55+ Living in Annapolis & Surrounding Communities

55+ Living in Annapolis

55+ living is about choosing a home that supports the life you want to live now — with comfort, simplicity, and peace of mind at the center. In Annapolis and throughout Anne Arundel County, 55+ communities and age-friendly homes offer options ranging from low-maintenance condominiums to thoughtfully designed single-level residences. Many provide features like accessible layouts, community amenities, and proximity to healthcare, dining, and waterfront recreation.

This page highlights current 55+ listings in Annapolis, Severna Park, Crofton, Gambrills, Edgewater, Odenton, and surrounding counties — homes well suited for those looking to downsize, simplify, or transition into a new chapter with confidence and ease.

$699,999
78 OLD MILL BOTTOM ROAD N #311
ANNAPOLIS, MD
2 Beds 2 Baths 1,723 Sqft
Pending
$699,000
940 ASTERN WAY #202
ANNAPOLIS, MD
3 Beds 3 Baths 2,113 Sqft
$689,900
76 OLD MILL BOTTOM ROAD N #301
ANNAPOLIS, MD
2 Beds 2 Baths 1,723 Sqft
Pending
$675,000
940 ASTERN WAY #602
ANNAPOLIS, MD
2 Beds 2 Baths 2,113 Sqft
$639,900
852 WOODMONT ROAD
ANNAPOLIS, MD
3 Beds 2 Baths 1,910 Sqft
Pending
$625,000
2551 JIGGER WAY
ANNAPOLIS, MD
3 Beds 3 Baths 2,640 Sqft
Active Under Contract
$550,000
2607 COMPASS DRIVE
ANNAPOLIS, MD
2 Beds 2 Baths 1,906 Sqft
Active Under Contract
$549,900
906 PERRY LANDING COURT
ANNAPOLIS, MD
2 Beds 2 Baths 2,569 Sqft
$530,000
78 OLD MILL BOTTOM ROAD N #409
ANNAPOLIS, MD
2 Beds 2 Baths 1,210 Sqft
Open House Coming Soon
$499,000
2608 QUIET WATER COVE #26
ANNAPOLIS, MD
2 Beds 2 Baths 1,410 Sqft
Active Under Contract
$485,000
2650 COMPASS DRIVE
ANNAPOLIS, MD
2 Beds 2 Baths 1,514 Sqft
$477,900
2627 COMPASS DRIVE
ANNAPOLIS, MD
2 Beds 2 Baths 1,234 Sqft
Active Under Contract
$465,000
2568 GLEN COVE
ANNAPOLIS, MD
3 Beds 2 Baths 1,512 Sqft
$444,883
78 OLD MILL BOTTOM ROAD N #209
ANNAPOLIS, MD
2 Beds 2 Baths 1,210 Sqft
Pending
$424,500
930 ASTERN WAY #204
ANNAPOLIS, MD
2 Beds 2 Baths 1,464 Sqft
Pending
$400,000
2646 QUIET WATER COVE
ANNAPOLIS, MD
3 Beds 2 Baths 2,354 Sqft
Pending
$310,000
940 ASTERN WAY #102A
ANNAPOLIS, MD
1 Beds 1 Baths 1,073 Sqft
$289,000
930 ASTERN WAY #510
ANNAPOLIS, MD
1 Beds 1 Baths 1,152 Sqft
$285,000
2900 SHIPMASTER WAY #119
ANNAPOLIS, MD
2 Beds 2 Baths 1,018 Sqft
Active Under Contract
$275,000
930 ASTERN WAY #304
ANNAPOLIS, MD
1 Beds 1 Baths 1,152 Sqft
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