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630 Warbler Way Unit #2212, Chester image
630 Warbler Way Unit #2212, Chester $499,990

Magothy || Available April 2026 This 2 bed, 2.5 bath home with a 1-car garage is designed with both comfort and convenience in mind. A dedicated home office with lited F...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

630 Warbler Way Unit #2211, Chester image
630 Warbler Way Unit #2211, Chester $524,900

Magothy || Available April 2026 This thoughtfully designed 2 bed, 2.5 bath home with a 1-car garage combines functionality with style. A welcoming home office with lited...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

259 Redstart Drive, Chester image
259 Redstart Drive, Chester $799,990

The Simone at Lot 547 features a well-balanced open-concept floorplan with a projected settlement date of March 2026, offering both style and functionality for modern liv...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

190 Harrier Way Unit #11, Chester image
190 Harrier Way Unit #11, Chester $520,000

Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell! Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich ...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

311 Kingfisher Lane, Chester image
311 Kingfisher Lane, Chester $879,990

The Tuscaloosa, located on Lot 588, is scheduled for an April 2026 settlement and offers generous space with 5 bedrooms, 4.5 baths, and a 3-car garage—ideal for growing h...

  • 5 Beds
  • 5 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

711 Warbler Way, Chester image
711 Warbler Way, Chester $769,990 ▼

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: 2403755074

233 Kingfisher Ln, Chester image
233 Kingfisher Ln, Chester $999,000 ▼

Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect...

  • 5 Beds
  • 5 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

132 Wheelhouse Way, Chester image
132 Wheelhouse Way, Chester $1,221,990

This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opp...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

111 Marshgrass Way Unit #21, Chester image
111 Marshgrass Way Unit #21, Chester $680,000

A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seaso...

  • 3 Beds
  • 3 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 2406308689

170 Harrier Way Unit #22, Chester image
170 Harrier Way Unit #22, Chester $499,000

For a limited time, the seller is offering $4,000 toward the capital contribution fee—an incredible opportunity to move into the sought-after Four Seasons at Kent Island ...

  • 2 Beds
  • 3 Baths
Courtesy of Keller Williams Select Realtors of Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: .

219 Broadwater Drive, Chester image
219 Broadwater Drive, Chester $643,000

Coming soon, professional photos coming today! **Lowest priced single-family home in Four Seasons — and better than new!** Why wait 7–8 months (and spend thousands more)...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

1000 Herons Nest Way Unit #22, Chester image
1000 Herons Nest Way Unit #22, Chester — Chester $485,000 ▼

BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wil...

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

Listing courtesy of RE/MAX Executive. Contact: 4432741900

111 Marshgrass Way Unit #43, Chester image
111 Marshgrass Way Unit #43, Chester $765,000

Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunr...

  • 2 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

215 Kingfisher Ln, Chester image
215 Kingfisher Ln, Chester $1,049,500 ▼

Price Reduced $50K – Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sou...

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

Listing courtesy of RE/MAX Executive. Contact: 4432741900

141 Redstart Drive, Chester image
141 Redstart Drive, Chester $879,990

The Kerr on Lot 529 offers a well-balanced layout with thoughtfully selected finishes, scheduled for a March 2026 settlement. Featuring 3 bedrooms, 3 baths, and a 3-car g...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

141 Switchgrass Way Unit #34, Chester image
141 Switchgrass Way Unit #34, Chester $668,500

**** NICE VIEWS OF THE CHESTER RIVER**** ***** LOWEST PRICED SEVERN MODEL**** K Hovnanian's Four Seasons at Kent Island is an active 55+...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

102 Boatswain Way Unit #2934, Chester image
102 Boatswain Way Unit #2934, Chester $969,990 ▼

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 KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

102 Boatswain Way Unit #2912, Chester image
102 Boatswain Way Unit #2912, Chester $599,990 ▼

Welcome to the Magothy, 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 KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

121 Wheelhouse Way Unit #2121, Chester image
121 Wheelhouse Way Unit #2121, Chester $704,900

Discover effortless elegance in this beautifully designed Severn condo, offering 3 bedrooms and 2.5 baths. With an open floorplan and high-end finishes throughout, this h...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

110 Boatswain Way Unit #3041, Chester image
110 Boatswain Way Unit #3041, Chester $949,990 ▼

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

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

110 Boatswain Way Unit #3043, Chester image
110 Boatswain Way Unit #3043, Chester $799,990 ▼

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 KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

121 Wheelhouse Way Unit #2142, Chester image
121 Wheelhouse Way Unit #2142, Chester $764,900

Experience low-maintenance luxury in this Chester condo, offering 2 bedrooms, 2.5 baths, and a versatile home office with lighted French doors—perfect for work-from-home ...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

170 Harrier Way Unit #34, Chester image
170 Harrier Way Unit #34, Chester $665,000

This is one of only two 3-bedroom condos on the market in Four Seasons with the immediate availability. Welcome to luxury condo living at Four Seasons at Kent Island, an...

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

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

Selling Office: .

154 Harrier Way, Chester image
154 Harrier Way, Chester $625,000

*** WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND*** Price Reduced! Lowest priced single family home in Four Seasons! Better than New! Custom Window Treatme...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

121 Wheelhouse Way Unit #2132, Chester image
121 Wheelhouse Way Unit #2132, Chester $659,900

Experience low-maintenance luxury in this Chester condo, offering 2 bedrooms, 2.5 baths, and a versatile home office with lighted French doors—perfect for work-from-home ...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

121 Wheelhouse Way Unit #2124, Chester image
121 Wheelhouse Way Unit #2124, Chester $704,900

This thoughtfully designed Severn condo offers 3 bedrooms and 2.5 bathrooms—blending comfort, style, and function. The owner’s suite features a private sitting room and s...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

621 Warbler Way, Chester image
621 Warbler Way, Chester $691,900

The Jenkins II home offers thoughtful single-level living with timeless design and modern comfort. Featuring 2 bedrooms, 2 baths, and a 2-car garage, this layout balances...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

121 Wheelhouse Way Unit #2112, Chester image
121 Wheelhouse Way Unit #2112, Chester $520,900

Experience stylish, low-maintenance living in this thoughtfully designed 2-bedroom, 2.5-bath Magothy condo, and curated finishes throughout. An open-concept layout, ample...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

121 Wheelhouse Way Unit #2111, Chester image
121 Wheelhouse Way Unit #2111, Chester $524,900

This Magothy condo offers low-maintenance luxury with a smart layout and designer features. With 2 bedrooms, 2.5 bathrooms, a 1-car garage, and a dedicated home office wi...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

266 Peregrine Dr, Chester image
266 Peregrine Dr, 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: 4432741900

110 Boatswain Way Unit #3032, Chester image
110 Boatswain Way Unit #3032, Chester $689,990 ▼

The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 ba...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

110 Boatswain Way Unit #3033, Chester image
110 Boatswain Way Unit #3033, Chester $699,990 ▼

The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 ba...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

110 Boatswain Way Unit #3034, Chester image
110 Boatswain Way Unit #3034, Chester $949,990 ▼

The Severn combines an open floorplan with thoughtful design elements, with a projected settlement date of November 2026. Designed for comfortable and modern living, this...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

110 Boatswain Way Unit #3031, Chester image
110 Boatswain Way Unit #3031, Chester $849,990 ▼

The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-c...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

110 Boatswain Way Unit #3021, Chester image
110 Boatswain Way Unit #3021, Chester $749,990 ▼

The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-c...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact: 2403755074

519 Warbler Way, Chester image
519 Warbler Way, Chester $799,990

Introducing the Kerr with a projected settlement date of January 2026. This home offers 3 bedrooms, 3 baths, and a spacious 3-car garage. Notable features include a hom...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

527 Warbler Way, Chester image
527 Warbler Way, Chester $784,990

Ready NOW! This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car ga...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

224 Bayberry Drive, Chester image
224 Bayberry Drive, Chester $550,000

Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, style, and resort-style living in this impeccably maintained, one-owner home — tu...

  • 2 Beds
  • 2 Baths
Courtesy of Realty Navigator

Listing courtesy of Realty Navigator. Contact:

Selling Office: .

117 Redstart Drive, Chester image
117 Redstart Drive, Chester $834,990

This stunning Taylor home offers an inviting open floor plan designed for both comfort and functionality. Featuring 2 bedrooms, 2.5 baths, and a spacious 3-car garage, th...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

170 Harrier Way Unit #11, Chester image
170 Harrier Way Unit #11, Chester $499,000

Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent I...

  • 2 Beds
  • 3 Baths
Courtesy of Redfin Corp

Listing courtesy of Redfin Corp. Contact:

Selling Office: .

176 Flagstaff Way Unit #2443, Chester image
176 Flagstaff Way Unit #2443, Chester $979,900 ▼

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: 2403755074

176 Flagstaff Way Unit #2433, Chester image
176 Flagstaff Way Unit #2433, Chester $799,990 ▼

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: 2403755074

176 Flagstaff Way Unit #2424, Chester image
176 Flagstaff Way Unit #2424, Chester $935,990

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: 2403755074

176 Flagstaff Way Unit #2412, Chester image
176 Flagstaff Way Unit #2412, Chester $659,990 ▼

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: 2403755074

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: 2403755074

4000 Herons Nest Way Unit #22, Chester image
4000 Herons Nest Way Unit #22, Chester $515,000 ▼

Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * Turn-key & Lovely 2nd Floor Condo in Elevator ...

  • 2 Beds
  • 3 Baths
Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

629 Warbler Way, Chester image
629 Warbler Way, Chester $694,900

Simone Home || Available December 2025 This thoughtfully designed 4 bed, 3 bath home with a 2-car garage offers both comfort and character. Enjoy a spacious screened pat...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

124 Nauset Lane, Chester image
124 Nauset Lane, Chester $825,000

10K price reduction!!! Better Than New – $175K+ in Upgrades and Lifestyle Ready Now Four Seasons at Kent Island – Killarney with Loft Model Why wait months—and spend thou...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

245 Peregrine Drive, Chester image
245 Peregrine Drive, Chester $700,000

This spacious 4-bedroom, 3-bathroom home offers the perfect balance of comfort, style, and functionality. Nestled in a tranquil and highly sought-after neighborhood, this...

  • 4 Beds
  • 3 Baths
Courtesy of Keller Williams Select Realtors of Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: .

201 Switchgrass Way Unit #1443, Chester image
201 Switchgrass Way Unit #1443, Chester $769,900

Welcome home to the Chester, a beautifully crafted 2-bedroom, 2.5-bath residence with a 1-car garage, offering low-maintenance luxury and stylish finishes throughout. Ide...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

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. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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