Call us at (540) 773-2470 to learn more about active adult communities near Winchester

Winchester, VA 55+ active adult communities & homes for sale - Page 2

82 communities near Winchester

Sort by:

Relevance

Relevance

Courts of Clarksburg
$600Ks - $700Ks
Courts of Clarksburg, Clarksburg, MD
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 140 homes
Village at Meadow Pointe
$200Ks - $300Ks
Village at Meadow Pointe, Harrisonburg, VA
Resale Only | 55+ age-restricted | Built 2003 - 2017 | 136 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
Gatherings at Cabin Branc...
$400Ks - $600Ks
Gatherings at Cabin Branc..., Clarksburg, MD
New Construction | 55+ age-restricted | Built 2024 - present | 135 homes
Regency North
$300Ks - $400Ks
Regency North, Fredericksburg, VA
New Construction | 55+ age-restricted | Built 2021 - present | 133 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Country Manor
$100Ks - $200Ks
Country Manor, Shippensburg, PA
Resale Only | 55+ age-restricted | Built 2000 - 2018 | 130 homes
Cedar Meadows
$400Ks
Cedar Meadows, White Post, VA
Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes
Barley Woods
$400Ks - $500Ks
Barley Woods, Fredericksburg, VA
New Construction | 55+ age-restricted | Built 2017 - present | 124 homes
Vistas at Lansdowne
$500Ks - $800Ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
Lexington 7
$800Ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 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
$300Ks - $400Ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 homes
Saintsbury Plaza
$300Ks - $400Ks
Saintsbury Plaza, Fairfax, VA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 111 homes
JerMae Estates
$400Ks - $500Ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
Albert Courts
$100Ks - $200Ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes
Havenwood Villas
$400Ks
Havenwood Villas, Fredericksburg, VA
New Construction | 55+ age-restricted | Built 2025 - present | 100 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
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
The Preserves at Cumberla...
$300Ks - $500Ks
The Preserves at Cumberla..., Gettysburg, PA
Resale Only | 55+ age-restricted | Built 2010 - present | 93 homes
Boxwood Villas
$500Ks - $600Ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
Legacy Woods
$400Ks
Legacy Woods, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 87 homes
5 rating (1 reviews) Keswick Villas
$400Ks - $600Ks
Keswick Villas, Spotsylvania, VA
New Construction | 55+ age-restricted | Built 2020 - present | 84 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 Village at Foxfield
$500Ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
Heritage Highlands
$300Ks - $400Ks
Heritage Highlands, Lovettsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes
3.7 rating (3 reviews) Four Seasons at Ashburn V...
$400Ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes
The Villages at Broadland...
$400Ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Cascades at Embrey Mill
$500Ks - $600Ks
Cascades at Embrey Mill, Stafford, VA
New Construction | 55+ age-restricted | Built 2021 - present | 78 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
1 rating (1 reviews) Downey Knolls
$200Ks - $400Ks
Downey Knolls, Elkton, VA
New and Resale | 55+ age-restricted | Built 2014 - present | 76 homes
Cadence at Lansdowne
$700Ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 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
CobbleStone Estates
$400Ks - $500Ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
River Crossing at Spring ...
$400Ks
River Crossing at Spring ..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2014 - present | 63 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
$300Ks
Liberty Grove, Manassas, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes
Turnberry East at Lee's H...
$300Ks
Turnberry East at Lee's H..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2007 - 2013 | 60 homes
Gatherings at Potomac Sta...
$400Ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes
Robinson Manor
$600Ks - $700Ks
Robinson Manor, Gainesville, VA
New Construction | 55+ age-restricted | Built 2023 - present | 50 homes
The Signature at Broadlan...
$300Ks - $400Ks
The Signature at Broadlan..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
The Villas of Salem Churc...
$400Ks
The Villas of Salem Churc..., Fredericksburg, VA
New Construction | 55+ age-restricted | Built 2020 - present | 45 homes
The Highlands at Blue Rid...
$400Ks - $700Ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes
Heritage Estates
$500Ks - $600Ks
Heritage Estates, Harrisonburg, VA
Resale Only | 55+ age-restricted | Built 1981 - 2020 | 39 homes
Mill Creek
$300Ks - $400Ks
Mill Creek, Spotsylvania, VA
Resale Only | 55+ age-restricted | Built 2006 - 2009 | 38 homes
Ballenger Run
$500Ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes
Celebrate 91 DENISON ST, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$528,000

3 beds

|

3 baths

|

2,588 sq ft

91 DENISON ST, FREDERICKSBURG, VA, 22406
Community: Celebrate
Penn National 3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222
$339,900

3 beds

|

4 baths

|

3,106 sq ft

3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172...
Community: Penn National
Heritage Hunt 6900 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155
$745,000

3 beds

|

4 baths

|

3,676 sq ft

6900 TRED AVON PL, GAINESVILLE, VA, 2015...
Community: Heritage Hunt
New Penn National 2365 ARONIMINK CIR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$239,000

2 beds

|

2 baths

|

1,254 sq ft

2365 ARONIMINK CIR, FAYETTEVILLE, PA, 17...
Community: Penn National
Penn National 6945 AUGUSTA NATIONAL, FAYETTEVILLE, PA,..., Fayetteville, PA 17222
$414,750

3 beds

|

4 baths

|

2,505 sq ft

6945 AUGUSTA NATIONAL, FAYETTEVILLE, PA,...
Community: Penn National
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Penn National 7010 FAIRWAY OAKS, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222
$379,900

3 beds

|

2 baths

7010 FAIRWAY OAKS, FAYETTEVILLE, PA, 172...
Community: Penn National
Penn National 6881 OLD COURSE RD, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$554,000

3 beds

|

3 baths

|

3,089 sq ft

6881 OLD COURSE RD, FAYETTEVILLE, PA, 17...
Community: Penn National
Spring Valley Estates 11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$388,900

4 beds

|

3 baths

|

2,035 sq ft

11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Penn National 6788 SAINT ANNES DR, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222
$649,900

4 beds

|

3 baths

|

4,310 sq ft

6788 SAINT ANNES DR, FAYETTEVILLE, PA, 1...
Community: Penn National
Spring Valley Estates 11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$388,900

4 beds

|

3 baths

|

2,035 sq ft

11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
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.
Spring Valley Estates 11845 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$364,900

3 beds

|

3 baths

|

1,800 sq ft

11845 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Spring Valley Estates 11823 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$364,900

3 beds

|

3 baths

|

1,800 sq ft

11823 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Spring Valley Estates 11819 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268
$364,900

3 beds

|

3 baths

|

1,800 sq ft

11819 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Penn National 6611 CONGRESSIONAL TER, FAYETTEVILLE, PA..., Fayetteville, PA 17222
$399,900

3 beds

|

3 baths

|

2,564 sq ft

6611 CONGRESSIONAL TER, FAYETTEVILLE, PA...
Community: Penn National
Penn National 5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222
$344,900

2 beds

|

3 baths

|

1,724 sq ft

5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1...
Community: Penn National
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Penn National 6041 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222
$325,000

3 beds

|

2 baths

|

1,974 sq ft

6041 GREENBRIAR TER, FAYETTEVILLE, PA, 1...
Community: Penn National
Penn National 6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$339,900

4 beds

|

3 baths

|

1,536 sq ft

6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17...
Community: Penn National
Country Manor 21 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$190,000

2 beds

|

2 baths

|

1,322 sq ft

21 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Penn National 3891 ALFALFA LN, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222
$289,900

2 beds

|

2 baths

|

1,576 sq ft

3891 ALFALFA LN, FAYETTEVILLE, PA, 17222
Community: Penn National
Country Manor 22 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$175,000

2 beds

|

2 baths

|

1,421 sq ft

22 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
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.
Country Manor 81 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$205,000

2 beds

|

2 baths

|

1,550 sq ft

81 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Penn National 2375 ARONIMINK CIR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222
$274,000

2 beds

|

2 baths

2375 ARONIMINK CIR, FAYETTEVILLE, PA, 17...
Community: Penn National
Penn National 5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P..., Fayetteville, PA 17222
$204,000

2 beds

|

2 baths

|

1,598 sq ft

|

Condo

5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P...
Community: Penn National
Penn National 6352 PENN NATIONAL DR, CHAMBERSBURG, PA,..., Chambersburg, PA 17201
$495,000

3 beds

|

2 baths

|

2,173 sq ft

6352 PENN NATIONAL DR, CHAMBERSBURG, PA,...
Community: Penn National
Penn National 6357 9TH VW, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222
$329,900

3 beds

|

2 baths

|

1,958 sq ft

|

Condo

6357 9TH VW, FAYETTEVILLE, PA, 17222
Community: Penn National
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Country Manor 84 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$184,900

2 beds

|

2 baths

|

1,438 sq ft

84 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
Crestwood Village 7043 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703
$339,999

2 beds

|

2 baths

|

1,225 sq ft

7043 BASSWOOD RD, FREDERICK, MD, 21703
Community: Crestwood Village
Trilogy® at Lake Frederick 108 BUNTING CT, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$745,000

3 beds

|

4 baths

|

5,284 sq ft

108 BUNTING CT, LAKE FREDERICK, VA, 2263...
Trilogy® at Lake Frederick 103 PLANETREE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$825,000

3 beds

|

3 baths

|

3,589 sq ft

103 PLANETREE CT, LAKE FREDERICK, VA, 22...
Trilogy® at Lake Frederick 102 PHOEBE CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$915,000

5 beds

|

4 baths

|

4,267 sq ft

102 PHOEBE CT, LAKE FREDERICK, VA, 22630
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.
Virginia Heritage at Lee's Parke 5910 W CARNIFEX FERRY RD, FREDERICKSBURG..., Fredericksburg, VA 22407
$525,000

3 beds

|

3 baths

|

3,004 sq ft

5910 W CARNIFEX FERRY RD, FREDERICKSBURG...
Regency at Dominion Valley 15110 HEATHER MILL LN APT 201, HAYMARKET..., Haymarket, VA 20169
$469,000

2 beds

|

2 baths

|

1,551 sq ft

|

Condo

15110 HEATHER MILL LN APT 201, HAYMARKET...
Keswick Villas 7704 COLBURN DR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$690,000

5 beds

|

4 baths

|

3,770 sq ft

7704 COLBURN DR, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
Regency at Dominion Valley 5484 RODRIQUEZ LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$745,000

3 beds

|

3 baths

|

2,598 sq ft

5484 RODRIQUEZ LN, HAYMARKET, VA, 20169
New Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 1006, LEESBURG, ..., Leesburg, VA 20176
$529,000

3 beds

|

3 baths

|

1,720 sq ft

|

Condo

19355 CYPRESS RIDGE TER 1006, LEESBURG, ...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Trilogy® at Lake Frederick 105 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630
$639,000

3 beds

|

4 baths

|

2,700 sq ft

105 CABBAGE WHITE DR, LAKE FREDERICK, VA...
Regency at Dominion Valley 15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20..., Haymarket, VA 20169
$750,000

3 beds

|

3 baths

|

3,309 sq ft

15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20...
Birchwood at Brambleton 23688 BOLTON CRESCENT TER APT 204, ASHBU..., Ashburn, VA 20148
$470,000

2 beds

|

2 baths

|

1,280 sq ft

|

Condo

23688 BOLTON CRESCENT TER APT 204, ASHBU...
Heritage Hunt 7065 HERITAGE HUNT DR 203, GAINESVILLE, ..., Gainesville, VA 20155
$450,000

2 beds

|

2 baths

|

1,421 sq ft

|

Condo

7065 HERITAGE HUNT DR 203, GAINESVILLE, ...
Community: Heritage Hunt
Falls Run 2 TURTLE CREEK WAY # 10-4, FREDERICKSBUR..., Fredericksburg, VA 22406
$377,000

2 beds

|

2 baths

|

1,657 sq ft

|

Condo

2 TURTLE CREEK WAY # 10-4, FREDERICKSBUR...
Community: Falls Run
123456…7

Frequently Asked Questions


Want more information about active adult communities around Winchester?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winchester?

Call us: (540) 773-2470
82 communities near Winchester
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.
© 2025 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: Dec 02, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top