Call us at (540) 452-4199 to learn more about active adult communities in Winchester Area

Winchester Area, VA 55+ active adult communities & homes for sale - Page 3

150 homes near Winchester Area

Sort by:

Relevance

Relevance

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
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 (2 reviews) Trilogy® at Lake Frederic...
$400ks - $800ks
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
Willow Run
$500ks - $600ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 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
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
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) 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.
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
Winchester Landing
$300ks - $400ks
Winchester Landing, Winchester, VA
Resale Only | 55+ age-restricted | Built 2023 - 2025
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
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 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
Lexington 7
$600ks - $700ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
Lexington Square
$800ks - $1Ms
Lexington Square, Ashburn, VA
New Construction | 55+ age-restricted | Built 2024 - present | 23 homes
Montebello
$500ks - $600ks
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 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) Gatherings at Wellington
$300ks - $400ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
Robinson Manor
$600ks - $700ks
Robinson Manor, Gainesville, VA
New Construction | 55+ age-restricted | Built 2023 - present | 50 homes
The Retreat at Poland Hil...
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 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 Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
5 rating (1 reviews) Willow Lawn Cottages
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
CobbleStone Estates
$400ks - $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
Liberty Grove
$200ks - $300ks
Liberty Grove, Manassas, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes
The Village at Foxfield
$300ks - $500ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
Cottage Glen
$400ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 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 Creekside
$700ks - $800ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 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
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
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
Boxwood Villas
$500ks - $600ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
Ballenger Run
$300ks - $400ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes
Abrams Chase
$400ks - $500ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 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
Woodbrook Village
$200ks - $300ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
The Village at Harvest Ri...
$400ks - $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes
Cross Creek Village
$300ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 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
Central Parke at Lowes Is...
$300ks - $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
1...2
The Woodlands of Urbana 3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$599,997

3 beds

|

3 baths

|

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704
Liberty Grove 8600 LIBERTY TRL 102, MANASSAS, VA, 2011..., Manassas, VA 20110
$290,000

1 beds

|

2 baths

|

1,131 sq ft

|

Condo

8600 LIBERTY TRL 102, MANASSAS, VA, 2011...
Community: Liberty Grove
CobbleStone Estates 9616 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740
$395,000

2 beds

|

2 baths

|

1,561 sq ft

9616 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
Potomac Green 44482 MALTESE FALCON SQ, ASHBURN, VA, 20..., Ashburn, VA 20147
$699,900

3 beds

|

3 baths

|

2,335 sq ft

44482 MALTESE FALCON SQ, ASHBURN, VA, 20...
Community: Potomac Green
The Flats at Heathcote Village by Del Webb 6156 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$679,990

3 beds

|

3 baths

|

2,625 sq ft

6156 AMBER LN, HAYMARKET, VA, 20169
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 6156 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169
$714,990

3 beds

|

3 baths

|

3,424 sq ft

6156 AMBER LN 2, HAYMARKET, VA, 20169
The Flats at Heathcote Village by Del Webb 6152 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$689,990

3 beds

|

3 baths

|

2,763 sq ft

6152 AMBER LN, HAYMARKET, VA, 20169
The Flats at Heathcote Village by Del Webb 6152 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169
$724,990

3 beds

|

3 baths

|

3,531 sq ft

6152 AMBER LN 2, HAYMARKET, VA, 20169
Lansdowne Woods of Virginia 19350 MAGNOLIA GROVE SQ UNIT 303, LEESBU..., Leesburg, VA 20176
$399,000

2 beds

|

2 baths

|

1,168 sq ft

|

Condo

19350 MAGNOLIA GROVE SQ UNIT 303, LEESBU...
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 Dominion Valley 15110 HEATHER MILL LN APT 305, HAYMARKET..., Haymarket, VA 20169
$460,000

2 beds

|

2 baths

|

1,551 sq ft

|

Condo

15110 HEATHER MILL LN APT 305, HAYMARKET...
Gatherings at Wellington 9202 CHARLESTON DR 406, MANASSAS, VA, 20..., Manassas, VA 20110
$375,000

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

9202 CHARLESTON DR 406, MANASSAS, VA, 20...
Birchwood at Brambleton 23630 HAVELOCK WALK TER UNIT 410, ASHBUR..., Ashburn, VA 20148
$549,900

2 beds

|

2 baths

|

1,212 sq ft

|

Condo

23630 HAVELOCK WALK TER UNIT 410, ASHBUR...
Gatherings at Wellington 10275 FOUNTAIN CIR 201, MANASSAS, VA, 20..., Manassas, VA 20110
$349,900

2 beds

|

2 baths

|

1,441 sq ft

|

Condo

10275 FOUNTAIN CIR 201, MANASSAS, VA, 20...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Birchwood at Brambleton 23630 HAVELOCK WALK TER UNIT 405, ASHBUR..., Ashburn, VA 20148
$435,000

2 beds

|

2 baths

|

1,059 sq ft

|

Condo

23630 HAVELOCK WALK TER UNIT 405, ASHBUR...
Lansdowne Woods of Virginia 19350 MAGNOLIA GROVE SQ 308, LEESBURG, V..., Leesburg, VA 20176
$435,000

2 beds

|

2 baths

|

1,444 sq ft

|

Condo

19350 MAGNOLIA GROVE SQ 308, LEESBURG, V...
Trilogy® at Lake Frederick 118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$600,000

3 beds

|

3 baths

|

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...
The Flats at Heathcote Village by Del Webb 6172 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$739,990

3 beds

|

4 baths

|

2,875 sq ft

6172 AMBER LN, HAYMARKET, VA, 20169
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 47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22..., Front Royal, VA 22630
$585,000

4 beds

|

4 baths

|

3,482 sq ft

47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22...
Winchester Landing 122 HARDY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602
$375,000

3 beds

|

3 baths

|

1,630 sq ft

122 HARDY WAY, WINCHESTER, VA, 22602
Community: Winchester Landing
The Village at Freedom Hills 13948 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740
$349,900

2 beds

|

2 baths

|

1,430 sq ft

13948 PATRIOT WAY, HAGERSTOWN, MD, 21740
Cottage Glen 129 DOONBEG CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$450,000

4 beds

|

3 baths

|

2,072 sq ft

129 DOONBEG CT, WINCHESTER, VA, 22602
Community: Cottage Glen
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 901, LEESBURG, V..., Leesburg, VA 20176
$515,000

3 beds

|

2 baths

|

1,534 sq ft

|

Condo

19375 CYPRESS RIDGE TER 901, LEESBURG, V...
Montebello 21630 HAWKSBILL HIGH CIR 204, STERLING, ..., Sterling, VA 20164
$620,000

2 beds

|

2 baths

|

1,640 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR 204, STERLING, ...
Community: Montebello
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 612, LEESBURG, V..., Leesburg, VA 20176
$575,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

19355 CYPRESS RIDGE TER 612, LEESBURG, V...
Winchester Landing 140 MCCORMICK CIR APT 302, WINCHESTER, V..., Winchester, VA 22602
$314,900

2 beds

|

2 baths

|

1,156 sq ft

140 MCCORMICK CIR APT 302, WINCHESTER, V...
Community: Winchester Landing
Montebello 21630 HAWKSBILL HIGH CIR UNIT 403, STERL..., Sterling, VA 20164
$545,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR UNIT 403, STERL...
Community: Montebello
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 112 BETONY CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$759,990

3 beds

|

3 baths

|

3,434 sq ft

112 BETONY CT, LAKE FREDERICK, VA, 22630
Trilogy® at Lake Frederick 114 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$724,900

3 beds

|

4 baths

|

3,333 sq ft

114 TURNSTONE LN, LAKE FREDERICK, VA, 22...
Birchwood at Brambleton 23590 RAYTOWN TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$789,795

3 beds

|

4 baths

|

2,742 sq ft

23590 RAYTOWN TER, ASHBURN, VA, 20148
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Birchwood at Brambleton 23664 HAVELOCK WALK TER APT 205, ASHBURN..., Ashburn, VA 20148
$628,482

2 beds

|

2 baths

|

1,553 sq ft

|

Condo

23664 HAVELOCK WALK TER APT 205, ASHBURN...
Birchwood at Brambleton 23664 HAVELOCK WALK TER APT 101, ASHBURN..., Ashburn, VA 20148
$657,468

2 beds

|

3 baths

|

1,576 sq ft

|

Condo

23664 HAVELOCK WALK TER APT 101, ASHBURN...
Cadence at Lansdowne 43917 MARITIME SONG TER, LEESBURG, VA, 2..., Leesburg, VA 20176
$750,000

3 beds

|

3 baths

|

2,389 sq ft

43917 MARITIME SONG TER, LEESBURG, VA, 2...
Emerald Pointe 13412 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$409,900

2 beds

|

2 baths

|

1,952 sq ft

13412 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Emerald Pointe 13218 ONYX DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$494,900

2 beds

|

2 baths

13218 ONYX DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
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 3412 ANGELICA WAY 402, FREDERICK, MD, 21..., Frederick, MD 21704
$525,000

2 beds

|

2 baths

|

Condo

3412 ANGELICA WAY 402, FREDERICK, MD, 21...
Heritage Hunt 7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155
$410,000

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
Birchwood at Brambleton 23630 WINTERDAY DR, ASHBURN, VA, 20148, Ashburn, VA 20148
$789,990

3 beds

|

4 baths

|

2,742 sq ft

23630 WINTERDAY DR, ASHBURN, VA, 20148
Birchwood at Brambleton 23631 HAVELOCK WALK TER 404, ASHBURN, VA..., Ashburn, VA 20148
$559,000

2 beds

|

2 baths

|

1,959 sq ft

|

Condo

23631 HAVELOCK WALK TER 404, ASHBURN, VA...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Woodbrook Village 203 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$374,000

2 beds

|

2 baths

|

1,590 sq ft

203 CRESTWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Emerald Pointe 13366 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$434,900

2 beds

|

2 baths

|

2,826 sq ft

13366 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe



Frequently Asked Questions


Connect with an agent
Want to learn more about 55+ communities in the Winchester Area?
  • Insights and market stats
  • Instant new home alerts
  • Answers from local 55+ experts

Call us now: (540) 452-4199

Want to learn more about 55+ communities in Winchester Area?

Call us: (540) 452-4199
150 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Feb 24, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top