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

33 communities near Ocean Pines

Sort by:

Relevance

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

Four Seasons at Hatteras ...

$400ks - $500ks

Four Seasons at Hatteras ..., Magnolia, DE

New Construction | 55+ age-restricted | Built 2023 - present | 400 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

Want to learn more about 55+ communities in Ocean Pines? 55places can help!

Questions? Call us: (667) 843-7291

5 rating (3 reviews)

Village of Eastridge

$300ks - $400ks

Village of Eastridge, Smyrna, DE

New Construction | 55+ age-restricted | Built 2014 - present | 189 homes

Independence

$400ks - $800ks

Independence, Millsboro, DE

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 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

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

Bay Crossing

$400ks - $600ks

Bay Crossing, Lewes, DE

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes

Auburn Meadows

$400ks - $500ks

Auburn Meadows, Smyrna, DE

New Construction | 55+ age-restricted | Built 2022 - present | 262 homes

Osprey Point

$300ks - $400ks

Osprey Point, Upper Township, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 149 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

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

Want to learn more about 55+ communities in Ocean Pines? 55places can help!

Questions? Call us: (667) 843-7291

Ashland

$300ks - $400ks

Ashland, Smyrna, DE

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes

Longacre Village

$300ks

Longacre Village, Dover, DE

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes

5 rating (1 reviews)

Bishop's Landing

$300ks - $500ks

Bishop's Landing, Millville, DE

New and Resale | Age-targeted | Built 2013 - present | 449 homes

Champions' Club

$300ks - $400ks

Champions' Club, Magnolia, DE

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 homes

Legacy at Cape May

$400ks - $500ks

Legacy at Cape May, Rio Grande, NJ

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 141 homes

5 rating (2 reviews)

Spring Meadow

$300ks - $400ks

Spring Meadow, Smyrna, DE

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes

Liberty West

$400ks

Liberty West, Georgetown, DE

New Construction | Age-targeted | Built 2025 - present | 181 homes

Wynndemere

$400ks

Wynndemere, Cape May Court House, NJ

Resale Only | 55+ age-restricted | Built 2001 - 2011 | 62 homes

4.5 rating (2 reviews)

Southern Meadow

$100ks - $200ks

Southern Meadow, Magnolia, DE

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 120 homes

Gatherings at Cape May

$500ks

Gatherings at Cape May, Rio Grande, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 115 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

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

3.3 rating (3 reviews)

Windstone

$400ks

Windstone, Milton, DE

Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes

SummersGate

$300ks

SummersGate, Salisbury, MD

New and Resale | 55+ age-restricted | Built 2008 - present | 216 homes

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

Fieldstone Village

$200ks - $300ks

Fieldstone Village, Dover, DE

Resale Only | 55+ age-restricted | Built 2002 - present | 98 homes

New Fieldstone Village

130 CLAYSTONE DR, DOVER, DE, 19901, Dover, DE 19901

$405,000

3 beds

2 baths

3,236 sq ft

130 CLAYSTONE DR, DOVER, DE, 19901

Community: Fieldstone Village

New Noble's Pond

169 WINDING CARRIAGE LN, DOVER, DE, 1990..., Dover, DE 19904

$385,000

3 beds

3 baths

1,820 sq ft

169 WINDING CARRIAGE LN, DOVER, DE, 1990...

Community: Noble's Pond

New Legacy at Cape May

1505 TIDEWATER AVE 1505, RIO GRANDE, NJ,..., Rio Grande, NJ 08242

$579,000

3 beds

3 baths

2,000 sq ft

Townhouse

1505 TIDEWATER AVE 1505, RIO GRANDE, NJ,...

Community: Legacy at Cape May

New Auburn Meadows

69 HEARTHINGTON HOLW, SMYRNA, DE, 19977, Smyrna, DE 19977

$448,990

3 beds

3 baths

2,151 sq ft

69 HEARTHINGTON HOLW, SMYRNA, DE, 19977

Community: Auburn Meadows

New Auburn Meadows

77 HEARTHINGTON HOLW, SMYRNA, DE, 19977, Smyrna, DE 19977

$428,115

3 beds

3 baths

1,936 sq ft

77 HEARTHINGTON HOLW, SMYRNA, DE, 19977

Community: Auburn Meadows

Want to learn more about 55+ communities in Ocean Pines? 55places can help!

Questions? Call us: (667) 843-7291

New Champions' Club

90 SHADOW CREEK RD, MAGNOLIA, DE, 19962, Magnolia, DE 19962

$350,000

3 beds

2 baths

1,600 sq ft

90 SHADOW CREEK RD, MAGNOLIA, DE, 19962

Community: Champions' Club

New Osprey Point

1731 ROUTE 9 OSPREY POINT, SEAVILLE, NJ,..., Seaville, NJ 08230

$569,000

2 beds

2 baths

Condo

1731 ROUTE 9 OSPREY POINT, SEAVILLE, NJ,...

Community: Osprey Point

New Osprey Point

1731 ROUTE 9 149, SEAVILLE, NJ, 08230, Seaville, NJ 08230

$569,000

2 beds

2 baths

Condo

1731 ROUTE 9 149, SEAVILLE, NJ, 08230

Community: Osprey Point

Legacy at Cape May

1607 TIDEWATER AVE 1607, RIO GRANDE, NJ,..., Rio Grande, NJ 08242

$569,000

3 beds

3 baths

2,140 sq ft

Townhouse

1607 TIDEWATER AVE 1607, RIO GRANDE, NJ,...

Community: Legacy at Cape May

Independence

29597 PATRICK HENRY CIR, MILLSBORO, DE, ..., Millsboro, DE 19966

$649,900

3 beds

3 baths

2,540 sq ft

29597 PATRICK HENRY CIR, MILLSBORO, DE, ...

Community: Independence

Longacre Village

75 N RED HAVEN LN, DOVER, DE, 19901, Dover, DE 19901

$339,000

2 beds

2 baths

1,280 sq ft

75 N RED HAVEN LN, DOVER, DE, 19901

Community: Longacre Village

Heritage Shores

110 WINGED FOOT DR, BRIDGEVILLE, DE, 199..., Bridgeville, DE 19933

$569,900

4 beds

3 baths

2,598 sq ft

110 WINGED FOOT DR, BRIDGEVILLE, DE, 199...

Community: Heritage Shores

The Villages at Red Mill Pond

34174 SPRING BROOK AVE, LEWES, DE, 19958, Lewes, DE 19958

$615,000

3 beds

2 baths

1,988 sq ft

34174 SPRING BROOK AVE, LEWES, DE, 19958

Community: The Villages at Red Mill Pond

Osprey Point

1731 ROUTE 9 98, OCEAN VIEW, NJ, 08230, Ocean View, NJ 08230

$549,000

2 beds

2 baths

Condo

1731 ROUTE 9 98, OCEAN VIEW, NJ, 08230

Community: Osprey Point

Gatherings at Cape May

30 LOCHALSH LN, RIO GRANDE, NJ, 08242, Rio Grande, NJ 08242

$575,000

2 beds

2 baths

2,206 sq ft

Other

30 LOCHALSH LN, RIO GRANDE, NJ, 08242

Community: Gatherings at Cape May

Silver Woods

8 OLD FORGE DR, OCEAN VIEW, DE, 19970, Ocean View, DE 19970

$799,995

3 beds

3 baths

3,026 sq ft

8 OLD FORGE DR, OCEAN VIEW, DE, 19970

Community: Silver Woods

Want to learn more about 55+ communities in Ocean Pines? 55places can help!

Questions? Call us: (667) 843-7291

Forest Landing at Bethany Beach

$799,995

3 beds

3 baths

3,026 sq ft

8 OLD FORGE DR, OCEAN VIEW, DE, 19970

Community: Forest Landing at Bethany Beach

Ashland

25 CYCLOPS TRL, SMYRNA, DE, 19977, Smyrna, DE 19977

$399,900

2 beds

2 baths

1,612 sq ft

25 CYCLOPS TRL, SMYRNA, DE, 19977

Community: Ashland

Village of Eastridge

131 LUPINE DR, SMYRNA, DE, 19977, Smyrna, DE 19977

$430,000

2 beds

2 baths

2,303 sq ft

131 LUPINE DR, SMYRNA, DE, 19977

Community: Village of Eastridge

Silver Woods

37252 BRENDA LN, FRANKFORD, DE, 19945, Frankford, DE 19945

$515,000

3 beds

3 baths

1,715 sq ft

37252 BRENDA LN, FRANKFORD, DE, 19945

Community: Silver Woods

Four Seasons at Belle Terre

21144 CONTI ST, LEWES, DE, 19958, Lewes, DE 19958

$699,900

3 beds

2 baths

2,080 sq ft

21144 CONTI ST, LEWES, DE, 19958

Community: Four Seasons at Belle Terre

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

Community: The Villages at Red Mill Pond

Wynndemere

$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...

Community: The Village of Cinderberry

Heritage Shores

$589,000

3 beds

3 baths

3,028 sq ft

329 HERITAGE SHORES CIR, BRIDGEVILLE, DE...

Community: Heritage Shores

Want to learn more about 55+ communities in Ocean Pines? 55places can help!

Questions? Call us: (667) 843-7291

Noble's Pond

1235 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904

$375,000

2 beds

2 baths

1,518 sq ft

1235 RESORT BLVD, DOVER, DE, 19904

Community: Noble's Pond

Auburn Meadows

264 HYDE AVE, SMYRNA, DE, 19977, Smyrna, DE 19977

$469,500

3 beds

2 baths

2,435 sq ft

264 HYDE AVE, SMYRNA, DE, 19977

Community: Auburn Meadows

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

Community: The Village of Cinderberry

Windstone

16779 BROOKSTONE DR, MILTON, DE, 19968, Milton, DE 19968

$459,000

3 beds

2 baths

2,000 sq ft

16779 BROOKSTONE DR, MILTON, DE, 19968

Community: Windstone

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

$549,500

4 beds

3 baths

2,800 sq ft

33285 LONE CEDAR LNDG, MILLVILLE, DE, 19...

Community: Bishop's Landing

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

Noble's Pond

1163 RESORT BLVD, DOVER, DE, 19904, Dover, DE 19904

$366,715

2 beds

2 baths

1,518 sq ft

1163 RESORT BLVD, DOVER, DE, 19904

Community: Noble's Pond

Four Seasons at Stone Harbor

308 OSPREY DR, CAPE MAY COURT HOUSE, NJ,..., Cape May Court House, NJ 08210

$699,000

3 beds

3 baths

2,220 sq ft

308 OSPREY DR, CAPE MAY COURT HOUSE, NJ,...

Community: Four Seasons at Stone Harbor

Auburn Meadows

76 SADDLEFORD RD, SMYRNA, DE, 19977, Smyrna, DE 19977

$397,990

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

$430,000

3 beds

2 baths

1,599 sq ft

133 CASSIUS LN, DOVER, DE, 19901

Community: Verona Woods

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

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

Community: The Villages at Red Mill Pond

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

Community: The Parke at Ocean Pines

Frequently Asked Questions

What size 55+ communities are there in Ocean Pines?

In Ocean Pines, there is 1 medium community with 500-1000 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Ocean Pines?

The smallest 55+ community in Ocean Pines has 503 homes, the largest has 503 homes, and the average community consists of 503 homes.

Are there gated 55+ communities in Ocean Pines?

No, there are no gated 55+ communities in Ocean Pines.

How long do listings in 55+ communities in Ocean Pines typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in Ocean Pines stay on the market for around 195 days. The average price of homes for sale in this community is approximately $427,581, though prices can range widely based on the size, location, and amenities of the community. For example, homes in The Parke at Ocean Pines average around $427,581.

Want more information about active adult communities around Ocean Pines?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Ocean Pines?

Call us: (667) 843-7291

33 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Apr 22, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

33 communities near Ocean Pines

195 homes near Ocean Pines

3 beds

2 baths

3,236 sq ft

3 beds

3 baths

1,820 sq ft

3 beds

3 baths

2,000 sq ft

Townhouse

3 beds

3 baths

2,151 sq ft

3 beds

3 baths

1,936 sq ft

3 beds

2 baths

1,600 sq ft

2 beds

2 baths

Condo

2 beds

2 baths

Condo

3 beds

3 baths

2,140 sq ft

Townhouse

3 beds

3 baths

2,540 sq ft

2 beds

2 baths

1,280 sq ft

4 beds

3 baths

2,598 sq ft

3 beds

2 baths

1,988 sq ft

2 beds

2 baths

Condo

2 beds

2 baths

2,206 sq ft

Other

3 beds

3 baths

3,026 sq ft

3 beds

3 baths

3,026 sq ft

2 beds

2 baths

1,612 sq ft

2 beds

2 baths

2,303 sq ft

3 beds

3 baths

1,715 sq ft

3 beds

2 baths

2,080 sq ft

3 beds

3 baths

2,140 sq ft

Townhouse

3 beds

2 baths

1,824 sq ft

2 beds

2 baths

Other

3 beds