Middletown, MD 55+ active adult communities & homes for sale - Page 9

582 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

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

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

Cameron Grove

$200ks - $400ks

Cameron Grove, Upper Marlboro, MD

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

Penn National

$100ks - $600ks

Penn National, Fayetteville, PA

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

Traditions of America at ...

$400ks - $600ks

Traditions of America at ..., Mechanicsburg, PA

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

The Village at Cabin Bran...

$500ks

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

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

5 rating (1 reviews)

Two Rivers

$500ks - $700ks

Two Rivers, Odenton, MD

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Gatherings at Cabin Branc...

$400ks - $600ks

Gatherings at Cabin Branc..., Clarksburg, MD

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

The Gatherings at Lakevie...

$300ks - $400ks

The Gatherings at Lakevie..., Reisterstown, MD

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

Spring Valley Estates

$300ks - $400ks

Spring Valley Estates, Waynesboro, PA

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

The Flats at Northside

$600ks - $1Ms

The Flats at Northside, Potomac, MD

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

Beechfield Manors

$200ks - $400ks

Beechfield Manors, Bowie, MD

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

5 rating (1 reviews)

Regency at Dominion Valle...

$300ks - $1Ms

Regency at Dominion Valle..., Haymarket, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes

Four Seasons at Virginia ...

$400ks - $500ks

Four Seasons at Virginia ..., Woodbridge, VA

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

Sagebrook

$300ks - $400ks

Sagebrook, Dover, PA

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

$300ks - $600ks

Snowden Overlook, Columbia, MD

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

The Crest of Alexandria

$400ks - $800ks

The Crest of Alexandria, Alexandria, VA

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

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

Carroll's Creek

$300ks

Carroll's Creek, Gambrills, MD

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes

Montebello

$500ks - $1Ms

Montebello, Sterling, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

5 rating (1 reviews)

Carroll Vista

$300ks

Carroll Vista, Taneytown, MD

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

Resale Only | 55+ age-restricted | Built 2023 - 2025

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

Questions? Call us: (240) 663-8229

Cortland Park

$300ks - $600ks

Cortland Park, Mechanicsburg, PA

New and Resale | 55+ age-restricted | Built 2020 - present | 104 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

Watershed

1238 CRESTED WOOD DR, LAUREL, MD, 20724, Laurel, MD 20724

$589,990

3 beds

4 baths

2,660 sq ft

1238 CRESTED WOOD DR, LAUREL, MD, 20724

Community: Watershed

Dunbarton

9712 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136

$635,000

2 beds

3 baths

3,882 sq ft

9712 SEAFIELD PL, BRISTOW, VA, 20136

Community: Dunbarton

Regency at Belmont

43909 EVELYN PATH TER, ASHBURN, VA, 2014..., Ashburn, VA 20147

$999,990

3 beds

4 baths

3,243 sq ft

43909 EVELYN PATH TER, ASHBURN, VA, 2014...

Community: Regency at Belmont

Heritage Hunt

13641 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$693,000

2 beds

2 baths

1,904 sq ft

13641 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

Leisure World® of Maryland

3100 N LEISURE WORLD BLVD 523, SILVER SP..., Silver Spring, MD 20906

$180,000

1 beds

2 baths

930 sq ft

Condo

3100 N LEISURE WORLD BLVD 523, 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

Heritage Hunt

13618 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$799,000

2 beds

3 baths

3,320 sq ft

13618 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

Leisure World® of Maryland

15115 INTERLACHEN DR 3-902, SILVER SPRIN..., Silver Spring, MD 20906

$159,900

1 beds

1 baths

850 sq ft

Condo

15115 INTERLACHEN DR 3-902, SILVER SPRIN...

Community: Leisure World® of Maryland

Carroll's Creek

1404 WIGEON WAY 304, GAMBRILLS, MD, 2105..., Gambrills, MD 21054

$429,000

3 beds

2 baths

1,786 sq ft

Condo

1404 WIGEON WAY 304, GAMBRILLS, MD, 2105...

Community: Carroll's Creek

Traditions of America at Silver Spring

122 INDEPENDENCE WAY, MECHANICSBURG, PA,..., Mechanicsburg, PA 17050

$537,500

3 beds

3 baths

2,490 sq ft

Condo

122 INDEPENDENCE WAY, MECHANICSBURG, PA,...

Community: Traditions of America at Silver Spring

Patapsco Overlook

11 CLAY LODGE LN 101, BALTIMORE, MD, 212..., Baltimore, MD 21228

$420,000

2 beds

2 baths

1,422 sq ft

Condo

11 CLAY LODGE LN 101, BALTIMORE, MD, 212...

Community: Patapsco Overlook

Carroll's Creek

1412 WIGEON WAY 301, GAMBRILLS, MD, 2105..., Gambrills, MD 21054

$432,500

3 beds

2 baths

1,782 sq ft

Condo

1412 WIGEON WAY 301, GAMBRILLS, MD, 2105...

Community: Carroll's Creek

Courtyards at Waverly Woods East

11150 CHAMBERS CT J, WOODSTOCK, MD, 2116..., Woodstock, MD 21163

$395,000

2 beds

2 baths

1,610 sq ft

Condo

11150 CHAMBERS CT J, WOODSTOCK, MD, 2116...

Community: Courtyards at Waverly Woods East

Gatherings at Ellicott Mills

8511 COLTRANE CT 204, ELLICOTT CITY, MD,..., Ellicott City, MD 21043

$439,990

2 beds

2 baths

1,500 sq ft

Condo

8511 COLTRANE CT 204, ELLICOTT CITY, MD,...

Community: Gatherings at Ellicott Mills

Heritage Hunt

6901 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$640,000

3 beds

3 baths

2,618 sq ft

6901 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Leisure World® of Maryland

3350 CHISWICK CT 57-1A, SILVER SPRING, M..., Silver Spring, MD 20906

$90,000

1 beds

1 baths

635 sq ft

Condo

3350 CHISWICK CT 57-1A, SILVER SPRING, M...

Community: Leisure World® of Maryland

The Village at Freedom Hills

13928 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$375,000

2 beds

2 baths

1,663 sq ft

13928 PATRIOT WAY, HAGERSTOWN, MD, 21740

110 SWITCHGRASS WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Four Seasons at Virginia Crossing

3664 TRAFORD LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193

$650,000

3 beds

3 baths

2,164 sq ft

3664 TRAFORD LN, WOODBRIDGE, VA, 22193

3 beds

3 baths

3,193 sq ft

11700 MYSTIC ROCK LN, WAYNESBORO, PA, 17...

Community: Spring Valley Estates

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

Questions? Call us: (240) 663-8229

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 404, LEESBURG, V..., Leesburg, VA 20176

$358,500

2 beds

2 baths

1,105 sq ft

Condo

19355 CYPRESS RIDGE TER 404, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Central Parke at Lowes Island

20745 ROYAL PALACE SQ 209, STERLING, VA,..., Sterling, VA 20165

$475,000

3 beds

2 baths

1,816 sq ft

Condo

20745 ROYAL PALACE SQ 209, STERLING, VA,...

Community: Central Parke at Lowes Island

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 111 days. The average price of homes for sale in this community is approximately $600,106, 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 $600,106.

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

582 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: Jul 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 9

141 communities near Middletown

582 homes near Middletown

3 beds

4 baths

2,660 sq ft

2 beds

3 baths

3,882 sq ft

3 beds

4 baths

3,243 sq ft

2 beds

2 baths

1,904 sq ft

1 beds

2 baths

930 sq ft

Condo

2 beds

3 baths

3,320 sq ft

1 beds

1 baths

850 sq ft

Condo

3 beds

2 baths

1,786 sq ft

Condo

3 beds

3 baths

2,490 sq ft

Condo

2 beds

2 baths

1,422 sq ft

Condo

3 beds

2 baths

1,782 sq ft

Condo

2 beds

2 baths

1,610 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

2,618 sq ft

1 beds

1 baths

635 sq ft

Condo

2 beds

2 baths

1,663 sq ft

2 beds

2 baths

1,445 sq ft

Condo

1 beds

2 baths

995 sq ft

Condo

3 beds

2 baths

1,850 sq ft

Condo

2 beds

2 baths

1,520 sq ft

Condo

3 beds

2 baths

1,735 sq ft

Condo