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230 Switchgrass Way Unit #12, Chester image
230 Switchgrass Way Unit #12, Chester $524,999 ▼

NEW INCENTIVE — THE OWNERS WILL COVER YOUR $8,000 COMMUNITY BUY-IN WITH ACCEPTABLE OFFER! Move-in ready condo with zero wait! This meticulously maintained, first-floor Ma...

  • 2 Beds
  • 3 Baths
Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

233 Peregrine Dr, Chester image
233 Peregrine Dr, Chester $724,999 ▼

Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4...

  • 4 Beds
  • 3 Baths
Courtesy of Rosendale Realty

Listing courtesy of Rosendale Realty. Contact: 4107580333

630 Warbler Way Unit #2224, Chester image
630 Warbler Way Unit #2224, Chester $699,990

Introducing the Severn Lot 2224, projected to settle in May 2026. This thoughtfully designed home offers 3 bedrooms, 2.5 baths, and a 1-car garage. Interior highlights ...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

1000 Herons Nest Way Unit #23, Chester image
1000 Herons Nest Way Unit #23, Chester $490,000

Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. ...

  • 2 Beds
  • 3 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

1000 Herons Nest Way Unit #402, Chester image
1000 Herons Nest Way Unit #402, Chester $570,000

Rarely on the market Penthouse level Chester model available immediately! Balcony views from the top floor leftside provide view of the Chester River, Macum Creek and t...

  • 2 Beds
  • 3 Baths
Courtesy of RE/MAX United Real Estate

Listing courtesy of RE/MAX United Real Estate. Contact:

Selling Office: .

1000 Herons Nest Way Unit #43, Chester image
1000 Herons Nest Way Unit #43, Chester $595,000 ▼

Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun ...

  • 2 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

528 Warbler Way, Chester image
528 Warbler Way, Chester $799,500

Like-new luxury living in Four Seasons at Kent Island. Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine,...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

2000 Herons Nest Way Unit #401, Chester image
2000 Herons Nest Way Unit #401, Chester $700,000 ▼

Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resor...

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

Listing courtesy of Real Broker, LLC. Contact: 8504500442

255 Redstart Drive, Chester image
255 Redstart Drive, Chester $780,000

The Simone is a beautifully designed home with a projected settlement of May 2026, offering the space and features you are looking for. With 4 bedrooms, 3 full baths, and...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

630 Warbler Way Unit #2233, Chester image
630 Warbler Way Unit #2233, Chester $599,900

The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-ca...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

630 Warbler Way Unit #2232, Chester image
630 Warbler Way Unit #2232, Chester $612,500

The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-ca...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

630 Warbler Way Unit #2223, Chester image
630 Warbler Way Unit #2223, Chester $559,900

Introducing the Chester Lot 2223, projected to settle in May 2026. This beautiful home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Interior highlights include a d...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

132 Wheelhouse Way Unit #11, Chester image
132 Wheelhouse Way Unit #11, Chester $699,000 ▼

Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its repl...

  • 2 Beds
  • 3 Baths
Courtesy of Real Broker, LLC

Listing courtesy of Real Broker, LLC. Contact: 8504500442

129 Sailcloth Way, Chester image
129 Sailcloth Way, Chester $764,900

Welcome to 129 Sailcloth Way in the resort-style community of Four Seasons at Kent Island! This beautifully upgraded Kilarney model offers over 2300 square feet of singl...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

630 Warbler Way Unit #2221, Chester image
630 Warbler Way Unit #2221, Chester $706,900

Magothy || Available May 2026 This thoughtfully designed home features 3 bedrooms, 2.5 baths, and a 1-car garage. Inside, you’ll find an open layout complemented by a dr...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

630 Warbler Way Unit #2222, Chester image
630 Warbler Way Unit #2222, Chester $514,990

Chester|| Available May 2026 This home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Standout features include a dry bar, an electric fireplace, and a dedicated home...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

539 Warbler Way, Chester image
539 Warbler Way, Chester $769,990

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: .

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: .

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

215 Kingfisher Ln, Chester image
215 Kingfisher Ln, Chester $995,000 ▼

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 sought-after Kingfisher ...

  • 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: .

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

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: .

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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