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

438 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...

$100Ks - $500Ks

Leisure World® of Marylan..., Silver Spring, MD

Resale Only | 55+ age-restricted | Built 1966 - 2009 | 5,600 homes

3.7 rating (6 reviews)

Amblebrook

$300Ks - $1Ms

Amblebrook, Gettysburg, PA

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

5 rating (3 reviews)

Heritage Hunt

$300Ks - $800Ks

Heritage Hunt, Gainesville, VA

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

2 rating (1 reviews)

Birchwood at Brambleton

$500Ks - $1Ms

Birchwood at Brambleton, Ashburn, VA

New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes

5 rating (2 reviews)

Potomac Green

$300Ks - $900Ks

Potomac Green, Ashburn, VA

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

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$300Ks - $600Ks

Lansdowne Woods of Virgin..., Lansdowne, VA

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

No reviews yet

Penn National

$200Ks - $500Ks

Penn National, Fayetteville, PA

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

5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400Ks - $900Ks

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 ...

$500Ks - $600Ks

Four Seasons at Historic ..., Dumfries, VA

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

5 rating (1 reviews)

Two Rivers

$600Ks - $900Ks

Two Rivers, Odenton, MD

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

No reviews yet

Cameron Grove

$300Ks - $500Ks

Cameron Grove, Upper Marlboro, MD

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

5 rating (2 reviews)

Central Parke at Victoria...

$300Ks - $400Ks

Central Parke at Victoria..., Laurel, MD

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

No reviews yet

The Woodlands of Urbana

$400Ks - $900Ks

The Woodlands of Urbana, Urbana, MD

New Construction | 55+ age-restricted | Built 2019 - present | 565 homes

5 rating (1 reviews)

Crestwood Village

$200Ks - $400Ks

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

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

1 rating (1 reviews)

Dunbarton

$600Ks - $600Ks

Dunbarton, Bristow, VA

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

No reviews yet

The Courtyards at Waverly...

$400Ks - $900Ks

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 - $300Ks

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

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

No reviews yet

Village Crest

$300Ks - $600Ks

Village Crest, Ellicott City, MD

New and Resale | 55+ age-restricted | Built 2005 - 2010 | 406 homes

No reviews yet

Courtyards at Waverly Woo...

$600Ks - $700Ks

Courtyards at Waverly Woo..., Woodstock, MD

Resale Only | 55+ age-restricted | Built 2006 - 2010 | 383 homes

5 rating (1 reviews)

Snowden Overlook

$600Ks - $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 - $400Ks

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

$800Ks - $800Ks

Spring Hill, Lorton, VA

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes

No reviews yet

The Enclave at Ellicott H...

$300Ks - $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 - $700Ks

Regency at Ashburn, Ashburn, VA

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

No reviews yet

The Crest of Alexandria

$600Ks - $900Ks

The Crest of Alexandria, Alexandria, VA

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

Colonial Charles

$400Ks - $500Ks

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 - $600Ks

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

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

No reviews yet

Eden Brook

$300Ks - $300Ks

Eden Brook, Odenton, MD

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 224 homes

No reviews yet

The Retreat at Poland Hil...

$700Ks - $900Ks

The Retreat at Poland Hil..., Chantilly, VA

Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes

1 2 3 4

Leisure World® of Maryland

3330 N LEISURE WORLD BLVD 5-919, SILVER ..., Silver Spring, MD 20906

$425,000

2 beds

2 baths

1,317 sq ft

Condo

3330 N LEISURE WORLD BLVD 5-919, SILVER ...

Community: Leisure World® of Maryland

The Courtyards at Waverly Woods

11243 GENTLE ROLLING DR, MARRIOTTSVILLE,..., Marriottsville, MD 21104

$759,900

3 beds

2 baths

2,228 sq ft

11243 GENTLE ROLLING DR, MARRIOTTSVILLE,...

Community: The Courtyards at Waverly Woods

Crestwood Village

7061 CATALPA RD, FREDERICK, MD, 21703, Frederick, MD 21703

$359,000

2 beds

1 baths

1,233 sq ft

7061 CATALPA RD, FREDERICK, MD, 21703

Community: Crestwood Village

Emerald Pointe

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$395,000

2 beds

2 baths

2,574 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Colonial Charles

10496 SUNSHINE PL, WALDORF, MD, 20603, Waldorf, MD 20603

$489,600

3 beds

3 baths

2,729 sq ft

10496 SUNSHINE PL, WALDORF, MD, 20603

Community: Colonial Charles

Crestwood Village

5673 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703

2 beds

3 baths

2,673 sq ft

19409 MOONSTONE DR, HAGERSTOWN, MD, 2174...

Community: Emerald Pointe

JerMae Estates

31 TOCATI ST, THURMONT, MD, 21788, Thurmont, MD 21788

$540,000

4 beds

3 baths

2,402 sq ft

31 TOCATI ST, THURMONT, MD, 21788

Community: JerMae Estates

The Enclave at Ellicott Hills

2540 KENSINGTON GDNS UNIT 201, ELLICOTT ..., Ellicott City, MD 21043

$380,000

2 beds

2 baths

1,440 sq ft

Condo

2540 KENSINGTON GDNS UNIT 201, ELLICOTT ...

Community: The Enclave at Ellicott Hills

Leisure World® of Maryland

3294 GLENEAGLES DR # 66-F, SILVER SPRING..., Silver Spring, MD 20906

$218,000

2 beds

3 baths

1,600 sq ft

Condo

3294 GLENEAGLES DR # 66-F, SILVER SPRING...

Community: Leisure World® of Maryland

The Enclave at Ellicott Hills

2500 KENSINGTON GDNS 406, ELLICOTT CITY,..., Ellicott City, MD 21043

$450,000

2 beds

2 baths

1,630 sq ft

Condo

2500 KENSINGTON GDNS 406, ELLICOTT CITY,...

Community: The Enclave at Ellicott Hills

Gatherings at Cabin Branch

13220 PETREL ST UNIT 4103, CLARKSBURG, M..., Clarksburg, MD 20871

$429,990

1 beds

1 baths

1,203 sq ft

Condo

13220 PETREL ST UNIT 4103, CLARKSBURG, M...

Community: Gatherings at Cabin Branch

The Village at Cabin Branch

$429,990

1 beds

1 baths

1,203 sq ft

Condo

13220 PETREL ST UNIT 4103, CLARKSBURG, M...

Community: The Village at Cabin Branch

Gatherings at Cabin Branch

13210 PETREL ST UNIT 3305, CLARKSBURG, M..., Clarksburg, MD 20871

$489,990

2 beds

2 baths

1,529 sq ft

Condo

Community: The Enclave at Ellicott Hills

Ellicott's Retreat

8580 SUNELL LN, ELLICOTT CITY, MD, 21043, Ellicott City, MD 21043

$1,350,000

6 beds

7 baths

4,241 sq ft

8580 SUNELL LN, ELLICOTT CITY, MD, 21043

Community: Ellicott's Retreat

Leisure World® of Maryland

2901 S LEISURE WORLD BLVD 303, SILVER SP..., Silver Spring, MD 20906

$350,000

2 beds

2 baths

1,288 sq ft

Condo

2901 S LEISURE WORLD BLVD 303, SILVER SP...

Community: Leisure World® of Maryland

Gatherings® at Quarry Place

510 QUARRY VIEW CT UNIT 308, REISTERSTOW..., Reisterstown, MD 21136

$399,900

2 beds

2 baths

1,390 sq ft

Condo

510 QUARRY VIEW CT UNIT 308, REISTERSTOW...

Community: Gatherings® at Quarry Place

Leisure World® of Maryland

3210 N LEISURE WORLD BLVD APT 815, SILVE..., Silver Spring, MD 20906

$195,000

1 beds

2 baths

910 sq ft

3210 N LEISURE WORLD BLVD APT 815, SILVE...

Community: Leisure World® of Maryland

The Village at Cabin Branch

13230 PETREL ST # 2207, CLARKSBURG, MD, ..., Clarksburg, MD 20871

$649,990

3 beds

2 baths

2,031 sq ft

Condo

13230 PETREL ST # 2207, CLARKSBURG, MD, ...

Community: The Village at Cabin Branch

Gatherings at Cabin Branch

$649,990

3 beds

2 baths

2,031 sq ft

Condo

13230 PETREL ST # 2207, CLARKSBURG, MD, ...

Community: Gatherings at Cabin Branch

Carroll Vista

122 PONYTAIL LN # 118, TANEYTOWN, MD, 21..., Taneytown, MD 21787

$345,000

1 beds

2 baths

1,419 sq ft

Condo

122 PONYTAIL LN # 118, TANEYTOWN, MD, 21...

Community: Carroll Vista

Winifred Manor

2001 RUDY SERRA DR UNIT 1D, ELDERSBURG, ..., Eldersburg, MD 21784

2 beds

2 baths

1,167 sq ft

Condo

14809 PENNFIELD CIR 209, SILVER SPRING, ...

Community: Leisure World® of Maryland

1 2 3 4 5 6 7 8 9 10 11

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.

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.

438 homes near Middletown

Remove Boundaries ×

Map Satellite

Want to learn more about 55+ communities in Middletown?

Call us: (240) 663-8229

Call Us Call Us

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

123 communities near Middletown

438 homes near Middletown

2 beds

2 baths

1,317 sq ft

Condo

3 beds

2 baths

2,228 sq ft

2 beds

1 baths

1,233 sq ft

2 beds

2 baths

2,574 sq ft

3 beds

3 baths

2,729 sq ft

2 beds

2 baths

1,315 sq ft

2 beds

2 baths

1,601 sq ft

Condo

2 beds

2 baths

2,170 sq ft

Condo

2 beds

2 baths

1,152 sq ft

Condo

3 beds

2 baths

1,194 sq ft

Condo

2 beds

2 baths

1,280 sq ft

Condo

2 beds

2 baths

1,513 sq ft

Condo

2 beds

2 baths

1,520 sq ft

Condo

1 beds

2 baths

945 sq ft

Condo

2 beds

2 baths

1,688 sq ft

Condo

2 beds

3 baths

2,673 sq ft

4 beds

3 baths

2,402 sq ft

2 beds

2 baths

1,440 sq ft

Condo

2 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

1,630 sq ft

Condo

1 beds

1 baths

1,203 sq ft

Condo