Homes with Pools for Sale in Chester, MD

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3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add mod

$899,000

3 beds2.5 baths2,464 sq ft

148 Elinor St, Chester, MD 21619

Updated staircase • Extensive renovation • Upgraded lighting

(703) 378-8810

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Professional photography and more remarks coming soon…. Come and see the largest model end-unit in Queens Landing with a stunning water-view of the pond. Schedule your showings today,

$459,000

3 beds2.5 baths2,008 sq ft

43-A Queen Neva Ct, Chester, MD 21619

$535 HOA • Community pool • Built 1994

(410) 224-3600

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedroom enhanced by a three-foot extension. A first-floor study offers flexible space for a home office, den, or possible fourth bedroom. Thoughtfully designed and exceptionally well-maintained, the home offers numerous updates and features, including a new roof installed in 2026 with a transferable manufacturer’s warranty and a new kitchen completed in 2022 featuring GE Café appliances, including a professional 36” six-burner range with convection oven, an additional oven in the island, and an Advantiu

$819,900

3 beds2.5 baths2,479 sq ft

207 Thomas White Blvd, Chester, MD 21619

New kitchen • Ge cafe appliances • New roof

(443) 353-5281

OPEN WED, 11AM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Welcome Home!!! Open DAILY by Appointment! * * * If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds. * * * Barely lived in and offering over $75,000 in builder upgrades, this home still feels like new, allowing you to move right in without the wait or additional costs of new construction (i. e. transfer tax split, etc). Designed for easy everyday living, the Simone model offers the convenience of having the majority of the home's daily living spaces on the main level. The gourmet kitchen, dining and living areas, screened porch, primary suite, second bedroom, office, full bath, and lau

$747,900

4 beds3 baths3,142 sq ft

209 Harrier Way, Chester, MD 21619

Community amenities • Gourmet kitchen • Screened porch

(410) 643-2244

COMING SOON

$345,000

3 beds1.5 baths1,080 sq ft

1609 Crab Alley Dr, Chester, MD 21619

0.46 acre lot • 2 garage spots • Pool

(703) 570-7307

Property at 320 Bayberry Dr, Chester, MD 21619, 3 beds, 2 baths

$897,750

3 beds2 baths2,331 sq ft

320 Bayberry Dr, Chester, MD 21619

(410) 486-4504

Property at 313 Thomas White Blvd, Chester, MD 21619, 4 beds, 2.5 baths

$825,000

4 beds2.5 baths3,291 sq ft

313 Thomas White Blvd, Chester, MD 21619

(443) 906-3848

Property at 134 Richard Ingle Way, Chester, MD 21619, 4 beds, 3.5 baths

$749,000

4 beds3.5 baths2,185 sq ft

134 Richard Ingle Way, Chester, MD 21619

Property at 214 Bayberry Dr, Chester, MD 21619, 3 beds, 3 baths

$924,000

3 beds3 baths2,745 sq ft

214 Bayberry Dr, Chester, MD 21619

(410) 822-6665

Property at 113 Bentons Pleasure Rd, Chester, MD 21619, 4 beds, 2.5 baths

$868,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

(410) 823-0033

Property at 108 Blenny Ln, Chester, MD 21619, 3 beds, 2.5 baths

$389,900

3 beds2.5 baths1,899 sq ft

108 Blenny Ln, Chester, MD 21619

(410) 224-3200

Property at 201 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$859,500

3 beds2.5 baths2,602 sq ft

201 Switchgrass Way #34, Chester, MD 21619

(410) 280-5600

Property at 111 Flycatcher Way, Chester, MD 21619, 5 beds, 4.5 baths

$1,200,000

5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 536 Warbler Way, Chester, MD 21619, 2 beds, 2.5 baths

$799,990

2 beds2.5 baths2,010 sq ft

536 Warbler Way, Chester, MD 21619

(410) 208-3500

Property at 117 Flycatcher Way, Chester, MD 21619, 3 beds, 3.5 baths

$1,200,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 230 Switchgrass Way #12, Chester, MD 21619, 2 beds, 2.5 baths

$525,000

2 beds2.5 baths2,003 sq ft

230 Switchgrass Way #12, Chester, MD 21619

(855) 450-0442

Property at 233 Peregrine Dr, Chester, MD 21619, 4 beds, 3 baths

$724,999

4 beds3 baths3,151 sq ft

233 Peregrine Dr, Chester, MD 21619

(410) 758-0333

Property at 1012 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$599,900

3 beds3.5 baths2,076 sq ft

1012 Auckland Way, Chester, MD 21619

Property at 2855 Cox Neck Rd, Chester, MD 21619, 4 beds, 4.5 baths

$1,195,000

4 beds4.5 baths4,413 sq ft

2855 Cox Neck Rd, Chester, MD 21619

(410) 304-2250

Property at 121 Merlin Dr, Chester, MD 21619, 2 beds, 2 baths

$719,900

2 beds2 baths2,118 sq ft

121 Merlin Dr, Chester, MD 21619

(410) 263-8686

Property at 330 Serenity Ln, Chester, MD 21619, 7 beds, 8 baths

$5,400,000

7 beds8 baths10,667 sq ft

330 Serenity Ln, Chester, MD 21619

(410) 280-5600

Property at 123 Flycatcher Way, Chester, MD 21619, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,789 sq ft

123 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 111 Marshgrass Way #41, Chester, MD 21619, 3 beds, 2.5 baths

$998,000

3 beds2.5 baths— sq ft

111 Marshgrass Way #41, Chester, MD 21619

(410) 770-3600

Property at 106 Bodys Neck Rd, Chester, MD 21619, 3 beds, 2.5 baths

$435,000

3 beds2.5 baths1,595 sq ft

106 Bodys Neck Rd, Chester, MD 21619

(410) 643-3404

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

$515,000

2 beds2.5 baths1,586 sq ft

34-E Queen Anne Way, Chester, MD 21619

(301) 970-2447

Property at 232 Evelyne St, Chester, MD 21619, 4 beds, 3.5 baths

$840,000

4 beds3.5 baths3,312 sq ft

232 Evelyne St, Chester, MD 21619

(410) 673-3344

Property at 114 Merganser Ct, Chester, MD 21619, 2 beds, 2 baths

$287,500

2 beds2 baths1,069 sq ft

114 Merganser Ct, Chester, MD 21619

(443) 988-0483

Property at 807 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$425,500

3 beds3.5 baths2,100 sq ft

807 Auckland Way, Chester, MD 21619

(855) 450-0442

Property at 323 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$949,990

5 beds4.5 baths3,225 sq ft

323 Kingfisher Ln, Chester, MD 21619

(410) 208-3500

Property at 54-D Queen Caroline Ct, Chester, MD 21619, 3 beds, 2.5 baths

$309,900

3 beds2.5 baths1,440 sq ft

54-D Queen Caroline Ct, Chester, MD 21619

(410) 643-4131

Property at 1000 Herons Nest Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$595,000

2 beds2.5 baths1,832 sq ft

1000 Herons Nest Way #43, Chester, MD 21619

(410) 224-2200

Property at 132 Wheelhouse Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$700,000

2 beds2.5 baths2,003 sq ft

132 Wheelhouse Way #11, Chester, MD 21619

(855) 450-0442

Property at 54F Queen Caroline Ct, Chester, MD 21619, 3 beds, 2.5 baths

$349,900

3 beds2.5 baths1,440 sq ft

54F Queen Caroline Ct, Chester, MD 21619

(410) 643-2244

Property at 215 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$995,000

5 beds4.5 baths3,225 sq ft

215 Kingfisher Ln, Chester, MD 21619

(443) 274-1900

Property at 45-G Queen Neva Ct, Chester, MD 21619, 2 beds, 2.5 baths

$349,500

2 beds2.5 baths1,312 sq ft

45-G Queen Neva Ct, Chester, MD 21619

(410) 263-8686

Property at 208 Blenny Ln, Chester, MD 21619, 3 beds, 3 baths

$385,900

3 beds3 baths1,899 sq ft

208 Blenny Ln, Chester, MD 21619

(443) 274-1900

Property at 1000 Herons Nest Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$485,000

2 beds2.5 baths1,900 sq ft

1000 Herons Nest Way #22, Chester, MD 21619

(443) 274-1900

Property at 540 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$929,990

3 beds3 baths2,789 sq ft

540 Warbler Way, Chester, MD 21619

(410) 208-3500

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

$479,000

2 beds2.5 baths2,003 sq ft

3000 Herons Nest Way #11, Chester, MD 21619

(410) 263-8686

Property at 8-F Queen Victoria Way, Chester, MD 21619, 1 bed, 1 bath

$240,000

1 bed1 bath724 sq ft

8-F Queen Victoria Way, Chester, MD 21619

(410) 643-2244

Property at 111 Marshgrass Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$765,000

2 beds2.5 baths— sq ft

111 Marshgrass Way #43, Chester, MD 21619

(410) 263-8686

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Homes with Pools for Sale in Chester

There are currently 45 homes with pools for sale in Chester at a median listing price of $574K. 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 77 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 15 homes have been sold in Chester. In addition to houses in Chester, there were also 17 condos, 21 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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