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Ocean Pines, MD 55+ active adult communities & homes for sale

33 communities near Ocean Pines

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5 rating (2 reviews) Heritage Shores
$200ks - $500ks
Heritage Shores, Bridgeville, DE
New and Resale | 55+ age-restricted | Built 2004 - present | 1,816 homes
5 rating (2 reviews) Noble's Pond
$200ks - $300ks
Noble's Pond, Dover, DE
New and Resale | 55+ age-restricted | Built 2007 - present | 800 homes
1.7 rating (3 reviews) Silver Woods
$400ks - $500ks
Silver Woods, Ocean View, DE
New and Resale | Age-targeted | Built 2005 - present | 111 homes
2.8 rating (4 reviews) The Villages at Red Mill ...
$400ks - $600ks
The Villages at Red Mill ..., Lewes, DE
New and Resale | Age-targeted | Built 2009 - present | 520 homes
Four Seasons at Hatteras ...
$400ks - $500ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
5 rating (3 reviews) Village of Eastridge
$300ks - $400ks
Village of Eastridge, Smyrna, DE
New Construction | 55+ age-restricted | Built 2014 - present | 189 homes
The Village of Cinderberr...
$200ks - $300ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 homes
3 rating (5 reviews) Heritage Creek
$300ks - $500ks
Heritage Creek, Milton, DE
New and Resale | Age-targeted | Built 2008 - present | 400 homes
Forest Landing at Bethany...
$300ks - $500ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
Verona Woods
$300ks - $400ks
Verona Woods, Dover, DE
Resale Only | 55+ age-restricted | Built 2020 - present | 148 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Independence
$400ks - $800ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 homes
Ashland
$300ks - $400ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
4.5 rating (2 reviews) Southern Meadow
$100ks - $200ks
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes
5 rating (1 reviews) Bishop's Landing
$300ks - $500ks
Bishop's Landing, Millville, DE
New and Resale | Age-targeted | Built 2013 - present | 449 homes
Liberty West
$400ks
Liberty West, Georgetown, DE
New Construction | Age-targeted | Built 2025 - present | 181 homes
5 rating (2 reviews) Spring Meadow
$300ks - $400ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
3.3 rating (3 reviews) Windstone
$400ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
5 rating (2 reviews) The Parke at Ocean Pines
$200ks - $600ks
The Parke at Ocean Pines, Ocean Pines, MD
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 503 homes
Four Seasons at Stone Har...
$600ks - $700ks
Four Seasons at Stone Har..., Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 60 homes
Bay Crossing
$400ks - $600ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Four Seasons at Belle Ter...
$400ks - $600ks
Four Seasons at Belle Ter..., Lewes, DE
New Construction | 55+ age-restricted | Built 2019 - present | 269 homes
Auburn Meadows
$400ks - $500ks
Auburn Meadows, Smyrna, DE
New Construction | 55+ age-restricted | Built 2022 - present | 262 homes
Champions' Club
$300ks - $400ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 homes
Osprey Point
$300ks - $400ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
SummersGate
$300ks
SummersGate, Salisbury, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 216 homes
Legacy at Cape May
$400ks - $500ks
Legacy at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 141 homes
Longacre Village
$300ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Roesville
$300ks
Roesville, Felton, DE
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes
Gatherings at Cape May
$500ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 homes
Gateway Shores
$200ks - $300ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Cedar Bay
$200ks - $300ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
Wynndemere
$400ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 homes
Fieldstone Village
$200ks - $300ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
New The Villages at Red Mill Pond 14692 PLEASANT POND WAY, LEWES, DE, 1995..., Lewes, DE 19958
$599,900

3 beds

|

2 baths

|

2,185 sq ft

14692 PLEASANT POND WAY, LEWES, DE, 1995...
Heritage Shores 110 WINGED FOOT DR, BRIDGEVILLE, DE, 199..., Bridgeville, DE 19933
$549,000

4 beds

|

3 baths

|

2,598 sq ft

110 WINGED FOOT DR, BRIDGEVILLE, DE, 199...
Community: Heritage Shores
Verona Woods 76 BALTHASAR DR, DOVER, DE, 19901, Dover, DE 19901
$434,000

3 beds

|

2 baths

|

1,704 sq ft

76 BALTHASAR DR, DOVER, DE, 19901
Community: Verona Woods
Verona Woods 302 ALEZACH DR, DOVER, DE, 19901, Dover, DE 19901
$439,900

3 beds

|

2 baths

|

1,800 sq ft

302 ALEZACH DR, DOVER, DE, 19901
Community: Verona Woods
The Parke at Ocean Pines 8 LONG POINT CT, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$549,900

4 beds

|

3 baths

|

2,808 sq ft

8 LONG POINT CT, OCEAN PINES, MD, 21811
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Noble's Pond 135 CASSELBERRY LN, DOVER, DE, 19904, Dover, DE 19904
$359,000

2 beds

|

2 baths

|

1,283 sq ft

135 CASSELBERRY LN, DOVER, DE, 19904
Community: Noble's Pond
Heritage Shores 134 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$319,900

2 beds

|

2 baths

|

1,320 sq ft

134 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
New Gatherings at Cape May 207 ABERDEEN WAY, RIO GRANDE, NJ, 08242, Rio Grande, NJ 08242
$565,000

2 beds

|

2 baths

|

1,920 sq ft

|

Other

207 ABERDEEN WAY, RIO GRANDE, NJ, 08242
New Village of Eastridge 105 OSCAR MILL LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$439,000

3 beds

|

3 baths

|

2,171 sq ft

105 OSCAR MILL LN, SMYRNA, DE, 19977
New The Village of Cinderberry 7 FRANKENBERRY DR, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$385,000

3 beds

|

2 baths

|

1,670 sq ft

7 FRANKENBERRY DR, GEORGETOWN, DE, 19947
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
New Four Seasons at Hatteras Hills 37 FRISCO DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$509,990

3 beds

|

3 baths

|

1,778 sq ft

37 FRISCO DR, MAGNOLIA, DE, 19962
Noble's Pond 86 COUNTRY CLUB DR, DOVER, DE, 19904, Dover, DE 19904
$438,000

3 beds

|

2 baths

|

2,514 sq ft

86 COUNTRY CLUB DR, DOVER, DE, 19904
Community: Noble's Pond
Heritage Shores 12 LINKS DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$425,000

3 beds

|

2 baths

|

1,795 sq ft

12 LINKS DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Silver Woods 248 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$484,990

3 beds

|

3 baths

|

2,070 sq ft

248 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Windstone 29817 SANDSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$524,900

3 beds

|

2 baths

|

2,165 sq ft

29817 SANDSTONE DR, MILTON, DE, 19968
Community: Windstone
Village of Eastridge 88 FELIX VIEW CT, SMYRNA, DE, 19977, Smyrna, DE 19977
$483,500

2 beds

|

3 baths

|

2,040 sq ft

88 FELIX VIEW CT, SMYRNA, DE, 19977
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Heritage Shores 2 WHISTLING DUCK DR, BRIDGEVILLE, DE, 19..., Bridgeville, DE 19933
$420,000

3 beds

|

2 baths

|

2,200 sq ft

2 WHISTLING DUCK DR, BRIDGEVILLE, DE, 19...
Community: Heritage Shores
Auburn Meadows 44 SADDLEFORD DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$458,900

3 beds

|

3 baths

|

2,151 sq ft

44 SADDLEFORD DR, SMYRNA, DE, 19977
Community: Auburn Meadows
Forest Landing at Bethany Beach 37109 FAIRWAY DR, FRANKFORD, DE, 19945, Frankford, DE 19945
$499,900

4 beds

|

3 baths

|

1,950 sq ft

|

Condo

37109 FAIRWAY DR, FRANKFORD, DE, 19945
The Villages at Red Mill Pond 34438 SPRING BROOK AVE, LEWES, DE, 19958, Lewes, DE 19958
$575,000

3 beds

|

2 baths

|

2,082 sq ft

34438 SPRING BROOK AVE, LEWES, DE, 19958
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Parke at Ocean Pines 7 LONG POINT CT, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$599,900

4 beds

|

3 baths

|

2,808 sq ft

7 LONG POINT CT, OCEAN PINES, MD, 21811
Spring Meadow 603 SORRELL CIR, SMYRNA, DE, 19977, Smyrna, DE 19977
$345,000

3 beds

|

2 baths

|

1,589 sq ft

603 SORRELL CIR, SMYRNA, DE, 19977
Community: Spring Meadow
The Parke at Ocean Pines 95 CHATHAM CT, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$549,900

4 beds

|

3 baths

|

2,357 sq ft

95 CHATHAM CT, OCEAN PINES, MD, 21811
Heritage Shores 32 RUDDY DUCK LN, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$425,000

2 beds

|

2 baths

|

1,896 sq ft

32 RUDDY DUCK LN, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
The Villages at Red Mill Pond 30418 COHENS DR, LEWES, DE, 19958, Lewes, DE 19958
$549,000

3 beds

|

2 baths

|

1,956 sq ft

30418 COHENS DR, LEWES, DE, 19958
Roesville 453 ASTON VILLA DR, FELTON, DE, 19943, Felton, DE 19943
$353,000

3 beds

|

2 baths

|

1,818 sq ft

453 ASTON VILLA DR, FELTON, DE, 19943
Community: Roesville
Heritage Creek 210 HERITAGE BLVD, MILTON, DE, 19968, Milton, DE 19968
$475,000

3 beds

|

3 baths

|

1,714 sq ft

210 HERITAGE BLVD, MILTON, DE, 19968
Community: Heritage Creek
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Verona Woods 401 ALEZACH DR, DOVER, DE, 19901, Dover, DE 19901
$430,000

3 beds

|

2 baths

|

1,356 sq ft

401 ALEZACH DR, DOVER, DE, 19901
Community: Verona Woods
Four Seasons at Stone Harbor 308 OSPREY 308 - TOWNHOUSE, CAPE MAY COU..., Cape May Court House, NJ 08210
$690,000

4 beds

|

3 baths

|

2,200 sq ft

|

Condo

308 OSPREY 308 - TOWNHOUSE, CAPE MAY COU...
Four Seasons at Stone Harbor 308 OSPREY CT NO, CAPE MAY COURT HOUSE, ..., Cape May Court House, NJ 08210
$690,000

4 beds

|

3 baths

|

2,220 sq ft

|

Townhouse

308 OSPREY CT NO, CAPE MAY COURT HOUSE, ...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Heritage Creek 205 HERITAGE BLVD, MILTON, DE, 19968, Milton, DE 19968
$549,900

4 beds

|

4 baths

|

3,384 sq ft

205 HERITAGE BLVD, MILTON, DE, 19968
Community: Heritage Creek
Heritage Shores 60 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$329,000

2 beds

|

2 baths

|

1,735 sq ft

60 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
Heritage Shores 391 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$354,000

2 beds

|

2 baths

|

1,416 sq ft

391 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Wynndemere 20 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ..., Cape May Court House, NJ 08210
$460,000

2 beds

|

2 baths

|

1,515 sq ft

|

Other

20 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ...
Community: Wynndemere
Southern Meadow 106 FOXTAIL LN 32, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$169,000

2 beds

|

2 baths

|

1,384 sq ft

106 FOXTAIL LN 32, MAGNOLIA, DE, 19962
Community: Southern Meadow
Auburn Meadows 38 ARDMONT DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$409,950

2 beds

|

2 baths

|

1,778 sq ft

38 ARDMONT DR, SMYRNA, DE, 19977
Community: Auburn Meadows
Noble's Pond 631 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$479,900

2 beds

|

2 baths

631 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Southern Meadow 121 BLUEBELL DR 11, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$159,900

2 beds

|

2 baths

|

1,092 sq ft

121 BLUEBELL DR 11, MAGNOLIA, DE, 19962
Community: Southern Meadow
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Village of Eastridge 54 OSCAR MILL LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$415,000

2 beds

|

2 baths

|

2,218 sq ft

54 OSCAR MILL LN, SMYRNA, DE, 19977
Four Seasons at Hatteras Hills 895 BUXTON CIR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$439,990

3 beds

|

2 baths

|

2,499 sq ft

895 BUXTON CIR, MAGNOLIA, DE, 19962
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

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