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228 Bayberry Dr, Chester image
228 Bayberry Dr, Chester $665,000

OPEN SUNDAY 11:00AM-1:00 Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/private ENS...

  • 2 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

136 Nauset Lane, Chester image
136 Nauset Lane, Chester $799,000

Welcome to 136 Nauset Lane, an upgraded Lille model in Four Seasons at Kent Island, a premier 55+ resort-style community. Situated on a corner lot, this Coastal Tradition...

  • 3 Beds
  • 3 Baths
Courtesy of RE/MAX One

Listing courtesy of RE/MAX One. Contact:

Selling Office: .

266 Peregrine Drive, Chester image
266 Peregrine Drive, Chester $707,000

Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features...

  • 4 Beds
  • 3 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

176 Flagstaff Way Unit #2443, Chester image
176 Flagstaff Way Unit #2443, Chester $979,990

The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers plann...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

641 Warbler Way, Chester image
641 Warbler Way, Chester $639,990 ▼

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

711 Warbler Way, Chester image
711 Warbler Way, Chester $739,990

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces i...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

275 Warbler Way, Chester image
275 Warbler Way, Chester $930,000 ▼

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

110 Boatswain Way Unit #3012, Chester image
110 Boatswain Way Unit #3012, Chester $619,990 ▼

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern ...

  • 2 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

176 Flagstaff Way Unit #2433, Chester image
176 Flagstaff Way Unit #2433, Chester $769,990

The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers ...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

176 Flagstaff Way Unit #2424, Chester image
176 Flagstaff Way Unit #2424, Chester $875,000

The Severn, located on Lot 2424, is scheduled for a August 2026 settlement and offers a well-designed layout with 3 bedrooms, 2.5 baths, and a 1-car garage—perfect for lo...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

154 Bluebell Court, Chester image
154 Bluebell Court, Chester $965,000

Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in th...

  • 3 Beds
  • 3 Baths
Courtesy of Wilson Realty & Staging LLC

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: .

176 Flagstaff Way Unit #2412, Chester image
176 Flagstaff Way Unit #2412, Chester $589,990

The Magothy at Lot 2412 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting ho...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

176 Flagstaff Way Unit #2411, Chester image
176 Flagstaff Way Unit #2411, Chester $599,990

The Magothy at Lot 2411 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting ho...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

536 Warbler Way, Chester image
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

200 Harrier Way Unit #21, Chester image
200 Harrier Way Unit #21, Chester $639,900

Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with pl...

  • 3 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

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

Selling Office: .

property image
169 Harrier Way, Chester $775,000

None

  • 2 Beds
  • 2 Baths
Courtesy of CENTURY 21 New Millennium

Listing courtesy of CENTURY 21 New Millennium. Contact:

Selling Office: .

216 Kingfisher Lane, Chester image
216 Kingfisher Lane, Chester $1,200,000

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 bat...

  • 2 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

Selling Office: .

135 Nauset Lane, Chester image
135 Nauset Lane, Chester $787,500

If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Isla...

  • 3 Beds
  • 3 Baths
Courtesy of Real Broker, LLC - Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: .

214 Bayberry Dr, Chester image
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

118 Broadwater Dr, Chester image
118 Broadwater Dr, Chester $660,000

Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with th...

  • 2 Beds
  • 2 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact: 4432741900

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

123 Flycatcher Way, Chester image
123 Flycatcher Way, Chester $1,100,000

The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opport...

  • 3 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

117 Flycatcher Way, Chester image
117 Flycatcher Way, Chester $1,100,000 ▼

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

111 Flycatcher Way, Chester image
111 Flycatcher Way, Chester $1,200,000

The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement...

  • 5 Beds
  • 5 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

209 Harrier Way, Chester image
209 Harrier Way, Chester $737,900 ▼

LESS MONEY OUT OF YOUR POCKET!!! With an accepted contract by 9/30/26 - the sellers are offering up to $7500 toward your closing costs or to use toward a rate buydown if ...

  • 4 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

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

193 Spinnaker Way, Chester image
193 Spinnaker Way, Chester $856,000

Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. ...

  • 3 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

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

307 Kingfisher Lane, Chester image
307 Kingfisher Lane, Chester $860,000

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-conce...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

212 Switchgrass Way Unit #34, Chester image
212 Switchgrass Way Unit #34, Chester $735,000

Best View of the Chester River. Check it out! Experience elevated Eastern Shore living in this beautifully appointed corner residence overlooking the Chester River in the...

  • 3 Beds
  • 3 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

127 Flycatcher Way, Chester image
127 Flycatcher Way, Chester $880,000

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 re...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

102 Boatswain Way Unit #2912, Chester image
102 Boatswain Way Unit #2912, Chester $609,990

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. T...

  • 2 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

190 Harrier Way Unit #21, Chester image
190 Harrier Way Unit #21, Chester $640,000

Impeccably finished and immediately available, this corner residence provides the ease and comfort of luxury condo living surrounded by the natural beauty of the Chesapea...

  • 3 Beds
  • 3 Baths
Courtesy of The KW Collective

Listing courtesy of The KW Collective. Contact:

Selling Office: .

132 Kestrel Lane, Chester image
132 Kestrel Lane, Chester $925,000

Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully desig...

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

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...

  • 2 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

110 Kinglet Court, Chester image
110 Kinglet Court, Chester $834,990

The Tuscaloosa home offers a thoughtfully designed layout with elevated finishes throughout, with a projected settlement of April 2026. Featuring 2 bedrooms, 2.5 baths, a...

  • 5 Beds
  • 5 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

249 Warbler Way, Chester image
249 Warbler Way, Chester $625,000

No waiting on the Builder for 8+ months!! This just like brand new Jenkins II Model built in June 2025 boasts soaring, coffered and vaulted ceilings in the 2,025 sf of s...

  • 2 Beds
  • 2 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

110 Boatswain Way Unit #3044, Chester image
110 Boatswain Way Unit #3044, Chester $999,990

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern c...

  • 3 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 #2911, Chester image
102 Boatswain Way Unit #2911, Chester $619,990 ▼

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. T...

  • 2 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

323 Kingfisher Ln, Chester image
323 Kingfisher Ln, Chester $949,990 ▼

Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort a...

  • 5 Beds
  • 5 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

723 Warbler Way, Chester image
723 Warbler Way, Chester $749,990 ▼

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces i...

  • 4 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

715 Warbler Way, Chester image
715 Warbler Way, Chester $779,990 ▼

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces i...

  • 4 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

532 Warbler Way, Chester image
532 Warbler Way, Chester $899,990 ▼

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

  • 3 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 #2933, Chester image
102 Boatswain Way Unit #2933, 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...

  • 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 #2921, Chester image
102 Boatswain Way Unit #2921, Chester $869,990

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern ...

  • 3 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

121 Kinglet Court, Chester image
121 Kinglet Court, Chester $937,990

Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home ...

  • 5 Beds
  • 5 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

110 Boatswain Way Unit #3042, Chester image
110 Boatswain Way Unit #3042, Chester $699,990 ▼

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

  • 2 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

540 Warbler Way, Chester image
540 Warbler Way, Chester $929,990 ▼

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

  • 3 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

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

121 Merlin Dr, Chester image
121 Merlin Dr, Chester $697,900 ▼

Assumable VA Loan available w/interest rate in 5's to qualified buyers! Experience the ease of elegant one-level living in this exceptional home, located in one of Maryla...

  • 2 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

Four Seasons At Kent Island Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Four Seasons At Kent Island, Chester MD. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

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