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

489 homes near Middletown

Sort by:

Relevance

No reviews yet

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

Cadence at Lansdowne

43899 SIREN SONG TER, LEESBURG, VA, 2017..., Leesburg, VA 20176

$785,000

3 beds

4 baths

2,780 sq ft

43899 SIREN SONG TER, LEESBURG, VA, 2017...

Community: Cadence at Lansdowne

Trilogy® at Lake Frederick

118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$650,000

3 beds

3 baths

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Gatherings at Wellington

9204 CHARLESTON DR UNIT 404, MANASSAS, V..., Manassas, VA 20110

$379,000

2 beds

2 baths

1,504 sq ft

Condo

9204 CHARLESTON DR UNIT 404, MANASSAS, V...

Community: Gatherings at Wellington

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER UNIT 418, LEESBU..., Leesburg, VA 20176

$499,900

2 beds

2 baths

1,441 sq ft

Condo

19375 CYPRESS RIDGE TER UNIT 418, LEESBU...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

117 HARVESTER DR, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$899,000

4 beds

5 baths

6,096 sq ft

117 HARVESTER DR, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (240) 663-8229

Belmont Bay

645 ANGELFISH WAY, WOODBRIDGE, VA, 22191, Woodbridge, VA 22191

$836,090

4 beds

4 baths

2,705 sq ft

645 ANGELFISH WAY, WOODBRIDGE, VA, 22191

Community: Belmont Bay

Birchwood at Brambleton

43016 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$880,862

3 beds

4 baths

2,742 sq ft

43016 DEBONAIR TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Gatherings at Wellington

10273 FOUNTAIN CIR 306, MANASSAS, VA, 20..., Manassas, VA 20110

$390,000

2 beds

2 baths

1,558 sq ft

Condo

10273 FOUNTAIN CIR 306, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Birchwood at Brambleton

43257 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$999,900

3 beds

4 baths

4,338 sq ft

43257 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

The Crest of Alexandria

7765 MOUNT CALVARY DR, ALEXANDRIA, VA, 2..., Alexandria, VA 22315

$979,000

3 beds

4 baths

2,848 sq ft

7765 MOUNT CALVARY DR, ALEXANDRIA, VA, 2...

Community: The Crest of Alexandria

Heritage Hunt

13457 VICTORY GALLOP WAY, GAINESVILLE, V..., Gainesville, VA 20155

$605,000

2 beds

2 baths

1,957 sq ft

13457 VICTORY GALLOP WAY, GAINESVILLE, V...

Community: Heritage Hunt

Heritage Hunt

17680 GLASS RIDGE PL, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$675,000

3 beds

3 baths

2,920 sq ft

17680 GLASS RIDGE PL, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 423, LEESBURG, V..., Leesburg, VA 20176

$399,900

2 beds

2 baths

1,315 sq ft

Condo

19355 CYPRESS RIDGE TER 423, LEESBURG, V...

Community: Lansdowne Woods of Virginia

River Ridge

1853 FAVERSHAM WAY, WOODBRIDGE, VA, 2219..., Woodbridge, VA 22192

$655,500

2 beds

2 baths

1,960 sq ft

1853 FAVERSHAM WAY, WOODBRIDGE, VA, 2219...

Community: River Ridge

Regency at Creekside

5966 BOWES CREEK PL, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$1,320,000

4 beds

5 baths

5,614 sq ft

5966 BOWES CREEK PL, GAINESVILLE, VA, 20...

Community: Regency at Creekside

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

Questions? Call us: (240) 663-8229

Birchwood at Brambleton

43011 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$881,202

3 beds

4 baths

2,742 sq ft

43011 DEBONAIR TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Potomac Green

20763 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$879,900

3 beds

3 baths

2,810 sq ft

20763 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

Central Parke at Lowes Island

20745 ROYAL PALACE SQ UNIT 207, STERLING..., Sterling, VA 20165

$429,900

2 beds

2 baths

1,692 sq ft

Condo

20745 ROYAL PALACE SQ UNIT 207, STERLING...

Community: Central Parke at Lowes Island

Regency at Dominion Valley

15236 WEISKOPF CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$887,000

2 beds

3 baths

3,994 sq ft

15236 WEISKOPF CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Birchwood at Brambleton

23631 HAVELOCK WALK TER 313, ASHBURN, VA..., Ashburn, VA 20148

$485,000

2 beds

2 baths

1,403 sq ft

Condo

23631 HAVELOCK WALK TER 313, ASHBURN, VA...

Community: Birchwood at Brambleton

Birchwood at Brambleton

43089 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$983,060

3 beds

3 baths

2,491 sq ft

43089 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Four Seasons at Historic Virginia

3949 SOLSTICE LN, DUMFRIES, VA, 22025, Dumfries, VA 22025

$625,000

4 beds

3 baths

3,192 sq ft

3949 SOLSTICE LN, DUMFRIES, VA, 22025

Community: Four Seasons at Historic Virginia

The Village at Harvest Ridge

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

$655,000

4 beds

3 baths

4,385 sq ft

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

Community: The Village at Harvest Ridge

Trilogy® at Lake Frederick

118 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$484,900

2 beds

2 baths

1,632 sq ft

118 MILKWEED DR, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Birchwood at Brambleton

42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$853,586

4 beds

4 baths

2,742 sq ft

42972 TRUMAN TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

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

Questions? Call us: (240) 663-8229

Saintsbury Plaza

2905 SAINTSBURY PLZ 315, FAIRFAX, VA, 22..., Fairfax, VA 22031

$425,000

2 beds

2 baths

1,264 sq ft

Condo

2905 SAINTSBURY PLZ 315, FAIRFAX, VA, 22...

Community: Saintsbury Plaza

Central Parke at Lowes Island

20898 PRINCE LOWES TER, STERLING, VA, 20..., Sterling, VA 20165

$750,000

3 beds

4 baths

3,239 sq ft

20898 PRINCE LOWES TER, STERLING, VA, 20...

Community: Central Parke at Lowes Island

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 815, LEESBURG, V..., Leesburg, VA 20176

$498,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER 815, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Potomac Green

20759 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$865,000

3 beds

4 baths

2,973 sq ft

20759 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

Birchwood at Brambleton

42874 FIREFLY SONATA TER APT 107, ASHBUR..., Ashburn, VA 20148

$465,000

2 beds

2 baths

1,268 sq ft

Condo

42874 FIREFLY SONATA TER APT 107, ASHBUR...

Community: Birchwood at Brambleton

Heritage Hunt

6824 DERBY RUN WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$775,000

3 beds

3 baths

3,774 sq ft

6824 DERBY RUN WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Birchwood at Brambleton

42920 FIREFLY SONATA TER UNIT 307, ASHBU..., Ashburn, VA 20148

$590,000

3 beds

2 baths

1,630 sq ft

Condo

42920 FIREFLY SONATA TER UNIT 307, ASHBU...

Community: Birchwood at Brambleton

Gatherings at Wellington

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20..., Manassas, VA 20110

$415,000

3 beds

2 baths

2,006 sq ft

Condo

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20...

Community: Gatherings at Wellington

The Atrium at MetroWest

2960 VADEN DR # 2-307, FAIRFAX, VA, 2203..., Fairfax, VA 22031

$774,900

2 beds

2 baths

1,546 sq ft

Condo

2960 VADEN DR # 2-307, FAIRFAX, VA, 2203...

Community: The Atrium at MetroWest

The Atrium at MetroWest

2960 VADEN DR # 2-103, FAIRFAX, VA, 2203..., Fairfax, VA 22031

$825,000

1 beds

2 baths

1,546 sq ft

Condo

2960 VADEN DR # 2-103, FAIRFAX, VA, 2203...

2,404 sq ft

20754 ADAMS MILL PL, ASHBURN, VA, 20147

Community: Potomac Green

1 2 3 4 5 6 7 8 9 10 11 12…13

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

489 homes near Middletown

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.
© 2025 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: Oct 24, 2025.
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

131 communities near Middletown

489 homes near Middletown

3 beds

4 baths

2,780 sq ft

3 beds

3 baths

2,523 sq ft

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

1,441 sq ft

Condo

4 beds

5 baths

6,096 sq ft

4 beds

4 baths

2,705 sq ft

3 beds

4 baths

2,742 sq ft

2 beds

2 baths

1,558 sq ft

Condo

3 beds

4 baths

4,338 sq ft

3 beds

4 baths

2,848 sq ft

2 beds

2 baths

1,957 sq ft

3 beds

3 baths

2,920 sq ft

2 beds

2 baths

1,315 sq ft

Condo

2 beds

2 baths

1,960 sq ft

4 beds

5 baths

5,614 sq ft

3 beds

4 baths

2,742 sq ft

3 beds

3 baths

2,810 sq ft

2 beds

2 baths

1,692 sq ft

Condo

2 beds

3 baths

3,994 sq ft

2 beds

2 baths

1,403 sq ft

Condo

3 beds

3 baths

2,491 sq ft

4 beds

3 baths

3,192 sq ft

4 beds

3 baths

4,385 sq ft

2 beds

2 baths