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

82 communities near Winchester

Sort by:

Relevance

5 rating (1 reviews)

Willow Lawn Cottages

$300Ks - $300Ks

Willow Lawn Cottages, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes

Cross Creek Village

$300Ks - $400Ks

Cross Creek Village, Winchester, VA

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes

The Village at Harvest Ri...

$500Ks - $600Ks

The Village at Harvest Ri..., Winchester, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes

Woodbrook Village

$300Ks - $300Ks

Woodbrook Village, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes

Cottage Glen

$400Ks - $400Ks

Cottage Glen, Winchester, VA

New and Resale | Age-targeted | Built 2018 - present | 25 homes

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

Abrams Chase

$500Ks - $500Ks

Abrams Chase, Winchester, VA

New Construction | 55+ age-restricted | Built 2020 - present | 13 homes

5 rating (3 reviews)

Heritage Hunt

$400Ks - $800Ks

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

5 rating (2 reviews)

Potomac Green

$800Ks - $900Ks

Potomac Green, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 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.

Penn National

$200Ks - $500Ks

Penn National, Fayetteville, PA

New and Resale | Age-targeted | Built 1968 - present | 1,100 homes

3.1 rating (7 reviews)

Celebrate

$300Ks - $600Ks

Celebrate, Fredericksburg, VA

New and Resale | 55+ age-restricted | Built 2008 - present | 1,100 homes

5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400Ks - $1Ms

Trilogy® at Lake Frederic..., Lake Frederick, VA

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

5 rating (1 reviews)

Regency at Dominion Valle...

$400Ks - $800Ks

Regency at Dominion Valle..., Haymarket, VA

Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes

5 rating (1 reviews)

Four Seasons at Historic ...

$600Ks - $700Ks

Four Seasons at Historic ..., Dumfries, VA

Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

4.4 rating (5 reviews)

Virginia Heritage at Lee'...

$500Ks - $600Ks

Virginia Heritage at Lee'..., Fredericksburg, VA

Resale Only | 55+ age-restricted | Built 2005 - 2021 | 795 homes

4.3 rating (3 reviews)

Falls Run

$300Ks - $400Ks

Falls Run, Fredericksburg, VA

Resale Only | 55+ age-restricted | Built 2002 - 2005 | 781 homes

The Woodlands of Urbana

$600Ks - $600Ks

The Woodlands of Urbana, Urbana, MD

New Construction | 55+ age-restricted | Built 2019 - present | 565 homes

5 rating (1 reviews)

Crestwood Village

$300Ks - $300Ks

Crestwood Village, Frederick, MD

Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes

Carter's Mill

$400Ks - $700Ks

Carter's Mill, Haymarket, VA

New Construction | 55+ age-restricted | Built 2020 - present | 480 homes

3 rating (2 reviews)

Dunbarton

$600Ks - $600Ks

Dunbarton, Bristow, VA

Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes

Montebello

$600Ks - $1Ms

Montebello, Sterling, VA

New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes

Twin Lake Villas

$300Ks - $400Ks

Twin Lake Villas, Locust Grove, VA

New Construction | 55+ age-restricted | Built 2021 - present | 340 homes

Spring Hill

$500Ks - $800Ks

Spring Hill, Lorton, VA

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes

Four Seasons at Charlotte...

$400Ks - $500Ks

Four Seasons at Charlotte..., Ruckersville, VA

Resale Only | 55+ age-restricted | Built 2005 - present | 275 homes

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

Regency at Ashburn

$800Ks - $900Ks

Regency at Ashburn, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes

ThreeOaks™

$400Ks - $800Ks

ThreeOaks™, Culpeper, VA

New Construction | 55+ age-restricted | Built 2024 - present | 268 homes

Emerald Pointe

$300Ks - $400Ks

Emerald Pointe, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes

River Ridge

$500Ks - $700Ks

River Ridge, Woodbridge, VA

Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes

Signature Club at Greenvi...

$400Ks - $900Ks

Signature Club at Greenvi..., New Market, MD

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes

Regency at Chancellorsvil...

$400Ks - $400Ks

Regency at Chancellorsvil..., Fredericksburg, VA

Resale Only | 55+ age-restricted | Built 2004 - 2019 | 225 homes

The Retreat at Poland Hil...

$700Ks - $900Ks

The Retreat at Poland Hil..., Chantilly, VA

Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes

Regency at Creekside

$900Ks - $900Ks

Regency at Creekside, Gainesville, VA

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes

The Atrium at MetroWest

$700Ks - $700Ks

The Atrium at MetroWest, Fairfax, VA

New Construction | 55+ age-restricted | Built 2018 - present | 206 homes

Four Seasons at Virginia ...

$400Ks - $600Ks

Four Seasons at Virginia ..., Woodbridge, VA

New Construction | 55+ age-restricted | Built 2021 - present | 185 homes

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

Central Parke at Lowes Is...

$400Ks - $700Ks

Central Parke at Lowes Is..., Sterling, VA

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes

Summerlake

$300Ks - $300Ks

Summerlake, Fredericksburg, VA

Resale Only | 55+ age-restricted | Built 1987 - 1997 | 161 homes

Belmont Bay

$400Ks - $800Ks

Belmont Bay, Woodbridge, VA

New and Resale | Age-targeted | Built 2007 - present | 155 homes

Regency at Belmont

$900Ks - $900Ks

Regency at Belmont, Ashburn, VA

New Construction | 55+ age-restricted | Built 2021 - present | 145 homes

Courts of Clarksburg

$600Ks - $700Ks

Courts of Clarksburg, Clarksburg, MD

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 140 homes

1 2...3

River Ridge

12221 SEAFORD CT, WOODBRIDGE, VA, 22192, Woodbridge, VA 22192

$584,900

3 beds

3 baths

1,962 sq ft

12221 SEAFORD CT, WOODBRIDGE, VA, 22192

Community: River Ridge

New Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER UNIT 404, LEESBU..., Leesburg, VA 20176

$340,000

2 beds

2 baths

1,038 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 404, LEESBU...

Community: Lansdowne Woods of Virginia

Heritage Hunt

6159 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$800,000

3 beds

3 baths

2,846 sq ft

6159 FERRIER CT, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Central Parke at Lowes Island

20745 ROYAL PALACE SQ UNIT 207, STERLING..., Sterling, VA 20165

$429,900

2 beds

2 baths

1,692 sq ft

Condo

20745 ROYAL PALACE SQ UNIT 207, STERLING...

Community: Central Parke at Lowes Island

The Village at Cabin Branch

13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871

$399,990

1 beds

1 baths

1,203 sq ft

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...

Community: The Village at Cabin Branch

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

Gatherings at Cabin Branch

$399,990

1 beds

1 baths

1,203 sq ft

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...

Community: Gatherings at Cabin Branch

The Retreat at Poland Hill

43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152

$945,000

4 beds

4 baths

3,553 sq ft

43441 BETTYS FARM DR, CHANTILLY, VA, 201...

Community: The Retreat at Poland Hill

Woodbrook Village

222 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$379,000

2 beds

2 baths

1,260 sq ft

222 CRESTWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

Regency at Chancellorsville

12524 REGIMENT LN, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22407

$427,500

2 beds

2 baths

1,802 sq ft

12524 REGIMENT LN, FREDERICKSBURG, VA, 2...

Community: Regency at Chancellorsville

Regency at Dominion Valley

15201 ROYAL CREST DR APT 407, HAYMARKET,..., Haymarket, VA 20169

$440,000

2 beds

2 baths

1,538 sq ft

Condo

15201 ROYAL CREST DR APT 407, HAYMARKET,...

Community: Regency at Dominion Valley

Trilogy® at Lake Frederick

118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$650,000

3 beds

3 baths

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

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

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 815, LEESBURG, V..., Leesburg, VA 20176

$498,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER 815, LEESBURG, V...

Community: Lansdowne Woods of Virginia

River Crossing at Spring Arbor

5806 SPRING ARBOR LN, FREDERICKSBURG, VA..., Fredericksburg, VA 22407

$465,000

3 beds

3 baths

1,925 sq ft

5806 SPRING ARBOR LN, FREDERICKSBURG, VA...

Community: River Crossing at Spring Arbor

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...

Community: Trilogy® at Lake Frederick

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

Four Seasons at Virginia Crossing

14035 MADRONA LN, WOODBRIDGE, VA, 22193, Woodbridge, VA 22193

$669,900

3 beds

3 baths

2,192 sq ft

14035 MADRONA LN, WOODBRIDGE, VA, 22193

Community: Four Seasons at Virginia Crossing

Celebrate

35 MONTAUK AVE, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406

$475,000

2 beds

2 baths

1,642 sq ft

35 MONTAUK AVE, FREDERICKSBURG, VA, 2240...

Community: Celebrate

Cascades at Embrey Mill

241 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554

$644,000

4 beds

4 baths

3,291 sq ft

Condo

241 SMOKEBUSH DR, STAFFORD, VA, 22554

Community: Cascades at Embrey Mill

New Heritage Hunt

6013 PINEY GROVE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$750,000

3 beds

3 baths

2,608 sq ft

6013 PINEY GROVE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

New Falls Run

2 TURTLE CREEK WAY # 10-4, FREDERICKSBUR..., Fredericksburg, VA 22406

$379,000

2 beds

2 baths

1,657 sq ft

Condo

2 TURTLE CREEK WAY # 10-4, FREDERICKSBUR...

Community: Falls Run

New Regency at Ashburn

20862 SABER JET PL, ASHBURN, VA, 20147, Ashburn, VA 20147

$915,000

3 beds

4 baths

4,150 sq ft

20862 SABER JET PL, ASHBURN, VA, 20147

Community: Regency at Ashburn

New Regency at Dominion Valley

15251 ROYAL CREST DR APT 103, HAYMARKET,..., Haymarket, VA 20169

$470,000

2 beds

2 baths

1,499 sq ft

Condo

15251 ROYAL CREST DR APT 103, HAYMARKET,...

Community: Regency at Dominion Valley

New Potomac Green

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$749,000

3 beds

3 baths

2,447 sq ft

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

New Four Seasons at Historic Virginia

17401 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025

$625,000

3 beds

2 baths

2,453 sq ft

17401 FOUR SEASONS DR, DUMFRIES, VA, 220...

Community: Four Seasons at Historic Virginia

New Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 601, LEESBURG, V..., Leesburg, VA 20176

$529,900

3 beds

2 baths

1,534 sq ft

Condo

19375 CYPRESS RIDGE TER 601, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

Four Seasons at Historic Virginia

16529 SPARKLING BROOK LOOP, DUMFRIES, VA..., Dumfries, VA 22025

$610,500

2 beds

2 baths

2,391 sq ft

16529 SPARKLING BROOK LOOP, DUMFRIES, VA...

Community: Four Seasons at Historic Virginia

Four Seasons at Ashburn Village

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,..., Ashburn, VA 20147

$429,900

2 beds

2 baths

1,612 sq ft

Condo

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,...

Community: Four Seasons at Ashburn Village

Potomac Green

44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147

$913,000

4 beds

4 baths

2,709 sq ft

44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,...

Community: Potomac Green

Trilogy® at Lake Frederick

118 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$479,900

2 beds

2 baths

1,632 sq ft

118 MILKWEED DR, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

New Potomac Green

20432 ISLAND WEST SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$739,999

3 beds

3 baths

2,253 sq ft

20432 ISLAND WEST SQ, ASHBURN, VA, 20147

Community: Potomac Green

Four Seasons at Ashburn Village

44485 CHAMBERLAIN TER UNIT 200, ASHBURN,..., Ashburn, VA 20147

$450,000

2 beds

2 baths

1,763 sq ft

Condo

44485 CHAMBERLAIN TER UNIT 200, ASHBURN,...

Community: Four Seasons at Ashburn Village

Heritage Hunt

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$864,997

4 beds

3 baths

4,486 sq ft

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Heritage Hunt

13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$630,000

3 beds

3 baths

2,090 sq ft

13963 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

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

Potomac Green

20742 ADAMS MILL PL, ASHBURN, VA, 20147, Ashburn, VA 20147

$800,000

3 beds

2 baths

1,670 sq ft

20742 ADAMS MILL PL, ASHBURN, VA, 20147

Community: Potomac Green

Want to learn more about 55+ communities in Winchester? 55places can help!

Questions? Call us: (540) 773-2470

New 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

Community: Regency at Dominion Valley

Virginia Heritage at Lee's Parke

5503 BALLS BLUFF RD, FREDERICKSBURG, VA,..., Fredericksburg, VA 22407

$549,999

3 beds

3 baths

2,102 sq ft

5503 BALLS BLUFF RD, FREDERICKSBURG, VA,...

Community: Virginia Heritage at Lee's Parke

New Spring Hill

8912 YELLOW DAISY PL, LORTON, VA, 22079, Lorton, VA 22079

$879,900

3 beds

3 baths

2,342 sq ft

8912 YELLOW DAISY PL, LORTON, VA, 22079

Community: Spring Hill

Birchwood at Brambleton

23630 HAVELOCK WALK TER UNIT 405, ASHBUR..., Ashburn, VA 20148

$445,000

2 beds

2 baths

1,059 sq ft

Condo

23630 HAVELOCK WALK TER UNIT 405, ASHBUR...

Community: Birchwood at Brambleton

Gatherings at Wellington

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20..., Manassas, VA 20110

$415,000

3 beds

2 baths

2,006 sq ft

Condo

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20...

Community: Gatherings at Wellington

1 2 3 4 5 6 7…8

Frequently Asked Questions

What size 55+ communities are there in Winchester?

In Winchester, there are no large communities, no medium communities, and 6 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winchester?

The smallest 55+ communities in Winchester has 13 homes, the largest has 120 homes, and the average communities consists of 68 homes.

Are there new 55+ homes available in Winchester?

Yes, there are new 55+ homes available in Winchester. The most recent communities started in Winchester include Abrams Chase, Cottage Glen, The Village at Harvest Ridge. There are also 2 communities in Winchester that offer new construction homes, including Abrams Chase, Cottage Glen.

Are there gated 55+ communities in Winchester?

Yes, there is gated 55+ communities in Winchester. Approximately 16.7% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes.

How long do listings in 55+ communities in Winchester typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winchester stay on the market for around 534 days. The average price of homes for sale in these communities is approximately $455,982, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Village at Harvest Ridge average around $569,950, while homes in Cottage Glen average around $479,500.

Want more information about active adult communities around Winchester?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

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

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: Nov 18, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

82 communities near Winchester

287 homes near Winchester

3 beds

3 baths

1,962 sq ft

2 beds

2 baths

1,038 sq ft

Condo

3 beds

3 baths

2,846 sq ft

2 beds

2 baths

1,692 sq ft

Condo

1 beds

1 baths

1,203 sq ft

Condo

1 beds

1 baths

1,203 sq ft

Condo

4 beds

4 baths

3,553 sq ft

2 beds

2 baths

1,260 sq ft

2 beds

2 baths

1,802 sq ft

2 beds

2 baths

1,538 sq ft

Condo

3 beds

3 baths

2,523 sq ft

5 beds

4 baths

3,770 sq ft

3 beds

2 baths

1,475 sq ft

Condo

3 beds

3 baths

1,925 sq ft

3 beds

4 baths

5,284 sq ft

3 beds

3 baths

2,192 sq ft

2 beds

2 baths

1,642 sq ft

4 beds

4 baths

3,291 sq ft

Condo

3 beds

3 baths

2,608 sq ft

2 beds

2 baths

1,657 sq ft

Condo

3 beds

4 baths

4,150 sq ft

2 beds

2 baths

1,499 sq ft

Condo

3 beds

3 baths