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

155 homes near Winchester Area

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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

No reviews yet

Cedar Meadows

$400Ks - $400Ks

Cedar Meadows, White Post, VA

Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes

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

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

Questions? Call us: (540) 452-4199

No reviews yet

Woodbrook Village

$300Ks - $300Ks

Woodbrook Village, Winchester, VA

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

No reviews yet

Heritage Highlands

$300Ks - $400Ks

Heritage Highlands, Lovettsville, VA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes

No reviews yet

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

No reviews yet

Cottage Glen

$400Ks - $400Ks

Cottage Glen, Winchester, VA

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

No reviews yet

Abrams Chase

$500Ks - $500Ks

Abrams Chase, Winchester, VA

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

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5 rating (3 reviews)

Heritage Hunt

$600Ks - $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

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

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

Questions? Call us: (540) 452-4199

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

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

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

Central Parke at Lowes Is...

$400Ks - $700Ks

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 Area? 55places can help!

Questions? Call us: (540) 452-4199

No reviews yet

Regency at Belmont

$900Ks - $900Ks

Regency at Belmont, Ashburn, VA

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

No reviews yet

Vistas at Lansdowne

$500Ks - $800Ks

Vistas at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes

No reviews yet

Lexington 7

$700Ks - $800Ks

Lexington 7, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes

No reviews yet

Suffield Meadows

$300Ks - $400Ks

Suffield Meadows, Warrenton, VA

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 homes

No reviews yet

JerMae Estates

$400Ks - $500Ks

JerMae Estates, Thurmont, MD

Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes

No reviews yet

Albert Courts

$100Ks - $200Ks

Albert Courts, Thurmont, MD

Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes

5 rating (1 reviews)

Four Seasons at Vint Hill

$600Ks - $600Ks

Four Seasons at Vint Hill, Warrenton, VA

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes

No reviews yet

Boxwood Villas

$500Ks - $600Ks

Boxwood Villas, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes

No reviews yet

The Village at Foxfield

$300Ks - $500Ks

The Village at Foxfield, Middletown, MD

Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes

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

Questions? Call us: (540) 452-4199

3.7 rating (3 reviews)

Four Seasons at Ashburn V...

$400Ks - $400Ks

Four Seasons at Ashburn V..., Ashburn, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes

No reviews yet

The Villages at Broadland...

$400Ks - $400Ks

The Villages at Broadland..., Ashburn, VA

New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes

No reviews yet

Cadence at Lansdowne

$700Ks - $700Ks

Cadence at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes

No reviews yet

The Village at Freedom Hi...

$300Ks - $300Ks

The Village at Freedom Hi..., Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes

No reviews yet

CobbleStone Estates

$400Ks - $500Ks

CobbleStone Estates, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes

1...2

Central Parke at Lowes Island

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

$499,900

3 beds

2 baths

1,989 sq ft

Condo

20810 NOBLE TER 205, STERLING, VA, 20165

Community: Central Parke at Lowes Island

Birchwood at Brambleton

23630 HAVELOCK WALK TER UNIT 317, ASHBUR..., Ashburn, VA 20148

$525,000

3 beds

2 baths

1,518 sq ft

Condo

23630 HAVELOCK WALK TER UNIT 317, ASHBUR...

Community: Birchwood at Brambleton

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

Willow Lawn Cottages

1818 KERSHAW LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$382,500

2 beds

2 baths

1,271 sq ft

1818 KERSHAW LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Montebello

46440 BEARTOWN DR, STERLING, VA, 20164, Sterling, VA 20164

$915,000

3 beds

3 baths

2,251 sq ft

46440 BEARTOWN DR, STERLING, VA, 20164

Community: Montebello

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

Questions? Call us: (540) 452-4199

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 Square

44506 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$837,656

3 beds

3 baths

2,969 sq ft

44506 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

Lexington 7

$837,656

3 beds

3 baths

2,969 sq ft

44506 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington 7

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

Heritage Hunt

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

$775,000

3 beds

4 baths

3,192 sq ft

13882 CINCH LN, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 1002, LEESBURG, ..., Leesburg, VA 20176

$375,000

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 1002, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Regency at Dominion Valley

15218 BRIER CREEK DR, HAYMARKET, VA, 201..., Haymarket, VA 20169

$749,990

3 beds

3 baths

3,386 sq ft

15218 BRIER CREEK DR, HAYMARKET, VA, 201...

Community: Regency at Dominion Valley

Birchwood at Brambleton

23688 BOLTON CRESCENT TER APT 204, ASHBU..., Ashburn, VA 20148

$475,000

2 beds

2 baths

1,280 sq ft

Condo

23688 BOLTON CRESCENT TER APT 204, ASHBU...

Community: Birchwood at Brambleton

Gatherings at Wellington

9202 CHARLESTON DR 307, MANASSAS, VA, 20..., Manassas, VA 20110

$421,000

3 beds

2 baths

2,006 sq ft

Condo

9202 CHARLESTON DR 307, MANASSAS, VA, 20...

Community: Gatherings at Wellington

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

Questions? Call us: (540) 452-4199

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

Heritage Hunt

6769 ARTHUR HILLS DR, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$849,900

4 beds

4 baths

5,410 sq ft

6769 ARTHUR HILLS DR, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Trilogy® at Lake Frederick

102 BETONY CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$785,990

3 beds

3 baths

3,434 sq ft

102 BETONY CT, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Birchwood at Brambleton

42785 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$799,900

3 beds

3 baths

2,669 sq ft

42785 CUMULUS TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Trilogy® at Lake Frederick

102 PHACELIA WAY, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$410,000

3 beds

4 baths

2,200 sq ft

102 PHACELIA WAY, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Cadence at Lansdowne

18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176

$755,000

3 beds

3 baths

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

New 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

The Woodlands of Urbana

3207 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704

$619,900

3 beds

2 baths

1,677 sq ft

3207 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

The Village at Foxfield

1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769

$574,900

3 beds

3 baths

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

Emerald Pointe

13323 DIAMOND POINTE DR, HAGERSTOWN, MD,..., Hagerstown, MD 21742

$449,900

2 beds

2 baths

1,884 sq ft

13323 DIAMOND POINTE DR, HAGERSTOWN, MD,...

Community: Emerald Pointe

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

Questions? Call us: (540) 452-4199

New Crestwood Village

5765 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$335,000

2 beds

1 baths

1,113 sq ft

5765 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

The Woodlands of Urbana

2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704

$725,000

3 beds

4 baths

3,634 sq ft

2928 HERB GARDEN DR, FREDERICK, MD, 2170...

Community: The Woodlands of Urbana

CobbleStone Estates

9616 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740

$399,000

2 beds

2 baths

1,561 sq ft

9616 COBBLE STONE CT, HAGERSTOWN, MD, 21...

Community: CobbleStone Estates

Emerald Pointe

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$359,900

2 beds

2 baths

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Emerald Pointe

13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$449,900

2 beds

2 baths

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Emerald Pointe

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742

$429,000

2 beds

3 baths

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...

Community: Emerald Pointe

Crestwood Village

5653 SANDY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$445,000

2 beds

2 baths

1,297 sq ft

5653 SANDY CT, FREDERICK, MD, 21703

Community: Crestwood Village

Albert Courts

9 EASY ST, THURMONT, MD, 21788, Thurmont, MD 21788

$349,900

3 beds

3 baths

1,740 sq ft

9 EASY ST, THURMONT, MD, 21788

Community: Albert Courts

The Woodlands of Urbana

3272 PINE NEEDLE CIR UNIT 202, FREDERICK..., Frederick, MD 21704

$425,000

2 beds

2 baths

Condo

3272 PINE NEEDLE CIR UNIT 202, FREDERICK...

Community: The Woodlands of Urbana

Emerald Pointe

19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742

$484,900

2 beds

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...

Community: Emerald Pointe

1 2 3 4

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Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

In the Winchester Area, there are no large communities, 1 medium community with 500-1000 homes, and 9 small communities with less than 500 homes.

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

The smallest 55+ communities in the Winchester Area has 13 homes, the largest has 950 homes, and the average communities consists of 161 homes.

Are there new 55+ homes available in the Winchester Area?

Yes, there are new 55+ homes available in the Winchester Area. The most recent communities started in the Winchester Area include Abrams Chase, Cottage Glen, The Highlands at Blue Ridge Shadows. There are also 3 communities in the Winchester Area that offer new construction homes, including Abrams Chase, Trilogy® at Lake Frederick, Cottage Glen.

Are there gated 55+ communities in the Winchester Area?

Yes, there are gated 55+ communities in the Winchester Area. Approximately 30.0% of 55+ communities in the area are gated. For instance, Cedar Meadows is a gated communities with 129 homes, and Trilogy® at Lake Frederick is another gated communities with 950 homes.

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

On average, listings in 55+ communities in the Winchester Area stay on the market for around 602 days. The average price of homes for sale in these communities is approximately $484,040, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Highlands at Blue Ridge Shadows average around $615,000, while homes in Cottage Glen average around $479,500.

Want to learn more about 55+ communities in the Winchester Area?

Insights and market stats
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Answers from local 55+ experts

Want to learn more about 55+ communities in Winchester Area?

Call us: (540) 452-4199

155 homes near Winchester Area

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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: Oct 23, 2025.
This application does not include information on all of the properties available for sale at this time.

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

46 communities near Winchester Area

155 homes near Winchester Area

3 beds

2 baths

1,989 sq ft

Condo

3 beds

2 baths

1,518 sq ft

Condo

2 beds

2 baths

1,625 sq ft

Condo

2 beds

2 baths

1,271 sq ft

3 beds

3 baths

2,251 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

2,969 sq ft

3 beds

3 baths

2,969 sq ft

2 beds

2 baths

1,967 sq ft

Condo

3 beds

4 baths

3,192 sq ft

2 beds

2 baths

1,038 sq ft

Condo

3 beds

3 baths

3,386 sq ft

2 beds

2 baths

1,280 sq ft

Condo

3 beds

2 baths

2,006 sq ft

Condo

2 beds

3 baths

1,743 sq ft

Condo

4 beds

4 baths

5,410 sq ft

3 beds

3 baths

3,434 sq ft

3 beds

3 baths

2,669 sq ft

3 beds

4 baths

2,200 sq ft

3 beds

3 baths

2,649 sq ft

2 beds

2 baths

1,225 sq ft

3 beds

2 baths

1,677 sq ft