Homes with Pools for Sale in Dutchess County, NY

230 homes

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ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Welcome to Rombout Retreat! A spacious four bedroom, three bath home offering over 3,000 square feet of beautifully maintained living space on two private acres surrounded by protected agricultural land. This thoughtfully designed home offers multiple living spaces, each with its own warm and inviting atmosphere, with fireplaces in every sitting room as well as an additional fireplace in the primary suite. Blending traditional charm with a contemporary feel, the home offers an easy, comfortable flow throughout that feels both timeless and move-in ready. The first floor opens to a spacious deck perfect for entertaining and enjoying the peaceful surroundings, overlooking lush gardens, a tranq

$950,000

4 beds2.5 baths4,221 sq ft

136 Rombout Rd, Pleasant Valley, NY 12603

Private acres • Spacious deck • Lush gardens

Listing by Houlihan Lawrence Inc.

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Idyllically perched on the corner of Blue Hill and Shenandoah, this Hudson Valley gem, where heritage meets modern warmth, 319 Blue Hill Road awaits. A timeless property, perfectly move-in ready features three bedrooms, two updated baths, seamlessly integrated central air conditioning and new luxury vinyl plank flooring. The magnificent fully roofed front porch spans the entire width of the home inviting you for morning coffee, spectacular sunsets -- (the view!)-- your happy place. Sloping lawn with gardens and above ground pool create your own personal oasis. A commuters dream location just moments from the Taconic State Parkway and I-84. Less than one half mile is the Lime Kiln Recreatio

$475,000

3 beds2 baths1,976 sq ft

319 Blue Hill Rd, Hopewell Junction, NY 12533

Above ground pool • Sloping lawn • Gardens

Listing by K. Fortuna Realty, Inc.

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Welcome to this lovely Hudson Valley estate where timeless architecture and exceptional privacy come together on 13.7 breathtaking park-like acres in the heart of LaGrange, just minutes from the Village of Millbrook. A picturesque quarter-mile, partially pine-lined driveway creates a country approach, setting the stage for this remarkable property. Perfectly positioned with a coveted southwest-facing orientation, the home is bathed in natural light throughout the day while showcasing spectacular sunset views over the surrounding landscape. This beautifully maintained 4-bedroom, 2.5-bath home offers an effortless blend of elegance, warmth, and everyday comfort. The inviting living room featu

$725,000

4 beds2.5 baths3,263 sq ft

32 Cole Rd, Pleasant Valley, NY 12569

13.7 park-like acres • Natural light • Hudson valley estate

Listing by Houlihan Lawrence Inc.

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Welcome to this spacious 5-bedroom contemporary home in the highly sought-after Streamside Knolls community, located in the Beacon School District. Enter through a grand archway with double doors into a dramatic foyer leading to the living room with cathedral ceilings, fireplace, and sliding doors to a balcony overlooking peaceful woods. Hardwood floors run throughout the home. The kitchen features stainless steel appliances, abundant cabinetry, breakfast nook, and bar seating, with a formal dining room nearby. The main-level primary suite offers two walk-in closets and a beautifully updated bath with Jacuzzi tub, separate shower, and double vanity. The walkout lower level includes a large

$729,000

5 beds4 baths3,416 sq ft

19 Ash Rd, Wappingers Falls, NY 12590

Cathedral ceilings • Grand archway • Dramatic foyer

Listing by eXp Realty

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Vacant and Price Reduced for Quick Sale! Owners have relocated to full-time sunshine! Move right into this lovely split-level home, offering 4 bedrooms and 2 full baths. Recent improvements include a newly installed hi-tech camera security system and a newly stained double deck! Pool and hot tub as-is. Small fenced yard area, perfect for pets or gardening! Also available for lease. Book your private tour today!

$595,900

4 beds2 baths2,160 sq ft

5 Verplanck Ave, Hopewell Junction, NY 12533

Bright living space • Hot tub • Double deck

Listing by Amalie Industries, LLC

Property at 135 Sterling St #135, Beacon, NY 12508, 2 beds, 1.5 baths

$240,000

2 beds1.5 baths1,050 sq ft

135 Sterling St #135, Beacon, NY 12508

Listing by Compass Greater NY, LLC

Property at 22 Hemlock Ct, Fishkill, NY 12524, 2 beds, 1.5 baths

$425,000

2 beds1.5 baths1,495 sq ft

22 Hemlock Ct, Fishkill, NY 12524

Listing by Century 21 Alliance Rlty Group

Property at 31 Roundtree Ct, Beacon, NY 12508, 3 beds, 1.5 baths

$349,000

3 beds1.5 baths1,576 sq ft

31 Roundtree Ct, Beacon, NY 12508

Listing by eXp Realty

Property at 5012 Albany Post, Staatsburg, NY 12580, 3 beds, 2 baths

$949,000

3 beds2 baths2,100 sq ft

5012 Albany Post, Staatsburg, NY 12580

Listing by Owner Entry.com

Property at 11 Potters Ln, Lagrangeville, NY 12540, 5 beds, 3.5 baths

$995,000

5 beds3.5 baths3,463 sq ft

11 Potters Ln, Lagrangeville, NY 12540

Listing by BHHS Hudson Valley Properties

Property at 26 Monroe Dr, Poughkeepsie, NY 12601, 3 beds, 1.5 baths

$499,888

3 beds1.5 baths2,311 sq ft

26 Monroe Dr, Poughkeepsie, NY 12601

Listing by Epique Realty

Property at 2 Merry Hill Rd, Poughkeepsie, NY 12603, 4 beds, 2 baths

$509,000

4 beds2 baths2,196 sq ft

2 Merry Hill Rd, Poughkeepsie, NY 12603

Listing by BHHS Hudson Valley Properties

Property at 702 Scenic Ln, Poughkeepsie, NY 12603, 2 beds, 3 baths

$349,900

2 beds3 baths1,190 sq ft

702 Scenic Ln, Poughkeepsie, NY 12603

Listing by RE/MAX Classic Realty

Property at 194 Devon Farms Rd, Stormville, NY 12582, 4 beds, 3.5 baths

$1,099,000

4 beds3.5 baths4,690 sq ft

194 Devon Farms Rd, Stormville, NY 12582

Listing by Direct Choice Realty

Property at 1668 Route 9 Unit 3N, Wappingers Falls, NY 12590, 1 bed, 1 bath

$245,000

1 bed1 bath772 sq ft

1668 Route 9 Unit 3N, Wappingers Falls, NY 12590

Listing by Robert A. McCaffrey Realty Inc

Property at 39 Brothers Rd, Poughquag, NY 12570, 3 beds, 1 bath

$479,000

3 beds1 bath1,200 sq ft

39 Brothers Rd, Poughquag, NY 12570

Listing by Sunbelt Sales & Development

Property at 287 Norton Rd, Red Hook, NY 12571, 3 beds, 2 baths

$539,000

3 beds2 baths2,025 sq ft

287 Norton Rd, Red Hook, NY 12571

Listing by eXp Realty

Property at 416 Saratoga Ln, Fishkill, NY 12524, 2 beds, 2 baths

$425,000

2 beds2 baths1,227 sq ft

416 Saratoga Ln, Fishkill, NY 12524

Listing by BHHS Hudson Valley Properties

Property at 7 Fox Run, Wappingers Falls, NY 12590, 3 beds, 3.5 baths

$789,000

3 beds3.5 baths3,250 sq ft

7 Fox Run, Wappingers Falls, NY 12590

Listing by BHHS Hudson Valley Properties

Property at 50 Glanhope Rd #21, Hopewell Junction, NY 12533, 3 beds, 1 bath

$55,000

3 beds1 bath750 sq ft

50 Glanhope Rd #21, Hopewell Junction, NY 12533

Listing by Houlihan Lawrence Inc.

Property at 28 Crimson Hill Rd, Rhinebeck, NY 12572, 3 beds, 2.5 baths

$1,350,000

3 beds2.5 baths4,722 sq ft

28 Crimson Hill Rd, Rhinebeck, NY 12572

Listing by Four Seasons Sothebys Intl

Property at 6 Kipsbergen Dr, Rhinebeck, NY 12572, 4 beds, 2 baths

$650,000

4 beds2 baths2,078 sq ft

6 Kipsbergen Dr, Rhinebeck, NY 12572

Listing by BHHS Hudson Valley Properties

Property at 427 Vassar Pl, Fishkill, NY 12524, 3 beds, 2.5 baths

$664,900

3 beds2.5 baths2,537 sq ft

427 Vassar Pl, Fishkill, NY 12524

Listing by McGough Realty Corp

Property at 57 Buhleir Rd, Pawling, NY 12564, 3 beds, 2 baths

$619,900

3 beds2 baths1,768 sq ft

57 Buhleir Rd, Pawling, NY 12564

Listing by Berkshire Hathaway HS NE Prop.

Property at 13 Spy Glass Ln, Staatsburg, NY 12580, 3 beds, 3.5 baths

$1,385,000

3 beds3.5 baths3,730 sq ft

13 Spy Glass Ln, Staatsburg, NY 12580

Listing by BHHS Hudson Valley Properties

Property at 38 Kelsey Rd, Poughkeepsie, NY 12601, 3 beds, 2 baths

$450,000

3 beds2 baths1,456 sq ft

38 Kelsey Rd, Poughkeepsie, NY 12601

Listing by Exit Realty Group

Property at 334 Browning Rd, Salt Point, NY 12578, 4 beds, 3 baths

$1,695,000

4 beds3 baths2,200 sq ft

334 Browning Rd, Salt Point, NY 12578

Property at 250 Maloney Rd, Wappingers Falls, NY 12590, 3 beds, 3.5 baths

$780,000

3 beds3.5 baths4,553 sq ft

250 Maloney Rd, Wappingers Falls, NY 12590

Listing by Cronin & Company Real Estate

Property at 22 Oriole Dr, Poughkeepsie, NY 12601, 3 beds, 1.5 baths

$469,900

3 beds1.5 baths1,457 sq ft

22 Oriole Dr, Poughkeepsie, NY 12601

Listing by Keller Williams Realty Partner

Property at 614 Sacandaga Loop, Wappingers Falls, NY 12590, 2 beds, 3 baths

$995,000

2 beds3 baths2,057 sq ft

614 Sacandaga Loop, Wappingers Falls, NY 12590

Listing by Compass Greater NY, LLC

Property at 160 Academy St Unit 3P, Poughkeepsie, NY 12601, 1 bed, 1 bath

$100,000

1 bed1 bath650 sq ft

160 Academy St Unit 3P, Poughkeepsie, NY 12601

Listing by Epique Realty

Property at 320 Hudson View Ter, Hyde Park, NY 12538, 2 beds, 3 baths

$499,900

2 beds3 baths1,980 sq ft

320 Hudson View Ter, Hyde Park, NY 12538

Listing by KW MidHudson

Property at 296-302 Stanford Rd, Millbrook, NY 12545, 4 beds, 4 baths

$4,250,000

4 beds4 baths4,253 sq ft

296-302 Stanford Rd, Millbrook, NY 12545

Listing by Corcoran Country Living

Property at 5 Red Tail Ct, Pawling, NY 12564, 4 beds, 2.5 baths

$600,000

4 beds2.5 baths2,924 sq ft

5 Red Tail Ct, Pawling, NY 12564

Listing by Houlihan Lawrence Inc.

Property at 36 Liberty St, Chelsea, NY 12512, 4 beds, 2.5 baths

$2,750,000

4 beds2.5 baths2,570 sq ft

36 Liberty St, Chelsea, NY 12512

Listing by Corcoran Country Living

Property at 12 Fenton Way, Hopewell Junction, NY 12533, 3 beds, 2.5 baths

$700,000

3 beds2.5 baths2,200 sq ft

12 Fenton Way, Hopewell Junction, NY 12533

Listing by BHHS Hudson Valley Properties

Property at 30 Tally-ho Dr, Dover Plains, NY 12522, 2 beds, 2 baths

$130,000

2 beds2 baths1,000 sq ft

30 Tally-ho Dr, Dover Plains, NY 12522

Listing by eXp Realty

Property at 1197 Bulls Head Rd, Clinton Corners, NY 12514, 4 beds, 4 baths

$2,700,000

4 beds4 baths4,032 sq ft

1197 Bulls Head Rd, Clinton Corners, NY 12514

Listing by Compass Greater NY, LLC

Property at 57 Sheafe Rd, Poughkeepsie, NY 12601, 3 beds, 2 baths

$92,000

3 beds2 baths1,100 sq ft

57 Sheafe Rd, Poughkeepsie, NY 12601

Listing by Curasi Realty, Inc.

Property at 2 Greenwood Dr, Beacon, NY 12508, 4 beds, 2 baths

$799,000

4 beds2 baths1,915 sq ft

2 Greenwood Dr, Beacon, NY 12508

Listing by Atlantica East Associates LLC

Property at 17 Audubon Trl, Salt Point, NY 12578, 4 beds, 4 baths

$1,350,000

4 beds4 baths4,552 sq ft

17 Audubon Trl, Salt Point, NY 12578

Listing by BHHS Hudson Valley Properties

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Based on information submitted to the MLS GRID as of Sun Sep 20 2026. 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 230 homes with pools for sale in Dutchess County at a median listing price of $550K. 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 61 days and receive 3 offers. This map is refreshed with the newest listings in Dutchess County every 15 minutes.

In the past month, 239 homes have been sold in Dutchess County. In addition to houses in Dutchess County, there were also 115 condos, 1 townhouse, and 76 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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