Four Seasons At Kent Island Real Estate

Welcome to Four Seasons At Kent Island, a premier 55+ active adult community located in Chester, Maryland. Situated in Queen Anne's County on the picturesque Kent Island, this neighborhood offers a serene and peaceful setting for retirees and active adults looking to enjoy a resort-style lifestyle.

Four Seasons At Kent Island features beautifully designed single-family homes and luxurious amenities, including a clubhouse, fitness center, swimming pool, tennis courts, and walking trails. Residents can socialize with neighbors, participate in various clubs and activities, and take advantage of the vibrant community atmosphere.

Living in Four Seasons At Kent Island provides easy access to nearby shopping, dining, and entertainment options, as well as stunning waterfront views of the Chesapeake Bay. The community is also conveniently located near major highways, making it easy to explore the charming towns and attractions of the Eastern Shore.

Experience the best of luxury living and leisure at Four Seasons At Kent Island, where every day feels like a vacation. Come and discover your dream home in this exclusive enclave on Kent Island, Maryland.

Newest Listings in Four Seasons At Kent Island

641 Warbler Way, Chester $649,990 ▼

Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful desig...

2 Beds
2 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

275 Warbler Way, Chester $944,900

Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and a...

3 Beds
3 Baths

Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

736 Warbler Way Unit #2733, Chester image

736 Warbler Way Unit #2733, Chester $719,990

Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, fun...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

536 Warbler Way, Chester $749,990 ▼

Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for ...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

214 Bayberry Dr, Chester $924,000

Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This ...

3 Beds
3 Baths

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

201 Switchgrass Way Unit #34, Chester image

201 Switchgrass Way Unit #34, Chester $835,000 ▼

Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking...

3 Beds
3 Baths

Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

320 Bayberry Dr, Chester $862,750 ▼

THE SELLER WILL ACCEPT OFFERS WITH MOST FURNITURE INCLUDED. SOME SMALL DECORATIONS AND A FEW PICTURES ARE RESERVED. THE MOVING VAN IS ALREADY SCHEDULED. Be part of the fa...

3 Beds
2 Baths

Courtesy of Mr. Lister Realty

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478

117 Flycatcher Way, Chester $1,200,000

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...

3 Beds
4 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

209 Harrier Way, Chester $747,900

Welcome Home!!! Open DAILY by Appointment - Or stop by one of our OPEN HOUSES***If you're looking for the ease of primarily one-level living with flexible space for guest...

4 Beds
3 Baths

Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

111 Marshgrass Way Unit #41, Chester image

111 Marshgrass Way Unit #41, Chester $998,000

Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabul...

3 Beds
3 Baths

Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

102 Boatswain Way Unit #2943, Chester image

102 Boatswain Way Unit #2943, Chester $919,990 ▼

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

102 Boatswain Way Unit #2932, Chester image

102 Boatswain Way Unit #2932, Chester $819,990 ▼

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...