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Isle of Wight, VA 55+ active adult communities & homes for sale - Page 2

41 communities near Isle of Wight

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The Landings at Bennett's...
$600Ks - $700Ks
The Landings at Bennett's..., Suffolk, VA
New and Resale | 55+ age-restricted | Built 2020 - present | 23 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Want to learn more about 55+ rental communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
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.
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Questions? Call us: (888) 625-4885
Ford's Colony 104 PORTLAND, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$919,900

4 beds

|

3 baths

|

3,614 sq ft

|

Detached

104 PORTLAND, WILLIAMSBURG, VA, 23188
Community: Ford's Colony
Retreat at Edinburgh Farms 2008 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$586,740

4 beds

|

2 baths

|

2,584 sq ft

|

Townhome

2008 MUNRO LN, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2021 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$584,990

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

2021 BARTON LN, CHESAPEAKE, VA, 23322
Ford's Colony 124 AUGUSTA, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$610,000

3 beds

|

3 baths

|

2,475 sq ft

|

Detached

124 AUGUSTA, WILLIAMSBURG, VA, 23188
Community: Ford's Colony
New Kingsmill 120 ROFFINGHAMS WAY, WILLIAMSBURG, VA, 2..., Williamsburg, VA 23185
$1,100,000

4 beds

|

4 baths

|

3,755 sq ft

|

Detached

120 ROFFINGHAMS WAY, WILLIAMSBURG, VA, 2...
Community: Kingsmill
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New Colonial Heritage 6342 CORDELIA RD, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23188
$525,000

3 beds

|

3 baths

|

1,936 sq ft

|

Detached

6342 CORDELIA RD, WILLIAMSBURG, VA, 2318...
Community: Colonial Heritage
Oak Crest Townhomes 8691 COASTAL TER, MECHANICSVILLE, VA, 23..., Mechanicsville, VA 23111
$459,990

3 beds

|

3 baths

|

1,960 sq ft

|

Condo

8691 COASTAL TER, MECHANICSVILLE, VA, 23...
Community: Oak Crest Townhomes
Retreat at Edinburgh Farms 2142 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$557,990

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2142 EDWIN DR, CHESAPEAKE, VA, 23322
New Town 5406 BEVERLY LN, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$499,000

3 beds

|

3 baths

|

1,826 sq ft

|

Townhome

5406 BEVERLY LN, WILLIAMSBURG, VA, 23188
Community: New Town
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 Villages at West Neck 2709 BROWNING DR, VIRGINIA BEACH, VA, 23..., Virginia Beach, VA 23456
$418,900

3 beds

|

2 baths

|

1,756 sq ft

|

Townhome

2709 BROWNING DR, VIRGINIA BEACH, VA, 23...
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Colonial Heritage 3931 ISAAC CIR, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$699,900

5 beds

|

4 baths

|

3,400 sq ft

|

Detached

3931 ISAAC CIR, WILLIAMSBURG, VA, 23188
Community: Colonial Heritage
New New Town 4907 SETTLERS MARKET BLVD, WILLIAMSBURG,..., Williamsburg, VA 23188
$559,000

3 beds

|

4 baths

|

2,360 sq ft

|

Townhome

4907 SETTLERS MARKET BLVD, WILLIAMSBURG,...
Community: New Town
Ford's Colony 105 GULLANE, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$849,900

4 beds

|

5 baths

|

4,873 sq ft

|

Detached

105 GULLANE, WILLIAMSBURG, VA, 23188
Community: Ford's Colony
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
New Eagle Pointe at Cahoon Plantation 551 DUNNING LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$465,000

3 beds

|

2 baths

|

1,760 sq ft

|

Townhome

551 DUNNING LN, CHESAPEAKE, VA, 23322
Kingsmill 230 PADGETTS ORDINARY, WILLIAMSBURG, VA,..., Williamsburg, VA 23185
$380,000

3 beds

|

3 baths

|

1,560 sq ft

|

Townhome

230 PADGETTS ORDINARY, WILLIAMSBURG, VA,...
Community: Kingsmill
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Questions? Call us: (888) 625-4885
Kingsmill 215 PADGETTS ORDINARY, WILLIAMSBURG, VA,..., Williamsburg, VA 23185
$299,900

2 beds

|

2 baths

|

1,230 sq ft

|

Townhome

215 PADGETTS ORDINARY, WILLIAMSBURG, VA,...
Community: Kingsmill
Kingsmill 713 GRAVES ORDINARY, WILLIAMSBURG, VA, 2..., Williamsburg, VA 23185
$415,000

3 beds

|

3 baths

|

1,752 sq ft

|

Townhome

713 GRAVES ORDINARY, WILLIAMSBURG, VA, 2...
Community: Kingsmill
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.
Kingsmill 122 PELHAMS ORDINARY, WILLIAMSBURG, VA, ..., Williamsburg, VA 23185
$289,900

2 beds

|

2 baths

|

1,190 sq ft

|

Townhome

122 PELHAMS ORDINARY, WILLIAMSBURG, VA, ...
Community: Kingsmill
Ford's Colony 109 WOODHALL SPA, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23188
$725,000

3 beds

|

4 baths

|

3,445 sq ft

|

Detached

109 WOODHALL SPA, WILLIAMSBURG, VA, 2318...
Community: Ford's Colony
Kingsmill 214 ARCHERS MEAD, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23185
$479,000

3 beds

|

3 baths

|

2,262 sq ft

|

Townhome

214 ARCHERS MEAD, WILLIAMSBURG, VA, 2318...
Community: Kingsmill
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Retreat at Edinburgh Farms 2152 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$530,740

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2152 EDWIN DR, CHESAPEAKE, VA, 23322
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
Ford's Colony 1240 TREVISO BAY, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23188
$649,990

4 beds

|

2 baths

|

2,714 sq ft

|

Townhome

1240 TREVISO BAY, WILLIAMSBURG, VA, 2318...
Community: Ford's Colony
Walnut Farm 1106 HITCHENS LN, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23188
$483,000

3 beds

|

2 baths

|

1,737 sq ft

|

Detached

1106 HITCHENS LN, WILLIAMSBURG, VA, 2318...
Community: Walnut Farm
The Retreat at Western Branch 4719 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$498,575

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

4719 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Retreat at Edinburgh Farms 2212 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$574,990

3 beds

|

3 baths

|

2,314 sq ft

|

Townhome

2212 EDWIN DR, CHESAPEAKE, VA, 23322
Want to learn more about 55+ rental communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
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.
Retreat at Edinburgh Farms 2144 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$569,990

3 beds

|

3 baths

|

2,314 sq ft

|

Townhome

2144 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2017 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$554,990

4 beds

|

3 baths

|

2,781 sq ft

|

Townhome

2017 BARTON LN, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2013 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$584,990

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

2013 BARTON LN, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2216 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$574,990

3 beds

|

3 baths

|

2,314 sq ft

|

Townhome

2216 EDWIN DR, CHESAPEAKE, VA, 23322
The Retreat at Western Branch 4723 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$493,248

4 beds

|

3 baths

|

2,880 sq ft

|

Townhome

4723 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Meredith Place 7752 HOMEPLACE CT, MECHANICSVILLE, VA, 2..., Mechanicsville, VA 23111
$415,000

2 beds

|

2 baths

|

1,536 sq ft

|

House

7752 HOMEPLACE CT, MECHANICSVILLE, VA, 2...
Community: Meredith Place
The Groves at New Kent 7571 SOUTHAMPTONSHIRE WAY, NEW KENT, VA,..., New Kent, VA 23124
$435,000

2 beds

|

2 baths

|

1,744 sq ft

|

House

7571 SOUTHAMPTONSHIRE WAY, NEW KENT, VA,...
Meredith Place 8125 JANICE AVE, MECHANICSVILLE, VA, 231..., Mechanicsville, VA 23111
$435,000

3 beds

|

2 baths

|

1,796 sq ft

|

House

8125 JANICE AVE, MECHANICSVILLE, VA, 231...
Community: Meredith Place
Walnut Farm 1212 HITCHENS LN, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23188
$695,000

4 beds

|

3 baths

|

2,875 sq ft

|

Detached

1212 HITCHENS LN, WILLIAMSBURG, VA, 2318...
Community: Walnut Farm
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 Cottages at Viniterra 8614 TERROIR LN, NEW KENT, VA, 23124, New Kent, VA 23124
$735,000

4 beds

|

3 baths

|

2,475 sq ft

|

House

8614 TERROIR LN, NEW KENT, VA, 23124
Want to learn more about 55+ rental communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
New The Villages at West Neck 2831 ROSE GARDEN WAY, VIRGINIA BEACH, VA..., Virginia Beach, VA 23456
$369,900

3 beds

|

2 baths

|

1,778 sq ft

|

Townhome

2831 ROSE GARDEN WAY, VIRGINIA BEACH, VA...
Colonial Heritage 6752 TARPLEYS TAVERN RD, WILLIAMSBURG, V..., Williamsburg, VA 23188
$610,000

3 beds

|

2 baths

|

3,048 sq ft

|

Detached

6752 TARPLEYS TAVERN RD, WILLIAMSBURG, V...
Community: Colonial Heritage
The Villages at West Neck 3532 WINDING TRAIL CIR, VIRGINIA BEACH, ..., Virginia Beach, VA 23456
$327,500

3 beds

|

2 baths

|

1,554 sq ft

|

Townhome

3532 WINDING TRAIL CIR, VIRGINIA BEACH, ...
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
The Villages at West Neck 3418 MISTY DAWN CT, VIRGINIA BEACH, VA, ..., Virginia Beach, VA 23456
$435,000

3 beds

|

2 baths

|

1,876 sq ft

|

Townhome

3418 MISTY DAWN CT, VIRGINIA BEACH, VA, ...
The Commons at Hunningdon Lakes 809 MASON CT, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320
$440,000

3 beds

|

2 baths

|

2,225 sq ft

|

Detached

809 MASON CT, CHESAPEAKE, VA, 23320

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