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

248 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

$400Ks - $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 - $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

$400Ks - $900Ks

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

$200Ks - $800Ks

Penn National, Fayetteville, PA

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

2.8 rating (6 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 - $800Ks

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 - $600Ks

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'...

$400Ks - $600Ks

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

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

4.3 rating (3 reviews)

Falls Run

$400Ks - $400Ks

Falls Run, Fredericksburg, VA

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

No reviews yet

The Woodlands of Urbana

$400Ks - $900Ks

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

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

$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

Regency at Ashburn

$600Ks - $600Ks

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...

$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 - $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 - $500Ks

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 - $500Ks

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

$900Ks - $900Ks

Regency at Belmont, Ashburn, VA

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

No reviews yet

Four Seasons at Charlotte...

$400Ks - $500Ks

Four Seasons at Charlotte..., Ruckersville, VA

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

No reviews yet

Courts of Clarksburg

$600Ks - $700Ks

Courts of Clarksburg, Clarksburg, MD

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

1 2...3

New Keswick Villas

8816 SELBY CT, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551

$440,625

3 beds

4 baths

2,145 sq ft

8816 SELBY CT, SPOTSYLVANIA, VA, 22551

Community: Keswick Villas

New Keswick Villas

8812 SELBY CT, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551

$475,375

3 beds

4 baths

2,145 sq ft

8812 SELBY CT, SPOTSYLVANIA, VA, 22551

Community: Keswick Villas

Four Seasons at Virginia Crossing

3720 HAVERTILL LN UNIT 303, WOODBRIDGE, ..., Woodbridge, VA 22193

$475,000

2 beds

2 baths

1,706 sq ft

Condo

3720 HAVERTILL LN UNIT 303, WOODBRIDGE, ...

Community: Four Seasons at Virginia Crossing

Liberty Grove

8600 LIBERTY TRL 102, MANASSAS, VA, 2011..., Manassas, VA 20110

$320,000

1 beds

2 baths

1,131 sq ft

Condo

8600 LIBERTY TRL 102, MANASSAS, VA, 2011...

Community: Liberty Grove

Liberty Grove

8600 LIBERTY TRL UNIT 303, MANASSAS, VA,..., Manassas, VA 20110

$370,000

2 beds

3 baths

1,743 sq ft

Condo

8600 LIBERTY TRL UNIT 303, MANASSAS, VA,...

Community: Liberty Grove

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

Questions? Call us: (540) 773-2470

Montebello

21899 HAWKSBILL HIGH CIR, STERLING, VA, ..., Sterling, VA 20164

$890,000

3 beds

3 baths

2,218 sq ft

21899 HAWKSBILL HIGH CIR, STERLING, VA, ...

Community: Montebello

Falls Run

227 SMITHFIELD WAY, FREDERICKSBURG, VA, ..., Fredericksburg, VA 22406

$478,500

3 beds

3 baths

2,334 sq ft

227 SMITHFIELD WAY, FREDERICKSBURG, VA, ...

Community: Falls Run

Regency at Chancellorsville

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

$487,500

2 beds

2 baths

1,802 sq ft

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

Community: Regency at Chancellorsville

Regency at Ashburn

44589 YORK CREST TER APT 300, ASHBURN, V..., Ashburn, VA 20147

$609,900

3 beds

2 baths

1,825 sq ft

Condo

44589 YORK CREST TER APT 300, ASHBURN, V...

Community: Regency at Ashburn

Falls Run

12 BRUNSWICK DR, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406

$475,000

3 beds

3 baths

2,492 sq ft

12 BRUNSWICK DR, FREDERICKSBURG, VA, 224...

Community: Falls Run

Birchwood at Brambleton

23630 HAVELOCK WALK TER UNIT 218, ASHBUR..., Ashburn, VA 20148

$569,900

2 beds

2 baths

1,967 sq ft

Condo

23630 HAVELOCK WALK TER UNIT 218, ASHBUR...

Community: Birchwood at Brambleton

The Retreat at Poland Hill

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

$969,950

4 beds

4 baths

3,553 sq ft

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

Community: The Retreat at Poland Hill

New Four Seasons at Charlottesville

795 FOUR SEASONS DR, RUCKERSVILLE, VA, 2..., Ruckersville, VA 22968

$448,800

3 beds

2 baths

1,825 sq ft

795 FOUR SEASONS DR, RUCKERSVILLE, VA, 2...

Community: Four Seasons at Charlottesville

Heritage Hunt

$369,000

2 beds

2 baths

1,206 sq ft

Condo

7065 HERITAGE HUNT DR APT 101, GAINESVIL...

Community: Heritage Hunt

Virginia Heritage at Lee's Parke

6020 E GREENBRIER RIVER RD, FREDERICKSBU..., Fredericksburg, VA 22407

$609,000

4 beds

3 baths

3,317 sq ft

6020 E GREENBRIER RIVER RD, FREDERICKSBU...

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

Montebello

46394 ROSE RIVER TER, STERLING, VA, 2016..., Sterling, VA 20164

$774,900

2 beds

2 baths

1,688 sq ft

46394 ROSE RIVER TER, STERLING, VA, 2016...

Community: Montebello

Trilogy® at Lake Frederick

135 SKIPPER DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$635,500

4 beds

4 baths

2,907 sq ft

135 SKIPPER DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

104 FOAM FLOWER DR, LAKE FREDERICK, VA, ..., Lake Frederick, VA 22630

$525,000

2 beds

2 baths

1,632 sq ft

104 FOAM FLOWER DR, LAKE FREDERICK, VA, ...

Community: Trilogy® at Lake Frederick

Virginia Heritage at Lee's Parke

6200 E DRANESVILLE DR, FREDERICKSBURG, V..., Fredericksburg, VA 22407

$599,999

3 beds

4 baths

2,566 sq ft

6200 E DRANESVILLE DR, FREDERICKSBURG, V...

Community: Virginia Heritage at Lee's Parke

Keswick Villas

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

$415,000

3 beds

2 baths

1,388 sq ft

8859 MARLOW DR, SPOTSYLVANIA, VA, 22551

Community: Keswick Villas

Regency at Dominion Valley

15691 ALDERBROOK DR, HAYMARKET, VA, 2016..., Haymarket, VA 20169

$899,000

2 beds

3 baths

4,124 sq ft

15691 ALDERBROOK DR, HAYMARKET, VA, 2016...

Community: Regency at Dominion Valley

Heritage Hunt

$405,000

2 beds

2 baths

1,388 sq ft

Condo

7065 HERITAGE HUNT DR APT 309, GAINESVIL...

Community: Heritage Hunt

Falls Run

11 LUCKETTS DR, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406

$399,400

2 beds

2 baths

1,552 sq ft

11 LUCKETTS DR, FREDERICKSBURG, VA, 2240...

Community: Falls Run

Saintsbury Plaza

2907 SAINTSBURY PLZ 206, FAIRFAX, VA, 22..., Fairfax, VA 22031

$450,000

2 beds

2 baths

1,368 sq ft

Condo

2907 SAINTSBURY PLZ 206, FAIRFAX, VA, 22...

Community: Saintsbury Plaza

Heritage Hunt

6037 CALUMET CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$725,000

2 beds

4 baths

2,710 sq ft

6037 CALUMET CT, GAINESVILLE, VA, 20155

Community: Heritage Hunt

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

Questions? Call us: (540) 773-2470

Cross Creek Village

109 CRANBERRY CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$425,000

2 beds

2 baths

1,686 sq ft

109 CRANBERRY CT, WINCHESTER, VA, 22602

Community: Cross Creek Village

Gatherings at Potomac Station

700 MOUNT AIRY TER NE UNIT 403A, LEESBUR..., Leesburg, VA 20176

$484,999

2 beds

2 baths

1,410 sq ft

Condo

700 MOUNT AIRY TER NE UNIT 403A, LEESBUR...

Community: Gatherings at Potomac Station

Falls Run

95 ASPEN HILL DR, FREDERICKSBURG, VA, 22..., Fredericksburg, VA 22406

$300,000

2 beds

2 baths

1,226 sq ft

Condo

95 ASPEN HILL DR, FREDERICKSBURG, VA, 22...

Community: Falls Run

Gatherings at Wellington

10275 FOUNTAIN CIR 206, MANASSAS, VA, 20..., Manassas, VA 20110

$405,000

2 beds

2 baths

1,558 sq ft

Condo

10275 FOUNTAIN CIR 206, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Four Seasons at Vint Hill

3607 MAUCHLEY CT, WARRENTON, VA, 20187, Warrenton, VA 20187

$624,950

2 beds

2 baths

2,156 sq ft

3607 MAUCHLEY CT, WARRENTON, VA, 20187

Community: Four Seasons at Vint Hill

Belmont Bay

609 ANGELFISH WAY, WOODBRIDGE, VA, 22191, Woodbridge, VA 22191

$821,211

3 beds

4 baths

2,849 sq ft

609 ANGELFISH WAY, WOODBRIDGE, VA, 22191

Community: Belmont Bay

Legacy Woods

$475,000

4 beds

3 baths

2,565 sq ft

11901 LEGACY WOODS DR, FREDERICKSBURG, V...

Community: Legacy Woods

Central Parke at Lowes Island

20810 NOBLE TER 205, STERLING, VA, 20165, Sterling, VA 20165

$510,000

3 beds

2 baths

1,989 sq ft

Condo

20810 NOBLE TER 205, STERLING, VA, 20165

Community: Central Parke at Lowes Island

New Trilogy® at Lake Frederick

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

$749,000

3 beds

3 baths

2,937 sq ft

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

Community: Trilogy® at Lake Frederick

New Virginia Heritage at Lee's Parke

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

$529,900

4 beds

4 baths

3,552 sq ft

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

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

Gatherings at Potomac Station

750 MOUNT AIRY TER NE UNIT 402, LEESBURG..., Leesburg, VA 20176

$569,900

2 beds

2 baths

1,625 sq ft

Condo

750 MOUNT AIRY TER NE UNIT 402, LEESBURG...

Community: Gatherings at Potomac Station

Potomac Green

20559 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$865,000

3 beds

3 baths

2,267 sq ft

20559 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

Belmont Bay

13825 ESTUARY PL, WOODBRIDGE, VA, 22191, Woodbridge, VA 22191

$819,999

4 beds

4 baths

3,144 sq ft

13825 ESTUARY PL, WOODBRIDGE, VA, 22191

Community: Belmont Bay

Virginia Heritage at Lee's Parke

5810 NEW BERNE RD, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22407

$649,900

3 beds

4 baths

3,354 sq ft

5810 NEW BERNE RD, FREDERICKSBURG, VA, 2...

Community: Virginia Heritage at Lee's Parke

Celebrate

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

$484,000

2 beds

2 baths

1,445 sq ft

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

Community: Celebrate

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.

Want to learn more about 55+ communities in Winchester?

Call us: (540) 773-2470

248 homes near Winchester

Remove Boundaries ×

Map Satellite

Call Us Call Us

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

81 communities near Winchester

248 homes near Winchester

3 beds

4 baths

2,145 sq ft

3 beds

4 baths

2,145 sq ft

2 beds

2 baths

1,706 sq ft

Condo

1 beds

2 baths

1,131 sq ft

Condo

2 beds

3 baths

1,743 sq ft

Condo

3 beds

3 baths

2,218 sq ft

3 beds

3 baths

2,334 sq ft

2 beds

2 baths

1,802 sq ft

3 beds

2 baths

1,825 sq ft

Condo

3 beds

3 baths

2,492 sq ft

2 beds

2 baths

1,967 sq ft

Condo

4 beds

4 baths

3,553 sq ft

3 beds

2 baths

1,825 sq ft

2 beds

2 baths

1,206 sq ft

Condo

4 beds

3 baths

3,317 sq ft

2 beds

2 baths

1,688 sq ft

4 beds

4 baths

2,907 sq ft

2 beds

2 baths

1,632 sq ft

3 beds

4 baths

2,566 sq ft

3 beds

2 baths

1,388 sq ft

2 beds

3 baths

4,124 sq ft

2 beds

2 baths

1,388 sq ft

Condo

2 beds

2 baths

1,552 sq ft

2 beds