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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 - $600Ks
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 - $500Ks
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
Roesville
$300Ks
Roesville, Felton, DE
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes
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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
Four Seasons at Hatteras ...
$400Ks - $500Ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
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.
Forest Landing at Bethany...
$400Ks - $500Ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
Four Seasons at Belle Ter...
$600Ks - $700Ks
Four Seasons at Belle Ter..., Lewes, DE
New Construction | 55+ age-restricted | Built 2019 - present | 269 homes
Auburn Meadows
$400Ks
Auburn Meadows, Smyrna, DE
New Construction | 55+ age-restricted | Built 2022 - present | 262 homes
3.3 rating (3 reviews) Windstone
$400Ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
Bay Crossing
$400Ks - $700Ks
Bay Crossing, Lewes, DE
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes
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Longacre Village
$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
SummersGate
$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
The Village of Cinderberr...
$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.
Ashland
$400Ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
Osprey Point
$400Ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
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
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes
Gatherings at Cape May
$400Ks - $500Ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 homes
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Questions? Call us: (667) 843-7291
1.7 rating (3 reviews) Silver Woods
$400Ks
Silver Woods, Ocean View, DE
New and Resale | Age-targeted | Built 2005 - present | 111 homes
Fieldstone Village
$300Ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes
Cedar Bay
$200Ks - $300Ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
Gateway Shores
$200Ks - $300Ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
Wynndemere
$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.
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 34944 COMPASS CV, LEWES, DE, 19958, Lewes, DE 19958
$649,900

3 beds

|

3 baths

|

2,400 sq ft

34944 COMPASS CV, LEWES, DE, 19958
Community: Bay Crossing
Heritage Shores 3 AMANDAS TEAL DR, BRIDGEVILLE, DE, 1993..., Bridgeville, DE 19933
$399,900

3 beds

|

2 baths

|

2,420 sq ft

3 AMANDAS TEAL DR, BRIDGEVILLE, DE, 1993...
Community: Heritage Shores
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
New Four Seasons at Belle Terre 21227 DAUPHINE ST, LEWES, DE, 19958, Lewes, DE 19958
$659,900

3 beds

|

2 baths

|

2,002 sq ft

21227 DAUPHINE ST, LEWES, DE, 19958
Heritage Shores 338 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$474,900

3 beds

|

2 baths

|

1,576 sq ft

338 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
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Questions? Call us: (667) 843-7291
Noble's Pond 809 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$339,810

3 beds

|

2 baths

|

1,453 sq ft

809 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
New Bishop's Landing 33298 LONE CEDAR LNDG # 5802, MILLVILLE,..., Millville, DE 19967
$588,900

4 beds

|

3 baths

|

2,600 sq ft

33298 LONE CEDAR LNDG # 5802, MILLVILLE,...
Community: Bishop's Landing
Four Seasons at Hatteras Hills 253 BUXTON CIR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$405,990

3 beds

|

2 baths

|

1,627 sq ft

253 BUXTON CIR, MAGNOLIA, DE, 19962
Silver Woods 136 KINGSTON AVE, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$441,990

3 beds

|

3 baths

|

2,267 sq ft

136 KINGSTON AVE, OCEAN VIEW, DE, 19970
Community: Silver Woods
Longacre Village 133 CANDOR LN, DOVER, DE, 19901, Dover, DE 19901
$300,000

2 beds

|

2 baths

|

1,198 sq ft

133 CANDOR LN, DOVER, DE, 19901
Community: Longacre Village
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 Shores 108 EMILYS PINTAIL DR, BRIDGEVILLE, DE, ..., Bridgeville, DE 19933
$385,000

4 beds

|

3 baths

|

2,400 sq ft

108 EMILYS PINTAIL DR, BRIDGEVILLE, DE, ...
Community: Heritage Shores
Independence 29688 PATRICK HENRY CIR, MILLSBORO, DE, ..., Millsboro, DE 19966
$659,900

3 beds

|

2 baths

|

2,156 sq ft

29688 PATRICK HENRY CIR, MILLSBORO, DE, ...
Community: Independence
Champions' Club 34 SAHALEE CT, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$415,000

3 beds

|

3 baths

|

2,109 sq ft

34 SAHALEE CT, MAGNOLIA, DE, 19962
Community: Champions' Club
Champions' Club 515 NICKLAUS LN, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$375,000

2 beds

|

2 baths

|

1,636 sq ft

515 NICKLAUS LN, MAGNOLIA, DE, 19962
Community: Champions' Club
Ashland 2 CYCLOPS TRL, SMYRNA, DE, 19977, Smyrna, DE 19977
$459,000

2 beds

|

2 baths

|

1,612 sq ft

2 CYCLOPS TRL, SMYRNA, DE, 19977
Community: Ashland
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Bay Crossing 34743 MARITIME WAY, LEWES, DE, 19958, Lewes, DE 19958
$539,900

3 beds

|

3 baths

|

2,125 sq ft

34743 MARITIME WAY, LEWES, DE, 19958
Community: Bay Crossing
Heritage Shores 8 HARLEQUIN LOOP, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$345,900

3 beds

|

2 baths

|

1,845 sq ft

8 HARLEQUIN LOOP, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Heritage Shores 33 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$425,000

2 beds

|

2 baths

|

1,952 sq ft

33 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Auburn Meadows 15 SADDLEFORD RD, SMYRNA, DE, 19977, Smyrna, DE 19977
$411,318

2 beds

|

2 baths

|

1,728 sq ft

15 SADDLEFORD RD, SMYRNA, DE, 19977
Community: Auburn Meadows
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
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.
Auburn Meadows 43 ARDMONT DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$409,818

2 beds

|

2 baths

|

1,778 sq ft

43 ARDMONT DR, SMYRNA, DE, 19977
Community: Auburn Meadows
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 643 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$467,900

2 beds

|

2 baths

|

1,575 sq ft

643 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 631 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$487,900

2 beds

|

2 baths

|

1,800 sq ft

631 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
Southern Meadow 112 LAVENDER DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$194,900

2 beds

|

2 baths

|

1,740 sq ft

112 LAVENDER DR, 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
The Villages at Red Mill Pond 36396 BABBLING BROOK WAY, LEWES, DE, 199..., Lewes, DE 19958
$650,000

4 beds

|

3 baths

|

2,600 sq ft

36396 BABBLING BROOK WAY, LEWES, DE, 199...
Four Seasons at Hatteras Hills 88 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$499,990

3 beds

|

2 baths

|

1,951 sq ft

88 WANCHESE DR, MAGNOLIA, DE, 19962
New Heritage Shores 31 HARLEQUIN LOOP, BRIDGEVILLE, DE, 1993..., Bridgeville, DE 19933
$419,000

3 beds

|

2 baths

|

1,859 sq ft

31 HARLEQUIN LOOP, BRIDGEVILLE, DE, 1993...
Community: Heritage Shores
Heritage Shores 8 GADWALL CIR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$350,000

3 beds

|

3 baths

|

2,200 sq ft

8 GADWALL CIR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Heritage Shores 30 AMANDAS TEAL DR, BRIDGEVILLE, DE, 199..., Bridgeville, DE 19933
$355,000

3 beds

|

2 baths

|

2,010 sq ft

30 AMANDAS TEAL DR, BRIDGEVILLE, DE, 199...
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.
Heritage Shores 106 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$399,900

4 beds

|

3 baths

|

1,859 sq ft

106 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Bay Crossing 34729 MARITIME WAY, LEWES, DE, 19958, Lewes, DE 19958
$550,000

3 beds

|

3 baths

|

2,761 sq ft

34729 MARITIME WAY, LEWES, DE, 19958
Community: Bay Crossing
Roesville 438 ASTON VILLA DR, FELTON, DE, 19943, Felton, DE 19943
$399,000

3 beds

|

2 baths

|

1,998 sq ft

438 ASTON VILLA DR, FELTON, DE, 19943
Community: Roesville
Silver Woods 354 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$499,990

4 beds

|

4 baths

|

2,443 sq ft

354 GALLAGHER DR, OCEAN VIEW, DE, 19970
Community: Silver Woods
Forest Landing at Bethany Beach 354 GALLAGHER DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$499,990

4 beds

|

4 baths

|

2,443 sq ft

354 GALLAGHER DR, OCEAN VIEW, DE, 19970
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Silver Woods HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE..., Ocean View, DE 19970
$479,990

3 beds

|

3 baths

|

2,070 sq ft

HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE...
Community: Silver Woods
Forest Landing at Bethany Beach HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE..., Ocean View, DE 19970
$479,990

3 beds

|

3 baths

|

2,070 sq ft

HOMESITE 22 GALLAGHER DR, OCEAN VIEW, DE...
Silver Woods 185 MERRICK WAY, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$419,990

3 beds

|

3 baths

|

2,201 sq ft

185 MERRICK WAY, OCEAN VIEW, DE, 19970
Community: Silver Woods
Bishop's Landing 17010 BELLEVUE CT, MILLVILLE, DE, 19967, Millville, DE 19967
$614,000

5 beds

|

4 baths

|

3,010 sq ft

17010 BELLEVUE CT, MILLVILLE, DE, 19967
Community: Bishop's Landing
Silver Woods 207 LACKAWANNA LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$424,990

3 beds

|

3 baths

|

2,178 sq ft

207 LACKAWANNA LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
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31 communities near Ocean Pines
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