Homes with Pools for Sale in Chester, MD

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OPEN SUN, 12PM TO 2PM3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
OPEN HOUSE SAT OCT 10th 10-12PM & SUN OCT 11TH 12-2PM! It's rare to find a designer home on a 1.4 acre lot with an in-ground saltwater pool and direct waterfront access on Kent Island at this price tag. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own 90 foot pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle b

$1,199,900

5 beds3 baths3,000 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

Updated kitchen • 90 foot pier • 1.4 acre lot

(443) 901-2200

OPEN OCT 17, 11AM TO 1PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Open House 10/17 11-1pm. Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, offering the convenience of * * true one-level living with no steps * * , three spacious bedrooms, and one of the largest garage configurations available in the community. Unlike many Killarney models designed with two bedrooms and a loft, this home features three true bedrooms, a dedicated laundry room, and an additional bump-out ideal for a home office or den. The open-concept interior features an Ultra Gourmet Kitchen with quartz countertops, upgraded cabinetry and appliances, double wall ovens, a French-door refrigerator, and a large center island perfect for gathering and en

$790,000

3 beds2 baths2,331 sq ft

117 Harrier Way, Chester, MD 21619

Waterfront clubhouse • 6,378 sq ft lot • 3 garage spots

(443) 274-1900

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Welcome to 223 Evelyne Street in Gibson’s Grant! Built by Koch Homes, this expanded Ashford model combines the convenience of a main-level primary bedroom with spacious living areas and an oversized garage with an enlarged family room above. Hardwood floors, plantation shutters throughout the home, and a beautiful stone-surround fireplace add warmth and timeless style. The spacious living room, kitchen, and dining area offer a welcoming setting for everyday living and entertaining, while a separate office provides a dedicated space for work or study. A beautiful Andersen sliding door opens to the deck and hardscaped patio, creating an inviting outdoor space for dining, relaxing, and g

$799,000

3 beds2.5 baths2,575 sq ft

223 Evelyne St, Chester, MD 21619

Separate office • Plantation shutters • Expanded family room

(703) 378-8810

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
Shore living doesn’t get much better than this! Wake up in this waterfront community perfectly tucked along the Chester River in the vibrant community of Queens Landing. Enjoy the easy, breezy coastal lifestyle with open living spaces, a sunlit kitchen, and a spacious primary suite with a private balcony and cozy fireplace. Private balcony offers the perfect spot for your morning coffee or evening cocktails—all with peaceful pond views you’ll never get tired of and two patios for your own private peaceful time outdoors. This two bedroom two bath end unit has been fully updated with a beautiful kitchen. Located just minutes from Route 50, this home is a c

$400,000

2 beds2 baths1,260 sq ft

1-F Queen Victoria Ct, Chester, MD 21619

Two patios • Peaceful pond views • Sunlit kitchen

(410) 255-3690

ABOUT THIS HOME
Home with a Pool for sale in Chester, MD:
New Listing! Bayside Condos * End Unit with Garage * Direct Water Views * Direct View of Castle Harbor Marina * Best Location in the Community * Potential to See Your Boat From Your Window * Many Upgrades * Renovated Kitchen * Renovated Primary Bath * Balcony Off Primary w Water Views * Large Walk-In Closet * Dramatic Ship Lap Accent Wall * Waterside Double Width Deck * Dual Zoned HVAC * Community Pool, Hot Tub, Tennis, Volleyball, Exercise Room and On-Site Property Manager * Condo Dues Cover Roof, Siding, Gutters, Lawn Care, Grass Cutting, Pest Control * Public Water, Public Sewer * Gas Fireplace * Convenient Chester Location Close To Shopping and Grocery

$599,900

3 beds3.5 baths2,100 sq ft

208 Widgeon Way, Chester, MD 21619

Renovated kitchen • Direct water views • Large walk-in closet

(410) 224-3200

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

$744,900

2 beds2.5 baths1,900 sq ft

111 Marshgrass Way #43, Chester, MD 21619

(410) 643-2244

Property at 1010 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$595,000

3 beds3.5 baths2,100 sq ft

1010 Auckland Way, Chester, MD 21619

(410) 505-9700

Property at 402 Macum Creek Dr, Chester, MD 21619, 3 beds, 2.5 baths

$789,000

3 beds2.5 baths2,787 sq ft

402 Macum Creek Dr, Chester, MD 21619

(703) 378-8810

Property at 326 Castle Marina Rd, Chester, MD 21619, 5 beds, 3.5 baths

$525,000

5 beds3.5 baths3,552 sq ft

326 Castle Marina Rd, Chester, MD 21619

(410) 643-5005

Property at 231 Evelyne St, Chester, MD 21619, 4 beds, 2.5 baths

$815,000

4 beds2.5 baths2,870 sq ft

231 Evelyne St, Chester, MD 21619

(410) 304-2250

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 34 Queen Anne Way Unit A, Chester, MD 21619, 2 beds, 2 baths

$570,000

2 beds2 baths1,380 sq ft

34 Queen Anne Way Unit A, Chester, MD 21619

(443) 274-1900

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

$859,900

3 beds2 baths2,331 sq ft

320 Bayberry Dr, Chester, MD 21619

(410) 224-3200

Property at 129 Wheelhouse Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$585,000

2 beds2.5 baths2,003 sq ft

129 Wheelhouse Way #11, Chester, MD 21619

(443) 274-1900

Property at 228 Bayberry Dr, Chester, MD 21619, 2 beds, 2.5 baths

$665,000

2 beds2.5 baths1,993 sq ft

228 Bayberry Dr, Chester, MD 21619

(410) 544-4000

Property at 15-E Queen Anne Way Unit E, Chester, MD 21619, 2 beds, 2.5 baths

$539,000

2 beds2.5 baths1,680 sq ft

15-E Queen Anne Way Unit E, Chester, MD 21619

(410) 822-6665

Property at 8-E Piney Narrows Rd, Chester, MD 21619

$40,000

— beds— baths830 sq ft

8-E Piney Narrows Rd, Chester, MD 21619

(410) 822-6665

Property at 7-B Queen Victoria Way Unit B, Chester, MD 21619, 2 beds, 2.5 baths

$499,000

2 beds2.5 baths1,680 sq ft

7-B Queen Victoria Way Unit B, Chester, MD 21619

(703) 522-1940

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

$829,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

(410) 823-0033

Property at 512 Auckland Way, Chester, MD 21619, 3 beds, 3 baths

$375,000

3 beds3 baths1,899 sq ft

512 Auckland Way, Chester, MD 21619

(410) 643-2244

Property at 53-E Queen Caroline Ct, Chester, MD 21619, 2 beds, 2.5 baths

$329,000

2 beds2.5 baths1,440 sq ft

53-E Queen Caroline Ct, Chester, MD 21619

(888) 860-7369

Property at 118 Broadwater Dr, Chester, MD 21619, 2 beds, 2 baths

$656,000

2 beds2 baths2,473 sq ft

118 Broadwater Dr, Chester, MD 21619

(443) 274-1900

Property at 168 Redstart Dr, Stevensville, MD 21619, 2 beds, 2.5 baths

$769,900

2 beds2.5 baths2,014 sq ft

168 Redstart Dr, Stevensville, MD 21619

(410) 224-3200

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

$1,125,000

4 beds4.5 baths4,413 sq ft

2855 Cox Neck Rd, Chester, MD 21619

(410) 304-2250

Property at 43-A Queen Neva Ct, Chester, MD 21619, 3 beds, 2.5 baths

$445,000

3 beds2.5 baths2,008 sq ft

43-A Queen Neva Ct, Chester, MD 21619

(410) 224-3600

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 510 Auckland Way, Chester, MD 21619, 3 beds, 2.5 baths

$410,000

3 beds2.5 baths1,899 sq ft

510 Auckland Way, Chester, MD 21619

(443) 292-6767

Property at 209 Harrier Way, Chester, MD 21619, 4 beds, 3 baths

$737,900

4 beds3 baths3,142 sq ft

209 Harrier Way, Chester, MD 21619

(410) 643-2244

Property at 830 Warbler Way #2843, Chester, MD 21619, 2 beds, 2.5 baths

$789,990

2 beds2.5 baths1,900 sq ft

830 Warbler Way #2843, Chester, MD 21619

(410) 208-3500

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

$369,900

3 beds2.5 baths1,899 sq ft

108 Blenny Ln, Chester, MD 21619

(410) 224-3200

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

$299,900

3 beds2.5 baths1,440 sq ft

54-D Queen Caroline Ct, Chester, MD 21619

(410) 643-4131

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

$429,900

3 beds2.5 baths1,595 sq ft

106 Bodys Neck Rd, Chester, MD 21619

(410) 643-3404

Property at 118 Kinglet Ct, Chester, MD 21619, 2 beds, 2.5 baths

$969,990

2 beds2.5 baths2,010 sq ft

118 Kinglet Ct, Chester, MD 21619

(410) 208-3500

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

$509,999

2 beds2.5 baths2,003 sq ft

230 Switchgrass Way #12, Chester, MD 21619

(855) 450-0442

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

$318,500

2 beds2.5 baths1,312 sq ft

45-G Queen Neva Ct, Chester, MD 21619

(410) 263-8686

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

$998,000

3 beds2.5 baths2,602 sq ft

111 Marshgrass Way #41, Chester, MD 21619

(410) 770-3600

Property at 830 Warbler Way #2833, Chester, MD 21619, 2 beds, 2.5 baths

$689,990

2 beds2.5 baths1,900 sq ft

830 Warbler Way #2833, Chester, MD 21619

(410) 208-3500

Property at 830 Warbler Way #2824, Chester, MD 21619, 3 beds, 2.5 baths

$749,990

3 beds2.5 baths2,602 sq ft

830 Warbler Way #2824, Chester, MD 21619

(410) 208-3500

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

$697,900

2 beds2 baths2,118 sq ft

121 Merlin Dr, Chester, MD 21619

(410) 263-8686

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 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

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Homes with Pools for Sale in Chester

There are currently 52 homes with pools for sale in Chester at a median listing price of $595K. 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 76 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, 26 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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