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Middletown, MD 55+ active adult communities & homes for sale - Page 15

593 homes near Middletown

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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
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.
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
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.
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
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.
123...4
Parklands 10609 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$409,990

3 beds

|

3 baths

|

1,917 sq ft

10609 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
Parklands 10635 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$423,890

3 beds

|

3 baths

|

2,195 sq ft

10635 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
Hawthorne Greene 6 GRAMBY CT, LA PLATA, MD, 20646, La Plata, MD 20646
$375,000

2 beds

|

2 baths

|

1,549 sq ft

6 GRAMBY CT, LA PLATA, MD, 20646
Community: Hawthorne Greene
Leisure World® of Maryland 15107 INTERLACHEN DR 2-321, SILVER SPRIN..., Silver Spring, MD 20906
$189,000

2 beds

|

2 baths

|

990 sq ft

15107 INTERLACHEN DR 2-321, SILVER SPRIN...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 918, SILVER SP..., Silver Spring, MD 20906
$299,500

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 918, SILVER SP...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
The Villages At Woodholme 8325 MEADOWSWEET RD 8325, BALTIMORE, MD,..., Baltimore, MD 21208
$500,000

3 beds

|

3 baths

|

3,144 sq ft

|

Condo

8325 MEADOWSWEET RD 8325, BALTIMORE, MD,...
Cameron Grove 13216 FOX BOW DR 403, UPPER MARLBORO, MD..., Upper Marlboro, MD 20774
$330,000

2 beds

|

2 baths

|

1,298 sq ft

|

Condo

13216 FOX BOW DR 403, UPPER MARLBORO, MD...
Community: Cameron Grove
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 920, LEESBURG, V..., Leesburg, VA 20176
$450,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19385 CYPRESS RIDGE TER 920, LEESBURG, V...
Parklands 10607 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$359,990

2 beds

|

2 baths

10607 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
Four Seasons at Virginia Crossing 3703 HAVERTILL LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193
$640,000

3 beds

|

3 baths

|

2,215 sq ft

3703 HAVERTILL LN, WOODBRIDGE, VA, 22193
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.
Birchwood at Brambleton 42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$853,586

3 beds

|

4 baths

|

2,742 sq ft

42972 TRUMAN TER, ASHBURN, VA, 20148
Leisure World® of Maryland 3500 FOREST EDGE DR 15-2E, SILVER SPRING..., Silver Spring, MD 20906
$180,000

2 beds

|

2 baths

|

1,157 sq ft

|

Condo

3500 FOREST EDGE DR 15-2E, SILVER SPRING...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 304, HAYMARKET, VA, 2..., Haymarket, VA 20169
$445,965

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 304, HAYMARKET, VA, 2...
Central Parke at Victoria Falls 13851 BELLE CHASSE BLVD 213, LAUREL, MD,..., Laurel, MD 20707
$395,000

2 beds

|

2 baths

|

1,703 sq ft

|

Condo

13851 BELLE CHASSE BLVD 213, LAUREL, MD,...
Four Seasons at Virginia Crossing 14035 MADRONA LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193
$635,000

3 beds

|

3 baths

|

2,192 sq ft

14035 MADRONA LN, WOODBRIDGE, VA, 22193
Leisure World® of Maryland 15101 INTERLACHEN DR 1-807, SILVER SPRIN..., Silver Spring, MD 20906
$189,000

2 beds

|

2 baths

|

990 sq ft

|

Condo

15101 INTERLACHEN DR 1-807, SILVER SPRIN...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Nells Acres 1909 LENNOX DR 90, ELDERSBURG, MD, 21784, Eldersburg, MD 21784
$330,000

3 beds

|

3 baths

|

1,620 sq ft

|

Condo

1909 LENNOX DR 90, ELDERSBURG, MD, 21784
Community: Nells Acres
Parklands 3958 KATMAI ST, WHITE PLAINS, MD, 20695, White Plains, MD 20695
$649,999

4 beds

|

4 baths

|

4,111 sq ft

3958 KATMAI ST, WHITE PLAINS, MD, 20695
Community: Parklands
Penn National 5860 FAIRWAY DR 4, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222
$180,000

2 beds

|

2 baths

|

1,598 sq ft

|

Condo

5860 FAIRWAY DR 4, FAYETTEVILLE, PA, 172...
Community: Penn National
Willow Run 118 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602
$549,990

3 beds

|

2 baths

|

1,958 sq ft

118 SCENTED ROSE WAY, WINCHESTER, VA, 22...
Community: Willow Run
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.
Leisure World® of Maryland 15300 BEAVERBROOK CT 88-2B, SILVER SPRIN..., Silver Spring, MD 20906
$269,000

2 beds

|

2 baths

|

1,043 sq ft

|

Condo

15300 BEAVERBROOK CT 88-2B, SILVER SPRIN...
Emerald Pointe 13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$399,900

2 beds

|

2 baths

|

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
The Atrium at MetroWest 2960 VADEN DR 2-312, FAIRFAX, VA, 22031, Fairfax, VA 22031
$768,980

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

2960 VADEN DR 2-312, FAIRFAX, VA, 22031
Beechfield Manors 4003 SEASIDE ALDER RD 0208 - ROSE, BOWIE..., Bowie, MD 20720
$378,850

2 beds

|

2 baths

|

1,294 sq ft

|

Condo

4003 SEASIDE ALDER RD 0208 - ROSE, BOWIE...
Community: Beechfield Manors
Beechfield Manors 4003 SEASIDE ALDER RD 0204 - VIOLET, BOW..., Bowie, MD 20720
$379,350

2 beds

|

2 baths

|

1,288 sq ft

|

Condo

4003 SEASIDE ALDER RD 0204 - VIOLET, BOW...
Community: Beechfield Manors
Beechfield Manors 4003 SEASIDE ALDER RD 0203- LILY, BOWIE,..., Bowie, MD 20720
$380,260

2 beds

|

2 baths

|

1,223 sq ft

|

Condo

4003 SEASIDE ALDER RD 0203- LILY, BOWIE,...
Community: Beechfield Manors
Amblebrook 104 CHOKEBERRY WAY, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$364,990

3 beds

|

2 baths

|

1,402 sq ft

104 CHOKEBERRY WAY, GETTYSBURG, PA, 1732...
Community: Amblebrook
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
The Gatherings at Lakeview Community 626 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$468,990

3 beds

|

3 baths

|

2,475 sq ft

|

Condo

626 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
The Gatherings at Lakeview Community 624 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$359,990

3 beds

|

3 baths

|

1,569 sq ft

|

Condo

624 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Sagebrook 907 SHADOWBROOKE DR, DOVER, PA, 17315, Dover, PA 17315
$401,990

2 beds

|

2 baths

907 SHADOWBROOKE DR, DOVER, PA, 17315
Community: Sagebrook
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.
Creek View 118 GLENRIDGE, CARLISLE, PA, 17015, Carlisle, PA 17015
$269,710

2 beds

|

2 baths

|

1,408 sq ft

118 GLENRIDGE, CARLISLE, PA, 17015
Community: Creek View
The Village at Cabin Branch 13210 PETREL ST 3304, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$474,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST 3304, CLARKSBURG, MD, 20...
Gatherings at Cabin Branch 13210 PETREL ST 3304, CLARKSBURG, MD, 20..., Clarksburg, MD 20871
$474,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST 3304, CLARKSBURG, MD, 20...

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