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

293 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 - $400Ks

Cross Creek Village, Winchester, VA

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

No reviews yet

The Village at Harvest Ri...

$500Ks - $600Ks

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

$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

$700Ks - $800Ks

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

$200Ks - $800Ks

Penn National, Fayetteville, PA

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

3.1 rating (7 reviews)

Celebrate

$300Ks - $500Ks

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 ...

$500Ks - $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

No reviews yet

The Woodlands of Urbana

$600Ks - $700Ks

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

No reviews yet

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

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

$400Ks - $400Ks

Twin Lake Villas, Locust Grove, VA

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

No reviews yet

Spring Hill

$500Ks - $800Ks

Spring Hill, Lorton, VA

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

No reviews yet

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

No reviews yet

ThreeOaks™

$400Ks - $800Ks

ThreeOaks™, Culpeper, VA

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

No reviews yet

Regency at Ashburn

$500Ks - $600Ks

Regency at Ashburn, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2013 - 2020 | 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...

$400Ks - $900Ks

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

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

No reviews yet

Regency at Chancellorsvil...

$400Ks - $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 - $800Ks

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

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

Questions? Call us: (540) 773-2470

No reviews yet

Central Parke at Lowes Is...

$400Ks - $700Ks

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

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

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

$900Ks - $900Ks

Regency at Belmont, Ashburn, VA

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

Heritage Hunt

13141 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$809,900

2 beds

4 baths

3,494 sq ft

13141 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

Heritage Hunt

13404 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$837,500

4 beds

4 baths

4,069 sq ft

13404 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Lexington Square

44486 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$827,046

3 beds

3 baths

3,128 sq ft

44486 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

Falls Run

286 BRIDGEWATER CIR, FREDERICKSBURG, VA,..., Fredericksburg, VA 22406

$450,000

3 beds

3 baths

2,604 sq ft

286 BRIDGEWATER CIR, FREDERICKSBURG, VA,...

Community: Falls Run

Lexington 7

$827,046

3 beds

3 baths

3,128 sq ft

44486 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington 7

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

Questions? Call us: (540) 773-2470

Celebrate

213 LONG POINT DR, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22406

$357,300

2 beds

2 baths

1,340 sq ft

213 LONG POINT DR, FREDERICKSBURG, VA, 2...

Community: Celebrate

Virginia Heritage at Lee's Parke

5307 W PHILIPPI PL, FREDERICKSBURG, VA, ..., Fredericksburg, VA 22407

$475,000

3 beds

3 baths

2,507 sq ft

5307 W PHILIPPI PL, FREDERICKSBURG, VA, ...

Community: Virginia Heritage at Lee's Parke

Heritage Hunt

13154 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$725,000

3 beds

4 baths

3,195 sq ft

13154 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

Regency at Dominion Valley

15463 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$759,000

3 beds

3 baths

3,814 sq ft

15463 LEGACY WAY, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Celebrate

183 LONG POINT DR, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22406

$479,000

3 beds

3 baths

2,406 sq ft

183 LONG POINT DR, FREDERICKSBURG, VA, 2...

Community: Celebrate

The Villas of Salem Church

5620 FINLEY ROSE CT, FREDERICKSBURG, VA,..., Fredericksburg, VA 22407

$400,000

3 beds

3 baths

1,767 sq ft

5620 FINLEY ROSE CT, FREDERICKSBURG, VA,...

Community: The Villas of Salem Church

Liberty Grove

8600 LIBERTY TRL 206, MANASSAS, VA, 2011..., Manassas, VA 20110

$349,900

2 beds

3 baths

1,743 sq ft

Condo

8600 LIBERTY TRL 206, MANASSAS, VA, 2011...

Community: Liberty Grove

Woodbrook Village

221 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$389,900

2 beds

2 baths

1,384 sq ft

221 CRESTWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

Celebrate

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

$538,850

3 beds

3 baths

2,420 sq ft

97 BATTERY POINT DR, FREDERICKSBURG, VA,...

Community: Celebrate

Birchwood at Brambleton

43044 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,050,000

4 beds

3 baths

3,753 sq ft

43044 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 773-2470

Falls Run

304 BRIDGEWATER CIR, FREDERICKSBURG, VA,..., Fredericksburg, VA 22406

$449,900

3 beds

3 baths

2,504 sq ft

304 BRIDGEWATER CIR, FREDERICKSBURG, VA,...

Community: Falls Run

Liberty Grove

8600 LIBERTY TRL UNIT 201, MANASSAS, VA,..., Manassas, VA 20110

$325,000

3 beds

3 baths

1,743 sq ft

Condo

8600 LIBERTY TRL UNIT 201, MANASSAS, VA,...

Community: Liberty Grove

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER UNIT 1115, LEESB..., Leesburg, VA 20176

$325,000

1 beds

1 baths

874 sq ft

Condo

19375 CYPRESS RIDGE TER UNIT 1115, LEESB...

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

Trilogy® at Lake Frederick

213 GREBE DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$765,000

3 beds

4 baths

3,191 sq ft

213 GREBE DR, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

153 LEATHER FLOWER DR, LAKE FREDERICK, V..., Lake Frederick, VA 22630

$520,000

4 beds

4 baths

2,719 sq ft

153 LEATHER FLOWER DR, LAKE FREDERICK, V...

Community: Trilogy® at Lake Frederick

Suffield Meadows

6704 HOLLY FARM LN UNIT 109, WARRENTON, ..., Warrenton, VA 20187

$375,000

2 beds

2 baths

Condo

6704 HOLLY FARM LN UNIT 109, WARRENTON, ...

Community: Suffield Meadows

Trilogy® at Lake Frederick

117 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$815,000

3 beds

4 baths

3,601 sq ft

117 MALLARD DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Heritage Hunt

6816 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155

$815,000

3 beds

3 baths

2,846 sq ft

6816 TRED AVON PL, GAINESVILLE, VA, 2015...

Community: Heritage Hunt

Regency at Dominion Valley

15211 ROYAL CREST DR UNIT 405, HAYMARKET..., Haymarket, VA 20169

$485,000

2 beds

2 baths

1,551 sq ft

Condo

15211 ROYAL CREST DR UNIT 405, HAYMARKET...

Community: Regency at Dominion Valley

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

Questions? Call us: (540) 773-2470

Trilogy® at Lake Frederick

114 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$729,900

3 beds

4 baths

3,333 sq ft

114 TURNSTONE LN, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Liberty Grove

8610 LIBERTY TRL UNIT 201, MANASSAS, VA,..., Manassas, VA 20110

$370,000

2 beds

3 baths

1,743 sq ft

Condo

8610 LIBERTY TRL UNIT 201, MANASSAS, VA,...

Community: Liberty Grove

Celebrate

196 DENISON ST, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406

$460,000

2 beds

2 baths

1,632 sq ft

196 DENISON ST, FREDERICKSBURG, VA, 2240...

Community: Celebrate

Regency at Chancellorsville

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

$450,000

2 beds

2 baths

1,802 sq ft

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

Community: Regency at Chancellorsville

Saintsbury Plaza

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

$395,000

2 beds

2 baths

1,125 sq ft

Condo

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

Community: Saintsbury Plaza

Barley Woods

12211 GLEN OAKS DR, FREDERICKSBURG, VA, ..., Fredericksburg, VA 22407

$499,900

2 beds

2 baths

1,981 sq ft

12211 GLEN OAKS DR, FREDERICKSBURG, VA, ...

Community: Barley Woods

Birchwood at Brambleton

1 HARDESTY TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$734,990

3 beds

3 baths

2,742 sq ft

1 HARDESTY TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Falls Run

21 BUCHANAN CT, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406

$440,000

3 beds

3 baths

2,229 sq ft

21 BUCHANAN CT, FREDERICKSBURG, VA, 2240...

Community: Falls Run

Celebrate

132 HYANNIS PL, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406

$469,900

3 beds

3 baths

2,056 sq ft

132 HYANNIS PL, FREDERICKSBURG, VA, 2240...

Community: Celebrate

Heritage Hunt

6524 BOX ELDER LOOP, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$600,000

3 beds

3 baths

2,153 sq ft

6524 BOX ELDER LOOP, GAINESVILLE, VA, 20...

Community: Heritage Hunt

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

Questions? Call us: (540) 773-2470

Four Seasons at Historic Virginia

3750 CHINA GROVE MEWS, DUMFRIES, VA, 220..., Dumfries, VA 22025

$584,999

2 beds

2 baths

2,107 sq ft

3750 CHINA GROVE MEWS, DUMFRIES, VA, 220...

Community: Four Seasons at Historic Virginia

Celebrate

15 POINT BLUFF ST, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22406

$478,950

2 beds

2 baths

1,646 sq ft

15 POINT BLUFF ST, FREDERICKSBURG, VA, 2...

Community: Celebrate

Keswick Villas

7704 COLBURN DR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551

$700,000

5 beds

4 baths

3,770 sq ft

7704 COLBURN DR, SPOTSYLVANIA, VA, 22551

Community: Keswick Villas

Keswick Villas

8859 MARLOW DR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551

$410,000

3 beds

2 baths

1,388 sq ft

8859 MARLOW DR, SPOTSYLVANIA, VA, 22551

Community: Keswick Villas

Birchwood at Brambleton

42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$839,000

3 beds

3 baths

2,669 sq ft

42788 MACBETH TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

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

293 homes near Winchester

Remove Boundaries ×

Map Satellite

Call Us Call Us

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

82 communities near Winchester

293 homes near Winchester

2 beds

4 baths

3,494 sq ft

4 beds

4 baths

4,069 sq ft

3 beds

3 baths

3,128 sq ft

3 beds

3 baths

2,604 sq ft

3 beds

3 baths

3,128 sq ft

2 beds

2 baths

1,340 sq ft

3 beds

3 baths

2,507 sq ft

3 beds

4 baths

3,195 sq ft

3 beds

3 baths

3,814 sq ft

3 beds

3 baths

2,406 sq ft

3 beds

3 baths

1,767 sq ft

2 beds

3 baths

1,743 sq ft

Condo

2 beds

2 baths

1,384 sq ft

3 beds

3 baths

2,420 sq ft

4 beds

3 baths

3,753 sq ft

3 beds

3 baths

2,504 sq ft

3 beds

3 baths

1,743 sq ft

Condo

1 beds

1 baths

874 sq ft

Condo

3 beds

3 baths

2,846 sq ft

3 beds

4 baths

3,191 sq ft

4 beds

4 baths

2,719 sq ft

2 beds

2 baths

Condo

3 beds

4 baths

3,601 sq ft

3 beds

3 baths

2,846 sq ft

2 beds

2 baths