Winchester Area, VA 55+ active adult communities & homes for sale - Page 5

202 homes near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

$300ks - $1Ms

Trilogy® at Lake Frederic..., Lake Frederick, VA

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

The Flats at Heathcote Vi...

$300ks - $500ks

The Flats at Heathcote Vi..., Haymarket, VA

New Construction | 55+ age-restricted | Built 2026 - present | 500 homes

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$200ks - $500ks

Lansdowne Woods of Virgin..., Lansdowne, VA

Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 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 (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes

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

Questions? Call us: (540) 452-4199

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

5 rating (1 reviews)

Regency at Dominion Valle...

$300ks - $1Ms

Regency at Dominion Valle..., Haymarket, VA

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

New Construction | 55+ age-restricted | Built 2026 - present

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.

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Montebello

$500ks - $1Ms

Montebello, Sterling, VA

New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

The Village at Freedom Hi...

$300ks

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

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes

Regency at Belmont

$600ks - $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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes

3.7 rating (3 reviews)

Four Seasons at Ashburn V...

$300ks - $400ks

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

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

The Retreat at Poland Hil...

$800ks

The Retreat at Poland Hil..., Chantilly, VA

Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes

Central Parke at Lowes Is...

$300ks - $600ks

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

New Construction | 55+ age-restricted | Built 2023 - present | 50 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 Highlands at Blue Rid...

$400ks - $600ks

The Highlands at Blue Rid..., Front Royal, VA

Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes

The Villages at Broadland...

$400ks

The Villages at Broadland..., Ashburn, VA

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

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

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

Questions? Call us: (540) 452-4199

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

New Construction | 55+ age-restricted | Built 2024 - present | 23 homes

1...2

Cedar Meadows

103 BLEEDING HEART DR, WHITE POST, VA, 2..., White Post, VA 22663

$460,000

3 beds

2 baths

1,493 sq ft

103 BLEEDING HEART DR, WHITE POST, VA, 2...

Community: Cedar Meadows

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 1111, LEESBURG, ..., Leesburg, VA 20176

$449,900

3 beds

2 baths

1,475 sq ft

Condo

19375 CYPRESS RIDGE TER 1111, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

104 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$739,990

3 beds

3 baths

2,457 sq ft

104 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

121 MILKWEED, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$879,900

3 beds

4 baths

4,213 sq ft

121 MILKWEED, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

110 COTTONTAIL DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$550,000

3 beds

3 baths

2,860 sq ft

110 COTTONTAIL DR, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Heritage Hunt

13703 CURRANT LOOP, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$565,000

3 beds

3 baths

2,050 sq ft

13703 CURRANT LOOP, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Willow Run

232 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$640,990

4 beds

3 baths

2,909 sq ft

232 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

Willow Run

234 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$636,990

4 beds

3 baths

2,865 sq ft

234 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

Willow Run

125 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$459,990

3 beds

2 baths

1,492 sq ft

125 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Willow Run

122 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$509,990

4 beds

3 baths

2,168 sq ft

122 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Trilogy® at Lake Frederick

118 TWINLEAF WAY, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$384,900

3 beds

3 baths

1,848 sq ft

118 TWINLEAF WAY, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Emerald Pointe

19553 TURQUOISE DR V222, HAGERSTOWN, MD,..., Hagerstown, MD 21742

$484,900

2 beds

2 baths

1,850 sq ft

19553 TURQUOISE DR V222, HAGERSTOWN, MD,...

Community: Emerald Pointe

Trilogy® at Lake Frederick

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

$599,900

3 beds

3 baths

2,721 sq ft

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

Community: Trilogy® at Lake Frederick

Crestwood Village

5661 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703

$415,000

2 beds

2 baths

1,297 sq ft

5661 CRABAPPLE DR, FREDERICK, MD, 21703

Community: Crestwood Village

Emerald Pointe

13301 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$404,900

2 beds

2 baths

1,726 sq ft

13301 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Cedar Meadows

108 TRUMPET VINE DR, WHITE POST, VA, 226..., White Post, VA 22663

$449,000

3 beds

2 baths

1,647 sq ft

108 TRUMPET VINE DR, WHITE POST, VA, 226...

Community: Cedar Meadows

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

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

3422 ANGELICA WAY 103, FREDERICK, MD, 21..., Frederick, MD 21704

$405,900

2 beds

2 baths

1,489 sq ft

Condo

3422 ANGELICA WAY 103, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 510, LEESBURG, V..., Leesburg, VA 20176

$419,000

2 beds

2 baths

1,251 sq ft

Condo

19365 CYPRESS RIDGE TER 510, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

107 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630

$659,920

4 beds

4 baths

3,190 sq ft

107 CABBAGE WHITE DR, LAKE FREDERICK, VA...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

106 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$749,990

2 beds

2 baths

2,058 sq ft

106 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Willow Lawn Cottages

1851 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$379,900

2 beds

2 baths

1,405 sq ft

1851 MELVOR LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 1115, LEESBURG, ..., Leesburg, VA 20176

$490,000

3 beds

2 baths

1,475 sq ft

Condo

19365 CYPRESS RIDGE TER 1115, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 802, LEESBURG, V..., Leesburg, VA 20176

$490,000

3 beds

2 baths

1,560 sq ft

Condo

19355 CYPRESS RIDGE TER 802, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 1122, LEESBURG, ..., Leesburg, VA 20176

$350,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 1122, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

107 YELLOW BIRCH, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$969,999

3 beds

5 baths

4,465 sq ft

107 YELLOW BIRCH, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

124 CHECKERSPOT WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$429,000

4 beds

4 baths

2,508 sq ft

124 CHECKERSPOT WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Emerald Pointe

13428 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$419,000

2 beds

2 baths

1,953 sq ft

13428 MARQUISE 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

Trilogy® at Lake Frederick

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

$600,000

2 beds

2 baths

2,089 sq ft

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

Community: Trilogy® at Lake Frederick

Willow Run

228 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$646,045

3 beds

2 baths

1,888 sq ft

228 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

Birchwood at Brambleton

23631 HAVELOCK WALK TER 421, ASHBURN, VA..., Ashburn, VA 20148

$540,000

3 beds

2 baths

1,906 sq ft

Condo

23631 HAVELOCK WALK TER 421, ASHBURN, VA...

Community: Birchwood at Brambleton

Rosehill Manor Villas

19604 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$374,900

2 beds

2 baths

1,767 sq ft

19604 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Willow Run

117 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602

$584,990

4 beds

3 baths

2,865 sq ft

117 SCENTED ROSE WAY, WINCHESTER, VA, 22...

Community: Willow Run

Cadence at Lansdowne

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

$735,500

3 beds

3 baths

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

Rosehill Manor Villas

13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742

$367,990

3 beds

2 baths

1,466 sq ft

13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...

Community: Rosehill Manor Villas

Rosehill Manor Villas

13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742

$379,999

3 beds

2 baths

1,687 sq ft

13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...

Community: Rosehill Manor Villas

Gatherings at Wellington

10275 FOUNTAIN CIR 201, MANASSAS, VA, 20..., Manassas, VA 20110

$339,900

2 beds

2 baths

1,441 sq ft

Condo

10275 FOUNTAIN CIR 201, MANASSAS, VA, 20...

Community: Gatherings at Wellington

The Village at Freedom Hills

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

$349,900

2 beds

2 baths

1,430 sq ft

13948 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

Trilogy® at Lake Frederick

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

$680,000

3 beds

4 baths

3,333 sq ft

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

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Emerald Pointe

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

$409,900

2 beds

2 baths

1,952 sq ft

13412 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 920, LEESBURG, V..., Leesburg, VA 20176

$450,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER 920, LEESBURG, V...

Community: Lansdowne Woods of Virginia

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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 10 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 173 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 Winchester Landing, Abrams Chase, Cottage Glen. There are also 4 communities in the Winchester Area that offer new construction homes, including Cottage Glen, Trilogy® at Lake Frederick, Willow Run.

Are there gated 55+ communities in the Winchester Area?

Yes, there are gated 55+ communities in the Winchester Area. Approximately 33.3% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes, and Cedar Meadows is another gated communities with 129 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 620 days. The average price of homes for sale in these communities is approximately $480,385, 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 $625,881, while homes in Cottage Glen average around $464,750.

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

Insights and market stats
Instant new home alerts
Answers from local 55+ experts

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

Call us: (540) 452-4199

202 homes

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© 2026 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: Jul 21, 2026.
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Winchester Area, VA 55+ active adult communities & homes for sale - Page 5

51 communities near Winchester Area

202 homes near Winchester Area

3 beds

2 baths

1,493 sq ft

3 beds

2 baths

1,475 sq ft

Condo

3 beds

3 baths

2,457 sq ft

3 beds

4 baths

4,213 sq ft

3 beds

3 baths

2,860 sq ft

3 beds

3 baths

2,050 sq ft

4 beds

3 baths

2,909 sq ft

4 beds

3 baths

2,865 sq ft

3 beds

2 baths

1,492 sq ft

4 beds

3 baths

2,168 sq ft

3 beds

3 baths

1,848 sq ft

2 beds

2 baths

1,850 sq ft

3 beds

3 baths

2,721 sq ft

2 beds

2 baths

1,297 sq ft

2 beds

2 baths

1,726 sq ft

3 beds

2 baths

1,647 sq ft

2 beds

2 baths

1,489 sq ft

Condo

2 beds

2 baths

1,251 sq ft

Condo

4 beds

4 baths

3,190 sq ft

2 beds

2 baths

2,058 sq ft

2 beds

2 baths

1,405 sq ft

3 beds

2 baths

1,475 sq ft

Condo

3 beds

2 baths

1,560 sq ft

Condo

2 beds

2 baths

1,038 sq ft