Homes with Pools for Sale in Dutchess County, NY

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ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
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. * *

$225,000

2 beds— baths3,444 sq ft

245 Hicks Hill Rd, Stanfordville, NY 12581

2.4 acre lot • Built 1951 • Listed 25 days

Listing by River Realty Services, Inc.

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
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,

$259,900

3 beds2 baths1,820 sq ft

16 Ryan Rd, Pine Plains, NY 12567

Close to schools • Large backyard • Ranch style

Listing by Compass Greater NY, LLC

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Welcome to The Woods in Rhinebeck. This lovely waterfront unit has tranquil pond views and beautiful late afternoon western light that fills the rooms with a warm glow. The main level features a bright eat-in kitchen, half bath and spacious living room with a wood burning fireplace as well as sliding glass doors to the rear deck overlooking the water. Upstairs are two ensuite bedrooms, the primary and a guest, along with a convenient laundry area and a loft-like den with a balcony perfectly positioned to take in the view. An attached one car garage has storage space, and the drive way offers ample private parking. The Woods offers paved walkways, a spacious community clubhouse, tennis court

$530,000

2 beds2.5 baths1,472 sq ft

14 Pond Dr E, Rhinebeck, NY 12572

Sliding glass doors • Rear deck • Waterfront unit

Listing by Rouse + Co Real Estate LLC

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Price Reduced! Spacious Nine Room, SIX Bedroom, THREE Bath Home Could Be A Great Investment Property Or Home For The Large Or Extended Family. All Types Of Multiple Living Arrangements Could Have Potential In This Brick Rowhouse Style, Tri-Level Which Includes Parking. Home Is Located Near Colleges, Train Station, Bus Routes, Library, Hospitals, Shopping And Restaurants Plus Many Major Roads In All Directions. What We Have Here Is A Newly Updated, Freshly Painted Multi-Level With All New Appliances, Allowing A Bathroom On Each Floor. Property Is Being Sold As Is. Agents, See Other Remarks.

$299,900

6 beds3 baths1,672 sq ft

212 Church St, Poughkeepsie, NY 12601

Centrally located • All new appliances • Freshly painted

Listing by Century 21 Hudson Valley Rlty.

ABOUT THIS HOME
Home with a Pool for sale in Dutchess County, NY:
Welcome home to 2 Spruce St. ! 2 full floors plus a completely finished walk out basement. Home has central air and heat. Completely updated and freshly painted, all you need to do is move in. Living room features a built in flue that can be opened up for adding a wood burning fireplace. 2 full primary bedrooms, each with it's own full bathroom, plus a powder room on the first floor. One of the bedrooms features a huge walk in closet. Home features include an office plus large flex space for a playroom/home theater, etc. Newer mechanicals. There is a walk out patio, plus a deck featuring a hard wired, lighted Sunsetter awning. Community features a large in-ground pool and clubhouse. Never

$399,999

2 beds2.5 baths1,838 sq ft

2 Spruce St, Pawling, NY 12564

Walk out patio • Huge walk in closet • Large in-ground pool

Listing by Hanson Real Estate Partners

Property at 62 Tamarack Hill Dr, Poughkeepsie, NY 12603, 3 beds, 1 bath

$429,000

3 beds1 bath1,753 sq ft

62 Tamarack Hill Dr, Poughkeepsie, NY 12603

Listing by Houlihan Lawrence Inc.

Property at 24 Villa Ln, Poughkeepsie, NY 12603, 4 beds, 4.5 baths

$2,495,000

4 beds4.5 baths4,356 sq ft

24 Villa Ln, Poughkeepsie, NY 12603

Listing by KW MidHudson

Property at 19 Grove St, Beacon, NY 12508, 4 beds, 2 baths

$639,000

4 beds2 baths1,894 sq ft

19 Grove St, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 56 Northrup Rd, Dover Plains, NY 12522, 4 beds, 4.5 baths

$2,475,000

4 beds4.5 baths2,412 sq ft

56 Northrup Rd, Dover Plains, NY 12522

Listing by Compass Greater NY, LLC

Property at 2203 Mulberry Ct, Poughkeepsie, NY 12603, 3 beds, 1.5 baths

$299,000

3 beds1.5 baths1,252 sq ft

2203 Mulberry Ct, Poughkeepsie, NY 12603

Listing by eXp Realty

Property at 104 Hillside Rd, Poughquag, NY 12570, 3 beds, 1.5 baths

$494,930

3 beds1.5 baths1,854 sq ft

104 Hillside Rd, Poughquag, NY 12570

Listing by RE/MAX Town & Country

Property at 29 Lewis Ave, Poughkeepsie, NY 12603, 4 beds, 1.5 baths

$354,999

4 beds1.5 baths1,251 sq ft

29 Lewis Ave, Poughkeepsie, NY 12603

Listing by VYLLA Home

Property at 48 E Van Buren Way, Hopewell Junction, NY 12533, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths2,951 sq ft

48 E Van Buren Way, Hopewell Junction, NY 12533

Listing by K. Fortuna Realty, Inc.

Property at 60 Hibiscus Cir #60, Hopewell Junction, NY 12533, 1 bed, 1 bath

$37,000

1 bed1 bath462 sq ft

60 Hibiscus Cir #60, Hopewell Junction, NY 12533

Listing by RE/MAX Town & Country

Property at 9 Apple Smt, Lagrangeville, NY 12540, 4 beds, 3.5 baths

$849,000

4 beds3.5 baths5,401 sq ft

9 Apple Smt, Lagrangeville, NY 12540

Listing by BHHS Hudson Valley Properties

Property at 126-128 Washington Ave, Beacon, NY 12508, 6 beds, 3 baths

$630,000

6 beds3 baths2,240 sq ft

126-128 Washington Ave, Beacon, NY 12508

Listing by Howard Hanna Rand Realty

Property at 5 Birch Dr, Holmes, NY 12531, 2 beds, 1 bath

$325,000

2 beds1 bath672 sq ft

5 Birch Dr, Holmes, NY 12531

Listing by RE/MAX Classic Realty

Property at 201 Rossway Rd, Pleasant Valley, NY 12569, 3 beds, 1 bath

$330,000

3 beds1 bath998 sq ft

201 Rossway Rd, Pleasant Valley, NY 12569

Listing by ReAttached

Property at 83 Sunny Ln, Stormville, NY 12582, 3 beds, 2.5 baths

$649,999

3 beds2.5 baths2,180 sq ft

83 Sunny Ln, Stormville, NY 12582

Listing by Keller Williams Realty

Property at 57 Kingwood Dr, Poughkeepsie, NY 12601, 5 beds, 2.5 baths

$885,000

5 beds2.5 baths3,707 sq ft

57 Kingwood Dr, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 82 Lake Rd, Pine Plains, NY 12567, 4 beds, 2.5 baths

$489,000

4 beds2.5 baths2,040 sq ft

82 Lake Rd, Pine Plains, NY 12567

Listing by Corcoran Country Living

Property at 634 Route 82, Hopewell Junction, NY 12533, 3 beds, 2 baths

$450,000

3 beds2 baths1,676 sq ft

634 Route 82, Hopewell Junction, NY 12533

Listing by KW MidHudson

Property at 12 Russell Rd, Wappingers Falls, NY 12590, 3 beds, 1 bath

$499,900

3 beds1 bath1,366 sq ft

12 Russell Rd, Wappingers Falls, NY 12590

Listing by Coldwell Banker Realty

Property at 85 W Hook Rd, Hopewell Junction, NY 12533, 2 beds, 1 bath

$349,999

2 beds1 bath1,412 sq ft

85 W Hook Rd, Hopewell Junction, NY 12533

Listing by K. Fortuna Realty, Inc.

Property at 1 Dean Ave, Wappingers Falls, NY 12590, 3 beds, 1 bath

$399,900

3 beds1 bath1,387 sq ft

1 Dean Ave, Wappingers Falls, NY 12590

Listing by K. Fortuna Realty, Inc.

Property at 228 Dog Tail Corners Rd, Wingdale, NY 12594, 2 beds, 1 bath

$350,000

2 beds1 bath1,296 sq ft

228 Dog Tail Corners Rd, Wingdale, NY 12594

Listing by McGrath Realty Inc

Property at 1 Four Winds Dr, Poughkeepsie, NY 12603, 4 beds, 3 baths

$649,999

4 beds3 baths2,809 sq ft

1 Four Winds Dr, Poughkeepsie, NY 12603

Listing by RE/MAX Prestige Properties

Property at 84 Rockefeller Ln, Red Hook, NY 12571, 4 beds, 3.5 baths

$855,000

4 beds3.5 baths3,152 sq ft

84 Rockefeller Ln, Red Hook, NY 12571

Listing by Houlihan Lawrence

Property at 29 Red Barn Rd, Hyde Park, NY 12538, 3 beds, 1 bath

$290,000

3 beds1 bath1,411 sq ft

29 Red Barn Rd, Hyde Park, NY 12538

Listing by K. Fortuna Realty, Inc.

Property at 13 Baldwin Dr, Wappingers Falls, NY 12590, 3 beds, 2 baths

$475,000

3 beds2 baths1,852 sq ft

13 Baldwin Dr, Wappingers Falls, NY 12590

Listing by Century 21 Alliance Rlty Group

Property at 2578 South Ave Unit South, Wappingers Falls, NY 12590, 6 beds, 3 baths

$540,000

6 beds3 baths2,994 sq ft

2578 South Ave Unit South, Wappingers Falls, NY 12590

Listing by RE/MAX Town & Country

Property at 3 Spring St, Chelsea, NY 12512, 5 beds, 1 bath

$599,000

5 beds1 bath2,088 sq ft

3 Spring St, Chelsea, NY 12512

Listing by K. Fortuna Realty, Inc.

Property at 70 Lakeview Dr, Holmes, NY 12531, 2 beds, 2 baths

$849,000

2 beds2 baths1,600 sq ft

70 Lakeview Dr, Holmes, NY 12531

Listing by BHHS Hudson Valley Properties

Property at 9 Bobcat Ln, Staatsburg, NY 12580, 2 beds, 1 bath

$340,000

2 beds1 bath768 sq ft

9 Bobcat Ln, Staatsburg, NY 12580

Listing by Four Seasons Sothebys Intl

Property at 6099 Route 82, Stanfordville, NY 12581, 3 beds, 2 baths

$299,900

3 beds2 baths3,841 sq ft

6099 Route 82, Stanfordville, NY 12581

Listing by Mondello Upstate Properties

Property at 88 Spackenkill Rd, Poughkeepsie, NY 12603, 4 beds, 3 baths

$549,000

4 beds3 baths1,680 sq ft

88 Spackenkill Rd, Poughkeepsie, NY 12603

Listing by ReAttached

Property at 2574-2576 South Ave, Wappingers Falls, NY 12590, 6 beds, 3 baths

$560,000

6 beds3 baths3,473 sq ft

2574-2576 South Ave, Wappingers Falls, NY 12590

Listing by RE/MAX Town & Country

Property at 93 Albany St, Poughkeepsie, NY 12601, 3 beds, 1.5 baths

$349,999

3 beds1.5 baths1,344 sq ft

93 Albany St, Poughkeepsie, NY 12601

Listing by Exit Realty Connections

Property at 2696 Route 52, Hopewell Junction, NY 12533, 3 beds, 3 baths

$535,000

3 beds3 baths2,357 sq ft

2696 Route 52, Hopewell Junction, NY 12533

Listing by Century 21 Alliance Rlty Group

Property at 8 Daniel Sabia Dr, Wappingers Falls, NY 12590, 3 beds, 1 bath

$425,000

3 beds1 bath1,684 sq ft

8 Daniel Sabia Dr, Wappingers Falls, NY 12590

Listing by KW MidHudson

Property at 88 Buckingham Ave, Poughkeepsie, NY 12601, 3 beds, 1 bath

$280,000

3 beds1 bath1,513 sq ft

88 Buckingham Ave, Poughkeepsie, NY 12601

Listing by Houlihan Lawrence Inc.

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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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