Middletown, MD 55+ active adult communities & homes for sale - Page 11

593 homes near Middletown

Sort by:

Relevance

3 rating (2 reviews)

Leisure World® of Marylan...

<$100k - $800ks

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 - $700ks

Amblebrook, Gettysburg, PA

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

5 rating (2 reviews)

Trilogy® at Lake Frederic...

$300ks - $1Ms

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

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

Parklands

$300ks - $500ks

Parklands, White Plains, MD

New Construction | 55+ age-restricted | Built 2025 - present | 586 homes

The Flats at Heathcote Vi...

$300ks - $500ks

The Flats at Heathcote Vi..., Haymarket, VA

New Construction | 55+ age-restricted | Built 2026 - present | 500 homes

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

Questions? Call us: (240) 663-8229

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$200ks - $500ks

Lansdowne Woods of Virgin..., Lansdowne, VA

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

The Flats at Northside

$600ks - $1Ms

The Flats at Northside, Potomac, MD

New Construction | Age-targeted | Built 2025 - present | 143 homes

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

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

Cameron Grove

$200ks - $400ks

Cameron Grove, Upper Marlboro, MD

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

Traditions of America at ...

$400ks - $600ks

Traditions of America at ..., Mechanicsburg, PA

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

Penn National

$100ks - $600ks

Penn National, Fayetteville, PA

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

The Village at Cabin Bran...

$500ks

The Village at Cabin Bran..., Clarksburg, MD

New Construction | 55+ age-restricted | Built 2021 - present

Gatherings at Cabin Branc...

$400ks - $600ks

Gatherings at Cabin Branc..., Clarksburg, MD

New Construction | 55+ age-restricted | Built 2024 - present | 135 homes

Four Seasons at Virginia ...

$400ks - $500ks

Four Seasons at Virginia ..., Woodbridge, VA

New Construction | 55+ age-restricted | Built 2021 - present | 185 homes

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

Questions? Call us: (240) 663-8229

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

New Construction | 55+ age-restricted | Built 2026 - present

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes

Spring Valley Estates

$300ks - $400ks

Spring Valley Estates, Waynesboro, PA

New Construction | 55+ age-restricted | Built 2019 - present | 140 homes

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

New Construction | 55+ age-restricted | Built 2022 - present | 177 homes

Carroll's Creek

$300ks

Carroll's Creek, Gambrills, MD

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 162 homes

The Gatherings at Lakevie...

$300ks - $400ks

The Gatherings at Lakevie..., Reisterstown, MD

New Construction | 55+ age-restricted | Built 2025 - present | 122 homes

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Beechfield Manors

$200ks - $400ks

Beechfield Manors, Bowie, MD

New Construction | 55+ age-restricted | Built 2024 - present

The Crest of Alexandria

$400ks - $800ks

The Crest of Alexandria, Alexandria, VA

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

The Village at Freedom Hi...

$300ks

The Village at Freedom Hi..., Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes

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

Questions? Call us: (240) 663-8229

The Atrium at MetroWest

$600ks - $700ks

The Atrium at MetroWest, Fairfax, VA

New Construction | 55+ age-restricted | Built 2018 - present | 206 homes

5 rating (2 reviews)

Central Parke at Victoria...

$300ks - $500ks

Central Parke at Victoria..., Laurel, MD

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

Sagebrook

$300ks - $400ks

Sagebrook, Dover, PA

New and Resale | 55+ age-restricted | Built 2020 - present | 194 homes

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes

Walden Woods

$500ks - $600ks

Walden Woods, Laurel, MD

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 97 homes

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes

5 rating (1 reviews)

Two Rivers

$500ks - $700ks

Two Rivers, Odenton, MD

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

5 rating (1 reviews)

Gatherings at Lyndwood

$300ks - $400ks

Gatherings at Lyndwood, Elkridge, MD

Resale Only | 55+ age-restricted | Built 2005 - 2008 | 216 homes

5 rating (1 reviews)

Snowden Overlook

$300ks - $600ks

Snowden Overlook, Columbia, MD

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

Watershed

$600ks - $700ks

Watershed, Laurel, MD

New Construction | 55+ age-restricted | 84 homes

Signature Club at Greenvi...

$400ks - $500ks

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

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

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

Questions? Call us: (240) 663-8229

Heritage at St. Charles

$300ks - $500ks

Heritage at St. Charles, White Plains, MD

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

The Villages At Woodholme

$400ks - $500ks

The Villages At Woodholme, Baltimore, MD

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

1 2 3...4

The Highlands at Blue Ridge Shadows

18 ALBATROSS CT, FRONT ROYAL, VA, 22630, Front Royal, VA 22630

$689,900

4 beds

4 baths

3,861 sq ft

18 ALBATROSS CT, FRONT ROYAL, VA, 22630

Community: The Highlands at Blue Ridge Shadows

Cameron Grove

13301 NEW ACADIA LN 109, UPPER MARLBORO,..., Upper Marlboro, MD 20774

$345,000

2 beds

2 baths

1,430 sq ft

Condo

13301 NEW ACADIA LN 109, UPPER MARLBORO,...

Community: Cameron Grove

Gatherings at Lyndwood

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

$400,000

2 beds

2 baths

1,500 sq ft

Condo

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

Community: Gatherings at Lyndwood

Leisure World® of Maryland

15300 PINE ORCHARD DR 85-2H, SILVER SPRI..., Silver Spring, MD 20906

$245,000

2 beds

2 baths

1,043 sq ft

Condo

15300 PINE ORCHARD DR 85-2H, SILVER SPRI...

Community: Leisure World® of Maryland

Carmella

$549,000

3 beds

4 baths

3,848 sq ft

Condo

427 CARMELLA DR, MECHANICSBURG, PA, 1705...

Community: Carmella

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

Questions? Call us: (240) 663-8229

Penn National

$379,900

3 beds

2 baths

1,676 sq ft

6342 PENN NATIONAL DR, FAYETTEVILLE, PA,...

Community: Penn National

Traditions of America at Silver Spring

228 LOYAL DR, MECHANICSBURG, PA, 17050, Mechanicsburg, PA 17050

$549,900

3 beds

3 baths

3,230 sq ft

Condo

228 LOYAL DR, MECHANICSBURG, PA, 17050

Community: Traditions of America at Silver Spring

Leisure World® of Maryland

3136 ADDERLEY CT 243-G, SILVER SPRING, M..., Silver Spring, MD 20906

$215,000

2 beds

3 baths

1,359 sq ft

Condo

3136 ADDERLEY CT 243-G, SILVER SPRING, M...

Community: Leisure World® of Maryland

The Village at Freedom Hills

13862 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$494,900

4 beds

2 baths

3,107 sq ft

13862 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

The Woodlands of Urbana

3422 ANGELICA WAY 103, FREDERICK, MD, 21..., Frederick, MD 21704

$430,000

2 beds

2 baths

1,489 sq ft

Condo

3422 ANGELICA WAY 103, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Amblebrook

85 QUIET CREEK DR, GETTYSBURG, PA, 17325, Gettysburg, PA 17325

$500,000

2 beds

2 baths

2,220 sq ft

85 QUIET CREEK DR, GETTYSBURG, PA, 17325

Community: Amblebrook

Penn National

6357 NINTH VW, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222

$299,000

3 beds

2 baths

1,958 sq ft

Condo

6357 NINTH VW, FAYETTEVILLE, PA, 17222

Community: Penn National

Central Parke at Victoria Falls

13401 BELLE CHASSE BLVD 312, LAUREL, MD,..., Laurel, MD 20707

$399,000

2 beds

2 baths

1,673 sq ft

Condo

13401 BELLE CHASSE BLVD 312, LAUREL, MD,...

Community: Central Parke at Victoria Falls

Crawfords Ridge

$849,900

5 beds

5 baths

4,162 sq ft

614 CRAWFORDS RIDGE RD, ODENTON, MD, 211...

Community: Crawfords Ridge

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 510, LEESBURG, V..., Leesburg, VA 20176

$435,000

2 beds

2 baths

1,251 sq ft

Condo

19365 CYPRESS RIDGE TER 510, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Amblebrook

192 HIGHLAND WAY 32, GETTYSBURG, PA, 173..., Gettysburg, PA 17325

$539,990

2 beds

3 baths

2,036 sq ft

192 HIGHLAND WAY 32, GETTYSBURG, PA, 173...

Community: Amblebrook

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

Questions? Call us: (240) 663-8229

Cedar Ridge at Piney Orchard

8604 WANDERING FOX TRL 301, ODENTON, MD,..., Odenton, MD 21113

$364,900

2 beds

2 baths

1,500 sq ft

Condo

8604 WANDERING FOX TRL 301, ODENTON, MD,...

Community: Cedar Ridge at Piney Orchard

Leisure World® of Maryland

15115 INTERLACHEN DR 3-1020, SILVER SPRI..., Silver Spring, MD 20906

$220,000

2 beds

2 baths

980 sq ft

Condo

15115 INTERLACHEN DR 3-1020, SILVER SPRI...

Community: Leisure World® of Maryland

Traditions of America at Silver Spring

126 CONGRESS DR, MECHANICSBURG, PA, 1705..., Mechanicsburg, PA 17050

$414,900

2 beds

2 baths

1,894 sq ft

Condo

126 CONGRESS DR, MECHANICSBURG, PA, 1705...

Community: Traditions of America at Silver Spring

Leisure World® of Maryland

3400 GLENEAGLES DR 73-3H, SILVER SPRING,..., Silver Spring, MD 20906

$95,000

1 beds

1 baths

800 sq ft

Condo

3400 GLENEAGLES DR 73-3H, SILVER SPRING,...

Community: Leisure World® of Maryland

Leisure World® of Maryland

3387 S LEISURE WORLD BLVD 91-G, SILVER S..., Silver Spring, MD 20906

$190,000

2 beds

3 baths

1,600 sq ft

Condo

3387 S LEISURE WORLD BLVD 91-G, SILVER S...

Community: Leisure World® of Maryland

Traditions of America at Silver Spring

406 GENERAL DR, MECHANICSBURG, PA, 17050, Mechanicsburg, PA 17050

$434,900

2 beds

2 baths

1,584 sq ft

Condo

406 GENERAL DR, MECHANICSBURG, PA, 17050

Community: Traditions of America at Silver Spring

Leisure World® of Maryland

15101 INTERLACHEN DR 1-806, SILVER SPRIN..., Silver Spring, MD 20906

$180,900

2 beds

2 baths

990 sq ft

Condo

15101 INTERLACHEN DR 1-806, SILVER SPRIN...

Community: Leisure World® of Maryland

The Woodlands of Urbana

3520 STARLIGHT ST 302, FREDERICK, MD, 21..., Frederick, MD 21704

$419,900

2 beds

2 baths

1,489 sq ft

Condo

3520 STARLIGHT ST 302, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Trilogy® at Lake Frederick

107 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630

$659,990

4 beds

4 baths

3,190 sq ft

107 CABBAGE WHITE DR, LAKE FREDERICK, VA...

Community: Trilogy® at Lake Frederick

Cameron Grove

14040 NEW ACADIA LN 105, UPPER MARLBORO,..., Upper Marlboro, MD 20774

$275,000

1 beds

1 baths

1,013 sq ft

Condo

14040 NEW ACADIA LN 105, UPPER MARLBORO,...

Community: Cameron Grove

Parklands

10327 YOSEMITE ST, WHITE PLAINS, MD, 206..., White Plains, MD 20695

$455,490

3 beds

2 baths

1,860 sq ft

10327 YOSEMITE ST, WHITE PLAINS, MD, 206...

Community: Parklands

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

Questions? Call us: (240) 663-8229

The Gatherings at Lakeview Community

578 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136

$374,990

3 beds

3 baths

1,569 sq ft

Condo

578 QUARRY PLACE CT, REISTERSTOWN, MD, 2...

Community: The Gatherings at Lakeview Community

Trilogy® at Lake Frederick

106 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$769,990

2 beds

2 baths

2,058 sq ft

106 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Blue Ridge

2229 CAROLINE LN, HARRISBURG, PA, 17110, Harrisburg, PA 17110

$389,000

3 beds

3 baths

2,038 sq ft

2229 CAROLINE LN, HARRISBURG, PA, 17110

Community: Blue Ridge

The Village at Freedom Hills

13880 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$382,000

2 beds

2 baths

1,543 sq ft

13880 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

Carroll's Creek

1406 WIGEON WAY 303, GAMBRILLS, MD, 2105..., Gambrills, MD 21054

$375,000

2 beds

2 baths

1,334 sq ft

Condo

1406 WIGEON WAY 303, GAMBRILLS, MD, 2105...

Community: Carroll's Creek

Willow Lawn Cottages

1851 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$389,900

2 beds

2 baths

1,405 sq ft

1851 MELVOR LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 1115, LEESBURG, ..., Leesburg, VA 20176

$515,000

3 beds

2 baths

1,475 sq ft

Condo

19365 CYPRESS RIDGE TER 1115, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Leisure World® of Maryland

15101 INTERLACHEN DR 1-112, SILVER SPRIN..., Silver Spring, MD 20906

$219,900

2 beds

2 baths

1,210 sq ft

Condo

15101 INTERLACHEN DR 1-112, SILVER SPRIN...

Community: Leisure World® of Maryland

Bloomfields 55+

2605 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$799,990

3 beds

4 baths

3,462 sq ft

2605 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Leisure World® of Maryland

15107 INTERLACHEN DR 2-1022, SILVER SPRI..., Silver Spring, MD 20906

$170,000

2 beds

2 baths

1,120 sq ft

Condo

15107 INTERLACHEN DR 2-1022, SILVER SPRI...

Community: Leisure World® of Maryland

Crestwood Village

5798 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$469,500

2 beds

2 baths

2,044 sq ft

5798 BOX ELDER 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

The Village at Harvest Ridge

153 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601

$639,900

4 beds

3 baths

3,157 sq ft

153 HARVEST RIDGE DR, WINCHESTER, VA, 22...

Community: The Village at Harvest Ridge

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 802, LEESBURG, V..., Leesburg, VA 20176

$490,000

3 beds

2 baths

1,560 sq ft

Condo

19355 CYPRESS RIDGE TER 802, LEESBURG, V...

Community: Lansdowne Woods of Virginia

1 2 3 4 5 6 7 8 9 10 11 12 13 14…15

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

593 homes

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 11

141 communities near Middletown

593 homes near Middletown

4 beds

4 baths

3,861 sq ft

2 beds

2 baths

1,430 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

1,043 sq ft

Condo

3 beds

4 baths

3,848 sq ft

Condo

3 beds

2 baths

1,676 sq ft

3 beds

3 baths

3,230 sq ft

Condo

2 beds

3 baths

1,359 sq ft

Condo

4 beds

2 baths

3,107 sq ft

2 beds

2 baths

1,489 sq ft

Condo

2 beds

2 baths

2,220 sq ft

3 beds

2 baths

1,958 sq ft

Condo

2 beds

2 baths

1,673 sq ft

Condo

5 beds

5 baths

4,162 sq ft

2 beds

2 baths

1,251 sq ft

Condo

2 beds

3 baths

2,036 sq ft

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

980 sq ft

Condo

2 beds

2 baths

1,894 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

3 baths

1,600 sq ft