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Winchester Area, VA 55+ active adult communities & homes for sale - Page 4

202 homes near Winchester Area

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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
The Flats at Heathcote Vi...
$300ks - $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction | 55+ age-restricted | Built 2026 - present | 500 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
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Willow Run
$500ks - $600ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 homes
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
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 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
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.
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
3 rating (2 reviews) Dunbarton
$300ks - $500ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
5 rating (2 reviews) Potomac Green
$400ks - $800ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
Montebello
$500ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 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 Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
5 rating (1 reviews) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
The Village at Foxfield
$300ks - $500ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 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
5 rating (1 reviews) Willow Lawn Cottages
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 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.
Regency at Belmont
$600ks - $900ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
5 rating (1 reviews) Gatherings at Wellington
$300ks - $400ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
Ballenger Run
$300ks - $400ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes
Gatherings at Potomac Sta...
$400ks - $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes
3.7 rating (3 reviews) Four Seasons at Ashburn V...
$300ks - $400ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes
The Retreat at Poland Hil...
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes
Central Parke at Lowes Is...
$300ks - $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Cedar Meadows
$300ks - $400ks
Cedar Meadows, White Post, VA
Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes
JerMae Estates
$300ks - $400ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
Liberty Grove
$200ks - $300ks
Liberty Grove, Manassas, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 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.
Suffield Meadows
$400ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 homes
Robinson Manor
$600ks - $700ks
Robinson Manor, Gainesville, VA
New Construction | 55+ age-restricted | Built 2023 - present | 50 homes
5 rating (1 reviews) Four Seasons at Vint Hill
$600ks
Four Seasons at Vint Hill, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes
Boxwood Villas
$500ks - $600ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
The Highlands at Blue Rid...
$400ks - $600ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes
The Villages at Broadland...
$400ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Albert Courts
$100ks - $200ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes
Regency at Creekside
$700ks - $800ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
CobbleStone Estates
$400ks - $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
Lexington Square
$800ks - $1Ms
Lexington Square, Ashburn, VA
New Construction | 55+ age-restricted | Built 2024 - present | 23 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.
1...2
Four Seasons at Ashburn Village 21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2..., Ashburn, VA 20147
$519,900

2 beds

|

2 baths

|

1,491 sq ft

|

Condo

21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2...
Rosehill Manor Villas 19601 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$374,900

3 beds

|

2 baths

|

1,735 sq ft

19601 LAVENDER LN, HAGERSTOWN, MD, 21742
Cedar Meadows 104 POPPY DR, WHITE POST, VA, 22663, White Post, VA 22663
$470,000

3 beds

|

2 baths

|

1,633 sq ft

104 POPPY DR, WHITE POST, VA, 22663
Community: Cedar Meadows
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 519, LEESBURG, V..., Leesburg, VA 20176
$325,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19385 CYPRESS RIDGE TER 519, LEESBURG, V...
Montebello 46408 REDDISH KNOB DR, STERLING, VA, 201..., Sterling, VA 20164
$1,000,000

3 beds

|

3 baths

|

2,381 sq ft

46408 REDDISH KNOB DR, STERLING, VA, 201...
Community: Montebello
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Dunbarton 9716 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136
$650,000

3 beds

|

3 baths

|

2,760 sq ft

9716 SEAFIELD PL, BRISTOW, VA, 20136
Community: Dunbarton
Trilogy® at Lake Frederick 124 YELLOW BIRCH, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$1,199,000

4 beds

|

5 baths

|

4,933 sq ft

124 YELLOW BIRCH, LAKE FREDERICK, VA, 22...
Willow Lawn Cottages 1856 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601
$369,900

2 beds

|

2 baths

|

1,219 sq ft

1856 MELVOR LN, WINCHESTER, VA, 22601
Heritage Hunt 6877 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$649,000

3 beds

|

2 baths

|

1,809 sq ft

6877 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Regency at Belmont 43909 EVELYN PATH TER, ASHBURN, VA, 2014..., Ashburn, VA 20147
$989,900

3 beds

|

4 baths

|

3,243 sq ft

43909 EVELYN PATH TER, ASHBURN, VA, 2014...
Community: Regency at Belmont
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.
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
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 7, HAYMARKET, VA, 201..., Haymarket, VA 20169
$474,990

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

5800 MOONSTONE WAY 7, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 6, HAYMARKET, VA, 201..., Haymarket, VA 20169
$374,990

1 beds

|

2 baths

|

995 sq ft

|

Condo

5800 MOONSTONE WAY 6, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 5, HAYMARKET, VA, 201..., Haymarket, VA 20169
$609,990

3 beds

|

2 baths

|

1,850 sq ft

|

Condo

5800 MOONSTONE WAY 5, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 4, HAYMARKET, VA, 201..., Haymarket, VA 20169
$549,990

2 beds

|

2 baths

|

1,520 sq ft

|

Condo

5800 MOONSTONE WAY 4, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 3, HAYMARKET, VA, 201..., Haymarket, VA 20169
$599,990

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

5800 MOONSTONE WAY 3, HAYMARKET, VA, 201...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 2, HAYMARKET, VA, 201..., Haymarket, VA 20169
$424,990

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...
The Flats at Heathcote Village by Del Webb 5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169
$494,990

2 beds

|

2 baths

|

1,475 sq ft

|

Condo

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...
Trilogy® at Lake Frederick 110 SWITCHGRASS WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630
$559,000

2 beds

|

2 baths

|

1,791 sq ft

110 SWITCHGRASS WAY, LAKE FREDERICK, VA,...
Gatherings at Wellington 9204 CHARLESTON DR 207, MANASSAS, VA, 20..., Manassas, VA 20110
$409,900

2 beds

|

2 baths

|

2,006 sq ft

|

Condo

9204 CHARLESTON DR 207, MANASSAS, VA, 20...
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 19355 CYPRESS RIDGE TER 1022, LEESBURG, ..., Leesburg, VA 20176
$368,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER 1022, LEESBURG, ...
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,...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 314, LEESBURG, V..., Leesburg, VA 20176
$334,990

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER 314, LEESBURG, V...
The Woodlands of Urbana 3411 ANGELICA WAY 401, FREDERICK, MD, 21..., Frederick, MD 21704
$495,000

2 beds

|

2 baths

|

1,785 sq ft

|

Condo

3411 ANGELICA WAY 401, FREDERICK, MD, 21...
Rosehill Manor Villas 19642 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$399,900

3 beds

|

2 baths

|

1,712 sq ft

19642 LAVENDER LN, HAGERSTOWN, MD, 21742
Trilogy® at Lake Frederick 105 TROUT LILY DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$399,900

3 beds

|

4 baths

|

2,327 sq ft

105 TROUT LILY DR, LAKE FREDERICK, VA, 2...
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER 306, LEESBURG, V..., Leesburg, VA 20176
$355,000

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

19365 CYPRESS RIDGE TER 306, LEESBURG, V...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Trilogy® at Lake Frederick 109 TUTELO LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$589,900

2 beds

|

3 baths

|

3,505 sq ft

109 TUTELO LN, LAKE FREDERICK, VA, 22630
Gatherings at Potomac Station 700 MOUNT AIRY TER 301, LEESBURG, VA, 20..., Leesburg, VA 20176
$589,000

2 beds

|

2 baths

|

1,809 sq ft

|

Condo

700 MOUNT AIRY TER 301, LEESBURG, VA, 20...
The Woodlands of Urbana 2913 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704
$849,000

3 beds

|

3 baths

|

2,712 sq ft

2913 HERB GARDEN DR, FREDERICK, MD, 2170...
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 19365 CYPRESS RIDGE TER 907, LEESBURG, V..., Leesburg, VA 20176
$585,000

3 beds

|

3 baths

|

1,720 sq ft

|

Condo

19365 CYPRESS RIDGE TER 907, LEESBURG, V...
Trilogy® at Lake Frederick 152 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$475,000

3 beds

|

2 baths

|

1,804 sq ft

152 MILKWEED DR, LAKE FREDERICK, VA, 226...
Rosehill Manor Villas 19704 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$449,990

3 beds

|

3 baths

|

1,895 sq ft

19704 OLEANDER CT, HAGERSTOWN, MD, 21742
Regency at Dominion Valley 15231 ROYAL CREST DR 204, HAYMARKET, VA,..., Haymarket, VA 20169
$450,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15231 ROYAL CREST DR 204, HAYMARKET, VA,...
Suffield Meadows 6715 HOLLY FARM LN, WARRENTON, VA, 20187, Warrenton, VA 20187
$575,000

3 beds

|

4 baths

|

3,350 sq ft

|

Condo

6715 HOLLY FARM LN, WARRENTON, VA, 20187
Community: Suffield Meadows
The Village at Foxfield 7 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$650,000

3 beds

|

3 baths

|

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769
Heritage Hunt 13972 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$775,000

4 beds

|

4 baths

|

3,256 sq ft

13972 REAL QUITE CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Birchwood at Brambleton 23665 HAVELOCK WALK TER 406, ASHBURN, VA..., Ashburn, VA 20148
$525,000

1 beds

|

2 baths

|

1,229 sq ft

|

Condo

23665 HAVELOCK WALK TER 406, ASHBURN, VA...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Crestwood Village 5738 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703
$325,000

2 beds

|

2 baths

|

1,264 sq ft

5738 BOX ELDER CT, FREDERICK, MD, 21703
Community: Crestwood Village
Heritage Hunt 13891 CHELMSFORD DR 110, GAINESVILLE, VA..., Gainesville, VA 20155
$425,000

3 beds

|

2 baths

|

1,424 sq ft

|

Condo

13891 CHELMSFORD DR 110, GAINESVILLE, VA...
Community: Heritage Hunt
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.



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REIN updates its listings on a daily basis. Data last updated: Jul 21, 2026.
This application does not include information on all of the properties available for sale at this time.

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