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

32 communities near Ocean Pines

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5 rating (2 reviews) Heritage Shores
$300ks - $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
5 rating (3 reviews) Village of Eastridge
$300ks - $400ks
Village of Eastridge, Smyrna, DE
New Construction | 55+ age-restricted | Built 2014 - present | 189 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
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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
Independence
$400ks - $800ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 homes
4.5 rating (2 reviews) Southern Meadow
$100ks - $200ks
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 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.
Ashland
$300ks - $400ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
3 rating (5 reviews) Heritage Creek
$300ks - $500ks
Heritage Creek, Milton, DE
New and Resale | Age-targeted | Built 2008 - present | 400 homes
Longacre Village
$300ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes
3.3 rating (3 reviews) Windstone
$400ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
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Four Seasons at Belle Ter...
$400ks - $600ks
Four Seasons at Belle Ter..., Lewes, DE
New Construction | 55+ age-restricted | Built 2019 - present | 269 homes
The Village of Cinderberr...
$200ks - $300ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 homes
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Champions' Club
$300ks - $400ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 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.
5 rating (1 reviews) Bishop's Landing
$300ks - $500ks
Bishop's Landing, Millville, DE
New and Resale | Age-targeted | Built 2013 - present | 449 homes
Bay Crossing
$400ks - $600ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
Forest Landing at Bethany...
$300ks - $500ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
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Cedar Bay
$200ks - $300ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
Auburn Meadows
$400ks - $500ks
Auburn Meadows, Smyrna, DE
New Construction | 55+ age-restricted | Built 2022 - present | 262 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
Want to learn more about 55+ rental communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
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.
Osprey Point
$300ks - $400ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
5 rating (2 reviews) Spring Meadow
$300ks - $400ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
Gateway Shores
$200ks - $300ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
Fieldstone Village
$200ks - $300ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
Roesville
$300ks
Roesville, Felton, DE
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Wynndemere
$400ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 homes
Gatherings at Cape May
$500ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 homes
New Osprey Point 1731 ROUTE 9 11, OCEAN VIEW, NJ, 08230, Ocean View, NJ 08230
$545,000

2 beds

|

2 baths

|

1,848 sq ft

|

Condo

1731 ROUTE 9 11, OCEAN VIEW, NJ, 08230
Community: Osprey Point
New The Parke at Ocean Pines 11423 MANKLIN CREEK RD UNIT 1, OCEAN PIN..., Ocean Pines, MD 21811
$295,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

11423 MANKLIN CREEK RD UNIT 1, OCEAN PIN...
New Noble's Pond 11 KINSALE PL, DOVER, DE, 19904, Dover, DE 19904
$389,000

3 beds

|

3 baths

|

2,306 sq ft

11 KINSALE PL, DOVER, DE, 19904
Community: Noble's Pond
New Longacre Village 147 N RED HAVEN LN, DOVER, DE, 19901, Dover, DE 19901
$339,900

2 beds

|

2 baths

|

1,280 sq ft

147 N RED HAVEN LN, DOVER, DE, 19901
Community: Longacre Village
New Longacre Village 103 CANDOR LN, DOVER, DE, 19901, Dover, DE 19901
$340,000

4 beds

|

3 baths

|

2,118 sq ft

103 CANDOR LN, DOVER, DE, 19901
Community: Longacre Village
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
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Questions? Call us: (667) 843-7291
New Ashland 26 CYCLOPS TRL, SMYRNA, DE, 19977, Smyrna, DE 19977
$425,000

3 beds

|

3 baths

|

1,848 sq ft

26 CYCLOPS TRL, SMYRNA, DE, 19977
Community: Ashland
Independence 29606 PATRICK HENRY CIR, MILLSBORO, DE, ..., Millsboro, DE 19966
$679,900

3 beds

|

2 baths

|

2,157 sq ft

29606 PATRICK HENRY CIR, MILLSBORO, DE, ...
Community: Independence
The Parke at Ocean Pines 8 LONG POINT CT, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$575,000

4 beds

|

3 baths

|

2,808 sq ft

8 LONG POINT CT, OCEAN PINES, MD, 21811
Four Seasons at Belle Terre 21336 DAUPHINE ST, LEWES, DE, 19958, Lewes, DE 19958
$670,000

3 beds

|

2 baths

|

2,087 sq ft

21336 DAUPHINE ST, 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.
Silver Woods 266 EXETER ST, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$499,900

3 beds

|

3 baths

|

2,178 sq ft

266 EXETER ST, OCEAN VIEW, DE, 19970
Community: Silver Woods
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Parke at Ocean Pines 11427 MANKLIN CREEK RD 7, OCEAN PINES, M..., Ocean Pines, MD 21811
$299,000

3 beds

|

2 baths

|

1,181 sq ft

|

Condo

11427 MANKLIN CREEK RD 7, OCEAN PINES, M...
Heritage Creek 322 MARINERS CIR, MILTON, DE, 19968, Milton, DE 19968
$565,000

3 beds

|

2 baths

|

1,836 sq ft

322 MARINERS CIR, MILTON, DE, 19968
Community: Heritage Creek
Bay Crossing 34825 CAPSTAN LN, LEWES, DE, 19958, Lewes, DE 19958
$750,000

4 beds

|

3 baths

|

2,400 sq ft

34825 CAPSTAN LN, LEWES, DE, 19958
Community: Bay Crossing
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Spring Meadow 219 WHEATSHEAF LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$430,000

3 beds

|

3 baths

|

3,117 sq ft

219 WHEATSHEAF LN, SMYRNA, DE, 19977
Community: Spring Meadow
Legacy at Cape May 407 SEACREST LN 407, RIO GRANDE, NJ, 082..., Rio Grande, NJ 08242
$599,000

3 beds

|

3 baths

|

Condo

407 SEACREST LN 407, RIO GRANDE, NJ, 082...
Community: Legacy at Cape May
Want to learn more about 55+ rental communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Heritage Shores 105 WHISTLING DUCK DR, BRIDGEVILLE, DE, ..., Bridgeville, DE 19933
$329,900

2 beds

|

2 baths

|

1,481 sq ft

105 WHISTLING DUCK DR, BRIDGEVILLE, DE, ...
Community: Heritage Shores
Noble's Pond 226 CARNEY CT, DOVER, DE, 19904, Dover, DE 19904
$359,900

3 beds

|

3 baths

|

2,142 sq ft

226 CARNEY CT, DOVER, DE, 19904
Community: Noble's Pond
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.
Noble's Pond 247 CARNEY CT, DOVER, DE, 19904, Dover, DE 19904
$348,990

3 beds

|

2 baths

|

1,453 sq ft

247 CARNEY CT, DOVER, DE, 19904
Community: Noble's Pond
Heritage Creek 200 FOX ST, MILTON, DE, 19968, Milton, DE 19968
$548,500

3 beds

|

3 baths

|

2,018 sq ft

200 FOX ST, MILTON, DE, 19968
Community: Heritage Creek
Heritage Shores 34 ROYAL VIEW DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$519,990

3 beds

|

4 baths

|

2,702 sq ft

34 ROYAL VIEW DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Independence 23843 BETSY ROSS LN, MILLSBORO, DE, 1996..., Millsboro, DE 19966
$525,000

3 beds

|

2 baths

|

2,280 sq ft

23843 BETSY ROSS LN, MILLSBORO, DE, 1996...
Community: Independence
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
The Villages at Red Mill Pond 34152 SPRING BROOK AVE, LEWES, DE, 19958, Lewes, DE 19958
$619,900

3 beds

|

2 baths

|

2,156 sq ft

34152 SPRING BROOK AVE, LEWES, DE, 19958
The Villages at Red Mill Pond 12137 SPICER CREEK AVE, LEWES, DE, 19958, Lewes, DE 19958
$545,000

3 beds

|

2 baths

|

1,703 sq ft

12137 SPICER CREEK AVE, LEWES, DE, 19958
Noble's Pond 42 STEEPLECHASE DR, DOVER, DE, 19904, Dover, DE 19904
$365,500

3 beds

|

2 baths

|

1,584 sq ft

42 STEEPLECHASE DR, DOVER, DE, 19904
Community: Noble's Pond
Windstone 29845 SANDSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$449,900

3 beds

|

2 baths

|

1,730 sq ft

29845 SANDSTONE DR, MILTON, DE, 19968
Community: Windstone
Want to learn more about 55+ rental communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
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.
Osprey Point 1731 ROUTE 9 25, OCEAN VIEW, NJ, 08230, Ocean View, NJ 08230
$519,000

2 beds

|

2 baths

|

Condo

1731 ROUTE 9 25, OCEAN VIEW, NJ, 08230
Community: Osprey Point
The Villages at Red Mill Pond 17547 CLOUD NINE DR, LEWES, DE, 19958, Lewes, DE 19958
$545,000

3 beds

|

2 baths

|

1,764 sq ft

17547 CLOUD NINE DR, LEWES, DE, 19958
The Villages at Red Mill Pond 34148 SPRING BROOK AVE, LEWES, DE, 19958, Lewes, DE 19958
$599,000

3 beds

|

2 baths

|

1,742 sq ft

34148 SPRING BROOK AVE, LEWES, DE, 19958
The Villages at Red Mill Pond 34497 SPRING BROOK AVE, LEWES, DE, 19958, Lewes, DE 19958
$544,900

3 beds

|

2 baths

|

1,628 sq ft

34497 SPRING BROOK AVE, LEWES, DE, 19958
Heritage Creek 215 MILL POND AVE, MILTON, DE, 19968, Milton, DE 19968
$469,900

3 beds

|

2 baths

|

1,979 sq ft

215 MILL POND AVE, 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
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Four Seasons at Hatteras Hills 59 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$499,990

3 beds

|

2 baths

|

1,951 sq ft

59 WANCHESE DR, MAGNOLIA, DE, 19962
Four Seasons at Hatteras Hills 73 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$469,990

3 beds

|

2 baths

|

1,627 sq ft

73 WANCHESE DR, MAGNOLIA, DE, 19962
Noble's Pond 631 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$486,500

2 beds

|

2 baths

|

1,800 sq ft

631 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 4 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$447,900

2 beds

|

2 baths

|

1,820 sq ft

4 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
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.
Noble's Pond 3 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$439,900

2 beds

|

2 baths

|

1,750 sq ft

3 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Want to learn more about 55+ rental communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Noble's Pond 2 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$420,900

2 beds

|

2 baths

|

1,510 sq ft

2 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 1 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$389,900

2 beds

|

2 baths

|

1,260 sq ft

1 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 498 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$512,000

3 beds

|

3 baths

|

2,373 sq ft

498 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
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Noble's Pond 643 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$450,400

2 beds

|

2 baths

|

1,575 sq ft

643 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 5 FAIRMONT LN, DOVER, DE, 19904, Dover, DE 19904
$453,900

3 beds

|

2 baths

|

1,820 sq ft

5 FAIRMONT LN, DOVER, DE, 19904
Community: Noble's Pond

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