Homes with Pools for Sale in Chester, NY

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COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Welcome to Whispering Hills! This inviting end-unit home offers a comfortable blend of everyday living, privacy, and convenience. Enjoy easy access to major commuter routes, highways, and bus service to NYC, making this an ideal choice for commuters seeking the comfort of home without sacrificing convenience. Come home to a welcoming community and enjoy all that this convenient location has to offer.

$299,000

2 beds1 bath1,084 sq ft

2124 Whispering Hls, Chester, NY 10918

$250 HOA • Garage • Community pool

Listing by Howard Hanna Rand Realty

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways. Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace, providing a welcoming space to relax or entertain. The kitchen boasts modern stainless-steel appliances, ample cabinetry, and a functional layout, making it a delight for cooking and meal prep. Living in Whispering Hills comes with a wealth of amenities. Enjoy sunny days by the community pool, play a match

$360,000

3 beds2.5 baths1,331 sq ft

3409 Whispering Hls, Chester, NY 10918

Handball courts • Community pool • Tennis courts

Listing by Howard Hanna Rand Realty

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange County within the Chester School District, this home offers space, privacy, and convenient access to shopping, dining, parks, recreation, commuter routes, and Hudson Valley attractions. Some listing photographs have been virtually decluttered and/or virtually staged for visualization purposes. Virt

$749,900

4 beds3 baths3,080 sq ft

20 Mountainside Dr, Chester, NY 10918

Covered porch • Central cooling • Gas heat

Listing by eXp Realty

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17. Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace, and a separate dining area ideal for entertaining. The kitchen has a tile backsplash, and a natural gas range. A convenient half bath and laundry area complete the first floor. Upstairs, the primary bedroom offers vaulted ceilings, a generous walk in closet and a full bath with private access to the hallway. The second bedroom is of ample

$290,000

2 beds1.5 baths1,072 sq ft

4008 Whispering Hills Dr, Chester, NY 10918

Natural gas range • Private access • Walk in closet

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the kitchen and family room, with a separate living room and formal dining room, plus laundry and a half bath. Upstairs, four bedrooms and two full baths provide ample space. The basement offers generous storage, and the 2-car garage completes the layout with a spacious driveway for multiple vehicles. T

$799,000

4 beds2.5 baths2,516 sq ft

3 Garnett Hill Rd, Chester, NY 10918

Wood molding • Sun deck • 3 tier trex deck

Listing by Keller Williams Realty

Property at 2522 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$369,000

3 beds2.5 baths1,331 sq ft

2522 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 412 Laroe Rd, Chester, NY 10918, 3 beds, 2 baths

$615,000

3 beds2 baths1,848 sq ft

412 Laroe Rd, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 11 Chandler Dr, Chester, NY 10918, 3 beds, 2.5 baths

$545,000

3 beds2.5 baths1,908 sq ft

11 Chandler Dr, Chester, NY 10918

Listing by Coldwell Banker Realty

Property at 7 Lakeview Dr, Chester, NY 10918, 4 beds, 2.5 baths

$549,999

4 beds2.5 baths2,098 sq ft

7 Lakeview Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 4114 Whispering Hls, Chester, NY 10918, 3 beds, 2 baths

$389,900

3 beds2 baths1,393 sq ft

4114 Whispering Hls, Chester, NY 10918

Listing by Coldwell Banker Realty

Property at 985 Craigville Rd, Chester, NY 10918, 4 beds, 3.5 baths

$750,000

4 beds3.5 baths3,100 sq ft

985 Craigville Rd, Chester, NY 10918

Listing by Serhant LLC

Property at 2113 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$295,000

2 beds1 bath1,084 sq ft

2113 Whispering Hls, Chester, NY 10918

Listing by Keller Williams Realty

Property at 2119 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$295,000

2 beds1.5 baths1,086 sq ft

2119 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 58 Nancy Ln, Chester, NY 10918, 3 beds, 2.5 baths

$749,999

3 beds2.5 baths2,718 sq ft

58 Nancy Ln, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 49 Stone Mountain Trl, Chester, NY 10918, 4 beds, 2.5 baths

$875,000

4 beds2.5 baths3,656 sq ft

49 Stone Mountain Trl, Chester, NY 10918

Listing by eRealty Advisors, Inc

Property at 2 Primrose Ln, Chester, NY 10918, 4 beds, 3 baths

$849,900

4 beds3 baths2,370 sq ft

2 Primrose Ln, Chester, NY 10918

Listing by Weichert Realtors

Property at 19 High St, Chester, NY 10918, 9 beds, 6.5 baths

$1,145,000

9 beds6.5 baths4,965 sq ft

19 High St, Chester, NY 10918

Listing by Keller Williams Realty

Property at 19 Greentree Ln, Chester, NY 10918, 4 beds, 4 baths

$3,400,000

4 beds4 baths7,750 sq ft

19 Greentree Ln, Chester, NY 10918

Listing by Serhant LLC

Property at 16 Lori Ln, Chester, NY 10918, 4 beds, 4 baths

$1,139,900

4 beds4 baths4,624 sq ft

16 Lori Ln, Chester, NY 10918

Listing by eXp Realty

Property at 12 Damian Ct, Chester, NY 10918, 5 beds, 4 baths

$949,000

5 beds4 baths3,136 sq ft

12 Damian Ct, Chester, NY 10918

Listing by MS Realty Group USA, Inc

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FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Welcome to this exceptional, sunny and spacious 4-bedroom, 3.5-bath home, perfectly situated on one of Monroe’s most secluded cul-de-sacs in the lovely Horizon Heights. Thoughtfully updated throughout, this distinctive property combines spacious interiors, high-end amenities, and resort-style outdoor living. Inside, hardwood floors and abundant natural light complement inviting living spaces, including a formal living room, formal dining room with a wood-burning brick fireplace and an expansive family room with a gas fireplace. The renovated chef’s kitchen features premium Viking and Thermador appliances, a large center island, generous cabinetry and an adjoining scullery/pantry

$699,000

4 beds3.5 baths2,860 sq ft

112 Mercury Ct, Monroe, NY 10950

Formal dining room • Formal living room • Cul-de-sac

Listing by Century 21 Realty Center

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Set at the end of a quiet cul-de-sac in the prestigious Farmingdale Heights neighborhood, this extraordinary custom-built residence offers an impressive combination of luxury, privacy, and exceptional indoor and outdoor living. From the moment you arrive, the professionally designed landscaping, expansive grounds, and striking architectural details set this home apart. With 5 bedrooms, 4.5 baths, and an abundance of thoughtfully designed living space, this home is built to impress while offering the comfort and privacy of a true retreat. A grand two-story foyer welcomes you with marble floors, an elegant staircase, crystal chandeliers, and dramatic floor-to-ceiling windows. Walnut-stained h

$1,499,000

5 beds4.5 baths3,586 sq ft

34 Woodcrest Ln, Goshen, NY 10924

Marble floors • Elegant staircase • Expansive grounds

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
* * A Rare Development & Investment Opportunity * * This is far more than three homes—it's a unique opportunity to acquire * * three adjoining properties totaling over 3 acres * * in one of the area's fastest-growing locations: * * 234 Prospect Road • 236 Prospect Road • 242 Prospect Road * * Being sold together, these three properties create a rare opportunity for * * larger land, greater development potential, and multiple income possibilities. * * The true value lies in the potential to * * combine the parcels and pursue a potential multi-lot subdivision * * , with the possibility of constructing multiple homes (subject to all municipal approva

$999,000

3 beds1.5 baths1,678 sq ft

242 Prospect Rd, Monroe, NY 10950

Over 3 acres • Substantial land • Existing income

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Welcome to Windridge! This well-maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfortable, carefree living in a convenient Hudson Valley location. The first floor features a spacious eat-in kitchen with new stainless-steel appliances, a powder room, and an open living/dining area with sliding doors leading to the patio. Upstairs offers two bedrooms, a full bath, and a spacious primary suite with a walk-in closet. Enjoy parking directly in front of your home, along with wonderful community amenities including two pools, two playgrounds, a clubhouse, basketball and tennis courts, and walking trails. Recent updates include brand-new siding, roof, stainless-steel appliances, cen

$355,000

3 beds2.5 baths1,585 sq ft

255 Heritage Ln, Monroe, NY 10950

Walk-in closet • Community amenities • Eat-in kitchen

Listing by Coldwell Banker Realty

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Welcome to 256 Ridge Road! Located in the Town of Hamptonburgh and in the Goshen School District, this 4 bedroom, 2.5 bath colonial will not disappoint. Enjoy scenic views of the surrounding horse farms, mountains and extraordinary sunsets from the covered front porch or second story bedroom picture window. Guests can be entertained in the private backyard, complete with flagstone patios and an 18’ X 36’ inground saltwater pool. The home boasts 2 fireplaces for chilly winter evenings and radiant heated floors. Energy efficient Mitsubishi mini split heating and cooling systems have recently been installed. The home has a finished basement that can function as a recreation room. F

$850,000

4 beds2.5 baths3,110 sq ft

256 Ridge Rd, Campbell Hall, NY 10916

Covered front porch • Private backyard • Finished basement

Listing by Curasi Realty, Inc.

ABOUT THIS HOME
Home with a Pool for sale in Chester, NY:
Welcome to 31 Still Road, a beautifully updated Cape Cod nestled in the heart of Monroe. Offering approximately 1,785 square feet of comfortable living space, this charming 3-bedroom, 2-bathroom home blends classic character with modern convenience. Step inside to find a warm and inviting interior with thoughtful updates throughout. The updated kitchen features modern appliances, generous counter space, and ample cabinetry, making it both functional and ideal for everyday living and entertaining. The home also offers abundant storage, a full attic, and a walk-out basement, providing plenty of flexibility for storage, recreation, or future use. Outside, enjoy your own private retreat on appr

$649,999

3 beds1.5 baths1,785 sq ft

31 Still Rd, Monroe, NY 10950

Landscaped backyard • Refreshing pool • Walk-out basement

Listing by Concrete Jungle NYC Realty

Property at 13 Lakeview Dr, Warwick, NY 10990, 4 beds, 2 baths

$490,000

4 beds2 baths2,005 sq ft

13 Lakeview Dr, Warwick, NY 10990

Listing by Cole Prime Realty

Property at 11 Hidden Creek Blvd, Monroe, NY 10950, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths2,176 sq ft

11 Hidden Creek Blvd, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 81 Lois Ln, Monroe, NY 10950, 2 beds, 1.5 baths

$329,000

2 beds1.5 baths1,168 sq ft

81 Lois Ln, Monroe, NY 10950

Listing by Keller Williams Valley Realty

Property at 607 Mountain Laurel Dr, Monroe, NY 10950, 3 beds, 2.5 baths

$299,000

3 beds2.5 baths1,320 sq ft

607 Mountain Laurel Dr, Monroe, NY 10950

Listing by Weichert Realtors

Property at 14 Robalene Dr, Goshen, NY 10924, 5 beds, 4 baths

$849,900

5 beds4 baths2,600 sq ft

14 Robalene Dr, Goshen, NY 10924

Listing by KW Hudson Valley United

Property at 7 Greenfield Dr, Warwick, NY 10990, 6 beds, 4 baths

$2,350,000

6 beds4 baths4,278 sq ft

7 Greenfield Dr, Warwick, NY 10990

Listing by Keller Williams Hudson Valley

Property at 7 Lake Ave, Monroe, NY 10950, 5 beds, 3.5 baths

$999,000

5 beds3.5 baths3,758 sq ft

7 Lake Ave, Monroe, NY 10950

Listing by Urbane Brokerage

Property at 1 Cedar Hill Dr, Warwick, NY 10990, 3 beds, 2.5 baths

$774,900

3 beds2.5 baths2,441 sq ft

1 Cedar Hill Dr, Warwick, NY 10990

Listing by Keller Williams Realty

Property at 213 Eagleton Dr, Monroe, NY 10950, 3 beds, 2.5 baths

$389,900

3 beds2.5 baths1,694 sq ft

213 Eagleton Dr, Monroe, NY 10950

Listing by Keller Williams Valley Realty

Property at 7 Briarwood Ave, Monroe, NY 10950, 4 beds, 2.5 baths

$625,000

4 beds2.5 baths2,892 sq ft

7 Briarwood Ave, Monroe, NY 10950

Listing by eRealty Advisors, Inc

Property at 127-129-131 Hill Rd, Goshen, NY 10924, 8 beds, 5.5 baths

$1,480,000

8 beds5.5 baths5,302 sq ft

127-129-131 Hill Rd, Goshen, NY 10924

Listing by Howard Hanna Rand Realty

Property at 14 Larchwood Dr, Goshen, NY 10924, 4 beds, 2 baths

$629,000

4 beds2 baths1,932 sq ft

14 Larchwood Dr, Goshen, NY 10924

Listing by HomeCoin.com

Property at 46 Mansion Ridge Blvd, Monroe, NY 10950, 3 beds, 2.5 baths

$924,990

3 beds2.5 baths2,994 sq ft

46 Mansion Ridge Blvd, Monroe, NY 10950

Listing by Terrie OConnor

Property at 154 Eagleton Dr, Monroe, NY 10950, 3 beds, 2.5 baths

$360,000

3 beds2.5 baths1,585 sq ft

154 Eagleton Dr, Monroe, NY 10950

Listing by Keller Williams Realty

Based on information submitted to the MLS GRID as of Tue Aug 25 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 Chester

There are currently 20 homes with pools for sale in Chester at a median listing price of $375K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 28 days and receive 4 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 4 homes have been sold in Chester. In addition to houses in Chester, there were also 13 condos, 1 townhouse, and 1 multi-family unit for sale in Chester last month. Find your dream home in Chester 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 Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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