy Land & Homes LLC

66 Ryan Rd, Pine Plains, NY 12567
/47
$595,000
- 4 Beds
- 2 Baths
- 2,605 Sq Ft
5 Myrtle Ave, Pine Plains, NY 12567

Beautiful Two Story, 4BR/2BA corner lot home with mountain views & quick walk to post office, shops, Stissing Lake & Stissing Mountain hiking trails. Experience the wonderful life of beautiful Pine Plains living! Wonderful large front, side & back yard on quiet sought after Myrtle Ave. Lovely front porch to sit & enjoy the scenery or head into the private back yard for a BBQ. Walk to school, post

Thomas Zengen Thomas Zengen

5 Myrtle Ave, Pine Plains, NY 12567
/25
$589,000
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
618 Bean River Rd, Millerton, NY 12546

PINE PLAINS 2-3 LOT DEVELOPMENT, 15+ acres for Family Compound or upscale development between Pine Plains Village and Millerton on quiet road off Route 199. The Development includes a 1400 SF 2BR/2BA RANCH with new well, w/2 large decks, all wood floors, wood siding + detached 2 car garage on 7+ acres subdividable into 4 acres with house and 3 acre vacant lot. Included is additional approved 8

David Birch Barns and Farms Realty LLC

618 Bean River Rd, Millerton, NY 12546
/29
$599,000
- 3 Beds
- 1.5 Baths
- 1,862 Sq Ft
43 Stissing Mountain Dr, Pine Plains, NY 12567

Welcome to 43 Stissing Mountain Drive — a peaceful and private retreat set on 2 beautifully wooded acres in the heart of the Hudson Valley. This great contemporary home offers 3 bedrooms and 2 bathrooms across 1,862 square feet of comfortable living space. With an open-concept layout, cathedral ceilings, and abundant natural light, the home blends style and function. A cozy fireplace anchors the

Richard Brenner Rich Brenner Realty, LLC

43 Stissing Mountain Dr, Pine Plains, NY 12567
/26
$2,250,000
- Land
- 34 Acres
- $66,430 per Acre
7702-7714 S Main St, Pine Plains, NY 12567

Prime 26.8-Acre Commercial Opportunity in Pine Plains, NYA rare investment opportunity awaits with this 26.8-acre commercial parcel—the last of its kind in the growing town of Pine Plains. Strategically located along South Main St (Route 82) with deeded right of way access from Route 83, this property is fully equipped for development and positioned to capitalize on the area’s increasing demand

Richard Brenner Rich Brenner Realty, LLC

7702-7714 S Main St, Pine Plains, NY 12567
/19
$995,000
- Land
- 29 Acres
- $34,669 per Acre
5-8 Lakeside Ln, Pine Plains, NY 12567

Welcome to your own slice of paradise! This beautiful 29-acre waterfront property offers the perfect canvass for your dream home. Nestled in the shadow of Stissing Mountain, you'll enjoy country views and ample space to build your oasis. Boasting approximately 800 feet of waterfront on Twin Island Lake, enjoy fishing, kayaking or just observing natures glory. Privacy is paramount on this property

Richard Brenner Rich Brenner Realty, LLC

5-8 Lakeside Ln, Pine Plains, NY 12567
/15
$89,000
- Land
- 2.60 Acres
- $34,231 per Acre
0 Finkle Rd, Pine Plains, NY 12567

Ready to build? Here's a great opportunity on 2.6 acres in Pine Plains NY. This cleared, mostly level lot has BOHA for a four bedroom home. Situated about halfway between Millerton and Pine Plains, this property offers country living while staying close to local amenities. This property is adjacent to 3977 Route 199

Richard Brenner Rich Brenner Realty, LLC

0 Finkle Rd, Pine Plains, NY 12567
/26
$379,000
- 3 Beds
- 2 Baths
- 1,280 Sq Ft
48 Woodside St, Pine Plains, NY 12567

Whether for starting out retirement or weekend use, 48 Woodside Street is an efficient, move-in-ready home. Pine Plains offers a number of attractions from fine dining at the Stissing House, or a relaxing kayak paddle on Thompson Pond. Nearby hiking trails offer options such as the Stissing Fire Tower, a challenging local favorite, and the Thompson Preserve an easy woodland stroll around a

Brad Rebillard Dutchess Country Realty, Inc.

48 Woodside St, Pine Plains, NY 12567
/15
$384,000
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
618 Bean River Rd, Pine Plains, NY 12567

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone Easy subdivision into 4 and 3 acre lots. Also available as Family Compound with adjoining 8 acre and 4 acre boha parcels for 699,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show unoccupied.

David Birch Barns & Farms Realty, LLC

618 Bean River Rd, Pine Plains, NY 12567
/6
$409,000
- Land
- 111 Acres
- $3,685 per Acre
0 Route 82 Unit 156245, Pine Plains, NY 12567

Large parcel with 1700 foot of frontage on 3 road. Lots of possibilities for estate, recreation or subdivision. Convenient to Taconic Parkway and Hudson.

David Birch Barns & Farms Realty, LLC

0 Route 82 Unit 156245, Pine Plains, NY 12567
/37
$320,000
- 2 Beds
- 2 Baths
- 1,620 Sq Ft
4 Antler Club Rd, Pine Plains, NY 12567

Located in the picturesque Antlers Club Lake Community, this 2-bedroom, 2-bath Cape Cod offers a peaceful retreat with beach access and your own dock for kayaking, fishing, or relaxing by the water. The home features a bright and inviting layout, with spacious living areas, a well-equipped kitchen, and a full bath on the main level. Upstairs, a large bedroom and another full bath provide a cozy

Michael Cahill HomeSmart Homes & Estates

4 Antler Club Rd, Pine Plains, NY 12567
/16
$389,000
- 2 Beds
- 1.5 Baths
- 1,336 Sq Ft
618 Bean River Rd, Millerton, NY 12546

Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone Easy subdivision into 4 and 3 acre lots. Also available as Family Compound with adjoining 8 acre and 4 acre boha parcels for 625,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show unoccupied.

David Birch Barns and Farms Realty LLC

618 Bean River Rd, Millerton, NY 12546
/12
$509,000
- 4 Beds
- 1.5 Baths
- 3,072 Sq Ft
7786 S Main St, Pine Plains, NY 12567

You wanted charm? You got it! This vintage 1903 village home in Pine Plains, NY formerly served as both the town pharmacy and library, and many of the bookshelves and all the quaint apothecary drawers remain intact. The large 3000sq foot home on a nicely landscaped yard of nearly a half an acre is filled with period details: wooden moldings, original door knobs and intricate iron hardware, a

David Norman Hall Houlihan Lawrence Inc.

7786 S Main St, Pine Plains, NY 12567
/13
$995,000
- Land
- 28 Acres
- $35,035 per Acre
390 Carpenter Hill Rd, Pine Plains, NY 12567

With magnificent Catskill Mountain views, this 28 acre estate property is the perfect site to build the home of your dreams. The land features exceptional privacy among gentle rolling fields and stunning sunsets over the valley and the Catskills. There is already a gravel driveway in place plus plans for building, landscaping and septic. Much of the surrounding land is forever protected through

Dan Kessler Compass Greater NY, LLC

390 Carpenter Hill Rd, Pine Plains, NY 12567
/7
$223,000
- Land
- 9 Acres
- $25,960 per Acre
622 Bean River Rd, Millerton, NY 12546

Great opportunity for 1 or 2 residence (property is in Hamlet Zone and subdividable).Very private with small pond, site back from road on Bean River Road, quiet town road, .8 miles North of Route 199 near border with Columbia County. Approved Septic design and existing shared driveway. (May need improvement). Adjoins 2BR2BA Ranch for sale on 7+ acres for $399,000. Owner financing possible with

David Birch Barns & Farms Realty, LLC

622 Bean River Rd, Millerton, NY 12546
/8
$632,200
- Land
- 32 Acres
- $20,000 per Acre
0 Skunks Misery Rd Unit 139025, Pine Plains, NY 12546

Spectacular piece of property with a hidden pasture to have secluded site for a home. This 31.61 acre piece of property is sited among larger parcels of property on a beautiful road in Dutchess County New York. Open field with option to do organic farming or raise livestock. Possibility of additional land. Property will be surveyed. 10 Minutes to Village of Millerton, Pine Plains, Amenia NY

Arleen Shepley Elyse Harney Real Estate

0 Skunks Misery Rd Unit 139025, Pine Plains, NY 12546
/10
$632,200
- Land
- 32 Acres
- $20,000 per Acre
0 Skunks Misery Rd Unit KEYM403150, Pine Plains, NY 12546

Property is on a beautiful road in Dutchess County, NY. Tucked away, a secret meadow adding privacy for a building site. 31.61 acres for sale in the town of Pine Plains located in the greater Hudson Valley. Panoramic view of the distant mountains and farms. This open field could be organic farming or raising livestock. This property is part of a larger farm which was once an active farm many

Arleen Shepley Elyse Harney Real Estate

0 Skunks Misery Rd Unit KEYM403150, Pine Plains, NY 12546

New York Dutchess County Millerton Pine Plains

Frequently Asked Questions Why Live in Pine Plains

Is Pine Plains a good place to live?

Pine Plains is a good place to live. Pine Plains is considered very car-dependent and somewhat bikeable. Pine Plains has 2 parks for recreational activities. It has a median age of 49. The average household income is $90,299 which is below the national average. College graduates make up 27.8% of residents. A majority of residents in Pine Plains are home owners, with 25.9% of residents renting and 74.1% of residents owning their home. A local real estate agent serving Pine Plains can help you decide if this neighborhood is the right one for you. Learn more on our Pine Plains neighborhood guide.

How much do you need to make to afford a house in Pine Plains?

The median home price in Pine Plains is $380,000. If you put a 20% down payment of $76,000 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $1,970 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $84K a year to afford the median home price in Pine Plains. The average household income in Pine Plains is $90K.

What are the best public schools in Pine Plains?

The best public schools that serve Pine Plains are:

Stissing Mountain High School has a C+ Niche grade, a student teacher ratio of 8:1 and an average review score of 3.5.

What are the most popular zip codes in Pine Plains, Millerton, NY?

The most popular zip codes in Pine Plains, Millerton, NY include 12567, 12581, 12503, 12546 and 12502.

What are the most popular neighborhoods near Pine Plains, Millerton, NY?

The most popular neighborhoods near Pine Plains, Millerton, NY are Stanford, North East, Milan, Amenia and Clinton.

Are home prices dropping in Pine Plains?

Yes, home prices in Pine Plains are down 38% in the last 12 months.

Learn more about living in Pine Plains

Home Trends in Pine Plains, NY

On average, homes in Pine Plains, Millerton sell after 66 days on the market compared to the national average of 70 days. The median sale price for homes in Pine Plains, Millerton over the last 12 months is $355,000, down 43% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$355,000

Median Single Family Sale Price

$365,000

Median Townhouse Sale Price

$499,000

Average Price Per Sq Ft

$204

Number of Homes for Sale

Last 12 months Home Sales

113

Months of Supply

0.30

Median List Price

$380,000

Median Change From 1st List Price

12%

Median Home Sale Price YoY Change

-43%

How to Buy a Home How to Finance a Home How to Sell a Home

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