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

278 homes 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

No reviews yet

Cross Creek Village

$300Ks - $300Ks

Cross Creek Village, Winchester, VA

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

No reviews yet

The Village at Harvest Ri...

$500Ks - $500Ks

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

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

No reviews yet

Woodbrook Village

$300Ks - $300Ks

Woodbrook Village, Winchester, VA

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

No reviews yet

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

No reviews yet

Abrams Chase

$500Ks - $500Ks

Abrams Chase, Winchester, VA

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

5 rating (3 reviews)

Heritage Hunt

$300Ks - $800Ks

Heritage Hunt, Gainesville, VA

Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes

2 rating (1 reviews)

Birchwood at Brambleton

$500Ks - $1Ms

Birchwood at Brambleton, Ashburn, VA

New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes

5 rating (2 reviews)

Potomac Green

$300Ks - $900Ks

Potomac Green, Ashburn, VA

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

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$300Ks - $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.

No reviews yet

Penn National

$300Ks - $500Ks

Penn National, Fayetteville, PA

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

2.8 rating (6 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 - $900Ks

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 - $400Ks

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 - $700Ks

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

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

4.3 rating (3 reviews)

Falls Run

$300Ks - $500Ks

Falls Run, Fredericksburg, VA

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

No reviews yet

The Woodlands of Urbana

$400Ks - $800Ks

The Woodlands of Urbana, Urbana, MD

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

5 rating (1 reviews)

Crestwood Village

$300Ks - $400Ks

Crestwood Village, Frederick, MD

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

No reviews yet

Carter's Mill

$400Ks - $700Ks

Carter's Mill, Haymarket, VA

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

1 rating (1 reviews)

Dunbarton

$600Ks - $600Ks

Dunbarton, Bristow, VA

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

No reviews yet

Montebello

$600Ks - $1Ms

Montebello, Sterling, VA

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

No reviews yet

Twin Lake Villas

$300Ks - $400Ks

Twin Lake Villas, Locust Grove, VA

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

No reviews yet

Spring Hill

$500Ks - $500Ks

Spring Hill, Lorton, VA

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

No reviews yet

Regency at Ashburn

$500Ks - $700Ks

Regency at Ashburn, Ashburn, VA

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

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

Questions? Call us: (540) 773-2470

No reviews yet

ThreeOaks™

$400Ks - $600Ks

ThreeOaks™, Culpeper, VA

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

No reviews yet

Emerald Pointe

$300Ks - $400Ks

Emerald Pointe, Hagerstown, MD

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

No reviews yet

River Ridge

$600Ks - $600Ks

River Ridge, Woodbridge, VA

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

No reviews yet

Signature Club at Greenvi...

$500Ks - $600Ks

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

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

No reviews yet

Regency at Chancellorsvil...

$500Ks - $500Ks

Regency at Chancellorsvil..., Fredericksburg, VA

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

No reviews yet

The Retreat at Poland Hil...

$700Ks - $900Ks

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

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

No reviews yet

Regency at Creekside

$900Ks - $900Ks

Regency at Creekside, Gainesville, VA

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

No reviews yet

The Atrium at MetroWest

$700Ks - $700Ks

The Atrium at MetroWest, Fairfax, VA

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

No reviews yet

Four Seasons at Virginia ...

$400Ks - $600Ks

Four Seasons at Virginia ..., Woodbridge, VA

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

No reviews yet

Central Parke at Lowes Is...

$400Ks - $400Ks

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? 55places can help!

Questions? Call us: (540) 773-2470

No reviews yet

Summerlake

$300Ks - $300Ks

Summerlake, Fredericksburg, VA

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

No reviews yet

Belmont Bay

$300Ks - $800Ks

Belmont Bay, Woodbridge, VA

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

No reviews yet

Regency at Belmont

$1Ms - $1Ms

Regency at Belmont, Ashburn, VA

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

No reviews yet

Four Seasons at Charlotte...

$500Ks - $500Ks

Four Seasons at Charlotte..., Ruckersville, VA

New and Resale | 55+ age-restricted | Built 2005 - present | 144 homes

No reviews yet

Spring Valley Estates

$300Ks - $300Ks

Spring Valley Estates, Waynesboro, PA

New Construction | 55+ age-restricted | Built 2019 - present | 140 homes

1 2 3

Birchwood at Brambleton

42743 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$875,000

3 beds

3 baths

2,832 sq ft

42743 CUMULUS TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Virginia Heritage at Lee's Parke

10207 IVERSON AVE, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22407

$585,000

3 beds

3 baths

2,596 sq ft

10207 IVERSON AVE, FREDERICKSBURG, VA, 2...

Community: Virginia Heritage at Lee's Parke

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 802, LEESBURG, V..., Leesburg, VA 20176

$524,900

3 beds

2 baths

1,560 sq ft

Condo

19355 CYPRESS RIDGE TER 802, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Four Seasons at Virginia Crossing

13970 ENGLEFIELD DR UNIT 207, WOODBRIDGE..., Woodbridge, VA 22193

$559,900

2 beds

2 baths

1,811 sq ft

Condo

13970 ENGLEFIELD DR UNIT 207, WOODBRIDGE...

Community: Four Seasons at Virginia Crossing

Birchwood at Brambleton

23650 HAVELOCK WALK TER UNIT 303, ASHBUR..., Ashburn, VA 20148

$610,000

2 beds

2 baths

1,553 sq ft

Condo

23650 HAVELOCK WALK TER UNIT 303, ASHBUR...

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 773-2470

Falls Run

19 HANOVER CT, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406

$470,000

3 beds

3 baths

2,279 sq ft

19 HANOVER CT, FREDERICKSBURG, VA, 22406

Community: Falls Run

Heritage Hunt

13460 VICTORY GALLOP WAY, GAINESVILLE, V..., Gainesville, VA 20155

$600,000

3 beds

3 baths

2,312 sq ft

13460 VICTORY GALLOP WAY, GAINESVILLE, V...

Community: Heritage Hunt

Montebello

21792 HAWKSBILL HIGH CIR, STERLING, VA, ..., Sterling, VA 20164

$895,000

2 beds

2 baths

1,445 sq ft

21792 HAWKSBILL HIGH CIR, STERLING, VA, ...

Community: Montebello

Four Seasons at Ashburn Village

21025 ROCKY KNOLL SQ 103, ASHBURN, VA, 2..., Ashburn, VA 20147

$459,000

2 beds

2 baths

1,359 sq ft

Condo

21025 ROCKY KNOLL SQ 103, ASHBURN, VA, 2...

Community: Four Seasons at Ashburn Village

Trilogy® at Lake Frederick

130 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$939,900

4 beds

4 baths

4,921 sq ft

130 GROSBEAK CT, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

110 FRITILLARY CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$430,000

3 beds

4 baths

2,325 sq ft

110 FRITILLARY CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$450,000

4 beds

4 baths

2,248 sq ft

111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Lansdowne Woods of Virginia

19370 MAGNOLIA GROVE SQ 208, LEESBURG, V..., Leesburg, VA 20176

$420,000

2 beds

2 baths

1,440 sq ft

Condo

19370 MAGNOLIA GROVE SQ 208, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Belmont Bay

620 ANGELFISH WAY, WOODBRIDGE, VA, 22191, Woodbridge, VA 22191

$849,950

3 beds

4 baths

3,240 sq ft

620 ANGELFISH WAY, WOODBRIDGE, VA, 22191

Community: Belmont Bay

Heritage Hunt

6046 GALLANT FOX CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$643,000

4 beds

3 baths

1,943 sq ft

6046 GALLANT FOX CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

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

Questions? Call us: (540) 773-2470

Heritage Hunt

13882 CINCH LN, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$835,000

3 beds

4 baths

3,192 sq ft

13882 CINCH LN, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Vistas at Lansdowne

44251 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176

$865,000

3 beds

4 baths

3,974 sq ft

44251 SILVERPALM GROVE TER, LEESBURG, VA...

Community: Vistas at Lansdowne

Heritage Hunt

6848 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155

$769,000

3 beds

3 baths

2,520 sq ft

6848 TRED AVON PL, GAINESVILLE, VA, 2015...

Community: Heritage Hunt

Trilogy® at Lake Frederick

142 RUFFED GROUSE CT, LAKE FREDERICK, VA..., Lake Frederick, VA 22630

$799,999

3 beds

3 baths

2,937 sq ft

142 RUFFED GROUSE CT, LAKE FREDERICK, VA...

Community: Trilogy® at Lake Frederick

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER UNIT 206, LEESBU..., Leesburg, VA 20176

$424,900

2 beds

2 baths

1,441 sq ft

Condo

19375 CYPRESS RIDGE TER UNIT 206, LEESBU...

Community: Lansdowne Woods of Virginia

Lexington Square

44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$818,236

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

Lexington 7

$818,236

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington 7

Lexington 7

44480 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$794,990

3 beds

3 baths

3,088 sq ft

44480 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington 7

Lexington Square

$794,990

3 beds

3 baths

3,088 sq ft

44480 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

Virginia Heritage at Lee's Parke

5639 CEDAR MOUNTAIN CT, FREDERICKSBURG, ..., Fredericksburg, VA 22407

$515,000

2 beds

2 baths

1,736 sq ft

5639 CEDAR MOUNTAIN CT, FREDERICKSBURG, ...

Community: Virginia Heritage at Lee's Parke

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

Questions? Call us: (540) 773-2470

Virginia Heritage at Lee's Parke

10205 IVERSON AVE, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22407

$569,900

4 beds

4 baths

3,552 sq ft

10205 IVERSON AVE, FREDERICKSBURG, VA, 2...

Community: Virginia Heritage at Lee's Parke

Abrams Chase

112 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$499,500

2 beds

2 baths

1,609 sq ft

112 AMBERFIELD CT, WINCHESTER, VA, 22602

Community: Abrams Chase

Celebrate

70 BATTERY POINT DR, FREDERICKSBURG, VA,..., Fredericksburg, VA 22406

$680,000

4 beds

3 baths

3,744 sq ft

70 BATTERY POINT DR, FREDERICKSBURG, VA,...

Community: Celebrate

Village at Meadow Pointe

521 HICKORY GROVE CIR, HARRISONBURG, VA,..., Harrisonburg, VA 22801

$374,000

2 beds

2 baths

1,910 sq ft

521 HICKORY GROVE CIR, HARRISONBURG, VA,...

Community: Village at Meadow Pointe

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER UNIT 921, LEESBU..., Leesburg, VA 20176

$495,000

2 beds

2 baths

1,509 sq ft

Condo

19355 CYPRESS RIDGE TER UNIT 921, LEESBU...

Community: Lansdowne Woods of Virginia

Heritage Hunt

13685 PADDOCK CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$775,000

3 beds

3 baths

2,951 sq ft

13685 PADDOCK CT, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Gatherings at Wellington

9200 CHARLESTON DR 408, MANASSAS, VA, 20..., Manassas, VA 20110

$375,000

2 beds

2 baths

1,417 sq ft

Condo

9200 CHARLESTON DR 408, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Saintsbury Plaza

2903 SAINTSBURY PLZ 310, FAIRFAX, VA, 22..., Fairfax, VA 22031

$420,000

2 beds

2 baths

1,125 sq ft

Condo

2903 SAINTSBURY PLZ 310, FAIRFAX, VA, 22...

Community: Saintsbury Plaza

Celebrate

14 PENSACOLA ST, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406

$489,900

2 beds

2 baths

1,445 sq ft

14 PENSACOLA ST, FREDERICKSBURG, VA, 224...

Community: Celebrate

Lexington Square

44470 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147

$977,626

4 beds

4 baths

4,089 sq ft

44470 COALPORT TER, ASHBURN, VA, 20147

Community: Lexington Square

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

Questions? Call us: (540) 773-2470

Lexington 7

$977,626

4 beds

4 baths

4,089 sq ft

44470 COALPORT TER, ASHBURN, VA, 20147

Community: Lexington 7

Regency at Dominion Valley

15130 HEATHER MILL LN 102, HAYMARKET, VA..., Haymarket, VA 20169

$415,000

2 beds

2 baths

1,499 sq ft

Condo

15130 HEATHER MILL LN 102, HAYMARKET, VA...

Community: Regency at Dominion Valley

Regency at Dominion Valley

15120 HEATHER MILL LN APT 304, HAYMARKET..., Haymarket, VA 20169

$465,000

2 beds

2 baths

1,499 sq ft

Condo

15120 HEATHER MILL LN APT 304, HAYMARKET...

Community: Regency at Dominion Valley

Woodbrook Village

201 ROSEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$375,000

2 beds

2 baths

1,692 sq ft

201 ROSEWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

Trilogy® at Lake Frederick

120 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$434,900

3 beds

3 baths

2,311 sq ft

120 BAYHILL TER, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

1 2 3 4 5 6 7

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 Cottage Glen, Abrams Chase.

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 160 days. The average price of homes for sale in these communities is approximately $457,410, 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 $564,900, 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.

278 homes near Winchester

Remove Boundaries ×

Map Satellite

Want to learn more about 55+ communities in Winchester?

Call us: (540) 773-2470

Call Us Call Us

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

81 communities near Winchester

278 homes near Winchester

3 beds

3 baths

2,832 sq ft

3 beds

3 baths

2,596 sq ft

3 beds

2 baths

1,560 sq ft

Condo

2 beds

2 baths

1,811 sq ft

Condo

2 beds

2 baths

1,553 sq ft

Condo

3 beds

3 baths

2,279 sq ft

3 beds

3 baths

2,312 sq ft

2 beds

2 baths

1,445 sq ft

2 beds

2 baths

1,359 sq ft

Condo

4 beds

4 baths

4,921 sq ft

3 beds

4 baths

2,325 sq ft

4 beds

4 baths

2,248 sq ft

2 beds

2 baths

1,440 sq ft

Condo

3 beds

4 baths

3,240 sq ft

4 beds

3 baths

1,943 sq ft

3 beds

4 baths

3,192 sq ft

3 beds

4 baths

3,974 sq ft

3 beds

3 baths

2,520 sq ft

3 beds

3 baths

2,937 sq ft

2 beds

2 baths

1,441 sq ft

Condo

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

3,088 sq ft

3 beds

3 baths