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201 Switchgrass Way Unit #1442, Chester image
201 Switchgrass Way Unit #1442, Chester $768,900

Experience the perfect balance of function and finesse in the Chester, a 2-bedroom, 2.5-bath home with a 1-car garage, designed for effortless living and elevated comfort...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

201 Switchgrass Way Unit #1433, Chester image
201 Switchgrass Way Unit #1433, Chester $669,900

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: .

509 Warbler Way, Chester image
509 Warbler Way, Chester $698,518

Settle into style with the Jenkins, a 2-bedroom, 2-bath home that balances cozy charm with functional upgrades. A 2-car garage, dedicated home office, and a screened pati...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

130 Sunrise Court, Chester image
130 Sunrise Court, Chester $935,000

Welcome to Four Seasons at Kent Island, where luxury and comfort meet coastal living. This stunning Santorini model at the end of a cul-de-sac with loft offers 3 bedrooms...

  • 3 Beds
  • 4 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

201 Switchgrass Way Unit #1421, Chester image
201 Switchgrass Way Unit #1421, Chester $689,900

Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

200 Harrier Way Unit #42, Chester image
200 Harrier Way Unit #42, Chester — 99999 $557,000

****** TOP FLOOR PENTHOUSE UNIT. NOBODY ABOVE YOU. SHOWS LIKE A MODEL****** ****** COMPARE OUR PRICE ...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

170 Harrier Way Unit #33, Chester image
170 Harrier Way Unit #33, Chester $485,000

This Chester model has scenic views of the river, beautiful sunrises, and an incredible display of wildlife in all seasons. Upgraded lighting package, dry bar, and fi...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

327 Kingfisher Lane, Chester image
327 Kingfisher Lane, Chester $934,900

Welcome to the Tuscaloosa, a stunning 5-bedroom, 4.5-bath home designed for flexible living and modern style. With a 3-car garage, open-concept layout, and high-end finis...

  • 5 Beds
  • 5 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

164 Redstart Drive, Chester image
164 Redstart Drive, Chester $844,900

Discover the charm and versatility of the Kerr, a thoughtfully designed 3-bedroom, 3-bath home offering an open layout, high-end finishes, and spaces tailored for comfort...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

3000 Herons Nest Way Unit #11, Chester image
3000 Herons Nest Way Unit #11, Chester $479,000 ▼

A price improvement has been made, making this unit the best value in the entire community. This home shows like a model with approximately $55,000.00 in upgrades. No nee...

  • 2 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

235 Bayberry Drive, Chester image
235 Bayberry Drive, Chester $910,000

Experience Kent Island living at its finest in this upgraded luxurious San Sebastian model in the prestigious Four Seasons community. Featuring an open floor plan with 10...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

255 Sailcloth Way, Chester image
255 Sailcloth Way, Chester $898,000

Welcome to 255 Sailcloth Way in Chester’s premier 55+ community—K. Hovnanian’s Four Seasons at Kent Island. This upgraded Santorini model is perfectly situated on a cul-d...

  • 4 Beds
  • 4 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

135 Nauset Ln, Chester image
135 Nauset Ln, Chester $799,999 ▼

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: 8554500442

242 Peregrine Drive, Chester image
242 Peregrine Drive, Chester $705,000

AVAILABLE IMMEDIATELY! Introducing the Simone – Where Modern Comfort Meets Farmhouse Charm. This 6 month old Simone offers the perfect blend of open-concept living and ...

  • 4 Beds
  • 3 Baths
Courtesy of Anchor Group Realty, LLC

Listing courtesy of Anchor Group Realty, LLC. Contact:

Selling Office: .

211 Switchgrass Way Unit #1524, Chester image
211 Switchgrass Way Unit #1524, Chester $624,900

The Severn home design offers a spacious and inviting living experience, combining an open floorplan with timeless Legacy design elements. With a projected settlement dat...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

211 Switchgrass Way Unit #1523, Chester image
211 Switchgrass Way Unit #1523, Chester $534,900

The Chester home design offers a spacious and inviting living experience, combining an open floorplan with timeless Legacy design elements. With a projected settlement da...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

211 Switchgrass Way Unit #1534, Chester image
211 Switchgrass Way Unit #1534, Chester $705,250

The Severn home design offers a spacious and inviting living experience, combining an open floorplan with timeless Legacy design elements. With a projected settlement dat...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

137 Warbler Way, Chester image
137 Warbler Way, Chester $721,000

No waiting on the builder here! Treat yourself to this STUNNING move-in-ready Four Seasons beauty- Boasting soaring ceilings, flooded with natural light, spacious, open-f...

  • 2 Beds
  • 2 Baths
Courtesy of Chaney Homes, LLC

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: .

516 Warbler Way, Chester image
516 Warbler Way, Chester $674,900

Charming Comfort & Elevated Style – Jenkins, Lot 602 | Move-In September 2025 Welcome to the Jenkins, a thoughtfully designed 2-bedroom, 2-bath home with a 2-car garage ...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

416 Warbler Way, Chester image
416 Warbler Way, Chester $654,900

Easy Living with Stylish Touches – Jenkins, Lot 597 | Move-In August 2025 Step into comfort and convenience with the Jenkins—a 2-bedroom, 2-bath home with a 2-car garage...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

211 Switchgrass Way Unit #1531, Chester image
211 Switchgrass Way Unit #1531, Chester $734,900

Discover effortless living in the Chester, a well-appointed 3-bedroom, 2.5-bath home with a 1-car garage, thoughtfully designed for both everyday comfort and style. This ...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

211 Switchgrass Way Unit #1511, Chester image
211 Switchgrass Way Unit #1511, Chester $500,900

The Magothy home design is a thoughtfully crafted residence that combines an open floorplan with the timeless elegance of Legacy design. With a projected settlement date ...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

211 Switchgrass Way Unit #1512, Chester image
211 Switchgrass Way Unit #1512, Chester $484,900

This Magothy home design offers a modern, open floorplan that blends seamlessly with Legacy design elements, creating a space that feels both expansive and inviting. Set ...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

223 Broadwater Drive, Chester image
223 Broadwater Drive, Chester $837,000

****************Welcome to Your Dream Home at Four Seasons on Kent Island******************* Step into refined elegance and low-maintenance luxury living with this stunni...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

524 Warbler Way, Chester image
524 Warbler Way, Chester $639,900

Easy Living Meets Timeless Style – Bernstein II, Lot 604 Available for settlement in Summer 2025, the Bernstein II is a beautifully designed 2-bedroom, 2-bath home offer...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

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

Jenkins Home Design - Projected Settlement Date: June 2025 Welcome to the Jenkins, a beautifully designed home located on Lot 374, offering both comfort and style in a ...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

132 Wheelhouse Way Unit #21, Chester image
132 Wheelhouse Way Unit #21, Chester $989,000

Don't wait for New Construction! This nearly NEW luxury condo is available NOW! Welcome to 132 Wheelhouse Way Unit 21, an extraordinary residence where elegance meets eas...

  • 3 Beds
  • 3 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

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: 4105463211

194 Sailcloth Way, Chester image
194 Sailcloth Way, Chester $790,000

Welcome to your dream home situated on a coveted premium lot that backs to the woods giving you endless views of wildlife. The first-floor living is ideal for all homeow...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

218 Switchgrass Way Unit #1732, Chester image
218 Switchgrass Way Unit #1732, Chester $829,900

Experience the perfect blend of form and function in the Chester, a thoughtfully designed 2-bedroom, 2.5-bath home with a 1-car garage and smart upgrades throughout. Whet...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

320 Bayberry Drive, Chester image
320 Bayberry Drive, Chester $775,000

Have it all at 320 Bayberry Drive in the award-winning Four Seasons at Kent Island! This stunning 2021-built home sits on a premium lot adjacent to open space, offering e...

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

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: .

510 Warbler Way, Chester image
510 Warbler Way, Chester $719,900

Introducing the Simone – Where Modern Comfort Meets Farmhouse Charm Projected for settlement on July 2025, the Simone home design offers the perfect blend of open-concep...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

218 Switchgrass Way Unit #1744, Chester image
218 Switchgrass Way Unit #1744, Chester $1,435,900

Stylish Comfort & Thoughtful Design – Severn Ready for June 2025 move-in, the Severn offers a refined take on condo living with 3 bedrooms, 2.5 baths, and a 1-car garage...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

218 Switchgrass Way Unit #1711, Chester image
218 Switchgrass Way Unit #1711, Chester $649,900

Magothy | Projected Settlement: June 2025 Welcome to the Magothy, a thoughtfully designed home with an anticipated move-in date of June 2025. This elegant residence off...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

121 Wheelhouse Way Unit #2142, Chester image
121 Wheelhouse Way Unit #2142, Chester $779,900

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: 2403755074

4000 Herons Nest Way Unit #11, Chester image
4000 Herons Nest Way Unit #11, Chester $540,000

Welcome to resort living at its finest, where active living meets luxury and convenience. This first-floor condo offers a unique blend of features and upgrades, making it...

  • 2 Beds
  • 3 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

170 Harrier Way Unit #32, Chester image
170 Harrier Way Unit #32, Chester $499,000

***HIGHLY MOTIVATED SELLERS*** PRICE REDUCED FOR AN OFFER ACCEPTED BY 6/23. SELLERS HAVE FOUND THEIR HOME OF CHOICE AND NEED TO MOVE QUICKLY! Welcome to Four Seasons a...

  • 2 Beds
  • 3 Baths
Courtesy of Redfin Corp

Listing courtesy of Redfin Corp. Contact:

Selling Office: .

148 Nighthawk Drive, Chester image
148 Nighthawk Drive, Chester $884,900

This Kerr is a beautifully designed home that offers both style and functionality, making it ideal for comfortable living and entertaining and estimated for completion Ap...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

212 Switchgrass Way Unit #1623, Chester image
212 Switchgrass Way Unit #1623, Chester $568,900

Nestled within the picturesque landscape of the Four Seasons active lifestyle community, Luxury Waterview Condos offer a harmonious blend of elegance, comfort, and unpara...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

200 Harrier Way Unit #44, Chester image
200 Harrier Way Unit #44, Chester $875,000

Four Seasons at Kent Island is an active 55+ community on Maryland's Eastern Shore, offering island resort-style & maintenance-free living at its finest! This Severn mode...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

246 Peregrine Drive, Chester image
246 Peregrine Drive, Chester $749,900

SPECIAL SAVINGS! Please see sales consultant for more information. This Simone is a stunning 4-bedroom, 3-bathroom home designed for modern living with a touch of class...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

212 Switchgrass Way Unit #1642, Chester image
212 Switchgrass Way Unit #1642, Chester $714,900

SPECIAL SAVINGS! Please see sales consultant for more information. The Chester is an elegant home that effortlessly blends a spacious open floorplan with timeless Legac...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

212 Switchgrass Way Unit #1644, Chester image
212 Switchgrass Way Unit #1644, Chester $714,900

Welcome to the Severn condominium design. This home is currently in the process of construction and is estimated to be completed by April 2025. This popular 2,600 sq. ft...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

212 Switchgrass Way Unit #1641, Chester image
212 Switchgrass Way Unit #1641, Chester $1,014,900

Welcome to this 3rd floor waterfront condominium with views of the Chester River. This home is currently in the process of construction and is estimated to be completed b...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

228 Warbler Way, Chester image
228 Warbler Way, Chester $649,900

The Simone is a beautifully designed home that seamlessly blends charm, sophistication, and functionality, making it perfect for both relaxation and entertaining. This ho...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

200 Harrier Way Unit #31, Chester image
200 Harrier Way Unit #31, Chester $651,000

Immediate Closing Available! Luxury Resort Style Living!! Four Seasons at Kent Island is an active 55+ community. When you are here it feels like a vacation. Move in rea...

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

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

Selling Office: .

212 Switchgrass Way Unit #1624, Chester image
212 Switchgrass Way Unit #1624, Chester $664,900

Nestled within the picturesque landscape of the Four Seasons active lifestyle community, Luxury Waterview Condos offer a harmonious blend of elegance, comfort, and unpara...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

212 Switchgrass Way Unit #1632, Chester image
212 Switchgrass Way Unit #1632, Chester $684,900

This Chester home is thoughtfully designed blending modern comfort with timeless style. Scheduled for settlement in April 2025, this two-bedroom, two-and-a-half-bath home...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

166 Warbler Way Unit #31, Chester image
166 Warbler Way Unit #31, Chester $824,900

Fabulous views and price on this end unit Severn Model! Filled with scenic water views of the Chester River and nature trail. Excellent fit and finish. Everything is...

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

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

Selling Office: .

261 Warbler Way, Chester image
261 Warbler Way, Chester $669,900

This beautiful home, projected for settlement in May 2025, offers a harmonious blend of open, airy spaces with classic design touches. With four spacious bedrooms and thr...

  • 4 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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