Browse All Four Seasons At Kent Island Properties for Sale

1000 Herons Nest Way Unit 23, Chester image

1000 Herons Nest Way Unit 23, Chester $480,000

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:

Selling Office: Redfin Corp.

154 Bluebell Ct, 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: Coldwell Banker Realty.

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:

132 Wheelhouse Way Unit 11, Chester image

132 Wheelhouse Way Unit 11, Chester $650,000

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:

Selling Office: Next Step Realty, LLC..

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: Compass.

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: Engel & Volkers Annapolis.

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: Unrepresented.

111 Marshgrass Way Unit 21, Chester image

111 Marshgrass Way Unit 21, Chester $660,000

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:

Selling Office: Next Step Realty, LLC..

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: Non Subscribing Office.

111 Marshgrass, Unit 12, Chester $519,900

Entering for comp purposes only

2 Beds
2 Baths

Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

1000 Herons Nest Way Unit 203, Chester $550,000

Welcome to 1000 Heron's Nest Way. This gorgeous 2 bedroom, 2.5 bath condominium was a *FORMER MODEL* and has never been lived in. This beautiful home has every conceiva...

2 Beds
3 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

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

220 Bayberry Dr, Chester $620,000

Beautiful 55 and older, single-level living with stunning features in the resort-like, amenity-rich community of Four Seasons at Kent Island. This beautiful home has it a...

3 Beds
3 Baths

Courtesy of Next Step Realty

Listing courtesy of Next Step Realty. Contact:

Selling Office: Beam Realty Group, Inc..

158 Sailcloth Way, Chester — None Available $876,000

Price reduction to SELL! EXQUISITE comes to mind in this fabulous 3 bdrm, 4bath Santorini Loft Edition. ALL OF THE UPGRADES that you could imagine PLUS! PREMIUM LOT that...

3 Beds
4 Baths

Courtesy of Long & Foster Real Estate, Inc.

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

Selling Office: Benson & Mangold, LLC.

133 Nighthawk Dr, Chester $917,981

None

3 Beds
3 Baths

Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: TTR Sotheby's International Realty.

136 Nighthawk Dr, Chester $885,565

None

3 Beds
2 Baths

Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: RE/MAX Executive.

126 Merlin Dr, Chester $644,900

Great detached option for 55+--beautiful community with water access, screened porch, HIGH ceilings, primary suite with two separate vanities, home office, second bedroom...

2 Beds
2 Baths

Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: Samson Properties.

111 Marshgrass Way Unit 42, Chester $634,900

This home is under construction and will be move in ready by early 2024! This home is located on the 4th floor of the condo building and features a fireplace, dry bar, l...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

111 Marshgrass Way Unit 33, Chester $549,900

This home is under construction and will be move in ready by early 2024! This home is located on the 3rd floor of the condo building and features a fireplace, dry bar, l...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

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

182 Sailcloth Way, Chester $846,698

None

3 Beds
2 Baths

Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: RE/MAX Executive.

4000 Herons Nest Way Unit 12, Chester $545,000

Why wait for new construction? Luxurious and Spacious 1st floor condo in highly sought-after Four Seasons at Kent Island-a vibrant, amenity filled 55+ community on the C...

2 Beds
3 Baths

Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

Selling Office: Engel & Volkers Annapolis.

125 Merlin Dr, Chester $667,025

None

2 Beds
2 Baths

Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: Schwartz Realty, Inc..

316 Bayberry Dr, Chester $860,000

Elegance abounds in this fabulous 3 bedroom, 3 full bath home. Coastal inspired vibes resonate throughout the home with many upgrades that include but are not limited t...

3 Beds
3 Baths

Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Keller Williams Realty Partners.

4000 Herons Nest Way Unit 34, Chester $643,160

**Island Living Awaits You - Immediate Move-In Available!**Seize the Summer - Your Dream Condo Awaits!** Escape to the idyllic island life this summer and make your move...

3 Beds
3 Baths

Courtesy of Realty Navigator

Listing courtesy of Realty Navigator. Contact:

Selling Office: Coastal Life Realty Group LLC.

3000 Herons Nest Way Unit 24, Chester $667,900

The Severn model is a spacious and airy 3 bedroom, 2.5 bath end-home unit boasting an expansive open floor plan with over 2600 square feet of luxurious living space. Th...

3 Beds
3 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Maryland Residential Realty.

200 Harrier Way Unit 942, Chester $649,900

Quick Move In! Move in by June 2023 and enjoy all the outdoor amenities the community has to offer. This Chester Model is located on the 4th floor of the condo building...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

111 Marshgrass Way Unit 24, Chester $633,900

This home is under construction and will be move in ready by early 2024. The Severn model is luxury living at its finest! Located at the end of each floor, this model ...

3 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Real Broker, LLC.

111 Marshgrass Way Unit 21, Chester $644,900

This home is under construction and will be move in ready by early 2024. The Severn model is luxury living at its finest! Located at the end of each floor, this model ...

3 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

111 Marshgrass Way Unit 32, Chester $584,900

This home is under construction and will be move in ready by late 2023/early 2024! This home is located on the 3rd floor of the condo building and features a fireplace, ...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

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

111 Marshgrass Way Unit 22, Chester $499,900

This home is under construction and will be move in ready by early 2024. This chester condo is located on the 2nd floor and features a fireplace as well as many upgrade...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

111 Marshgrass Way Unit 1112, Chester $519,900

This home is under construction and will be move in ready by late 2023/early 2024! Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discov...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

111 Marshgrass Way Unit 1111, Chester $514,900

This home is under construction and will be move in ready by late fall of 2023! Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover ...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Martz and Associates Real Estate LLC.

119 Marshgrass Way Unit 1243, Chester $647,900

This home is under construction and will be move in ready by late fall of 2023! Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover ...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

119 Marshgrass Way Unit 1232, Chester $549,900

This home is under construction and will be move in ready by early January 2024! Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

119 Marshgrass Way Unit 1242, Chester $649,900

This home is under construction and will be move in ready by late fall of 2023! Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover ...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

119 Marshgrass Way Unit 1233, Chester $594,900

This home is under construction and will be move in ready by late fall of 2023! Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover ...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

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:

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: Berkshire Hathaway HomeServices PenFed Realty.

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:

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:

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: Washington Fine Properties.

132 Kestrel Ln, 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: Berkshire Hathaway HomeServices PenFed Realty.

307 Kingfisher Ln, 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: Unrepresented.

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: Unrepresented.

121 Kinglet Ct, 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: Long & Foster Real Estate, Inc..

110 Boatswain Way Unit 3041, Chester image

110 Boatswain Way Unit 3041, Chester $924,990

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:

Selling Office: Unrepresented.

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:

219 Broadwater Dr, 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: Coldwell Banker Realty.

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: Taylor Properties.

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:

Selling Office: Corner House Realty.

110 Boatswain Way Unit 3032, Chester image

110 Boatswain Way Unit 3032, Chester $659,990

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:

Selling Office: Real Broker, LLC -.

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Four Seasons At Kent Island Real Estate & Homes

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