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

49 communities 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

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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

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Cottage Glen

$400Ks

Cottage Glen, Winchester, VA

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

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

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Questions? Call us: (540) 452-4199

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

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

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Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Regency at Dominion Valle...

$400Ks - $500Ks

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

Resale Only | 55+ age-restricted | Built 2019 - 2025 | 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

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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

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

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

Questions? Call us: (540) 452-4199

Rosehill Manor Villas

$300Ks

Rosehill Manor Villas, Hagerstown, MD

New Construction | 55+ age-restricted | Built 2022 - present | 177 homes

Regency at Belmont

$900Ks

Regency at Belmont, Ashburn, VA

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

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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

$700Ks - $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

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

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

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Questions? Call us: (540) 452-4199

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

1...2

New The Village at Freedom Hills

13948 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$374,900

2 beds

2 baths

1,430 sq ft

13948 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

The Woodlands of Urbana

3520 STARLIGHT ST 302, FREDERICK, MD, 21..., Frederick, MD 21704

$436,900

2 beds

2 baths

1,489 sq ft

Condo

3520 STARLIGHT ST 302, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Rosehill Manor Villas

19710 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,990

2 beds

2 baths

1,811 sq ft

19710 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Emerald Pointe

13412 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$424,900

2 beds

2 baths

1,952 sq ft

13412 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Emerald Pointe

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

$349,900

2 beds

2 baths

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

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

Questions? Call us: (540) 452-4199

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Crestwood Village

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

$339,000

2 beds

2 baths

1,264 sq ft

5722 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

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

The Woodlands of Urbana

3248 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704

$640,000

3 beds

4 baths

2,276 sq ft

3248 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

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

Emerald Pointe

13218 ONYX DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$494,900

2 beds

2 baths

13218 ONYX DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

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

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

The Woodlands of Urbana

3412 ANGELICA WAY 402, FREDERICK, MD, 21..., Frederick, MD 21704

$525,000

2 beds

2 baths

Condo

3412 ANGELICA WAY 402, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

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

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

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

$609,997

3 beds

3 baths

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

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

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

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

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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 Village at Freedom Hills

13946 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$379,900

2 beds

2 baths

1,484 sq ft

13946 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

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

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

New Winchester Landing

151 MCCORMICK CIR APT 203, WINCHESTER, V..., Winchester, VA 22602

$315,000

2 beds

2 baths

1,156 sq ft

Condo

151 MCCORMICK CIR APT 203, WINCHESTER, V...

Community: Winchester Landing

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New Birchwood at Brambleton

23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN..., Ashburn, VA 20148

$724,900

3 beds

2 baths

2,148 sq ft

Condo

23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN...

Community: Birchwood at Brambleton

Regency at Dominion Valley

5429 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$735,000

3 beds

3 baths

2,524 sq ft

5429 TREVINO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Lansdowne Woods of Virginia

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

$389,000

2 beds

2 baths

1,105 sq ft

Condo

19365 CYPRESS RIDGE TER UNIT 1102, LEESB...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

42783 FIREFLY SONATA TER, ASHBURN, VA, 2..., Ashburn, VA 20148

$760,000

2 beds

3 baths

2,406 sq ft

42783 FIREFLY SONATA TER, ASHBURN, VA, 2...

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER UNIT 522, LEESBU..., Leesburg, VA 20176

$370,000

2 beds

2 baths

1,101 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 522, LEESBU...

Community: Lansdowne Woods of Virginia

Heritage Hunt

$440,000

2 beds

2 baths

1,421 sq ft

Condo

7065 HERITAGE HUNT DR 203, GAINESVILLE, ...

Community: Heritage Hunt

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Four Seasons at Ashburn Village

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,..., Ashburn, VA 20147

$429,900

2 beds

2 baths

1,612 sq ft

Condo

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,...

Community: Four Seasons at Ashburn Village

New Trilogy® at Lake Frederick

108 GADWELL LN, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$714,900

3 beds

4 baths

3,464 sq ft

108 GADWELL LN, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

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New Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER UNIT 821, LEESBU..., Leesburg, VA 20176

$367,000

2 beds

2 baths

1,246 sq ft

Condo

19385 CYPRESS RIDGE TER UNIT 821, LEESBU...

Community: Lansdowne Woods of Virginia

Heritage Hunt

13879 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$725,000

4 beds

3 baths

3,151 sq ft

13879 CRABTREE WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Heritage Hunt

6880 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$749,000

2 beds

3 baths

3,087 sq ft

6880 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

The Village at Harvest Ridge

147 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601

$639,000

3 beds

3 baths

3,153 sq ft

147 HARVEST RIDGE DR, WINCHESTER, VA, 22...

Community: The Village at Harvest Ridge

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER UNIT 708, LEESBU..., Leesburg, VA 20176

$399,000

2 beds

2 baths

1,315 sq ft

Condo

19375 CYPRESS RIDGE TER UNIT 708, LEESBU...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 901, LEESBURG, V..., Leesburg, VA 20176

$515,000

3 beds

2 baths

1,534 sq ft

Condo

19375 CYPRESS RIDGE TER 901, LEESBURG, V...

Community: Lansdowne Woods of Virginia

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

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

$369,900

3 beds

3 baths

1,962 sq ft

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

Community: Trilogy® at Lake Frederick

New Cottage Glen

129 DOONBEG CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$450,000

4 beds

3 baths

2,072 sq ft

129 DOONBEG CT, WINCHESTER, VA, 22602

Community: Cottage Glen

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

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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

Woodbrook Village

203 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$379,000

2 beds

2 baths

1,590 sq ft

203 CRESTWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

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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?

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

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49 communities

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REIN updates its listings on a daily basis. Data last updated: Jan 07, 2026.
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Winchester Area, VA 55+ active adult communities & homes for sale

49 communities near Winchester Area

113 homes near Winchester Area

2 beds

2 baths

1,430 sq ft

2 beds

2 baths

1,489 sq ft

Condo

2 beds

2 baths

1,811 sq ft

2 beds

2 baths

1,952 sq ft

2 beds

2 baths

1,834 sq ft

2 beds

2 baths

1,264 sq ft

3 beds

3 baths

1,532 sq ft

3 beds

4 baths

2,276 sq ft

3 beds

3 baths

1,677 sq ft

2 beds

2 baths

2 beds

2 baths

3 beds

3 baths

3,161 sq ft

2 beds

2 baths

Condo

3 beds

3 baths

1,816 sq ft

2 beds

2 baths

2,826 sq ft

2 beds

1 baths

1,160 sq ft

2 beds

2 baths

2,615 sq ft

2 beds

2 baths

1,484 sq ft

2 beds

3 baths

2,739 sq ft

3 beds

4 baths

3,333 sq ft

2 beds

2 baths

1,156 sq ft

Condo

3 beds

2 baths

2,148 sq ft

Condo

3 beds

3 baths

2,524 sq ft

2 beds

2 baths

1,105 sq ft

Condo

2 beds

3 baths

2,406 sq ft