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Eastern Shore 55+ Community Homes

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Eastern Shore 55+ Community Homes

208 Topside Dr Unit #211, Stevensville image
208 Topside Dr Unit #211, Stevensville $625,000

Professional Photography Coming Soon! Professional interior photography and stunning drone photography are currently being scheduled and will be added soon. Stay tuned fo...

  • 2 Beds
  • 2 Baths
  • MDQA2018598 MLS
641 Warbler Way, Chester image
641 Warbler Way, Chester $649,990 ▼

Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful desig...

  • 2 Beds
  • 2 Baths
  • MDQA2018602 MLS
275 Warbler Way, Chester image
275 Warbler Way, Chester $944,900

Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and a...

  • 3 Beds
  • 3 Baths
  • MDQA2018566 MLS
736 Warbler Way Unit #2733, Chester image
736 Warbler Way Unit #2733, Chester $719,990

Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, fun...

  • 2 Beds
  • 3 Baths
  • MDQA2018548 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
139 Harmony Way, Centreville image
139 Harmony Way, Centreville $459,000

Perfect location for an afternoon walk to the pool and clubhouse! New roof with a warranty that conveys with the purchase of this lovely home. The updated kitchen is one ...

  • 2 Beds
  • 2 Baths
  • MDQA2018378 MLS
29580 Charles Dr, Easton image
29580 Charles Dr, Easton $549,900 ▼

Chesapeake by Del Webb. The Hillsboro model offers an exceptional combination of space, convenience, and comfortable living. Located directly across from the Community C...

  • 3 Beds
  • 3 Baths
  • MDTA2014814 MLS
536 Warbler Way, Chester image
536 Warbler Way, Chester $749,990 ▼

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
  • MDQA2018316 MLS
29403 Jobes St, Easton image
29403 Jobes St, Easton $389,990 ▼

Welcome to the Pacifica 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, t...

  • 2 Beds
  • 2 Baths
  • MDTA2014824 MLS
902 Moorings Cir Unit #10, Stevensville image
902 Moorings Cir Unit #10, Stevensville $565,000

Experience the relaxed coastal lifestyle you've been dreaming of at 902 Moorings Circle in the highly sought-after 55+ community of Bay Bridge Cove! This beautifully main...

  • 2 Beds
  • 2 Baths
  • MDQA2018168 MLS
29796 Lyons Dr, Easton image
29796 Lyons Dr, Easton $525,000

Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ commu...

  • 3 Beds
  • 3 Baths
  • MDTA2014802 MLS
214 Bayberry Dr, Chester image
214 Bayberry Dr, Chester $924,000

Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This ...

  • 3 Beds
  • 3 Baths
  • MDQA2018216 MLS
259 Topside Dr Unit #166, Stevensville image
259 Topside Dr Unit #166, Stevensville $685,000

Professional staging & photos coming soon! Welcome to 259 Topside Drive in Bay Bridge Cove, one of Kent Island’s most sought-after 55+ communities! This beautifully upgra...

  • 3 Beds
  • 3 Baths
  • MDQA2018214 MLS
201 Switchgrass Way Unit #34, Chester image
201 Switchgrass Way Unit #34, Chester $859,500

Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking...

  • 3 Beds
  • 3 Baths
  • MDQA2018120 MLS
29500 Cromwell Ln, Easton image
29500 Cromwell Ln, Easton $399,990

Welcome to the Pacifica II, a thoughtfully designed 1,385 sq. ft home offering 2 bedrooms, 2 bathrooms, and a 2-car garage. The lovely kitchen flows seamlessly into the a...

  • 2 Beds
  • 2 Baths
  • MDTA2014714 MLS
320 Bayberry Dr, Chester image
320 Bayberry Dr, Chester $862,750 ▼

Be part of the fastest growing 55+ community on Marylands Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior...

  • 3 Beds
  • 2 Baths
  • MDQA2018158 MLS
214 Harmony Way, Centreville image
214 Harmony Way, Centreville $439,900

First Floor Living at it's BEST! Welcome to Symphony Village at Centreville, a sought after Active Adult Community offering an impressive array of amenities and activitie...

  • 3 Beds
  • 2 Baths
  • MDQA2018148 MLS
117 Flycatcher Way, Chester image
117 Flycatcher Way, Chester $1,200,000

The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back...

  • 3 Beds
  • 4 Baths
  • MDQA2018162 MLS
209 Harrier Way, Chester image
209 Harrier Way, Chester $747,900

Welcome Home!!! Open DAILY by Appointment - Or stop by one of our OPEN HOUSES***If you're looking for the ease of primarily one-level living with flexible space for guest...

  • 4 Beds
  • 3 Baths
  • MDQA2018154 MLS
29720 Lyons Dr, Easton image
29720 Lyons Dr, Easton $465,000

Chesapeake by Del Webb. Thurston model single-story in the Easton Club East, 55+ active adult community. This rarely available, single-owner home is move-in ready and bo...

  • 2 Beds
  • 2 Baths
  • MDTA2014642 MLS
29833 Hillary Ave, Easton image
29833 Hillary Ave, Easton $495,000 ▼

Welcome to easy living in one of Easton's most sought-after 55+ communities. Situated on a desirable corner lot with mature landscaping, this well-maintained Thurston mod...

  • 3 Beds
  • 3 Baths
  • MDTA2014254 MLS
111 Marshgrass Way Unit #41, Chester image
111 Marshgrass Way Unit #41, Chester $998,000

Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabul...

  • 3 Beds
  • 3 Baths
  • MDQA2017940 MLS
1 Victoria Ct, Easton image
1 Victoria Ct, Easton $249,500

BUYER MUST FILL OUT APPLICATION AT HYDE PARK OFFICE AND BE APPROVED. NEW ROOF JUST INSTALLED MAY 2026! This charming and well maintained 2-bedroom, 3-bath rancher is loca...

  • 2 Beds
  • 3 Baths
  • MDTA2014592 MLS
102 Boatswain Way Unit #2943, Chester image
102 Boatswain Way Unit #2943, Chester $919,990 ▼

Welcome to the Chester, 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
  • MDQA2018010 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

  • Centreville
  • Chestertown
  • Queenstown
  • Grasonville
  • Chester
  • Stevensville / Kent Island
  • Easton
  • St Michaels
  • Wye Mills
  • Cordova
  • Church Hill
  • Sudlersville
  • Rock Hall
  • Worton
  • Millington
  • Galena
  • Goldsboro
  • Greensboro
  • Denton
  • Queen Anne
  • Ridgely
  • Oxford

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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