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

51 communities near Winchester Area

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5 rating (2 reviews) Trilogy® at Lake Frederic...
$300ks - $900ks
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
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 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 Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
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
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Winchester Landing
$300ks - $400ks
Winchester Landing, Winchester, VA
Resale Only | 55+ age-restricted | Built 2023 - 2025
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
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
5 rating (1 reviews) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
5 rating (1 reviews) Willow Lawn Cottages
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Village at Freedom Hi...
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
Montebello
$500ks - $700ks
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
Ballenger Run
$300ks - $400ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes
Suffield Meadows
$400ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 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.
3 rating (2 reviews) Dunbarton
$300ks - $500ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
Regency at Belmont
$600ks - $900ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
Gatherings at Potomac Sta...
$400ks - $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes
JerMae Estates
$300ks - $400ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
The Village at Foxfield
$300ks - $500ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
5 rating (2 reviews) Potomac Green
$400ks - $800ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
Cedar Meadows
$300ks - $400ks
Cedar Meadows, White Post, VA
Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Central Parke at Lowes Is...
$300ks - $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
Liberty Grove
$200ks - $300ks
Liberty Grove, Manassas, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 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
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 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 Signature at Broadlan...
$300ks - $400ks
The Signature at Broadlan..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 homes
Regency at Creekside
$700ks - $800ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
The Villages at Broadland...
$400ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Woodbrook Village
$200ks - $300ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Abrams Chase
$400ks - $500ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 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
Vistas at Lansdowne
$800ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Lexington Square
$800ks - $1Ms
Lexington Square, Ashburn, VA
New Construction | 55+ age-restricted | Built 2024 - present | 23 homes
Boxwood Villas
$500ks - $600ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 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
Heritage Hunt 7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155
$399,900

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
Trilogy® at Lake Frederick 109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$599,900

4 beds

|

4 baths

|

3,859 sq ft

109 EMPEROR DR, LAKE FREDERICK, VA, 2263...
New Dunbarton 9450 RAITH CT, BRISTOW, VA, 20136, Bristow, VA 20136
$800,000

5 beds

|

3 baths

|

4,124 sq ft

9450 RAITH CT, BRISTOW, VA, 20136
Community: Dunbarton
New Trilogy® at Lake Frederick 113 PINTAIL WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$820,000

3 beds

|

4 baths

|

4,159 sq ft

113 PINTAIL WAY, LAKE FREDERICK, VA, 226...
New Regency at Dominion Valley 15140 HEATHER MILL LN 404, HAYMARKET, VA..., Haymarket, VA 20169
$470,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15140 HEATHER MILL LN 404, HAYMARKET, VA...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
New Albert Courts 131 CODY DR 11, THURMONT, MD, 21788, Thurmont, MD 21788
$300,000

2 beds

|

2 baths

|

1,384 sq ft

|

Condo

131 CODY DR 11, THURMONT, MD, 21788
Community: Albert Courts
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 1122, LEESBURG, ..., Leesburg, VA 20176
$399,990

2 beds

|

2 baths

|

1,101 sq ft

|

Condo

19385 CYPRESS RIDGE TER 1122, LEESBURG, ...
Birchwood at Brambleton 42851 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148
$549,900

3 beds

|

3 baths

|

2,492 sq ft

|

Condo

42851 LITTLEHALES TER, ASHBURN, VA, 2014...
The Signature at Broadlands 43091 WYNRIDGE DR 201, BROADLANDS, VA, 2..., Broadlands, VA 20148
$429,900

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

43091 WYNRIDGE DR 201, BROADLANDS, VA, 2...
Gatherings at Wellington 9204 CHARLESTON DR 206, MANASSAS, VA, 20..., Manassas, VA 20110
$369,900

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

9204 CHARLESTON DR 206, 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.
Trilogy® at Lake Frederick 108 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$589,900

3 beds

|

3 baths

|

2,573 sq ft

108 VICEROY WAY, LAKE FREDERICK, VA, 226...
Liberty Grove 8605 LIBERTY TRL, MANASSAS, VA, 20110, Manassas, VA 20110
$549,900

3 beds

|

4 baths

|

2,988 sq ft

|

Condo

8605 LIBERTY TRL, MANASSAS, VA, 20110
Community: Liberty Grove
Regency at Dominion Valley 15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$799,419

3 beds

|

3 baths

|

4,050 sq ft

15508 HAGEN WAY, HAYMARKET, VA, 20169
Regency at Dominion Valley 5217 ARMOUR CT, HAYMARKET, VA, 20169, Haymarket, VA 20169
$725,000

3 beds

|

3 baths

|

2,427 sq ft

5217 ARMOUR CT, HAYMARKET, VA, 20169
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 514, LEESBURG, V..., Leesburg, VA 20176
$375,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER 514, LEESBURG, V...
Regency at Dominion Valley 15100 HEATHER MILL LN 103, HAYMARKET, VA..., Haymarket, VA 20169
$449,980

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15100 HEATHER MILL LN 103, HAYMARKET, VA...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Heritage Hunt 13281 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$739,000

3 beds

|

3 baths

|

2,520 sq ft

13281 FIELDSTONE WAY, GAINESVILLE, VA, 2...
Community: Heritage Hunt
Willow Lawn Cottages 1853 ROSSER LN, WINCHESTER, VA, 22601, Winchester, VA 22601
$400,000

2 beds

|

2 baths

|

1,186 sq ft

1853 ROSSER LN, WINCHESTER, VA, 22601
The Flats at Heathcote Village by Del Webb 15492 EMERALD WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$830,496

3 beds

|

3 baths

|

2,763 sq ft

15492 EMERALD WAY, HAYMARKET, VA, 20169
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER 615, LEESBURG, V..., Leesburg, VA 20176
$485,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19365 CYPRESS RIDGE TER 615, LEESBURG, V...
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 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...
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...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Winchester Landing 120 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602
$369,999

3 beds

|

3 baths

|

1,630 sq ft

120 MAURY WAY, WINCHESTER, VA, 22602
Community: Winchester Landing
Trilogy® at Lake Frederick 107 OSPREY DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$519,900

3 beds

|

4 baths

|

3,007 sq ft

107 OSPREY DR, LAKE FREDERICK, VA, 22630
Winchester Landing 126 MAURY, WINCHESTER, VA, 22602, Winchester, VA 22602
$389,900

3 beds

|

3 baths

|

1,630 sq ft

126 MAURY, WINCHESTER, VA, 22602
Community: Winchester Landing
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 Highlands at Blue Ridge Shadows 79 PUTTER CT, FRONT ROYAL, VA, 22630, Front Royal, VA 22630
$530,000

3 beds

|

2 baths

|

1,829 sq ft

79 PUTTER CT, FRONT ROYAL, VA, 22630
Heritage Hunt 6872 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$699,999

2 beds

|

2 baths

|

2,066 sq ft

6872 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Trilogy® at Lake Frederick 114 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$680,000

3 beds

|

4 baths

|

3,333 sq ft

114 TURNSTONE LN, LAKE FREDERICK, VA, 22...
Woodbrook Village 111 TANGLEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$369,900

2 beds

|

2 baths

|

1,400 sq ft

111 TANGLEWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Abrams Chase 131 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$465,000

2 beds

|

2 baths

|

1,811 sq ft

131 AMBERFIELD CT, WINCHESTER, VA, 22602
Community: Abrams Chase
Regency at Belmont 43931 NORMAN NEWS TER, ASHBURN, VA, 2014..., Ashburn, VA 20147
$1,085,000

3 beds

|

4 baths

|

3,255 sq ft

43931 NORMAN NEWS TER, ASHBURN, VA, 2014...
Community: Regency at Belmont
Heritage Hunt 6128 BETON CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155
$799,000

3 beds

|

3 baths

|

2,653 sq ft

6128 BETON CT, GAINESVILLE, VA, 20155
Community: Heritage Hunt
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 107, LEESBURG, V..., Leesburg, VA 20176
$315,000

1 beds

|

1 baths

|

874 sq ft

|

Condo

19385 CYPRESS RIDGE TER 107, LEESBURG, V...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Gatherings at Wellington 10275 FOUNTAIN CIR 306, MANASSAS, VA, 20..., Manassas, VA 20110
$380,000

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

10275 FOUNTAIN CIR 306, MANASSAS, VA, 20...
Birchwood at Brambleton 23669 GOLDEN EMBERS SQ 403, ASHBURN, VA,..., Ashburn, VA 20148
$729,900

3 beds

|

2 baths

|

2,148 sq ft

|

Condo

23669 GOLDEN EMBERS SQ 403, ASHBURN, VA,...
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: Aug 18, 2026.
This application does not include information on all of the properties available for sale at this time.

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