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Eastern Shore 55+ Community Homes

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Eastern Shore 55+ Community Homes

7196 Bobs Way, Easton image
7196 Bobs Way, Easton $520,000

Chesapeake by Del Webb. This one owner Merion model is sited on an end lot overlooking a pond and community open space. Living room/office, family room with gas firepla...

  • 3 Beds
  • 3 Baths
  • MDTA2015432 MLS
105 Symphony Way, Centreville image
105 Symphony Way, Centreville $619,000

Welcome to 105 Symphony Way in the sought after community of Symphony Village at Centreville. This is a rare find in the community, a Wagner Model located just steps fro...

  • 3 Beds
  • 3 Baths
  • MDQA2019118 MLS
122 Orchestra Pl, Centreville image
122 Orchestra Pl, Centreville $599,000

Don't miss this home in the Symphony Village at Centreville Active Adult Community. This home has so much to offer, starting with owned solar panels (please ask about ex...

  • 3 Beds
  • 3 Baths
  • MDQA2019120 MLS
313 Orchestra Pl, Centreville image
313 Orchestra Pl, Centreville — None Available $?

This bright, custom Vivaldi model in Centreville's premier Symphony Village community perfectly balances luxury and comfort. Featuring gleaming hardwood floors throughout...

  • 3 Beds
  • 2 Baths
  • MDQA2019112 MLS
  • None Available Bldg.
19 St James Ct, Easton image
19 St James Ct, Easton $149,900

Enjoy living in the sought after community of Hyde Park 55+ Adult Living. Located on a corner lot, close to the pool and clubhouse. Amenities also include walking trail...

  • 2 Beds
  • 2 Baths
  • MDTA2015396 MLS
14 Curzon Ct, Easton image
14 Curzon Ct, Easton $125,000

Opportunity Awaits in Sun Communities Hyde Park! This spacious 2-bedroom, 2-bath home features a welcoming front porch, a bright sunroom, and plenty of potential to make ...

  • 2 Beds
  • 2 Baths
  • MDTA2015378 MLS
830 Warbler Way Unit 2843, Chester image
830 Warbler Way Unit 2843, Chester $789,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish liv...

  • 2 Beds
  • 3 Baths
  • MDQA2018944 MLS
111 Marshgrass Way Unit 43, Chester image
111 Marshgrass Way Unit 43, Chester $744,900

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communit...

  • 2 Beds
  • 3 Baths
  • MDQA2018854 MLS
7598 Ward Brothers Cir, Easton image
7598 Ward Brothers Cir, Easton $554,990

The Bogart offers an open-concept design with classic details and a projected settlement date of February 2027. Designed for comfortable everyday living, this home featur...

  • 3 Beds
  • 2 Baths
  • MDTA2015276 MLS
117 Harrier Way, Chester image
117 Harrier Way, Chester $790,000

Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, offering true one-level living with no steps, three spacious bedrooms, and the larges...

  • 3 Beds
  • 2 Baths
  • MDQA2018792 MLS
64 Park Ln, Easton image
64 Park Ln, Easton $30,000

ONLINE AUCTION: Bidding begins 10/29/2026, 10:00 AM. Bidding ends 11/2/2026, 1:20 PM. List Price is Suggested Opening Bid. Deposit: $5,000. This auction takes place on th...

  • 2 Beds
  • 2 Baths
  • MDTA2015238 MLS
129 Wheelhouse Way Unit 21, Chester image
129 Wheelhouse Way Unit 21, Chester $1,399,000 ▼

Experience exceptional waterfront living in this stunning 3-bedroom, 2.5-bath condominium offering what are arguably the best views in the community. Positioned to captur...

  • 3 Beds
  • 3 Baths
  • MDQA2018858 MLS
129 Wheelhouse Way Unit 11, Chester image
129 Wheelhouse Way Unit 11, Chester $585,000

Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury,...

  • 2 Beds
  • 3 Baths
  • MDQA2018848 MLS
29574 Charles Dr, Easton image
29574 Charles Dr, Easton $525,000 ▼

Chesapeake by Del Webb. Gorgeous McDaniel style home has been remodeled with many upgrades in the past 4 years. Living room/office, formal dining room, family room with...

  • 3 Beds
  • 3 Baths
  • MDTA2015194 MLS
630 Warbler Way Unit 12, Chester image
630 Warbler Way Unit 12, Chester $549,950

Experience everything Four Seasons at Kent Island has to offer without the wait! Less than one year old, this beautifully maintained home shows like new and offers one of...

  • 2 Beds
  • 3 Baths
  • MDQA2018826 MLS
118 Kinglet Ct, Chester image
118 Kinglet Ct, Chester $969,990

Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for ...

  • 2 Beds
  • 3 Baths
  • MDQA2018806 MLS
114 Kinglet Ct, Chester image
114 Kinglet Ct, Chester $999,990

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for bo...

  • 3 Beds
  • 3 Baths
  • MDQA2018804 MLS
247 Redstart Dr, Chester image
247 Redstart Dr, Chester $899,990

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for bo...

  • 3 Beds
  • 3 Baths
  • MDQA2018802 MLS
830 Warbler Way Unit 2833, Chester image
830 Warbler Way Unit 2833, Chester $689,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish liv...

  • 2 Beds
  • 3 Baths
  • MDQA2018800 MLS
320 Bayberry Dr, Chester image
320 Bayberry Dr, Chester $859,900

None

  • 3 Beds
  • 2 Baths
  • MDQA2018766 MLS
228 Bayberry Dr, Chester image
228 Bayberry Dr, Chester $665,000

Immediate Occupancy-Be HOME for the HOLIDAYS! Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS c...

  • 2 Beds
  • 3 Baths
  • MDQA2018728 MLS
29496 Mason Ln, Easton image
29496 Mason Ln, Easton $489,990

Welcome to the Spring Lake II, a beautifully designed home that pairs an open-concept layout with timeless Loft elements. Offering 2 bedrooms, 2 baths, and a 2-car garage...

  • 2 Beds
  • 2 Baths
  • MDTA2015130 MLS
208 Topside Dr Unit 211, Stevensville image
208 Topside Dr Unit 211, Stevensville $610,000 ▼

Luxury, comfort, and resort-style living come together beautifully in this exceptional Bay Bridge Cove residence! This beautifully appointed home combines elegant finishe...

  • 2 Beds
  • 2 Baths
  • MDQA2018598 MLS
29812 Dustin Ave, Easton image
29812 Dustin Ave, Easton $480,000

Welcome to this beautifully maintained McDaniel model in Easton Club East, a sought-after 55+ active adult community in Easton. Offering 3 bedrooms and 2.5 baths, this sp...

  • 3 Beds
  • 3 Baths
  • MDTA2014530 MLS
6 Albion Ct, Easton image
6 Albion Ct, Easton $89,000

BUYER MUST BE APPROVED FOR PURCHASE BY THE HYDE PARK OFFICE BEFORE SUBMITTING AN OFFER. SUBJECT TO MONTHLY GROUND RENT THAT WILL INCREASE FROM $643 CURRENTLY TO $678 IN N...

  • 2 Beds
  • 2 Baths
  • MDTA2014876 MLS
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More Eastern Shore 55+ Communities

  • 55+ Bay Bridge Cove
  • Four Seasons at Kent Island
  • Easton Club East
  • Symphony Village

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Want to know more about our Eastern Shore 55+ Communities?

Brett Schrader is a local Agent that can assist with any questions you may have about these great communities, their models, HOA's and amenities. Call 410-490-6075


Explore Our Best Towns

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Centerville Communities

  • Bridgetown Estates
  • Claiborne Fields
  • North Brook
  • Providence Farms
  • Symphony Village
  • Three Creeks
  • Willow Branch

Stevensville / Kent Island Communities

  • Bay Bridge Cove
  • Cloverfields
  • Bay City
  • Cove Creek Club
  • Ellendale
  • Kent Island Estates

Easton Communities

  • Bretridge
  • Chapel Estates
  • Cooks Hope
  • Easton Club East
  • Hyde Park
  • Lakelands at Easton
  • Matthews Town Run
  • Stoney Ridge Farm

Chestertown Communities

  • Chesapeake Landing
  • Chester Harbor
  • Chester River Landing
  • Coventry Farms

Grasonville Communities

  • Chester River Beach
  • Prospect Bay

Queenstown Communities

  • Steamboat Village

Chester Communities

  • Gibson’s Grant

Denton Communities

  • Cattail Commons
  • Mallard Landing

Ridgely Communities

  • Lister Estates

  • Centreville
  • Chestertown
  • Easton
  • Grasonville
  • Stevensville

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Brett Schrader
Cell: 410-490-6075
Taylor Properties
Broker 800-913-4326
BrettSchrader6@gmail.com

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