Middletown, MD 55+ active adult communities & homes for sale - Page 4

141 communities near Middletown

Sort by:

Relevance

Belmont Bay

$300ks - $600ks

Belmont Bay, Woodbridge, VA

New and Resale | Age-targeted | Built 2007 - present | 155 homes

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

1 rating (1 reviews)

Legacy at Cherry Tree

$400ks - $500ks

Legacy at Cherry Tree, Laurel, MD

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 120 homes

Colonial Charles

$500ks

Colonial Charles, Waldorf, MD

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

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

Questions? Call us: (240) 663-8229

North Pointe Condominiums

$200ks - $300ks

North Pointe Condominiums, Hanover, PA

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 120 homes

Gatherings® at Quarry Pla...

$400ks - $500ks

Gatherings® at Quarry Pla..., Reisterstown, MD

Resale Only | 55+ age-restricted | Built 2014 - 2017 | 135 homes

5 rating (1 reviews)

Villas at Cattail Creek

$500ks - $1Ms

Villas at Cattail Creek, Glenwood, MD

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 93 homes

Enclave at Park Forest

$500ks - $600ks

Enclave at Park Forest, Elkridge, MD

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 45 homes

Hickory Crest

$400ks - $500ks

Hickory Crest, Columbia, MD

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 88 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.

Amesbury

$200ks - $300ks

Amesbury, Harrisburg, PA

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 106 homes

Courts of Clarksburg

$500ks - $700ks

Courts of Clarksburg, Clarksburg, MD

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 140 homes

Scot's Glen

$700ks - $800ks

Scot's Glen, Columbia, MD

Resale Only | 55+ age-restricted | Built 2006 - 2012 | 73 homes

3.5 rating (4 reviews)

Bent Creek Crossing

$300ks

Bent Creek Crossing, Mechanicsburg, PA

Resale Only | 55+ age-restricted | Built 1998 - 2004 | 110 homes

The Enclave at Ellicott S...

$400ks - $500ks

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

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 69 homes

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes

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

Questions? Call us: (240) 663-8229

Longstown Village

$100ks - $200ks

Longstown Village, York, PA

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

Washington Square

$200ks - $300ks

Washington Square, La Plata, MD

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 78 homes

5 rating (1 reviews)

Four Seasons at Vint Hill

$600ks

Four Seasons at Vint Hill, Warrenton, VA

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes

Roth's Farm Village

$200ks

Roth's Farm Village, Spring Grove, PA

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

Gatherings at Jefferson P...

$300ks - $400ks

Gatherings at Jefferson P..., Ellicott City, MD

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 74 homes

1 2 3 4

New Suffield Meadows

6708 STREAM VIEW LN, WARRENTON, VA, 2018..., Warrenton, VA 20187

$619,900

3 beds

3 baths

3,701 sq ft

Condo

6708 STREAM VIEW LN, WARRENTON, VA, 2018...

Community: Suffield Meadows

New Regency at Dominion Valley

15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$929,900

3 beds

3 baths

3,810 sq ft

15508 HAGEN WAY, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

New Cortland Park

770 AURORA DR, MECHANICSBURG, PA, 17055, Mechanicsburg, PA 17055

$534,900

4 beds

4 baths

2,256 sq ft

770 AURORA DR, MECHANICSBURG, PA, 17055

Community: Cortland Park

New The Courtyards at Waverly Woods

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

$400,000

2 beds

2 baths

1,438 sq ft

Condo

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

Community: The Courtyards at Waverly Woods

New Heritage Hunt

13749 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$730,000

3 beds

3 baths

2,626 sq ft

13749 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

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

Questions? Call us: (240) 663-8229

New Birchwood at Brambleton

23640 BOLTON CRESCENT TER 403, ASHBURN, ..., Ashburn, VA 20148

$759,900

3 beds

2 baths

1,908 sq ft

Condo

23640 BOLTON CRESCENT TER 403, ASHBURN, ...

Community: Birchwood at Brambleton

New Heritage at St. Charles

11271 YELLOWSTONE CT, WHITE PLAINS, MD, ..., White Plains, MD 20695

3 beds

2 baths

1,430 sq ft

43 CHOKEBERRY WAY, GETTYSBURG, PA, 17325

Community: Amblebrook

New The Courtyards at Waverly Woods

2415 ANDERSON HILL ST, MARRIOTTSVILLE, M..., Marriottsville, MD 21104

$900,000

3 beds

3 baths

5,380 sq ft

Condo

2415 ANDERSON HILL ST, MARRIOTTSVILLE, M...

Community: The Courtyards at Waverly Woods

New Traditions of America at Silver Spring

254 COLONIAL DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050

$499,500

2 beds

3 baths

2,529 sq ft

Condo

254 COLONIAL DR, MECHANICSBURG, PA, 1705...

Community: Traditions of America at Silver Spring

New Snowden Overlook

8633 VAST ROSE DR 14, COLUMBIA, MD, 2104..., Columbia, MD 21045

$679,000

2 beds

4 baths

3,542 sq ft

Condo

8633 VAST ROSE DR 14, COLUMBIA, MD, 2104...

Community: Snowden Overlook

New Potomac Green

44480 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147

$885,000

3 beds

3 baths

2,817 sq ft

44480 BLUERIDGE MEADOWS DR, ASHBURN, VA,...

Community: Potomac Green

New Potomac Green

44397 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$760,000

3 beds

3 baths

2,118 sq ft

44397 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

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

Questions? Call us: (240) 663-8229

New Courtyards at Waverly Woods East

11185 CHAMBERS CT G, WOODSTOCK, MD, 2116..., Woodstock, MD 21163

$385,500

2 beds

2 baths

1,358 sq ft

Condo

11185 CHAMBERS CT G, WOODSTOCK, MD, 2116...

Community: Courtyards at Waverly Woods East

New Ellicott's Retreat

8505 SUNELL LN, ELLICOTT CITY, MD, 21043, Ellicott City, MD 21043

$1,175,000

5 beds

5 baths

4,201 sq ft

8505 SUNELL LN, ELLICOTT CITY, MD, 21043

Community: Ellicott's Retreat

New Boxwood Villas

3816 FULHAM RD, FREDERICK, MD, 21704, Frederick, MD 21704

$759,900

3 beds

4 baths

3,383 sq ft

3816 FULHAM RD, FREDERICK, MD, 21704

Community: Boxwood Villas

New River Ridge

12357 ROMNEY MEWS, WOODBRIDGE, VA, 22192, Woodbridge, VA 22192

$719,900

3 beds

3 baths

3,760 sq ft

12357 ROMNEY MEWS, WOODBRIDGE, VA, 22192

Community: River Ridge

New Maple Highlands

8511 LALLYBROCH LN, FULTON, MD, 20759, Fulton, MD 20759

$1,150,000

4 beds

4 baths

4,098 sq ft

Condo

8511 LALLYBROCH LN, FULTON, MD, 20759

Community: Maple Highlands

New Cameron Grove

13220 FOX BOW DR 104, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774

$299,999

1 beds

1 baths

1,015 sq ft

Condo

13220 FOX BOW DR 104, UPPER MARLBORO, MD...

Community: Cameron Grove

New Village Crest

8220 ACADEMY RD 22, ELLICOTT CITY, MD, 2..., Ellicott City, MD 21043

$649,900

4 beds

4 baths

3,329 sq ft

Condo

8220 ACADEMY RD 22, ELLICOTT CITY, MD, 2...

Community: Village Crest

New Roth's Farm Village

1332 PLEASANT VIEW DR 75, SPRING GROVE, ..., Spring Grove, PA 17362

$245,000

2 beds

2 baths

1,104 sq ft

1332 PLEASANT VIEW DR 75, SPRING GROVE, ...

Community: Roth's Farm Village

New Regency at Belmont

43927 HURLEYS HUNT TER, ASHBURN, VA, 201..., Ashburn, VA 20147

$1,099,000

3 beds

4 baths

3,255 sq ft

43927 HURLEYS HUNT TER, ASHBURN, VA, 201...

Community: Regency at Belmont

New Scot's Glen

10737 MCGREGOR DR, COLUMBIA, MD, 21044, Columbia, MD 21044

$895,000

4 beds

5 baths

5,200 sq ft

Condo

10737 MCGREGOR DR, COLUMBIA, MD, 21044

Community: Scot's Glen

New Leisure World® of Maryland

3200 N LEISURE WORLD BLVD 712, SILVER SP..., Silver Spring, MD 20906

$310,000

2 beds

2 baths

1,260 sq ft

Condo

3200 N LEISURE WORLD BLVD 712, SILVER SP...

Community: Leisure World® of Maryland

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

Questions? Call us: (240) 663-8229

New Leisure World® of Maryland

14805 PENNFIELD CIR 309, SILVER SPRING, ..., Silver Spring, MD 20906

$375,000

$599,999

2 beds

2 baths

1,419 sq ft

Condo

21914 HAWKSBILL HIGH CIR 204, STERLING, ...

Community: Montebello

New Montebello

21630 HAWKSBILL HIGH CIR 202, STERLING, ..., Sterling, VA 20164

$735,999

3 beds

2 baths

1,940 sq ft

Condo

21630 HAWKSBILL HIGH CIR 202, STERLING, ...

Community: Montebello

New Heritage Hunt

13191 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$785

4 beds

5 baths

4,664 sq ft

13191 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

New Two Rivers

3068 SPRING PEEPER CT, ODENTON, MD, 2111..., Odenton, MD 21113

$545,000

2 beds

2 baths

1,614 sq ft

3068 SPRING PEEPER CT, ODENTON, MD, 2111...

Community: Two Rivers

New The Preserves at Cumberland Village

120 WOODHAVEN DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325

$475,000

2 beds

2 baths

1,718 sq ft

120 WOODHAVEN DR, GETTYSBURG, PA, 17325

Community: The Preserves at Cumberland Village

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

Questions? Call us: (240) 663-8229

New Trilogy® at Lake Frederick

134 ATLANTIS LN, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$635,000

3 beds

3 baths

2,173 sq ft

134 ATLANTIS LN, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

New Two Rivers

2859 DRAGON FLY WAY, ODENTON, MD, 21113, Odenton, MD 21113

$805,000

4 beds

4 baths

3,870 sq ft

2859 DRAGON FLY WAY, ODENTON, MD, 21113

Community: Two Rivers

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 138 days. The average price of homes for sale in this community is approximately $604,937, 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 $604,937.

Want more information about active adult communities around Middletown?

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 Middletown?

Call us: (240) 663-8229

141 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: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Middletown, MD 55+ active adult communities & homes for sale - Page 4

141 communities near Middletown

593 homes near Middletown

3 beds

3 baths

3,701 sq ft

Condo

3 beds

3 baths

3,810 sq ft

4 beds

4 baths

2,256 sq ft

2 beds

2 baths

1,438 sq ft

Condo

3 beds

3 baths

2,626 sq ft

3 beds

2 baths

1,908 sq ft

Condo

3 beds

2 baths

2,066 sq ft

2 beds

2 baths

1,366 sq ft

Condo

3 beds

2 baths

1,415 sq ft

Condo

2 beds

2 baths

2,370 sq ft

Condo

3 beds

2 baths

1,430 sq ft

3 beds

3 baths

5,380 sq ft

Condo

2 beds

3 baths

2,529 sq ft

Condo

2 beds

4 baths

3,542 sq ft

Condo

3 beds

3 baths

2,817 sq ft

3 beds

3 baths

2,118 sq ft

2 beds

2 baths

1,358 sq ft

Condo

5 beds

5 baths

4,201 sq ft

3 beds

4 baths

3,383 sq ft

3 beds

3 baths

3,760 sq ft

4 beds

4 baths

4,098 sq ft

Condo

1 beds

1 baths

1,015 sq ft