Middletown, MD 55+ active adult communities & homes for sale - Page 8

572 homes near Middletown

Sort by:

Relevance

5 rating (1 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...

- $900ks

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

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

Parklands

$300ks - $500ks

Parklands, White Plains, MD

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

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

Questions? Call us: (240) 663-8229

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

Cameron Grove

$200ks - $400ks

Cameron Grove, Upper Marlboro, MD

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

The Flats at Northside

$600ks - $1Ms

The Flats at Northside, Potomac, MD

New Construction | Age-targeted | Built 2025 - present | 143 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 (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

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

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

Beechfield Manors

$200ks - $400ks

Beechfield Manors, Bowie, MD

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

Penn National

$100ks - $600ks

Penn National, Fayetteville, PA

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

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

Questions? Call us: (240) 663-8229

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

The Village at Cabin Bran...

$500ks

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

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

The Atrium at MetroWest

$600ks - $700ks

The Atrium at MetroWest, Fairfax, VA

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

Gatherings at Cabin Branc...

$400ks - $600ks

Gatherings at Cabin Branc..., Clarksburg, MD

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

The Gatherings at Lakevie...

$300ks - $400ks

The Gatherings at Lakevie..., Reisterstown, MD

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

5 rating (1 reviews)

Four Seasons at Historic ...

$400ks - $600ks

Four Seasons at Historic ..., Dumfries, VA

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

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

Questions? Call us: (240) 663-8229

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Carroll Vista

$200ks - $300ks

Carroll Vista, Taneytown, MD

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

5 rating (1 reviews)

Two Rivers

$500ks - $700ks

Two Rivers, Odenton, MD

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

Cedar Ridge at Piney Orch...

$200ks - $300ks

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

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

Winifred Manor

$200ks

Winifred Manor, Eldersburg, MD

Resale Only | 55+ age-restricted | Built 1998 - 2002 | 152 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

Blue Ridge

$300ks - $400ks

Blue Ridge, Harrisburg, PA

New and Resale | Age-targeted | Built 2020 - present | 130 homes

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

Questions? Call us: (240) 663-8229

Carroll's Creek

$300ks

Carroll's Creek, Gambrills, MD

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Signature Club at Greenvi...

$400ks - $500ks

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

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

Traditions of America at ...

$400ks - $600ks

Traditions of America at ..., Mechanicsburg, PA

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

Four Seasons at Virginia ...

$400ks - $500ks

Four Seasons at Virginia ..., Woodbridge, VA

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

Sagebrook

$300ks - $400ks

Sagebrook, Dover, PA

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

The Crest of Alexandria

$400ks - $800ks

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

The Village at Freedom Hi...

$300ks

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

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

1 2 3...4

Trilogy® at Lake Frederick

124 CHECKERSPOT WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$435,000

4 beds

4 baths

2,508 sq ft

124 CHECKERSPOT WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

The Woodlands of Urbana

3264 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704

$567,000

3 beds

3 baths

1,817 sq ft

3264 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

Cedar Meadows

111 BLUETS DR, WHITE POST, VA, 22663, White Post, VA 22663

$469,900

3 beds

2 baths

1,619 sq ft

111 BLUETS DR, WHITE POST, VA, 22663

Community: Cedar Meadows

Trilogy® at Lake Frederick

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

$629,000

3 beds

3 baths

2,173 sq ft

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

Community: Trilogy® at Lake Frederick

Leisure World® of Maryland

15107 INTERLACHEN DR 2-716, SILVER SPRIN..., Silver Spring, MD 20906

$169,900

1 beds

1 baths

860 sq ft

Condo

15107 INTERLACHEN DR 2-716, 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

15115 INTERLACHEN DR 3-621, SILVER SPRIN..., Silver Spring, MD 20906

$386,000

3 beds

3 baths

1,530 sq ft

Condo

15115 INTERLACHEN DR 3-621, SILVER SPRIN...

Community: Leisure World® of Maryland

Cameron Grove

13310 NEW ACADIA LN 206, UPPER MARLBORO,..., Upper Marlboro, MD 20774

$285,000

2 beds

2 baths

1,287 sq ft

Condo

13310 NEW ACADIA LN 206, UPPER MARLBORO,...

Community: Cameron Grove

Gatherings at Wellington

9204 CHARLESTON DR 206, MANASSAS, VA, 20..., Manassas, VA 20110

$399,900

2 beds

2 baths

1,558 sq ft

Condo

9204 CHARLESTON DR 206, MANASSAS, VA, 20...

Community: Gatherings at Wellington

The Flats at Northside

1121 FORTUNE TER 310, POTOMAC, MD, 20854, Potomac, MD 20854

$918,209

2 beds

2 baths

1,534 sq ft

Condo

1121 FORTUNE TER 310, POTOMAC, MD, 20854

Community: The Flats at Northside

Birchwood at Brambleton

23603 GOLDEN EMBERS SQ, ASHBURN, VA, 201..., Ashburn, VA 20148

$919,900

4 beds

4 baths

4,071 sq ft

23603 GOLDEN EMBERS SQ, ASHBURN, VA, 201...

Community: Birchwood at Brambleton

Emerald Pointe

13428 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$434,000

2 beds

2 baths

1,953 sq ft

13428 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Lexington Square

44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$784,936

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

Lexington 7

$784,936

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington 7

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

Questions? Call us: (240) 663-8229

Potomac Green

20726 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

3 beds

3 baths

2,223 sq ft

61 BONESET DR, GETTYSBURG, PA, 17325

Community: Amblebrook

Amblebrook

371 QUIET CREEK DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325

$739,000

2 beds

2 baths

2,390 sq ft

371 QUIET CREEK DR, GETTYSBURG, PA, 1732...

Community: Amblebrook

Leisure World® of Maryland

3182 ADDERLEY CT 240-E, SILVER SPRING, M..., Silver Spring, MD 20906

$229,900

2 beds

3 baths

1,359 sq ft

Condo

3182 ADDERLEY CT 240-E, SILVER SPRING, M...

Community: Leisure World® of Maryland

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

Questions? Call us: (240) 663-8229

Signature Club at Greenview

5811 UPTON CIR 49, NEW MARKET, MD, 21774, New Market, MD 21774

$685,000

4 beds

4 baths

3,501 sq ft

5811 UPTON CIR 49, NEW MARKET, MD, 21774

Community: Signature Club at Greenview

Trilogy® at Lake Frederick

105 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$849,900

4 beds

4 baths

5,247 sq ft

105 TURNSTONE LN, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Willow Run

124 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$449,990

3 beds

2 baths

1,492 sq ft

124 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Winifred Manor

2010 RUDY SERRA DR D, SYKESVILLE, MD, 21..., Sykesville, MD 21784

2 beds

3 baths

1,359 sq ft

Condo

15002 EARDLEY CT 282-B, SILVER SPRING, M...

Community: Leisure World® of Maryland

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

Questions? Call us: (240) 663-8229

Bethany Glen

9676 WISHING WELL LN, ELLICOTT CITY, MD,..., Ellicott City, MD 21042

$824,985

3 beds

3 baths

9676 WISHING WELL LN, ELLICOTT CITY, MD,...

Community: Bethany Glen

Heritage at St. Charles

11265 YELLOWSTONE CT, WHITE PLAINS, MD, ..., White Plains, MD 20695

$524,900

3 beds

2 baths

2,010 sq ft

11265 YELLOWSTONE CT, WHITE PLAINS, MD, ...

Community: Heritage at St. Charles

Signature Club at Greenview

5915 JACOBEAN PL, NEW MARKET, MD, 21774, New Market, MD 21774

$659,999

4 beds

4 baths

3,454 sq ft

Condo

5915 JACOBEAN PL, NEW MARKET, MD, 21774

Community: Signature Club at Greenview

Robinson Manor

14712 GRAND CRU LOOP, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$699,000

3 beds

3 baths

2,270 sq ft

14712 GRAND CRU LOOP, GAINESVILLE, VA, 2...

Community: Robinson Manor

Abrams Chase

105 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$515,000

2 beds

2 baths

1,800 sq ft

105 AMBERFIELD CT, WINCHESTER, VA, 22602

Community: Abrams Chase

Leisure World® of Maryland

3005 S LEISURE WORLD BLVD APT 702, SILVE..., Silver Spring, MD 20906

$279,900

2 beds

2 baths

1,093 sq ft

Condo

3005 S LEISURE WORLD BLVD APT 702, SILVE...

Community: Leisure World® of Maryland

Two Rivers

2705 DRAGON FLY WAY, ODENTON, MD, 21113, Odenton, MD 21113

$786,000

3 beds

3 baths

3,456 sq ft

2705 DRAGON FLY WAY, ODENTON, MD, 21113

Community: Two Rivers

Dunbarton

9513 MOONEN BAY LN, BRISTOW, VA, 20136, Bristow, VA 20136

$639,999

4 beds

3 baths

2,711 sq ft

9513 MOONEN BAY LN, BRISTOW, VA, 20136

Community: Dunbarton

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

Questions? Call us: (240) 663-8229

Heritage Hunt

6595 ALDERWOOD WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$625,000

3 beds

3 baths

2,311 sq ft

6595 ALDERWOOD WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Central Parke at Victoria Falls

13218 WINDING TRAIL RD, LAUREL, MD, 2070..., Laurel, MD 20707

$460,000

3 beds

3 baths

1,464 sq ft

13218 WINDING TRAIL RD, LAUREL, MD, 2070...

Community: Central Parke at Victoria Falls

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 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?

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

572 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: Apr 10, 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 8

141 communities near Middletown

572 homes near Middletown

4 beds

4 baths

2,508 sq ft

3 beds

3 baths

1,817 sq ft

3 beds

2 baths

1,619 sq ft

3 beds

3 baths

2,173 sq ft

1 beds

1 baths

860 sq ft

Condo

3 beds

3 baths

1,530 sq ft

Condo

2 beds

2 baths

1,287 sq ft

Condo

2 beds

2 baths

1,558 sq ft

Condo

2 beds

2 baths

1,534 sq ft

Condo

4 beds

4 baths

4,071 sq ft

2 beds

2 baths

1,953 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

2,798 sq ft

3 beds

2 baths

1,900 sq ft

Condo

3 beds

2 baths

2,006 sq ft

Condo

2 beds

2 baths

1,520 sq ft

Condo

3 beds

3 baths

1,530 sq ft

Condo

3 beds

3 baths

2,223 sq ft

2 beds

2 baths

2,390 sq ft

2 beds

3 baths

1,359 sq ft

Condo

4 beds

4 baths

3,501 sq ft

4 beds