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Middletown, MD 55+ active adult communities & homes for sale - Page 14

572 homes near Middletown

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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
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
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
The Flats at Northside
$600ks - $1Ms
The Flats at Northside, Potomac, MD
New Construction | Age-targeted | Built 2025 - present | 143 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
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.
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
Beechfield Manors
$200ks - $400ks
Beechfield Manors, Bowie, MD
New Construction | 55+ age-restricted | Built 2024 - present
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
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Questions? Call us: (240) 663-8229
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
The Gatherings at Lakevie...
$300ks - $400ks
The Gatherings at Lakevie..., Reisterstown, MD
New Construction | 55+ age-restricted | Built 2025 - present | 122 homes
The Atrium at MetroWest
$600ks - $700ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 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.
Gatherings at Cabin Branc...
$400ks - $600ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 homes
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
5 rating (1 reviews) Gatherings at Wellington
$300ks - $400ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Cedar Ridge at Piney Orch...
$200ks - $300ks
Cedar Ridge at Piney Orch..., Odenton, MD
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 450 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 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
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.
Signature Club at Greenvi...
$400ks - $500ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
5 rating (1 reviews) Carroll Vista
$200ks - $300ks
Carroll Vista, Taneytown, MD
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 453 homes
Spring Valley Estates
$300ks - $400ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Four Seasons at Virginia ...
$400ks - $500ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
Blue Ridge
$300ks - $400ks
Blue Ridge, Harrisburg, PA
New and Resale | Age-targeted | Built 2020 - present | 130 homes
Winifred Manor
$200ks
Winifred Manor, Eldersburg, MD
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 152 homes
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
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) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 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 Village at Freedom Hi...
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
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 (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) Two Rivers
$500ks - $700ks
Two Rivers, Odenton, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 800 homes
123...4
Leisure World® of Maryland 3210 N LEISURE WORLD BLVD 1001, SILVER S..., Silver Spring, MD 20906
$435,000

3 beds

|

2 baths

|

1,544 sq ft

|

Condo

3210 N LEISURE WORLD BLVD 1001, SILVER S...
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
$195,000

2 beds

|

2 baths

|

990 sq ft

15107 INTERLACHEN DR 2-321, SILVER SPRIN...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Trilogy® at Lake Frederick 117 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$780,000

3 beds

|

4 baths

|

3,601 sq ft

117 MALLARD DR, LAKE FREDERICK, VA, 2263...
Leisure World® of Maryland 3200 N LEISURE WORLD BLVD 918, SILVER SP..., Silver Spring, MD 20906
$309,500

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

3200 N LEISURE WORLD BLVD 918, SILVER SP...
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
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.
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...
Penn National 6352 PENN NATIONAL DR, FAYETTEVILLE, PA,..., Fayetteville, PA 17222
$495,000

3 beds

|

2 baths

|

2,173 sq ft

6352 PENN NATIONAL DR, FAYETTEVILLE, PA,...
Community: Penn National
Parklands 5332 KINGS CANYON CT, WHITE PLAINS, MD, ..., White Plains, MD 20695
$488,000

4 beds

|

3 baths

|

2,728 sq ft

5332 KINGS CANYON CT, 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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
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
Saintsbury Plaza 2903 SAINTSBURY PLZ 310, FAIRFAX, VA, 22..., Fairfax, VA 22031
$375,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2903 SAINTSBURY PLZ 310, FAIRFAX, VA, 22...
Community: Saintsbury Plaza
Two Rivers 3148 SUNNY RIDGE DR, ODENTON, MD, 21113, Odenton, MD 21113
$737,900

3 beds

|

3 baths

|

2,056 sq ft

3148 SUNNY RIDGE DR, ODENTON, MD, 21113
Community: Two Rivers
Ellicott Meadows 11940 HAMPSTEAD GRN 73, ELLICOTT CITY, M..., Ellicott City, MD 21042
$800,000

4 beds

|

4 baths

|

4,171 sq ft

|

Condo

11940 HAMPSTEAD GRN 73, ELLICOTT CITY, M...
Community: Ellicott Meadows
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 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
$458,465

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 304, HAYMARKET, VA, 2...
Leisure World® of Maryland 3310 N LEISURE WORLD BLVD 325, SILVER SP..., Silver Spring, MD 20906
$205,000
|

1,115 sq ft

|

Condo

3310 N LEISURE WORLD BLVD 325, SILVER SP...
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,...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Four Seasons at Virginia Crossing 14035 MADRONA LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193
$649,900

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
$201,000

2 beds

|

2 baths

|

990 sq ft

|

Condo

15101 INTERLACHEN DR 1-807, SILVER SPRIN...
The Villages At Woodholme 8402 PRAIRIE ROSE 8402, PIKESVILLE, MD, ..., Pikesville, MD 21208
$450,000

3 beds

|

4 baths

|

3,800 sq ft

|

Condo

8402 PRAIRIE ROSE 8402, PIKESVILLE, MD, ...
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
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.
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
Willow Run 115 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602
$589,990

4 beds

|

3 baths

|

2,818 sq ft

115 SCENTED ROSE WAY, WINCHESTER, VA, 22...
Community: Willow Run
Penn National 5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P..., Fayetteville, PA 17222
$199,000

2 beds

|

2 baths

|

1,598 sq ft

|

Condo

5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P...
Community: Penn National
Amblebrook 318 RUSTIC WOOD DR, GETTYSBURG, PA, 1732..., Gettysburg, PA 17325
$475,000

2 beds

|

2 baths

|

1,860 sq ft

318 RUSTIC WOOD DR, GETTYSBURG, PA, 1732...
Community: Amblebrook
Parklands 10620 GREAT BASIN PL, WHITE PLAINS, MD, ..., White Plains, MD 20695
$399,990

3 beds

|

3 baths

10620 GREAT BASIN PL, WHITE PLAINS, MD, ...
Community: Parklands
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
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
Emerald Pointe 19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742
$464,900

2 beds

|

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...
Community: Emerald Pointe
The Gatherings at Lakeview Community 606 QUARRY PLACE CT, REISTERSTOWN, MD, 2..., Reisterstown, MD 21136
$476,990

3 beds

|

3 baths

|

2,475 sq ft

|

Condo

606 QUARRY PLACE CT, REISTERSTOWN, MD, 2...
Leisure World® of Maryland 2904 N LEISURE WORLD BLVD 211, SILVER SP..., Silver Spring, MD 20906
$224,900

2 beds

|

2 baths

|

1,041 sq ft

|

Condo

2904 N LEISURE WORLD BLVD 211, SILVER SP...
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.
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 0309- LILAC, BOWIE..., Bowie, MD 20720
$493,550

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

4003 SEASIDE ALDER RD 0309- LILAC, BOWIE...
Community: Beechfield Manors
Beechfield Manors 4003 SEASIDE ALDER RD 0208 - ROSE, BOWIE..., Bowie, MD 20720
$428,850

2 beds

|

2 baths

|

1,294 sq ft

|

Condo

4003 SEASIDE ALDER RD 0208 - ROSE, BOWIE...
Community: Beechfield Manors
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (240) 663-8229
Beechfield Manors 4003 SEASIDE ALDER RD 0204 - VIOLET, BOW..., Bowie, MD 20720
$419,350

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
$415,260

2 beds

|

2 baths

|

1,223 sq ft

|

Condo

4003 SEASIDE ALDER RD 0203- LILY, BOWIE,...
Community: Beechfield Manors

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