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320 Bayberry Dr, Chester image
320 Bayberry Dr, 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: RE/MAX Leading Edge.

233 Peregrine Dr, Chester image
233 Peregrine Dr, Chester $669,900

Welcome to the Simone home design. This home features a great room fireplace, screened patio, and plus shower in primary suite. This home is estimated for completion Augu...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Rosendale Realty.

254 Peregrine Dr, Chester image
254 Peregrine Dr, Chester $674,900

Welcome to the Simone home design. This home features a great room fireplace, laundry tub, and plus shower in primary suite. This home is estimated for completion Novembe...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

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

136 Merlin Dr, Chester image
136 Merlin Dr, Chester $585,900

The Bernstein II model is a show stopper! This home features a fireplace as well as a screened patio. For a full list of features please see a sales representative. Welc...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

243 King Fisher Dr, Chester image
243 King Fisher Dr, Chester $914,900

Welcome to the Franklin home design. This home features a screened patio and plus shower in primary suite. This home is estimated for completion October 2024. For a ful...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

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

118 Peregrine Dr, Chester image
118 Peregrine Dr, Chester $642,900

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: Non Subscribing Office.

237 Peregrine Dr, Chester image
237 Peregrine Dr, Chester $599,900

The Jenkins II model is first floor living at its finest. This home features a great room fireplace and a plus shower in primary suite. This home is available now! For a...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Engel & Volkers Annapolis.

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: Non Subscribing 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: Long & Foster Real Estate, Inc..

119 Peregrine Dr, Chester image
119 Peregrine Dr, Chester $634,900

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: RE/MAX Executive.

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: Non Subscribing Office.

211 Warbler Way, Chester image
211 Warbler Way, Chester $799,900

SPECIAL SAVINGS! Please see sales consultant for more information. This Kerr is a beautifully crafted home that blends sophistication with comfort, offering ideal space...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Maryland Residential Realty.

111 Peregrine Dr, Chester image
111 Peregrine Dr, Chester $779,900

This Kerr is a thoughtfully designed home that combines comfort, elegance, and functionality, perfect for both everyday living and special occasions and estimated for com...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Cummings & Co. Realtors.

234 Peregrine Dr, Chester image
234 Peregrine Dr, Chester $650,000

Welcome to the Simone home design. This home features a great room fireplace, laundry tub, and plus shower in primary suite. This home is estimated for completion Decembe...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

229 Peregrine Dr, Chester image
229 Peregrine Dr, Chester $574,900

Welcome to the Bernstein home design. This home features a screened patio and plus shower in primary suite. This home is estimated for completion August 2024. For a ful...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

207 Warbler Way, Chester image
207 Warbler Way, Chester $799,900

Welcome to the Kerr home design. This home features a screened patio and plus shower in primary suite. This home is estimated for completion October 2024. For a full li...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

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

135 Merlin Dr, Chester image
135 Merlin Dr, 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: Non Subscribing Office.

238 Peregrine Dr, Chester image
238 Peregrine Dr, Chester $657,200

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: Non Subscribing 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: Non Subscribing Office.

148 Nighthawk Dr, Chester image
148 Nighthawk Dr, 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: Unrepresented.

242 Peregrine Dr, Chester image
242 Peregrine Dr, Chester $684,900

Welcome to the Simone home design. This home features a great room fireplace, screened patio, and plus shower in primary suite. This home is estimated for completion Janu...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Anchor Group Realty, LLC.

106 Merlin Dr, Chester image
106 Merlin Dr, 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: Non Subscribing Office.

131 Merlin Dr, Chester image
131 Merlin Dr, 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: Non Subscribing Office.

139 Merlin Dr, Chester image
139 Merlin Dr, 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: Realty Navigator.

241 Peregrine Dr, Chester image
241 Peregrine Dr, Chester $604,900

The Jenkins II model is first floor living at its finest. This home features a great room fireplace and plus shower in primary suite. This home is estimated for completio...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

246 Peregrine Dr, Chester image
246 Peregrine Dr, 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: Non Subscribing Office.

203 Bayberry Dr, Chester image
203 Bayberry Dr, 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: Non Subscribing Office.

245 Peregrine Dr, Chester image
245 Peregrine Dr, Chester $637,900

Welcome to the Simone home design. This home features a great room fireplace, screened patio, and plus shower in primary suite. This home is estimated for completion Augu...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

125 Peregrine Dr, Chester image
125 Peregrine Dr, Chester $664,900

Welcome to the Simone home design. This home features a great room fireplace, screened patio, and plus shower in primary suite. This home is estimated for completion Dece...

  • 4 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: NOVA Brokers, LLC..

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: Coldwell Banker Waterman Realty.

126 Merlin Dr, Chester image
126 Merlin Dr, 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: Samson Properties.

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: Anne Arundel Properties, Inc..

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: Non Subscribing Office.

122 Merlin Dr, Chester image
122 Merlin Dr, 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: Real Broker, LLC.

136 Peregrine Dr, Chester image
136 Peregrine Dr, Chester $604,900

Welcome to the Bernstein home design. This home features a screened patio and plus shower in primary suite. This home is available now! For a full list of included feat...

  • 2 Beds
  • 2 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Coldwell Banker Realty.

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: Non Subscribing Office.

218 Peregrine Dr, Chester image
218 Peregrine Dr, Chester $805,000

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 Fe...

  • 3 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

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: TTR Sotheby's International Realty.

209 Harrier Way, Chester image
209 Harrier Way, Chester $705,000

This brand new, custom-built home offers 2791 square feet of luxurious living space, with premium upgrades throughout. Premium up-grades are valued over $75,000. (See pr...

  • 4 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

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

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: Washington Fine Properties.

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: Coldwell Banker Realty.

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: RE/MAX Realty Services.

119 Cavalier Ct, Chester image
119 Cavalier Ct, Chester $760,000

This gorgeous Santorini model is Move In Ready and located in the amenity rich 55+ community of Four Seasons. Built in 2019, this home provides a spacious floor plan offe...

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

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

Selling Office: Trademark Realty, Inc.

129 Wheelhouse Way Unit 2032, Chester image
129 Wheelhouse Way Unit 2032, Chester $734,900

Welcome to unparalleled waterfront luxury at 129 Wheelhouse Way, Unit 2032, in Chester, MD! This exquisite 2-bedroom, 2.5-bath condo features an open floor plan with brea...

  • 2 Beds
  • 3 Baths
Courtesy of Northrop Realty

Listing courtesy of Northrop Realty. Contact:

Selling Office: Unrepresented Buyer 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: Unrepresented Buyer Office.

212 Switchgrass Way Unit 1612, Chester image
212 Switchgrass Way Unit 1612, Chester $524,900

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: Non Subscribing Office.

129 Wheelhouse Way Unit 2011, Chester image
129 Wheelhouse Way Unit 2011, Chester $549,900

Luxury living at its finest! This ground floor waterfront unit is under construction and Move in Ready! Welcome to a new luxury active adult 55+ community on Maryland'...

  • 2 Beds
  • 3 Baths
Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

135 Broadwater Dr, Chester image
135 Broadwater Dr, Chester $669,000

The Donegal model is a spacious and airy 2 bedroom, 2 bath home boasting an expansive open floor plan with nearly 2000 square feet of luxurious living space on one level....

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

Listing courtesy of RE/MAX Executive. Contact:

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

252 Sailcloth Way, Chester image
252 Sailcloth Way, Chester $839,000

Welcome to your dream home in the prestigious Four Seasons community on Kent Island, Maryland. This exquisite property boasts a coveted premium lot, offering unparalleled...

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

Listing courtesy of Real Broker, LLC - Gaithersburg. Contact:

Selling Office: Coldwell Banker Realty.

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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