Homes with Pools for Sale in Dutchess County, NY

916 homes

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ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Chelsea Retreat – Where Quiet Luxury Meets the Hudson River. Now is your opportunity to own 25.57 scenic acres in the heart of the Hudson Valley, set high above the Hudson River boasting million-dollar water views. Enjoy the best of both worlds—peaceful country living with convenient access to train stations and highways, all less than an hour from Manhattan. Design your dream home or work with our team to bring your vision to life. Whether you’re seeking a weekend retreat or a year-round residence, this property offers endless potential for a custom-built lifestyle surrounded by nature and Hudson Valley charm Chelsea Retreat is a distinctive subdivision of luxury homes

$1,200,000

— beds— baths— sq ft

Lot #17 River Rd N, Chelsea, NY 12512

Scenic nature trails • Peaceful water views • Wooded paths

Listing by Corcoran Country Living

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Chelsea Retreat – Where Quiet Luxury Meets the Hudson River. Now is your opportunity to own 76.12 scenic acres in the heart of the Hudson Valley, set high above the Hudson River boasting million-dollar water views. Enjoy the best of both worlds—peaceful country living with convenient access to train stations and highways, all less than an hour from Manhattan. Design your dream home or work with our team to bring your vision to life. Whether you’re seeking a weekend retreat or a year-round residence, this property offers endless potential for a custom-built lifestyle surrounded by nature and Hudson Valley charm Chelsea Retreat is a distinctive subdivision of luxury ho

$1,800,000

— beds— baths— sq ft

Lot #16 River Rd N, Chelsea, NY 12512

Nature trails • Wooded paths • 76.12 acre lot

Listing by Corcoran Country Living

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
30 Acres | Stunning Mountain Views | Walk to Downtown Millerton | Direct Rail Trail Access Experience one of Millerton’s most coveted land offerings: 30 acres with sweeping mountain views and the rare ability to walk directly into downtown Millerton for coffee, dining, shops, The Moviehouse, the farmers market, and more. This property delivers the perfect combination of privacy, scale, and in-town convenience. The land features gently rolling terrain, a roughed-in driveway, and direct frontage on the Harlem Valley Rail Trail, providing instant access to hiking, biking, and year-round outdoor recreation. Bordering scenic farmland and set across from a picturesque stream, the property c

$550,000

— beds— baths— sq ft

0 Mill Rd, Millerton, NY 12546

Picturesque stream • 30 acres of land • Roughed-in driveway

Listing by eXp Realty

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Build Your Dream Home with Panoramic Hudson Valley Views. The perfect blend of privacy, beauty, and convenience on this 4.4-acre parcel tucked away at the end of a peaceful cul-de-sac in a beautiful Beekman neighborhood. Set atop a gentle slope, this property offers sweeping distant views of the Hudson Valley and the Shawangunk Ridge, including Mohonk Mountain—an amazing backdrop for your future home. The land has been partially cleared, including a driveway access, providing an easy start for construction and the flexibility to design your ideal layout. A current survey and Board of Health approval are already in place, with no fill required for the septic system—saving you tim

$198,000

— beds— baths— sq ft

Woodin Pl, Poughquag, NY 12570

4.4 acre parcel • Current survey • Driveway access

Listing by Houlihan Lawrence Inc.

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
This is a corner lot located at the intersection of Stanton Terrace and Regency Drive. Please check all zoning setbacks.

$8,000

— beds— baths— sq ft

Stanton Ter, Poughkeepsie, NY 12603

Corner lot • 3,485 sq ft lot • Listed 31 days

Listing by Epique Realty

$20,000

— beds— baths— sq ft

Echo Ln, Fishkill, NY 12508

Listing by Epique Realty

Property at Woodmont Rd, Hopewell Junction, NY

$195,000

— beds— baths— sq ft

Woodmont Rd, Hopewell Junction, NY

Listing by Serhant LLC

Property at 00 N Quaker Ln, Staatsburg, NY

$95,000

— beds— baths— sq ft

00 N Quaker Ln, Staatsburg, NY

Listing by Four Seasons Sothebys Intl

Property at 0 N Quaker Ln, Staatsburg, NY

$105,000

— beds— baths— sq ft

0 N Quaker Ln, Staatsburg, NY

Listing by Four Seasons Sothebys Intl

Property at 1436 Route 9G, Hyde Park, NY 12538

$1,500,000

— beds— baths— sq ft

1436 Route 9G, Hyde Park, NY 12538

Listing by Thomas Zengen

Property at 97 Reservoir Rd, Staatsburg, NY 12580

$409,000

— beds— baths— sq ft

97 Reservoir Rd, Staatsburg, NY 12580

Listing by Coldwell Banker Realty

Property at Round Lake Rd, Rhinebeck, NY 12572

$350,000

— beds— baths— sq ft

Round Lake Rd, Rhinebeck, NY 12572

Listing by BHHS Hudson Valley Properties

Property at 12 Deverly Rd, Holmes, NY 12531

$899,000

— beds— baths— sq ft

12 Deverly Rd, Holmes, NY 12531

Listing by McGrath Realty Inc

Property at 36 Fallkill Rd, Hyde Park, NY 12538

$159,900

— beds— baths— sq ft

36 Fallkill Rd, Hyde Park, NY 12538

Listing by Houlihan Lawrence Inc.

Property at Maloney Rd, Poughkeepsie, NY 12603

$175,000

— beds— baths— sq ft

Maloney Rd, Poughkeepsie, NY 12603

Listing by Keller Williams Realty

Property at 1830 Bruzgul Rd, Lagrangeville, NY 12540

$899,000

— beds— baths— sq ft

1830 Bruzgul Rd, Lagrangeville, NY 12540

Listing by Houlihan Lawrence Inc.

Property at 1196 82 Rte, Hopewell Junction, NY 12533

$4,499,000

— beds— baths— sq ft

1196 82 Rte, Hopewell Junction, NY 12533

Listing by Four Seasons Sothebys Intl

Property at Rt-55, Lagrangeville, NY 12540

$30,000

— beds— baths— sq ft

Rt-55, Lagrangeville, NY 12540

Listing by eXp Realty

Property at Stove Pipe Aly, Red Hook, NY 12571

$69,500

— beds— baths— sq ft

Stove Pipe Aly, Red Hook, NY 12571

Listing by BHHS Hudson Valley Properties

Property at 240 Boardman Rd, Poughkeepsie, NY 12603

$600,000

— beds— baths— sq ft

240 Boardman Rd, Poughkeepsie, NY 12603

Listing by BHHS Hudson Valley Properties

Property at 67 Jackson Rd, Poughkeepsie, NY 12603

$240,000

— beds— baths— sq ft

67 Jackson Rd, Poughkeepsie, NY 12603

Listing by RE/MAX Town & Country

$50,000

— beds— baths— sq ft

1875 New Hackensack Rd, Poughkeepsie, NY 12603

Listing by eXp Realty

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Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Dutchess County

There are currently 916 homes with pools for sale in Dutchess County at a median listing price of $545K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Dutchess County stay on the market for 56 days and receive 4 offers. This map is refreshed with the newest listings in Dutchess County every 15 minutes.

In the past month, 261 homes have been sold in Dutchess County. In addition to houses in Dutchess County, there were also 98 condos, 1 townhouse, and 71 multi-family units for sale in Dutchess County last month. Find your dream home in Dutchess County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Dutchess County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Dutchess County. If you're looking to sell your home in the Dutchess County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Dutchess County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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