Homes with Pools for Sale in Chester, MD

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NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The be

$1,400,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

Screened patio • Barn doors • Cozy fireplace

(240) 375-5074

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication. Standout features include a dedicated home office, an inviting fireplace, and a screened patio perfect for indoor–outdoor living. Custom design elements—such as barn doors, ceiling beams, and a striking feature wall—bring warmth, character, and craftsmanship to every corner. As a premium bonus, all model home furniture is included, providing a fully move-in-ready

$1,400,000

5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

Open-concept design • Screened patio • Inviting fireplace

(240) 375-5074

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Welcome to Bayside on Kent Island! This meticulously maintained 3-level townhome offers beautiful pond views and numerous updates throughout. Main level features an open floorplan with hardwood bamboo floors and upgraded lighting, Bright kitchen with white shaker cabinets, granite counters (2019), and updated fixtures. Upper level includes an oversized Primary Suite with a spa-like bath (2018), large walk-in closet with California Closets (2024 – $12K), and ceiling fan. Second bedroom features a large closet and is adjacent to the updated hall bath. Entry-level 3rd bedroom/office offers custom built-ins (2024) and direct access to the patio with serene pond views. Enjoy outdoor living

$349,000

3 beds2.5 baths1,747 sq ft

206 Ringneck Ct #78, Chester, MD 21619

Garage • Community pool • Built 1995

(443) 274-1900

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace, and professionally designed details such as a feature wall, crown molding, and sliding barn doors that add custom character to each space. As an added benefit, all model home furniture is included, providing a fully move-in-ready experience. The gourmet kitchen is equipped with a Profile range,

$1,300,000

3 beds3 baths2,789 sq ft

123 Flycatcher Way, Chester, MD 21619

Sliding barn doors • Feature wall • Inviting fireplace

(240) 375-5074

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a screened patio ideal for indoor–outdoor living. Elevated design moments—such as feature walls, ceiling beams, and barn doors—bring custom flair to each space. As a true bonus, all model home furniture is included, offering a completely move-in-ready experience. The chef-inspired ki

$1,100,000

2 beds2 baths1,993 sq ft

127 Flycatcher Way, Chester, MD 21619

Screened patio • Cozy fireplace • Open-concept layout

(240) 375-5074

$330,000

1 bed1 bath724 sq ft

10-B Queen Elizabeth Ct, Chester, MD 21619

(410) 643-2244

Property at 2907 Cox Neck Rd E, Chester, MD 21619, 4 beds, 5 baths

$1,899,000

4 beds5 baths3,460 sq ft

2907 Cox Neck Rd E, Chester, MD 21619

(410) 280-5600

Property at 132 Claiborne St, Chester, MD 21619, 2 beds, 3.5 baths

$659,000

2 beds3.5 baths2,400 sq ft

132 Claiborne St, Chester, MD 21619

(410) 263-8686

Property at 1916 Stevens Dr, Chester, MD 21619, 3 beds, 2 baths

$495,000

3 beds2 baths1,728 sq ft

1916 Stevens Dr, Chester, MD 21619

(410) 224-2200

Property at 162 Kirwans Landing Ln, Chester, MD 21619, 4 beds, 2.5 baths

$929,000

4 beds2.5 baths2,404 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

(410) 263-8686

Property at 112 Chessie Ct, Chester, MD 21619, 3 beds, 2.5 baths

$519,900

3 beds2.5 baths2,066 sq ft

112 Chessie Ct, Chester, MD 21619

(443) 249-7653

Property at 202 Mchenny Ct, Chester, MD 21619, 3 beds, 2.5 baths

$875,000

3 beds2.5 baths2,520 sq ft

202 Mchenny Ct, Chester, MD 21619

(410) 224-2200

Property at 203 Riverside Dr, Chester, MD 21619, 5 beds, 3.5 baths

$1,099,900

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

(301) 945-9010

Property at 302 Teal Ct Unit A, Chester, MD 21619, 2 beds, 1.5 baths

$294,000

2 beds1.5 baths1,073 sq ft

302 Teal Ct Unit A, Chester, MD 21619

(410) 451-3300

Property at 1906 Harbor Dr, Chester, MD 21619, 3 beds, 2 baths

$499,900

3 beds2 baths1,750 sq ft

1906 Harbor Dr, Chester, MD 21619

(240) 222-3200

Property at 1839 Harbor Dr, Chester, MD 21619, 4 beds, 2 baths

$384,999

4 beds2 baths2,035 sq ft

1839 Harbor Dr, Chester, MD 21619

(301) 970-2447

Property at 906 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$520,000

3 beds3.5 baths2,076 sq ft

906 Auckland Way, Chester, MD 21619

(410) 673-3344

Property at 1221 Cox Nck, Chester, MD 21619, 4 beds, 2.5 baths

$524,900

4 beds2.5 baths1,482 sq ft

1221 Cox Nck, Chester, MD 21619

(855) 550-0528

Property at 1870 Harbor Dr, Chester, MD 21619, 2 beds, 1 bath

$324,900

2 beds1 bath832 sq ft

1870 Harbor Dr, Chester, MD 21619

(443) 274-1900

Property at 1401 Calvert Rd, Chester, MD 21619, 2 beds, 2 baths

$454,900

2 beds2 baths1,444 sq ft

1401 Calvert Rd, Chester, MD 21619

(410) 643-5005

Property at Harbor Dr, Chester, MD 21619, 3 beds, 2 baths

$499,900

3 beds2 baths1,250 sq ft

Harbor Dr, Chester, MD 21619

(410) 643-5005

Property at 117 Redstart Dr, Chester, MD 21619, 2 beds, 2.5 baths

$879,900

2 beds2.5 baths2,010 sq ft

117 Redstart Dr, Chester, MD 21619

(240) 375-5074

Property at 30-C Queen Mary Ct, Chester, MD 21619, 2 beds, 2.5 baths

$339,900

2 beds2.5 baths1,440 sq ft

30-C Queen Mary Ct, Chester, MD 21619

(410) 255-3690

Property at 201 Golden Eye Ct, Chester, MD 21619, 2 beds, 2 baths

$285,000

2 beds2 baths1,073 sq ft

201 Golden Eye Ct, Chester, MD 21619

(410) 673-3344

Property at 2865 Cox Neck Rd, Chester, MD 21619, 4 beds, 3.5 baths

$2,259,000

4 beds3.5 baths5,122 sq ft

2865 Cox Neck Rd, Chester, MD 21619

(410) 721-1500

Property at 527 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$869,900

3 beds3 baths2,789 sq ft

527 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 1757 Harbor Dr, Chester, MD 21619, 4 beds, 3.5 baths

$1,125,000

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

Property at 3000 Herons Nest Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$555,900

2 beds2.5 baths2,003 sq ft

3000 Herons Nest Way #11, Chester, MD 21619

(410) 263-8686

Property at 630 Warbler Way #33, Chester, MD 21619, 2 beds, 2.5 baths

$644,900

2 beds2.5 baths1,900 sq ft

630 Warbler Way #33, Chester, MD 21619

Listing provided by Zillow

Property at 1405 Little Creek Rd, Chester, MD 21619, 2 beds, 1 bath

$19,500

2 beds1 bath764 sq ft

1405 Little Creek Rd, Chester, MD 21619

(302) 217-6692

Property at 519 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$879,900

3 beds3 baths2,789 sq ft

519 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 205 Anchor Ln, Chester, MD 21619, 6 beds, 3 baths

$535,000

6 beds3 baths3,500 sq ft

205 Anchor Ln, Chester, MD 21619

(443) 274-1900

Property at 312 Teal Ct Unit F, Chester, MD 21619, 2 beds, 2 baths

$305,000

2 beds2 baths1,073 sq ft

312 Teal Ct Unit F, Chester, MD 21619

(443) 292-6767

Property at 135 Nauset Ln, Chester, MD 21619, 3 beds, 3 baths

$814,900

3 beds3 baths2,399 sq ft

135 Nauset Ln, Chester, MD 21619

(855) 450-0442

Property at 630 Warbler Way #32, Chester, MD 21619, 2 beds, 2.5 baths

$644,990

2 beds2.5 baths1,900 sq ft

630 Warbler Way #32, Chester, MD 21619

Listing provided by Zillow

Property at 9-B Queen Victoria Way, Chester, MD 21619, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths1,680 sq ft

9-B Queen Victoria Way, Chester, MD 21619

(301) 490-5400

Property at 141 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$684,950

3 beds2.5 baths2,600 sq ft

141 Switchgrass Way #34, Chester, MD 21619

(443) 274-1900

Property at 132 Kestrel Ln, Chester, MD 21619, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths3,634 sq ft

132 Kestrel Ln, Chester, MD 21619

(410) 280-5600

Property at 34-E Queen Anne Way, Chester, MD 21619, 2 beds, 2.5 baths

$469,000

2 beds2.5 baths1,104 sq ft

34-E Queen Anne Way, Chester, MD 21619

(301) 970-2447

Property at 132 Wheelhouse Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way #43, Chester, MD 21619

Listing provided by Zillow

Property at 132 Wheelhouse Way, Chester, MD 21619, 2 beds, 2.5 baths

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way, Chester, MD 21619

(240) 375-5074

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Homes with Pools for Sale in Chester

There are currently 68 homes with pools for sale in Chester 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 Chester stay on the market for 75 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 14 homes have been sold in Chester. In addition to houses in Chester, there were also 16 condos, 12 townhouses, and 0 multi-family units 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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