Browse All Four Seasons At Kent Island Properties for Sale

110 Boatswain Way Unit 3033, Chester image

110 Boatswain Way Unit 3033, Chester $675,000

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:

Selling Office: Maryland Residential Realty.

110 Boatswain Way Unit 3034, Chester image

110 Boatswain Way Unit 3034, Chester $884,990

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:

Selling Office: Non Subscribing Office.

110 Boatswain Way Unit 3031, Chester image

110 Boatswain Way Unit 3031, Chester $830,000

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:

Selling Office: Long & Foster Real Estate, Inc..

255 Redstart Dr, 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: Unrepresented.

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: Keller Williams Flagship.

259 Redstart Dr, 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: The KW Collective.

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: Berkshire Hathaway HomeServices PenFed Realty.

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: KW Metro Center.

311 Kingfisher Ln, 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: Unrepresented.

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: RE/MAX Executive.

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: Unrepresented.

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: Unrepresented.

4000 Herons Nest Way Unit 22, Chester image

4000 Herons Nest Way Unit 22, Chester $492,500 ▼

Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, S...

2 Beds
3 Baths

Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

170 Harrier Way Unit 34, Chester — None Available $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: Benson & Mangold, LLC.

110 Kinglet Ct, 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: Unrepresented.

141 Redstart Dr, 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: Unrepresented.

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: Unrepresented.

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: Unrepresented.

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: Unrepresented.

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: Unrepresented.

3000 Herons Nest Way Unit 11, Chester image

3000 Herons Nest Way Unit 11, Chester $460,000 ▼

This highly sought-after first-floor condo offers the opportunity to own a fully upgraded 2,003 square foot Four Seasons Condo without waiting for new construction. Just...

2 Beds
3 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

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: Unrepresented.

117 Redstart Dr, 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: Unrepresented.

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: Real Broker, LLC.

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: Redfin Corp.

135 Nauset Ln, 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: Real Broker, LLC.

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: Unrepresented.

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: Unrepresented.

141 Switchgrass Way Unit 34, Chester image

141 Switchgrass Way Unit 34, Chester — None Available $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: RE/MAX Executive.

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: TTR Sotheby's International Realty.

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: RE/MAX Executive.

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: Unrepresented.

130 Sunrise Ct, 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: RE/MAX Executive.

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: Unrepresented.

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: Non Subscribing 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: Unrepresented Buyer Office.

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: RE/MAX Leading Edge.

245 Peregrine Dr, 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: EXP Realty, LLC.

124 Nauset Ln, 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: Compass.

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: Unrepresented.

223 Broadwater Dr, 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: Greater Annapolis Realty.

224 Bayberry Dr, 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: Coldwell Banker Realty.

235 Bayberry Dr, Chester — None Available $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: RE/MAX Executive.

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: Berkshire Hathaway HomeServices PenFed Realty.

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: Compass.

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: Unrepresented.

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: Unrepresented Buyer Office.

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: Douglas Realty LLC.

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: Unrepresented Buyer 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: Samson Properties.

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Four Seasons At Kent Island Real Estate & Homes

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