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

125 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

Willow Run

$400Ks - $600Ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

Cedar Meadows

$400Ks

Cedar Meadows, White Post, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$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

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

Questions? Call us: (540) 452-4199

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

Woodbrook Village, Winchester, VA

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

Heritage Highlands

$300Ks - $400Ks

Heritage Highlands, Lovettsville, VA

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

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

Cottage Glen

$400Ks

Cottage Glen, Winchester, VA

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

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Abrams Chase

$500Ks

Abrams Chase, Winchester, VA

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

Winchester Landing

$300Ks

Winchester Landing, Winchester, VA

Resale Only | 55+ age-restricted | Built 2023 - 2025

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

$600Ks - $800Ks

Potomac Green, Ashburn, VA

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

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

Questions? Call us: (540) 452-4199

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$300Ks - $400Ks

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 - $700Ks

Regency at Dominion Valle..., Haymarket, VA

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

The Woodlands of Urbana

$600Ks

The Woodlands of Urbana, Urbana, MD

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

5 rating (1 reviews)

Crestwood Village

$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

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

Regency at Ashburn

$800Ks - $900Ks

Regency at Ashburn, Ashburn, VA

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

Emerald Pointe

$300Ks - $400Ks

Emerald Pointe, Hagerstown, MD

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

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

Questions? Call us: (540) 452-4199

Regency at Creekside

$900Ks

Regency at Creekside, Gainesville, VA

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

Central Parke at Lowes Is...

$400Ks - $700Ks

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

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

Regency at Belmont

$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

Vistas at Lansdowne

$500Ks - $800Ks

Vistas at Lansdowne, Lansdowne, VA

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

Lexington 7

$800Ks

Lexington 7, Ashburn, VA

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

Suffield Meadows

$300Ks - $400Ks

Suffield Meadows, Warrenton, VA

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

JerMae Estates

$400Ks - $500Ks

JerMae Estates, Thurmont, MD

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

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

Four Seasons at Vint Hill, Warrenton, VA

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

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

Questions? Call us: (540) 452-4199

Boxwood Villas

$500Ks - $600Ks

Boxwood Villas, Urbana, MD

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

The Village at Foxfield

$500Ks

The Village at Foxfield, Middletown, MD

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

3.7 rating (3 reviews)

Four Seasons at Ashburn V...

$400Ks

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

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

The Villages at Broadland...

$400Ks

The Villages at Broadland..., Ashburn, VA

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

Cadence at Lansdowne

$700Ks

Cadence at Lansdowne, Lansdowne, VA

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

1...2

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

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

Lansdowne Woods of Virginia

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

$329,900

2 beds

2 baths

1,038 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 404, LEESBU...

Community: Lansdowne Woods of Virginia

Heritage Hunt

6920 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$625,000

2 beds

3 baths

2,745 sq ft

6920 NETHERSTONE CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER UNIT 1102, LEESB..., Leesburg, VA 20176

$399,000

2 beds

2 baths

1,105 sq ft

Condo

19365 CYPRESS RIDGE TER UNIT 1102, LEESB...

Community: Lansdowne Woods of Virginia

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

Questions? Call us: (540) 452-4199

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER UNIT 920, LEESBU..., Leesburg, VA 20176

$450,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 920, LEESBU...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

117 HARVESTER DR, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$899,000

4 beds

5 baths

6,096 sq ft

117 HARVESTER DR, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Liberty Grove

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

$329,900

2 beds

3 baths

1,743 sq ft

Condo

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

Community: Liberty Grove

Birchwood at Brambleton

23640 BOLTON CRESCENT TER # 13-204, ASHB..., Ashburn, VA 20148

$484,990

2 beds

2 baths

1,431 sq ft

Condo

23640 BOLTON CRESCENT TER # 13-204, ASHB...

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 114, LEESBURG, V..., Leesburg, VA 20176

$350,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 114, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

103 BURKWOOD TER, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$410,000

3 beds

3 baths

2,376 sq ft

103 BURKWOOD TER, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Birchwood at Brambleton

23631 HAVELOCK WALK TER 220, ASHBURN, VA..., Ashburn, VA 20148

$529,999

3 beds

2 baths

1,971 sq ft

Condo

23631 HAVELOCK WALK TER 220, ASHBURN, VA...

Community: Birchwood at Brambleton

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

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

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

Questions? Call us: (540) 452-4199

Montebello

21914 HAWKSBILL HIGH CIR UNIT 304, STERL..., Sterling, VA 20164

$599,000

2 beds

2 baths

1,640 sq ft

Condo

21914 HAWKSBILL HIGH CIR UNIT 304, STERL...

Community: Montebello

Trilogy® at Lake Frederick

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

$499,900

4 beds

4 baths

2,719 sq ft

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

Community: Trilogy® at Lake Frederick

Birchwood at Brambleton

23631 HAVELOCK WALK TER 318, ASHBURN, VA..., Ashburn, VA 20148

$499,900

2 beds

2 baths

1,967 sq ft

Condo

23631 HAVELOCK WALK TER 318, ASHBURN, VA...

Community: Birchwood at Brambleton

Gatherings at Wellington

9204 CHARLESTON DR UNIT 404, MANASSAS, V..., Manassas, VA 20110

$379,000

2 beds

2 baths

1,504 sq ft

Condo

9204 CHARLESTON DR UNIT 404, MANASSAS, V...

Community: Gatherings at Wellington

Birchwood at Brambleton

42729 AUTUMN DAY TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$925,000

3 beds

3 baths

2,802 sq ft

42729 AUTUMN DAY TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Heritage Hunt

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

$610,000

3 beds

3 baths

2,153 sq ft

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

Community: Heritage Hunt

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER UNIT 418, LEESBU..., Leesburg, VA 20176

$484,900

2 beds

2 baths

1,441 sq ft

Condo

19375 CYPRESS RIDGE TER UNIT 418, LEESBU...

Community: Lansdowne Woods of Virginia

Regency at Dominion Valley

5226 CANYON CREEK WAY, HAYMARKET, VA, 20..., Haymarket, VA 20169

$665,000

2 beds

2 baths

2,018 sq ft

5226 CANYON CREEK WAY, HAYMARKET, VA, 20...

Community: Regency at Dominion Valley

Lexington 7

44529 FIERY SKIPPER TER, ASHBURN, VA, 20..., Ashburn, VA 20147

$800,000

3 beds

4 baths

2,608 sq ft

44529 FIERY SKIPPER TER, ASHBURN, VA, 20...

Community: Lexington 7

Winchester Landing

113 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$369,900

3 beds

3 baths

1,505 sq ft

113 MAURY WAY, WINCHESTER, VA, 22602

Community: Winchester Landing

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

Questions? Call us: (540) 452-4199

Gatherings at Wellington

9202 CHARLESTON DR 405, MANASSAS, VA, 20..., Manassas, VA 20110

$365,000

2 beds

2 baths

1,504 sq ft

Condo

9202 CHARLESTON DR 405, MANASSAS, VA, 20...

Community: Gatherings at Wellington

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

Regency at Dominion Valley

5128 FALDO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$850,000

3 beds

4 baths

4,238 sq ft

5128 FALDO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Birchwood at Brambleton

43011 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$881,202

3 beds

4 baths

2,742 sq ft

43011 DEBONAIR TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Birchwood at Brambleton

42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$853,586

4 beds

4 baths

2,742 sq ft

42972 TRUMAN TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Trilogy® at Lake Frederick

144 COWBIRD ST, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$849,900

4 beds

4 baths

3,921 sq ft

144 COWBIRD ST, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Birchwood at Brambleton

42920 FIREFLY SONATA TER UNIT 307, ASHBU..., Ashburn, VA 20148

$590,000

3 beds

2 baths

1,630 sq ft

Condo

42920 FIREFLY SONATA TER UNIT 307, ASHBU...

Community: Birchwood at Brambleton

Albert Courts

215 STULL CT, THURMONT, MD, 21788, Thurmont, MD 21788

$299,999

3 beds

3 baths

1,532 sq ft

215 STULL CT, THURMONT, MD, 21788

Community: Albert Courts

Crestwood Village

6905 CHOKEBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$324,900

2 beds

1 baths

1,160 sq ft

6905 CHOKEBERRY CT, FREDERICK, MD, 21703

Community: Crestwood Village

Emerald Pointe

13366 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$434,900

2 beds

2 baths

2,826 sq ft

13366 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

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

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The Woodlands of Urbana

3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704

$615,000

3 beds

3 baths

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

The Village at Foxfield

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

$564,900

3 beds

3 baths

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

Crestwood Village

5722 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$349,000

2 beds

2 baths

1,264 sq ft

5722 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Emerald Pointe

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

$424,900

2 beds

2 baths

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

The Woodlands of Urbana

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

$609,900

3 beds

3 baths

1,677 sq ft

3207 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

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Virginia
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

125 homes near Winchester Area

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REIN updates its listings on a daily basis. Data last updated: Dec 11, 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

48 communities near Winchester Area

125 homes near Winchester Area

3 beds

3 baths

2,608 sq ft

3 beds

3 baths

2,649 sq ft

2 beds

2 baths

1,038 sq ft

Condo

2 beds

3 baths

2,745 sq ft

2 beds

2 baths

1,105 sq ft

Condo

3 beds

2 baths

1,475 sq ft

Condo

4 beds

5 baths

6,096 sq ft

2 beds

3 baths

1,743 sq ft

Condo

2 beds

2 baths

1,431 sq ft

Condo

2 beds

2 baths

1,038 sq ft

Condo

3 beds

3 baths

2,376 sq ft

3 beds

2 baths

1,971 sq ft

Condo

3 beds

4 baths

3,676 sq ft

2 beds

2 baths

1,059 sq ft

Condo

3 beds

2 baths

2,006 sq ft

Condo

2 beds

2 baths

1,640 sq ft

Condo

4 beds

4 baths

2,719 sq ft

2 beds

2 baths

1,967 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

3 beds

3 baths

2,802 sq ft

3 beds

3 baths

2,153 sq ft

2 beds

2 baths