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111 Bluebell Ct Bluebell Court, Chester image
111 Bluebell Ct Bluebell Court, Chester $527,500

If you are looking to move into a beautiful home in an incredible community, congratulations, this home is available! Welcome to Kent Island's Four Seasons community. Th...

  • 2 Beds
  • 2 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: .

105 Warbler Way, Chester image
105 Warbler Way, Chester $644,900

The Jenkins II model is first floor living at its finest. This home features a great room fireplace, screened patio, and plus shower in primary suite. This home is estima...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

152 Peregrine Drive, Chester image
152 Peregrine Drive, Chester $792,355

K Hovnanian Homes Tuscaloosa model with over 3,200 square feet. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-fil...

  • 5 Beds
  • 5 Baths
Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: .

166 Warbler Way Unit #22, Chester image
166 Warbler Way Unit #22, Chester $609,900

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

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

166 Warbler Way Unit #32, Chester image
166 Warbler Way Unit #32, Chester $684,900

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

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

166 Warbler Way Unit #33, Chester image
166 Warbler Way Unit #33, Chester $569,900

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

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

103 Spinnaker Way, Chester image
103 Spinnaker Way, Chester $825,000

PRICE DROP! Just reduced $10,000!! A must see in the sought after community of Four Seasons at Kent Island on the Eastern Shore of Maryland. Why wait for new constructi...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

2000 Herons Nest Way Unit #42, Chester image
2000 Herons Nest Way Unit #42, Chester $679,000

YOUZA! Don't miss out on this one-time opportunity to buy a hidden gem! This penthouse Chester condo is located within the acclaimed 55+ Four Seasons retirement communi...

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

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: .

137 Warbler Way, Chester image
137 Warbler Way, Chester $704,900

The Kelly model is first floor living at its finest. This home features a screened patio, fireplace, upgraded shower, and smart cooking appliances. For a full list of in...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

157 Sailcloth Way, Chester image
157 Sailcloth Way, Chester $595,000

Welcome to Kent Islands Finest Living. This home features 2 Bedrooms, both with Full Baths and an additional room for use as an Office or Bedroom. There is also a separ...

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

Listing courtesy of RE/MAX One. Contact:

Selling Office: .

143 Warbler Way, Chester image
143 Warbler Way, Chester $749,900

The Kerr model is a showstopper. This home features a fireplace, upgraded shower, and more. For a full list of included features please consult a sales representative. W...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

256 Sailcloth Way, Chester image
256 Sailcloth Way, Chester $859,000

Spectacular location inside the Four Seasons complex! Quiet cul de sac end unit on the pond and pristine open space in the rear of this gracious home. Spotless LVP floori...

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

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

Selling Office: .

166 Warbler Way Unit #31, Chester image
166 Warbler Way Unit #31, Chester $884,900

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

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

122 Warbler Way, Chester image
122 Warbler Way, Chester $634,900

The Jenkins II model is a show stopper! This home also features a covered patio and fireplace as well as upgraded shower. For a full list of features please see a sales...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

109 Warbler Way, Chester image
109 Warbler Way, Chester $684,900

The Simone model is a show stopper! This home includes a screened patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sale...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

135 Merlin Drive, Chester image
135 Merlin Drive, Chester $680,000

The Simone model is a show stopper! This home includes a screened patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sale...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

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

The Taylor model is a show stopper! This home includes a covered patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sales...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

property image
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: .

147 Warbler Way, Chester image
147 Warbler Way, Chester $734,900

The Kerr model is a show stopper! This home includes a covered patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sales r...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

158 Sailcloth Way, Chester image
158 Sailcloth Way, Chester $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: .

4000 Herons Nest Way Unit #12, Chester image
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: .

220 Bayberry Drive, Chester image
220 Bayberry Drive, 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: .

139 Merlin Drive, Chester image
139 Merlin Drive, Chester $634,900

The Jenkins II model is a show stopper! This home includes a stone fireplace to complete the great room, smart cooking suite in the kitchen, and classic plus shower. For...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

111 Marshgrass Way Unit #32, Chester image
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: .

1000 Herons Nest Way Unit #203, Chester image
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: .

316 Bayberry Drive, Chester image
316 Bayberry Drive, 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: .

111 Marshgrass Way Unit #42, Chester image
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: .

119 Marshgrass Way Unit #1232, Chester image
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: .

111 Marshgrass Way Unit #33, Chester image
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: .

111 Marshgrass Way Unit #1112, Chester image
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: .

111 Marshgrass Way Unit #1111, Chester image
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: .

106 Merlin Drive, Chester image
106 Merlin Drive, Chester $694,900

The Kelly model is first floor living at its finest. This home features a screened patio, fireplace, upgraded shower and detailed trim in the foyer and primary bedroom. ....

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

111 Marshgrass Way Unit #24, Chester image
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: .

111 Marshgrass Way Unit #21, Chester image
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: .

111 Marshgrass Way Unit #22, Chester image
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: .

133 Nighthawk Dr, Chester image
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: .

property image
136 Nighthawk Drive, Chester $885,565

None

  • 3 Beds
  • 2 Baths
Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: .

126 Merlin Drive, Chester image
126 Merlin Drive, 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: .

3000 Herons Nest Way Unit #24, Chester image
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: .

126 Merlin Drive, Chester image
126 Merlin Drive, Chester $644,900

The Jenkins II model is a show stopper! This home showcases a Loft look. This home also features a screened patio and fireplace as well as upgraded shower. For a full...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

122 Merlin Drive, Chester image
122 Merlin Drive, Chester $589,900

The Bernstein II model is a show stopper! This home includes a fireplace as well as an upgraded shower. This home features the Classic Look. For a full list of feature...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

119 Marshgrass Way Unit #1242, Chester image
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: .

119 Marshgrass Way Unit #1233, Chester image
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: .

property image
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: .

4000 Herons Nest Way Unit #34, Chester image
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: .

203 Bayberry Drive, Chester image
203 Bayberry Drive, Chester $589,900

The Ibiza model is first floor living at its finest. This home features a covered patio, custom backsplash, and a home office. For a full list of included features pleas...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: .

119 Marshgrass Way Unit #1243, Chester image
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: .

125 Merlin Drive, Chester image
125 Merlin Drive, Chester $667,025

None

  • 2 Beds
  • 2 Baths
Courtesy of Non Subscribing Office

Listing courtesy of Non Subscribing Office. Contact:

Selling Office: .

200 Harrier Way Unit #942, Chester image
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: .

131 Merlin Drive, Chester image
131 Merlin Drive, Chester $604,900

The Bernstein II model is a show stopper! In the kitchen you will find an upgraded cabinet with stacked glass cabinets on top, quartz countertops and a smart cooking su...

  • 2 Beds
  • 2 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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