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Ocean Pines, MD 55+ active adult communities & homes for sale - Page 2

186 homes 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
5 rating (3 reviews) Village of Eastridge
$300ks - $400ks
Village of Eastridge, Smyrna, DE
New Construction | 55+ age-restricted | Built 2014 - present | 189 homes
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Four Seasons at Hatteras ...
$400ks - $500ks
Four Seasons at Hatteras ..., Magnolia, DE
New Construction | 55+ age-restricted | Built 2023 - present | 400 homes
3 rating (5 reviews) Heritage Creek
$300ks - $500ks
Heritage Creek, Milton, DE
New and Resale | Age-targeted | Built 2008 - present | 400 homes
The Village of Cinderberr...
$200ks - $300ks
The Village of Cinderberr..., Georgetown, DE
New and Resale | 55+ age-restricted | Built 2003 - present | 170 homes
Forest Landing at Bethany...
$300ks - $500ks
Forest Landing at Bethany..., Frankford, DE
New and Resale | Age-targeted | Built 2012 - present | 280 homes
Independence
$400ks - $800ks
Independence, Millsboro, DE
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 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.
Verona Woods
$300ks - $400ks
Verona Woods, Dover, DE
Resale Only | 55+ age-restricted | Built 2020 - present | 148 homes
Osprey Point
$300ks - $400ks
Osprey Point, Upper Township, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 homes
Ashland
$300ks - $400ks
Ashland, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes
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
Bay Crossing
$400ks - $600ks
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
5 rating (1 reviews) Bishop's Landing
$300ks - $500ks
Bishop's Landing, Millville, DE
New and Resale | Age-targeted | Built 2013 - present | 449 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
4.5 rating (2 reviews) Southern Meadow
$100ks - $200ks
Southern Meadow, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes
Legacy at Cape May
$400ks - $500ks
Legacy at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 141 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.
Liberty West
$400ks
Liberty West, Georgetown, DE
New Construction | Age-targeted | Built 2025 - present | 181 homes
Champions' Club
$300ks - $400ks
Champions' Club, Magnolia, DE
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 homes
3.3 rating (3 reviews) Windstone
$400ks
Windstone, Milton, DE
Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes
5 rating (2 reviews) Spring Meadow
$300ks - $400ks
Spring Meadow, Smyrna, DE
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes
Longacre Village
$300ks
Longacre Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes
Fieldstone Village
$200ks - $300ks
Fieldstone Village, Dover, DE
Resale Only | 55+ age-restricted | Built 2002 - present | 98 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
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
SummersGate
$300ks
SummersGate, Salisbury, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 216 homes
Gatherings at Cape May
$500ks
Gatherings at Cape May, Rio Grande, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 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.
Gateway Shores
$200ks - $300ks
Gateway Shores, Cape May Court House, NJ
Resale Only | 55+ age-restricted | Built 1996 - 2002 | 66 homes
Cedar Bay
$200ks - $300ks
Cedar Bay, Ocean View, DE
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 72 homes
Roesville
$300ks
Roesville, Felton, DE
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes
Legacy at Cape May 2305 TIDEWATER AVE 2305, RIO GRANDE, NJ,..., Rio Grande, NJ 08242
$539,000

3 beds

|

3 baths

|

2,140 sq ft

|

Townhouse

2305 TIDEWATER AVE 2305, RIO GRANDE, NJ,...
Community: Legacy at Cape May
The Villages at Red Mill Pond 34258 SPRING BROOK AVE, LEWES, DE, 19958, Lewes, DE 19958
$550,000

3 beds

|

2 baths

|

1,824 sq ft

34258 SPRING BROOK AVE, LEWES, DE, 19958
Wynndemere 40 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ..., Cape May Court House, NJ 08210
$430,000

2 beds

|

2 baths

|

Other

40 WYNNDEMERE CT, CAPE MAY COURT HOUSE, ...
Community: Wynndemere
Longacre Village 392 WINESAP LN, DOVER, DE, 19901, Dover, DE 19901
$520,000

3 beds

|

3 baths

|

1,916 sq ft

392 WINESAP LN, DOVER, DE, 19901
Community: Longacre Village
The Village of Cinderberry 46 FRANKENBERRY DR, GEORGETOWN, DE, 1994..., Georgetown, DE 19947
$395,000

3 beds

|

2 baths

|

2,003 sq ft

46 FRANKENBERRY DR, GEORGETOWN, DE, 1994...
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Heritage Shores 329 HERITAGE SHORES CIR, BRIDGEVILLE, DE..., Bridgeville, DE 19933
$579,000

3 beds

|

3 baths

|

3,028 sq ft

329 HERITAGE SHORES CIR, BRIDGEVILLE, DE...
Community: Heritage Shores
Noble's Pond 1235 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904
$354,454

2 beds

|

2 baths

|

1,518 sq ft

1235 RESORT BLVD, DOVER, DE, 19904
Community: Noble's Pond
The Village of Cinderberry 26 CINDER WAY 38, GEORGETOWN, DE, 19947, Georgetown, DE 19947
$330,000

2 beds

|

2 baths

|

1,693 sq ft

26 CINDER WAY 38, GEORGETOWN, DE, 19947
Heritage Shores 78 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$349,800

2 beds

|

2 baths

|

1,728 sq ft

78 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
Bishop's Landing 33285 LONE CEDAR LNDG, MILLVILLE, DE, 19..., Millville, DE 19967
$537,500

4 beds

|

3 baths

|

2,800 sq ft

33285 LONE CEDAR LNDG, MILLVILLE, DE, 19...
Community: Bishop's Landing
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 11 BAY HILL RD, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$380,000

2 beds

|

2 baths

|

1,739 sq ft

11 BAY HILL RD, MAGNOLIA, DE, 19962
Community: Champions' Club
Four Seasons at Stone Harbor 308 OSPREY DR, CAPE MAY COURT HOUSE, NJ,..., Cape May Court House, NJ 08210
$694,900

3 beds

|

3 baths

|

2,220 sq ft

308 OSPREY DR, CAPE MAY COURT HOUSE, NJ,...
Auburn Meadows 76 SADDLEFORD RD, SMYRNA, DE, 19977, Smyrna, DE 19977
$389,918

2 beds

|

2 baths

|

1,728 sq ft

76 SADDLEFORD RD, SMYRNA, DE, 19977
Community: Auburn Meadows
Verona Woods 133 CASSIUS LN, DOVER, DE, 19901, Dover, DE 19901
$425,000

3 beds

|

2 baths

|

1,599 sq ft

133 CASSIUS LN, DOVER, DE, 19901
Community: Verona Woods
The Villages at Red Mill Pond 16511 GREENSPRING AVE, LEWES, DE, 19958, Lewes, DE 19958
$555,000

3 beds

|

2 baths

|

1,855 sq ft

16511 GREENSPRING AVE, LEWES, DE, 19958
The Parke at Ocean Pines 3 HATTERAS ST, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$335,000

2 beds

|

2 baths

|

1,187 sq ft

3 HATTERAS ST, 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 38 LEANDER DR, DOVER, DE, 19904, Dover, DE 19904
$469,000

2 beds

|

2 baths

|

2,242 sq ft

38 LEANDER DR, DOVER, DE, 19904
Community: Noble's Pond
Champions' Club 15 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 19..., Magnolia, DE 19962
$390,000

2 beds

|

2 baths

|

1,630 sq ft

15 AUGUSTA NATIONAL DR, MAGNOLIA, DE, 19...
Community: Champions' Club
Forest Landing at Bethany Beach 36427 BUNKER CT, FRANKFORD, DE, 19945, Frankford, DE 19945
$589,900

4 beds

|

3 baths

|

2,550 sq ft

|

Condo

36427 BUNKER CT, FRANKFORD, DE, 19945
The Villages at Red Mill Pond 16480 GREENSPRING AVE, LEWES, DE, 19958, Lewes, DE 19958
$619,000

4 beds

|

3 baths

|

2,477 sq ft

16480 GREENSPRING 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 Villages at Red Mill Pond 17563 CLOUD NINE DR, LEWES, DE, 19958, Lewes, DE 19958
$579,000

3 beds

|

2 baths

|

2,228 sq ft

17563 CLOUD NINE DR, LEWES, DE, 19958
Verona Woods 401 ALEZACH DR, DOVER, DE, 19901, Dover, DE 19901
$440,000

3 beds

|

2 baths

|

1,356 sq ft

401 ALEZACH DR, DOVER, DE, 19901
Community: Verona Woods
Spring Meadow 39 THISTLE CT, SMYRNA, DE, 19977, Smyrna, DE 19977
$328,000

2 beds

|

2 baths

|

1,410 sq ft

39 THISTLE CT, SMYRNA, DE, 19977
Community: Spring Meadow
Independence 23854 BETSY ROSS LN, MILLSBORO, DE, 1996..., Millsboro, DE 19966
$575,000

3 beds

|

2 baths

|

2,417 sq ft

23854 BETSY ROSS LN, MILLSBORO, DE, 1996...
Community: Independence
The Villages at Red Mill Pond 34273 SPRING BROOK AVE, LEWES, DE, 19958, Lewes, DE 19958
$649,000

3 beds

|

2 baths

|

2,267 sq ft

34273 SPRING BROOK AVE, LEWES, DE, 19958
Ashland 7 PEGASUS LN, SMYRNA, DE, 19977, Smyrna, DE 19977
$469,900

3 beds

|

3 baths

|

2,400 sq ft

7 PEGASUS LN, SMYRNA, DE, 19977
Community: Ashland
Independence 24032 BENJAMIN HARRISON CIR, MILLSBORO, ..., Millsboro, DE 19966
$509,900

3 beds

|

2 baths

|

1,675 sq ft

24032 BENJAMIN HARRISON CIR, MILLSBORO, ...
Community: Independence
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
The Parke at Ocean Pines 57 HATTERAS ST, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$389,000

3 beds

|

2 baths

|

1,408 sq ft

57 HATTERAS ST, OCEAN PINES, MD, 21811
The Village of Cinderberry 12 FRANKENBERRY DR, GEORGETOWN, DE, 1994..., Georgetown, DE 19947
$419,000

3 beds

|

2 baths

|

1,665 sq ft

12 FRANKENBERRY DR, GEORGETOWN, DE, 1994...
Heritage Creek 220 FOX ST, MILTON, DE, 19968, Milton, DE 19968
$539,000

3 beds

|

2,485 sq ft

220 FOX ST, MILTON, DE, 19968
Community: Heritage Creek
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 Beach 36725 PAR LN 98, FRANKFORD, DE, 19945, Frankford, DE 19945
$575,000

4 beds

|

3 baths

|

2,400 sq ft

|

Condo

36725 PAR LN 98, FRANKFORD, DE, 19945
Heritage Shores 32 WATERSIDE DR, BRIDGEVILLE, DE, 19933, Bridgeville, DE 19933
$549,900

4 beds

|

3 baths

|

2,650 sq ft

32 WATERSIDE DR, BRIDGEVILLE, DE, 19933
Community: Heritage Shores
Four Seasons at Hatteras Hills 62 FRISCO DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$509,990

3 beds

|

2 baths

|

1,951 sq ft

62 FRISCO DR, MAGNOLIA, DE, 19962
The Parke at Ocean Pines 10 CAMBRIDGE PL, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811
$699,000

4 beds

|

3 baths

|

3,080 sq ft

10 CAMBRIDGE PL, OCEAN PINES, MD, 21811
Auburn Meadows 614 VIRDIN DR, SMYRNA, DE, 19977, Smyrna, DE 19977
$439,000

2 beds

|

2 baths

|

1,797 sq ft

614 VIRDIN DR, SMYRNA, DE, 19977
Community: Auburn Meadows
Four Seasons at Hatteras Hills 1002 BUXTON CIR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$519,990

3 beds

|

2 baths

|

1,754 sq ft

1002 BUXTON CIR, MAGNOLIA, DE, 19962
Heritage Shores 42 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1..., Bridgeville, DE 19933
$329,000

2 beds

|

2 baths

|

1,683 sq ft

42 WHISTLING DUCK DR, BRIDGEVILLE, DE, 1...
Community: Heritage Shores
Forest Landing at Bethany Beach 36451 DOG LEG CT, FRANKFORD, DE, 19945, Frankford, DE 19945
$599,000

4 beds

|

3 baths

|

2,750 sq ft

|

Condo

36451 DOG LEG CT, FRANKFORD, DE, 19945
Want to learn more about 55+ communities in Ocean Pines? 55places can help!
Questions? Call us: (667) 843-7291
Heritage Shores 100 WHISTLING DUCK DR, BRIDGEVILLE, DE, ..., Bridgeville, DE 19933
$323,000

2 beds

|

2 baths

|

1,569 sq ft

100 WHISTLING DUCK DR, BRIDGEVILLE, DE, ...
Community: Heritage Shores
Four Seasons at Hatteras Hills 30 FRISCO DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962
$519,990

3 beds

|

3 baths

|

1,778 sq ft

30 FRISCO DR, 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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