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Ocean Pines, MD 55+ active adult communities & homes for sale - Page 3

118 homes near Ocean Pines

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5 rating (2 reviews) The Parke at Ocean Pines
$200Ks - $300Ks
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
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
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.
Champions' Club
$300Ks - $400Ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 homes
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
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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
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
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.
SummersGate
$400Ks
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
Ashland
$400Ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
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Questions? Call us: (667) 843-7291
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
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.
1.7 rating (3 reviews) Silver Woods
$400Ks - $500Ks
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
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Questions? Call us: (667) 843-7291
Four Seasons at Stone Har...
$600Ks
Four Seasons at Stone Har..., Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 60 homes
Heritage Shores 103 WINGED FOOT DR, BRIDGEVILLE, DE, 199..., Bridgeville, DE 19933
$399,900

3 beds

|

2 baths

|

1,952 sq ft

103 WINGED FOOT DR, BRIDGEVILLE, DE, 199...
Community: Heritage Shores
Bishop's Landing 33285 LONE CEDAR LNDG, MILLVILLE, DE, 19..., Millville, DE 19967
$565,000

4 beds

|

3 baths

|

2,800 sq ft

33285 LONE CEDAR LNDG, MILLVILLE, DE, 19...
Community: Bishop's Landing
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
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
Fieldstone Village 175 CLAYSTONE DR, DOVER, DE, 19901, Dover, DE 19901
$369,900

3 beds

|

2 baths

|

1,945 sq ft

175 CLAYSTONE DR, DOVER, DE, 19901
Community: Fieldstone Village
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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
Noble's Pond 3 NOBLES POND XING, DOVER, DE, 19904, Dover, DE 19904
$439,900

2 beds

|

2 baths

|

1,750 sq ft

3 NOBLES POND XING, DOVER, DE, 19904
Community: Noble's Pond
Heritage Shores 38 ROYAL VIEW DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$599,990

3 beds

|

3 baths

|

3,309 sq ft

38 ROYAL VIEW DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Heritage Shores 312 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$399,990

3 beds

|

2 baths

|

1,792 sq ft

312 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
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.
Village of Eastridge 00 FELIX VIEW CT BAYARD, SMYRNA, DE, 199..., Smyrna, DE 19977
$395,000

2 beds

|

2 baths

|

1,580 sq ft

00 FELIX VIEW CT BAYARD, SMYRNA, DE, 199...
Village of Eastridge 00 FELIX VIEW CT BAYARD CLASSIC, SMYRNA,..., Smyrna, DE 19977
$382,000

2 beds

|

2 baths

|

1,600 sq ft

00 FELIX VIEW CT BAYARD CLASSIC, SMYRNA,...
The Villages at Red Mill Pond 18682 GOLDEN SUNRISE PL, LEWES, DE, 1995..., Lewes, DE 19958
$489,900

3 beds

|

2 baths

|

1,498 sq ft

18682 GOLDEN SUNRISE PL, LEWES, DE, 1995...
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
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...
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
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
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 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
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
Silver Woods 138 KINGSTON AVE, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$424,990

3 beds

|

3 baths

|

2,088 sq ft

138 KINGSTON AVE, OCEAN VIEW, DE, 19970
Community: Silver Woods
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!
Questions? Call us: (667) 843-7291
Bay Crossing 34677 VILLA CIR 504, LEWES, DE, 19958, Lewes, DE 19958
$399,900

3 beds

|

2 baths

|

1,215 sq ft

34677 VILLA CIR 504, LEWES, DE, 19958
Community: Bay Crossing
Champions' Club 314 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1..., Magnolia, DE 19962
$325,000

2 beds

|

2 baths

|

1,566 sq ft

314 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 1...
Community: Champions' Club
Heritage Creek 202 HAY ST, MILTON, DE, 19968, Milton, DE 19968
$448,900

3 beds

|

3 baths

|

2,046 sq ft

202 HAY ST, MILTON, DE, 19968
Community: Heritage Creek
Village of Eastridge 00 FELIX VIEW CT ASTON, SMYRNA, DE, 1997..., Smyrna, DE 19977
$406,000

2 beds

|

2 baths

|

1,720 sq ft

00 FELIX VIEW CT ASTON, SMYRNA, DE, 1997...
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 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
Village of Eastridge 76 VOLPE WAY, SMYRNA, DE, 19977, Smyrna, DE 19977
$389,000

2 beds

|

2 baths

|

1,639 sq ft

76 VOLPE WAY, SMYRNA, DE, 19977
Ashland 7 PEGASUS LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$469,900

3 beds

|

3 baths

|

1,944 sq ft

7 PEGASUS LN, SMYRNA, DE, 19977
Community: Ashland
Heritage Shores 328 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$499,990

3 beds

|

2 baths

|

2,018 sq ft

328 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Heritage Shores 12 HARLEQUIN LOOP, BRIDGEVILLE, DE, 1993..., Bridgeville, DE 19933
$349,900

3 beds

|

2 baths

|

1,845 sq ft

12 HARLEQUIN LOOP, BRIDGEVILLE, DE, 1993...
Community: Heritage Shores
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Silver Woods 385 SCRANTON LN, OCEAN VIEW, DE, 19970, Ocean View, DE 19970
$449,990

3 beds

|

3 baths

|

2,178 sq ft

385 SCRANTON LN, OCEAN VIEW, DE, 19970
Community: Silver Woods
Noble's Pond 2 NOBLES POND XING, DOVER, DE, 19904, Dover, DE 19904
$420,900

2 beds

|

2 baths

|

1,510 sq ft

2 NOBLES POND XING, DOVER, DE, 19904
Community: Noble's Pond
Village of Eastridge 00 FELIX VIEW CT BRENFORD, SMYRNA, DE, 1..., Smyrna, DE 19977
$402,000

3 beds

|

2 baths

|

1,740 sq ft

00 FELIX VIEW CT BRENFORD, SMYRNA, DE, 1...
Village of Eastridge 00 FELIX VIEW CT ASBURY, SMYRNA, DE, 199..., Smyrna, DE 19977
$392,000

2 beds

|

2 baths

|

1,600 sq ft

00 FELIX VIEW CT ASBURY, SMYRNA, DE, 199...
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 211 PROSPECT ST, MILTON, DE, 19968, Milton, DE 19968
$494,900

3 beds

|

3 baths

|

2,046 sq ft

211 PROSPECT ST, MILTON, DE, 19968
Community: Heritage Creek
Noble's Pond 4 NOBLES POND XING, DOVER, DE, 19904, Dover, DE 19904
$447,900

2 beds

|

2 baths

|

1,820 sq ft

4 NOBLES POND XING, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 6 NOBLES POND XING, DOVER, DE, 19904, Dover, DE 19904
$453,900

3 beds

|

2 baths

|

1,820 sq ft

6 NOBLES POND XING, DOVER, DE, 19904
Community: Noble's Pond
Noble's Pond 1 NOBLES POND XING, DOVER, DE, 19904, Dover, DE 19904
$389,900

2 beds

|

2 baths

|

1,260 sq ft

1 NOBLES POND XING, DOVER, DE, 19904
Community: Noble's Pond

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