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

31 communities near Ocean Pines

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5 rating (2 reviews) The Parke at Ocean Pines
$200Ks - $500Ks
The Parke at Ocean Pines, Ocean Pines, MD
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 503 homes
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
$300Ks - $400Ks
Noble's Pond, Dover, DE
New and Resale | 55+ age-restricted | Built 2007 - present | 800 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
No reviews yet Roesville
$300Ks - $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
No reviews yet Independence
$100Ks - $700Ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 homes
5 rating (1 reviews) Bishop's Landing
$500Ks - $600Ks
Bishop's Landing, Millville, DE
New and Resale | Age-targeted | Built 2013 - present | 449 homes
3 rating (5 reviews) Heritage Creek
$400Ks - $500Ks
Heritage Creek, Milton, DE
New and Resale | Age-targeted | Built 2008 - present | 400 homes
No reviews yet Four Seasons at Hatteras ...
$400Ks - $500Ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
No reviews yet Champions' Club
$300Ks - $400Ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 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.
No reviews yet Forest Landing at Bethany...
$400Ks - $500Ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
No reviews yet Four Seasons at Belle Ter...
$600Ks - $700Ks
Four Seasons at Belle Ter..., Lewes, DE
New Construction | 55+ age-restricted | Built 2019 - present | 269 homes
No reviews yet Auburn Meadows
$400Ks - $400Ks
Auburn Meadows, Smyrna, DE
New Construction | 55+ age-restricted | Built 2022 - present | 262 homes
3.3 rating (3 reviews) Windstone
$400Ks - $400Ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
No reviews yet Bay Crossing
$400Ks - $700Ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
No reviews yet Longacre Village
$200Ks - $300Ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes
5 rating (2 reviews) Spring Meadow
$300Ks - $400Ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
No reviews yet SummersGate
$300Ks - $300Ks
SummersGate, Salisbury, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 216 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
No reviews yet The Village of Cinderberr...
$200Ks - $300Ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 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.
No reviews yet Ashland
$400Ks - $400Ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
No reviews yet Osprey Point
$400Ks - $400Ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
No reviews yet Legacy at Cape May
$400Ks - $500Ks
Legacy at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 141 homes
4.5 rating (2 reviews) Southern Meadow
$100Ks - $100Ks
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes
No reviews yet Gatherings at Cape May
$400Ks - $500Ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
1.7 rating (3 reviews) Silver Woods
$400Ks - $500Ks
Silver Woods, Ocean View, DE
New and Resale | Age-targeted | Built 2005 - present | 111 homes
No reviews yet Fieldstone Village
$300Ks - $300Ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
No reviews yet Cedar Bay
$200Ks - $300Ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
No reviews yet Gateway Shores
$200Ks - $300Ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
No reviews yet Wynndemere
$400Ks - $400Ks
Wynndemere, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 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.
No reviews yet Four Seasons at Stone Har...
$500Ks - $600Ks
Four Seasons at Stone Har..., Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 60 homes
Bay Crossing 34774 SCHOONER PASS, LEWES, DE, 19958, Lewes, DE 19958
$499,900

3 beds

|

3 baths

|

1,993 sq ft

34774 SCHOONER PASS, LEWES, DE, 19958
Community: Bay Crossing
Bay Crossing 34953 COMPASS CV, LEWES, DE, 19958, Lewes, DE 19958
$725,000

4 beds

|

4 baths

|

4,061 sq ft

34953 COMPASS CV, LEWES, DE, 19958
Community: Bay Crossing
Windstone 29635 RIVERSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$399,900

3 beds

|

2 baths

|

1,732 sq ft

29635 RIVERSTONE DR, MILTON, DE, 19968
Community: Windstone
Independence 23855 BETSY ROSS LN, MILLSBORO, DE, 1996..., Millsboro, DE 19966
$599,999

3 beds

|

2 baths

|

2,200 sq ft

23855 BETSY ROSS LN, MILLSBORO, DE, 1996...
Community: Independence
Four Seasons at Stone Harbor 308 OSPREY DR, CAPE MAY COURT HOUSE, NJ,..., Cape May Court House, NJ 08210
$635,000

4 beds

|

3 baths

|

2,220 sq ft

|

Townhouse

308 OSPREY DR, CAPE MAY COURT HOUSE, NJ,...
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Four Seasons at Stone Harbor 100 OSPREY DR # 100, CAPE MAY COURT HOUS..., Cape May Court House, NJ 08210
$699,000

3 beds

|

3 baths

|

2,545 sq ft

|

Townhouse

100 OSPREY DR # 100, CAPE MAY COURT HOUS...
Osprey Point 1731 ROUTE 9 28, OCEAN VIEW, NJ, 08230, Ocean View, NJ 08230
$549,900

2 beds

|

2 baths

|

2,002 sq ft

|

Condo

1731 ROUTE 9 28, OCEAN VIEW, NJ, 08230
Community: Osprey Point
Wynndemere 90 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ..., Cape May Court House, NJ 08210
$449,000

2 beds

|

2 baths

|

1,338 sq ft

|

Other

90 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ...
Community: Wynndemere
Gateway Shores 144 LEE LN, CAPE MAY COURT HOUSE, NJ, 08..., Cape May Court House, NJ 08210
$259,000

1 beds

|

2 baths

|

Condo

144 LEE LN, CAPE MAY COURT HOUSE, NJ, 08...
Community: Gateway Shores
Four Seasons at Stone Harbor 3 WHIMBREL WAY, CAPE MAY COURT HOUSE, NJ..., Cape May Court House, NJ 08210
$599,000

3 beds

|

3 baths

|

2,087 sq ft

|

Condo

3 WHIMBREL WAY, CAPE MAY COURT HOUSE, NJ...
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 Stone Harbor 11 SANDERLING CT # 23, CAPE MAY COURT HO..., Cape May Court House, NJ 08210
$794,500

3 beds

|

3 baths

|

2,545 sq ft

|

Townhouse

11 SANDERLING CT # 23, CAPE MAY COURT HO...
Gateway Shores 147 LEE LN # 147, CAPE MAY COURT HOUSE, ..., Cape May Court House, NJ 08210
$309,900

2 beds

|

2 baths

|

1,160 sq ft

|

Condo

147 LEE LN # 147, CAPE MAY COURT HOUSE, ...
Community: Gateway Shores
The Villages at Red Mill Pond 36396 BABBLING BROOK WAY, LEWES, DE, 199..., Lewes, DE 19958
$650,000

4 beds

|

4 baths

|

2,600 sq ft

36396 BABBLING BROOK WAY, LEWES, DE, 199...
Heritage Creek 217 FOX ST, MILTON, DE, 19968, Milton, DE 19968
$575,000

3 beds

|

3 baths

|

2,182 sq ft

217 FOX ST, MILTON, DE, 19968
Community: Heritage Creek
New Noble's Pond 135 CASSELBERRY LN, DOVER, DE, 19904, Dover, DE 19904
$365,000

2 beds

|

2 baths

|

1,283 sq ft

135 CASSELBERRY LN, DOVER, DE, 19904
Community: Noble's Pond
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
New Village of Eastridge 100 NEW VILLAGE LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$479,500

3 beds

|

2 baths

|

1,842 sq ft

100 NEW VILLAGE LN, SMYRNA, DE, 19977
Heritage Shores 9 LINKS DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$440,000

3 beds

|

2 baths

|

1,810 sq ft

9 LINKS DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Bishop's Landing 30195 BRANDYWINE DR, MILLVILLE, DE, 1996..., Millville, DE 19967
$665,000

4 beds

|

4 baths

|

3,152 sq ft

30195 BRANDYWINE DR, MILLVILLE, DE, 1996...
Community: Bishop's Landing
The Villages at Red Mill Pond 17927 TORRY PINES PL, LEWES, DE, 19958, Lewes, DE 19958
$529,000

3 beds

|

3 baths

|

3,736 sq ft

17927 TORRY PINES PL, LEWES, DE, 19958
Auburn Meadows 1012 VIRDIN DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$429,359

3 beds

|

2 baths

|

1,878 sq ft

1012 VIRDIN DR, SMYRNA, DE, 19977
Community: Auburn Meadows
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 Auburn Meadows 1000 VIRDIN DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$437,531

3 beds

|

3 baths

|

2,386 sq ft

1000 VIRDIN DR, SMYRNA, DE, 19977
Community: Auburn Meadows
Forest Landing at Bethany Beach 37092 FAIRWAY DR, FRANKFORD, DE, 19945, Frankford, DE 19945
$569,900

4 beds

|

3 baths

|

2,400 sq ft

|

Condo

37092 FAIRWAY DR, FRANKFORD, DE, 19945
Noble's Pond 247 CARNEY CT, DOVER, DE, 19904, Dover, DE 19904
$354,900

3 beds

|

2 baths

|

1,453 sq ft

247 CARNEY CT, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 227 CARNEY CT, DOVER, DE, 19904, Dover, DE 19904
$369,245

3 beds

|

3 baths

|

2,142 sq ft

227 CARNEY CT, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 208 CARNEY CT, DOVER, DE, 19904, Dover, DE 19904
$371,647

3 beds

|

3 baths

|

2,142 sq ft

208 CARNEY CT, DOVER, DE, 19904
Community: Noble's Pond
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Windstone 29575 FIELDSTONE DR, MILTON, DE, 19968, Milton, DE 19968
$475,000

3 beds

|

2 baths

|

2,056 sq ft

29575 FIELDSTONE DR, MILTON, DE, 19968
Community: Windstone
Independence 29432 ANDREW JACKSON DR, MILLSBORO, DE, ..., Millsboro, DE 19966
$715,000

3 beds

|

2 baths

|

2,900 sq ft

29432 ANDREW JACKSON DR, MILLSBORO, DE, ...
Community: Independence
Heritage Shores 134 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$344,900

2 beds

|

2 baths

|

1,320 sq ft

134 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Heritage Shores 3 AMANDAS TEAL DR, BRIDGEVILLE, DE, 1993..., Bridgeville, DE 19933
$420,000

3 beds

|

2 baths

|

2,420 sq ft

3 AMANDAS TEAL DR, BRIDGEVILLE, DE, 1993...
Community: Heritage Shores
New Heritage Shores 99 EMILYS PINTAIL DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$429,900

4 beds

|

3 baths

|

3,091 sq ft

99 EMILYS PINTAIL DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
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.
Longacre Village 45 HARCREST CT, DOVER, DE, 19901, Dover, DE 19901
$359,900

3 beds

|

3 baths

|

2,010 sq ft

45 HARCREST CT, DOVER, DE, 19901
Community: Longacre Village
Heritage Shores 338 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$478,000

3 beds

|

2 baths

|

1,576 sq ft

338 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Village of Eastridge 131 HENGST FARM LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$457,351

2 beds

|

2 baths

|

1,684 sq ft

131 HENGST FARM LN, SMYRNA, DE, 19977
Village of Eastridge 123 HENGST FARM LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$487,803

2 beds

|

2 baths

|

1,581 sq ft

123 HENGST FARM LN, SMYRNA, DE, 19977
Independence 23792 SAMUEL ADAMS CIR, MILLSBORO, DE, 1..., Millsboro, DE 19966
$715,000

4 beds

|

3 baths

|

3,142 sq ft

23792 SAMUEL ADAMS CIR, MILLSBORO, DE, 1...
Community: Independence
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Longacre Village 21 STARFIRE CT, DOVER, DE, 19901, Dover, DE 19901
$299,900

2 beds

|

2 baths

|

1,198 sq ft

21 STARFIRE CT, DOVER, DE, 19901
Community: Longacre Village
Independence 26446 COTTONTAIL CV, MILLSBORO, DE, 1996..., Millsboro, DE 19966
$150,000

3 beds

|

2 baths

|

1,344 sq ft

26446 COTTONTAIL CV, MILLSBORO, DE, 1996...
Community: Independence
Silver Woods 392 SCRANTON LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$479,990

3 beds

|

3 baths

|

2,267 sq ft

392 SCRANTON LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Forest Landing at Bethany Beach HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE..., Ocean View, DE 19970
$489,990

3 beds

|

3 baths

|

2,070 sq ft

HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE...
Silver Woods HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE..., Ocean View, DE 19970
$489,990

3 beds

|

3 baths

|

2,070 sq ft

HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE...
Community: Silver Woods
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31 communities near Ocean Pines
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