Middletown, MD 55+ active adult communities & homes for sale

489 homes near Middletown

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The Village at Foxfield

$300Ks - $500Ks

The Village at Foxfield, Middletown, MD

Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes

5 rating (1 reviews)

Leisure World® of Marylan...

<$100k - $500Ks

Leisure World® of Marylan..., Silver Spring, MD

Resale Only | 55+ age-restricted | Built 1966 - 2009 | 5,600 homes

4.3 rating (11 reviews)

Amblebrook

$300Ks - $1Ms

Amblebrook, Gettysburg, PA

New Construction | 55+ age-restricted | Built 2018 - present | 2,000 homes

5 rating (3 reviews)

Heritage Hunt

$600Ks - $800Ks

Heritage Hunt, Gainesville, VA

Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes

2 rating (1 reviews)

Birchwood at Brambleton

$400Ks - $1Ms

Birchwood at Brambleton, Ashburn, VA

New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes

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

Questions? Call us: (240) 663-8229

5 rating (2 reviews)

Potomac Green

$700Ks - $800Ks

Potomac Green, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$300Ks - $500Ks

Lansdowne Woods of Virgin..., Lansdowne, VA

Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes

No reviews yet

Penn National

$200Ks - $800Ks

Penn National, Fayetteville, PA

New and Resale | Age-targeted | Built 1968 - present | 1,100 homes

5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400Ks - $1Ms

Trilogy® at Lake Frederic..., Lake Frederick, VA

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

5 rating (1 reviews)

Regency at Dominion Valle...

$400Ks - $800Ks

Regency at Dominion Valle..., Haymarket, VA

Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 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.

5 rating (1 reviews)

Four Seasons at Historic ...

$600Ks - $700Ks

Four Seasons at Historic ..., Dumfries, VA

Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes

5 rating (1 reviews)

Two Rivers

$500Ks - $800Ks

Two Rivers, Odenton, MD

New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes

No reviews yet

Cameron Grove

$300Ks - $400Ks

Cameron Grove, Upper Marlboro, MD

Resale Only | 55+ age-restricted | Built 1999 - 2013 | 740 homes

5 rating (2 reviews)

Central Parke at Victoria...

$300Ks - $600Ks

Central Parke at Victoria..., Laurel, MD

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 609 homes

No reviews yet

The Woodlands of Urbana

$600Ks - $700Ks

The Woodlands of Urbana, Urbana, MD

New Construction | 55+ age-restricted | Built 2019 - present | 565 homes

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

Questions? Call us: (240) 663-8229

5 rating (1 reviews)

Crestwood Village

$300Ks - $300Ks

Crestwood Village, Frederick, MD

Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes

No reviews yet

Traditions of America at ...

$400Ks - $500Ks

Traditions of America at ..., Mechanicsburg, PA

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 517 homes

No reviews yet

Carter's Mill

$400Ks - $700Ks

Carter's Mill, Haymarket, VA

New Construction | 55+ age-restricted | Built 2020 - present | 480 homes

3 rating (2 reviews)

Dunbarton

$600Ks - $600Ks

Dunbarton, Bristow, VA

Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes

No reviews yet

The Courtyards at Waverly...

$300Ks - $600Ks

The Courtyards at Waverly..., Marriottsville, MD

Resale Only | 55+ age-restricted | Built 2012 - 2018 | 462 homes

5 rating (1 reviews)

Carroll Vista

$300Ks - $500Ks

Carroll Vista, Taneytown, MD

Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes

No reviews yet

Cedar Ridge at Piney Orch...

$300Ks - $400Ks

Cedar Ridge at Piney Orch..., Odenton, MD

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes

No reviews yet

Montebello

$600Ks - $1Ms

Montebello, Sterling, VA

New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes

No reviews yet

Village Crest

$400Ks - $600Ks

Village Crest, Ellicott City, MD

New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes

No reviews yet

Courtyards at Waverly Woo...

$300Ks - $400Ks

Courtyards at Waverly Woo..., Woodstock, MD

Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes

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

Questions? Call us: (240) 663-8229

5 rating (1 reviews)

Snowden Overlook

$400Ks - $700Ks

Snowden Overlook, Columbia, MD

Resale Only | 55+ age-restricted | Built 2005 - 2010 | 350 homes

No reviews yet

Creek View

$100Ks - $200Ks

Creek View, Carlisle, PA

New and Resale | 55+ age-restricted | Built 2004 - present | 305 homes

No reviews yet

Longstown Village

$100Ks - $200Ks

Longstown Village, York, PA

Resale Only | Age-targeted | Built 1997 - 2000 | 304 homes

No reviews yet

Heritage at St. Charles

$400Ks - $500Ks

Heritage at St. Charles, White Plains, MD

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 300 homes

No reviews yet

The Villages At Woodholme

$400Ks - $500Ks

The Villages At Woodholme, Baltimore, MD

Resale Only | 55+ age-restricted | Built 2002 - 2007 | 286 homes

No reviews yet

Spring Hill

$500Ks - $800Ks

Spring Hill, Lorton, VA

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes

No reviews yet

The Enclave at Ellicott H...

$400Ks - $400Ks

The Enclave at Ellicott H..., Ellicott City, MD

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 280 homes

No reviews yet

Regency at Ashburn

$500Ks - $600Ks

Regency at Ashburn, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes

No reviews yet

Emerald Pointe

$300Ks - $400Ks

Emerald Pointe, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes

No reviews yet

The Crest of Alexandria

$900Ks - $900Ks

The Crest of Alexandria, Alexandria, VA

New and Resale | 55+ age-restricted | Built 2017 - present | 250 homes

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

Questions? Call us: (240) 663-8229

No reviews yet

Colonial Charles

$400Ks - $400Ks

Colonial Charles, Waldorf, MD

Resale Only | 55+ age-restricted | Built 2006 - 2018 | 240 homes

No reviews yet

River Ridge

$600Ks - $600Ks

River Ridge, Woodbridge, VA

Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes

No reviews yet

Signature Club at Greenvi...

$400Ks - $900Ks

Signature Club at Greenvi..., New Market, MD

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes

No reviews yet

Eden Brook

$300Ks - $300Ks

Eden Brook, Odenton, MD

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 224 homes

No reviews yet

Roth's Farm Village

$200Ks - $200Ks

Roth's Farm Village, Spring Grove, PA

New and Resale | 55+ age-restricted | Built 2006 - present | 224 homes

1 2 3...4

Leisure World® of Maryland

3376 CHISWICK CT 52-3C, SILVER SPRING, M..., Silver Spring, MD 20906

$149,000

2 beds

1 baths

1,035 sq ft

Condo

3376 CHISWICK CT 52-3C, SILVER SPRING, M...

Community: Leisure World® of Maryland

The Courtyards at Waverly Woods

2507 SOPHIA CHASE DR, MARRIOTTSVILLE, MD..., Marriottsville, MD 21104

$699,000

3 beds

4 baths

3,604 sq ft

2507 SOPHIA CHASE DR, MARRIOTTSVILLE, MD...

Community: The Courtyards at Waverly Woods

The Villages At Woodholme

8525 MEADOWSWEET RD # 8525, BALTIMORE, M..., Baltimore, MD 21208

$459,000

3 beds

4 baths

3,800 sq ft

Condo

8525 MEADOWSWEET RD # 8525, BALTIMORE, M...

Community: The Villages At Woodholme

The Courtyards at Waverly Woods

2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M..., Marriottsville, MD 21104

$410,000

2 beds

2 baths

1,438 sq ft

Condo

2241 JOHN GRAVEL RD M, MARRIOTTSVILLE, M...

Community: The Courtyards at Waverly Woods

Leisure World® of Maryland

15301 PINE ORCHARD DR 86-3E, SILVER SPRI..., Silver Spring, MD 20906

$289,999

3 beds

2 baths

1,340 sq ft

Condo

15301 PINE ORCHARD DR 86-3E, SILVER SPRI...

Community: Leisure World® of Maryland

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

Questions? Call us: (240) 663-8229

Leisure World® of Maryland

3365 S LEISURE WORLD BLVD 95-1C, SILVER ..., Silver Spring, MD 20906

$120,000

1 beds

1 baths

990 sq ft

Condo

3365 S LEISURE WORLD BLVD 95-1C, SILVER ...

Community: Leisure World® of Maryland

Leisure World® of Maryland

15030 WESTHOLM CT # 268-C, SILVER SPRING..., Silver Spring, MD 20906

$299,000

3 beds

2 baths

1,194 sq ft

Condo

15030 WESTHOLM CT # 268-C, SILVER SPRING...

Community: Leisure World® of Maryland

Carroll Vista

127 PONYTAIL LN # 133, TANEYTOWN, MD, 21..., Taneytown, MD 21787

$337,900

2 beds

2 baths

1,419 sq ft

Condo

127 PONYTAIL LN # 133, TANEYTOWN, MD, 21...

Community: Carroll Vista

Cedar Ridge at Piney Orchard

8615 FLUTTERING LEAF TRL 404, ODENTON, M..., Odenton, MD 21113

$389,000

2 beds

2 baths

1,500 sq ft

Condo

8615 FLUTTERING LEAF TRL 404, ODENTON, M...

Community: Cedar Ridge at Piney Orchard

Carroll's Creek

1412 WIGEON WAY UNIT 307, GAMBRILLS, MD,..., Gambrills, MD 21054

$395,000

2 beds

2 baths

1,695 sq ft

Condo

1412 WIGEON WAY UNIT 307, GAMBRILLS, MD,...

Community: Carroll's Creek

Leisure World® of Maryland

2900 N LEISURE WORLD BLVD APT 209, SILVE..., Silver Spring, MD 20906

$265,000

2 beds

2 baths

1,261 sq ft

Condo

2900 N LEISURE WORLD BLVD APT 209, SILVE...

Community: Leisure World® of Maryland

Leisure World® of Maryland

15000 PENNFIELD CIR 311, SILVER SPRING, ..., Silver Spring, MD 20906

$275,000

2 beds

2 baths

1,123 sq ft

Condo

15000 PENNFIELD CIR 311, SILVER SPRING, ...

Community: Leisure World® of Maryland

Emerald Pointe

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742

$429,000

2 beds

3 baths

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...

Community: Emerald Pointe

Leisure World® of Maryland

15101 GLADE DR 10-3D, SILVER SPRING, MD,..., Silver Spring, MD 20906

$225,000

2 beds

2 baths

1,273 sq ft

Condo

15101 GLADE DR 10-3D, SILVER SPRING, MD,...

Community: Leisure World® of Maryland

Two Rivers

1326 STONEFLY LN, ODENTON, MD, 21113, Odenton, MD 21113

$799,900

3 beds

3 baths

3,052 sq ft

1326 STONEFLY LN, ODENTON, MD, 21113

Community: Two Rivers

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

Questions? Call us: (240) 663-8229

Gatherings® at Quarry Place

601 QUICKSILVER CT UNIT 408, REISTERSTOW..., Reisterstown, MD 21136

$370,000

2 beds

2 baths

1,390 sq ft

Condo

601 QUICKSILVER CT UNIT 408, REISTERSTOW...

Community: Gatherings® at Quarry Place

Colonial Charles

3141 LADY BANKS LN, WALDORF, MD, 20603, Waldorf, MD 20603

$450,000

3 beds

3 baths

2,400 sq ft

3141 LADY BANKS LN, WALDORF, MD, 20603

Community: Colonial Charles

Leisure World® of Maryland

3302 DENSMORE CT # 204-B, SILVER SPRING,..., Silver Spring, MD 20906

$459,000

$230,000

2 beds

2 baths

Condo

2001 RUDY SERRA DR UNIT 1D, ELDERSBURG, ...

Community: Winifred Manor

Crestwood Village

5653 SANDY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$445,000

2 beds

2 baths

1,297 sq ft

5653 SANDY CT, FREDERICK, MD, 21703

Community: Crestwood Village

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

Questions? Call us: (240) 663-8229

Winifred Manor

2016 RUDY SERRA DR C, SYKESVILLE, MD, 21..., Sykesville, MD 21784

1 beds

1 baths

1,203 sq ft

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...

Community: Gatherings at Cabin Branch

The Village at Cabin Branch

$399,990

1 beds

1 baths

1,203 sq ft

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...

Community: The Village at Cabin Branch

Leisure World® of Maryland

15115 INTERLACHEN DR 3-209, SILVER SPRIN..., Silver Spring, MD 20906

$330,000

3 beds

3 baths

1,615 sq ft

Condo

15115 INTERLACHEN DR 3-209, SILVER SPRIN...

Community: Leisure World® of Maryland

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

Questions? Call us: (240) 663-8229

Leisure World® of Maryland

15101 INTERLACHEN DR 1-807, SILVER SPRIN..., Silver Spring, MD 20906

$226,000

2 beds

2 baths

990 sq ft

Condo

15101 INTERLACHEN DR 1-807, SILVER SPRIN...

Community: Leisure World® of Maryland

Albert Courts

9 EASY ST, THURMONT, MD, 21788, Thurmont, MD 21788

$349,900

3 beds

3 baths

1,740 sq ft

9 EASY ST, THURMONT, MD, 21788

Community: Albert Courts

Gatherings at Lyndwood

6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210..., Elkridge, MD 21075

$425,000

2 beds

2 baths

1,500 sq ft

Condo

6155 SHADYWOOD RD 204, ELKRIDGE, MD, 210...

Community: Gatherings at Lyndwood

Leisure World® of Maryland

15100 INTERLACHEN DR 4-717, SILVER SPRIN..., Silver Spring, MD 20906

$265,000

2 beds

2 baths

1,317 sq ft

Condo

15100 INTERLACHEN DR 4-717, SILVER SPRIN...

Community: Leisure World® of Maryland

Central Parke at Victoria Falls

13851 BELLE CHASSE BLVD UNIT 213, LAUREL..., Laurel, MD 20707

$410,000

2 beds

2 baths

1,703 sq ft

Condo

13851 BELLE CHASSE BLVD UNIT 213, LAUREL...

Community: Central Parke at Victoria Falls

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Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there is 1 small community with less than 500 homes.

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

The smallest 55+ community in Middletown has 81 homes, the largest has 81 homes, and the average community consists of 81 homes.

Are there gated 55+ communities in Middletown?

No, there are no gated 55+ communities in Middletown.

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

On average, listings in 55+ community in Middletown stay on the market for around 58 days. The average price of homes for sale in this community is approximately $550,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in The Village at Foxfield average around $550,000.

Want more information about active adult communities around Middletown?

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Want to learn more about 55+ communities in Middletown?

Call us: (240) 663-8229

489 homes near Middletown

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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.
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REIN updates its listings on a daily basis. Data last updated: Oct 24, 2025.
This application does not include information on all of the properties available for sale at this time.

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Middletown, MD 55+ active adult communities & homes for sale

131 communities near Middletown

489 homes near Middletown

2 beds

1 baths

1,035 sq ft

Condo

3 beds

4 baths

3,604 sq ft

3 beds

4 baths

3,800 sq ft

Condo

2 beds

2 baths

1,438 sq ft

Condo

3 beds

2 baths

1,340 sq ft

Condo

1 beds

1 baths

990 sq ft

Condo

3 beds

2 baths

1,194 sq ft

Condo

2 beds

2 baths

1,419 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

1,695 sq ft

Condo

2 beds

2 baths

1,261 sq ft

Condo

2 beds

2 baths

1,123 sq ft

Condo

2 beds

3 baths

2,739 sq ft

2 beds

2 baths

1,273 sq ft

Condo

3 beds

3 baths

3,052 sq ft

2 beds

2 baths

1,390 sq ft

Condo

3 beds

3 baths

2,400 sq ft

3 beds

2 baths

1,193 sq ft

Condo

3 beds

4 baths

2,660 sq ft

3 beds

2 baths

1,320 sq ft

2 beds

2 baths

1,500 sq ft