Call us at (888) 625-4885 to learn more about active adult communities in Isle of Wight

Isle of Wight, VA 55+ active adult communities & homes for sale - Page 3

269 homes near Isle of Wight

Sort by:

Relevance

Relevance

South Harbor Towns
$300Ks - $400Ks
South Harbor Towns, Isle of Wight, VA
New Construction | 55+ age-restricted | Built 2023 - present | 300 homes
5 rating (2 reviews) Ford's Colony
$500Ks - $1Ms
Ford's Colony, Williamsburg, VA
New and Resale | Age-targeted | Built 1987 - present | 3,250 homes
Kingsmill
$200Ks - $1Ms
Kingsmill, Williamsburg, VA
New and Resale | Age-targeted | Built 1975 - present | 2,354 homes
4.3 rating (15 reviews) Colonial Heritage
$400Ks - $600Ks
Colonial Heritage, Williamsburg, VA
New and Resale | 55+ age-restricted | Built 2004 - present | 1,800 homes
4 rating (3 reviews) The Villages at West Neck
$300Ks - $500Ks
The Villages at West Neck, Virginia Beach, VA
Resale Only | 55+ age-restricted | Built 2001 - 2014 | 936 homes
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
The Governor's Land at Tw...
$700Ks - $3Ms
The Governor's Land at Tw..., Williamsburg, VA
New and Resale | Age-targeted | 750 homes
4.4 rating (5 reviews) Eagle Pointe at Cahoon Pl...
$300Ks - $600Ks
Eagle Pointe at Cahoon Pl..., Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2005 - present | 501 homes
4.5 rating (12 reviews) The Groves at New Kent
$300Ks - $400Ks
The Groves at New Kent, New Kent, VA
New and Resale | 55+ age-restricted | Built 2010 - present | 455 homes
The Settlement at Powhata...
$400Ks - $600Ks
The Settlement at Powhata..., Williamsburg, VA
Resale Only | 55+ age-restricted | Built 2008 - 2017 | 400 homes
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.
New Town
$400Ks - $500Ks
New Town, Williamsburg, VA
New and Resale | Age-targeted | Built 2005 - present | 250 homes
The Retreat at Greenbrier
$400Ks
The Retreat at Greenbrier, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2003 - 2015 | 184 homes
4.5 rating (4 reviews) Settler's Ridge
$300Ks - $500Ks
Settler's Ridge, Richmond, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 166 homes
The Villas at Rose Hill
$400Ks - $500Ks
The Villas at Rose Hill, Mechanicsville, VA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 157 homes
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (1 reviews) Cobblestone
$300Ks
Cobblestone, Hopewell, VA
Resale Only | 55+ age-restricted | Built 1998 - 2014 | 154 homes
The Parke at Cypress Cree...
$500Ks - $700Ks
The Parke at Cypress Cree..., Smithfield, VA
New Construction | 55+ age-restricted | Built 2020 - present | 152 homes
Tinsley Charter
$200Ks - $300Ks
Tinsley Charter, Prince George, VA
Resale Only | 55+ age-restricted | Built 2003 - 2019 | 150 homes
Cherry Grove
$400Ks
Cherry Grove, Mechanicsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 130 homes
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 Bluffs at Bell Creek
$300Ks - $400Ks
The Bluffs at Bell Creek, Mechanicsville, VA
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 128 homes
Church Square
$300Ks - $400Ks
Church Square, Smithfield, VA
New and Resale | 55+ age-restricted | Built 2007 - present | 120 homes
5 rating (1 reviews) The Cottages at Viniterra
$400Ks - $600Ks
The Cottages at Viniterra, New Kent, VA
New Construction | 55+ age-restricted | Built 2021 - present | 118 homes
Whittakers Mill
$400Ks
Whittakers Mill, Williamsburg, VA
New and Resale | Age-targeted | Built 2018 - present | 106 homes
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
Retreat at Edinburgh Farm...
$500Ks
Retreat at Edinburgh Farm..., Chesapeake, VA
New Construction | 55+ age-restricted | Built 2023 - present | 102 homes
The Vineyards at Hallstea...
$400Ks
The Vineyards at Hallstea..., Suffolk, VA
New Construction | 55+ age-restricted | Built 2021 - present | 102 homes
The Retreat at Harbour Co...
$400Ks - $500Ks
The Retreat at Harbour Co..., Suffolk, VA
New Construction | 55+ age-restricted | Built 2022 - present | 101 homes
Meredith Place
$400Ks
Meredith Place, Mechanicsville, VA
Resale Only | 55+ age-restricted | Built 2011 - 2015 | 100 homes
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.
Stags Trail
$400Ks - $700Ks
Stags Trail, Mechanicsville, VA
New Construction | 55+ age-restricted | Built 2023 - present | 98 homes
Sommerton
$500Ks
Sommerton, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 90 homes
Villas at Five Forks
$300Ks - $400Ks
Villas at Five Forks, Williamsburg, VA
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 90 homes
Legacy at Burbage Lake
$200Ks - $400Ks
Legacy at Burbage Lake, Suffolk, VA
New Construction | 55+ age-restricted | 90 homes
The Commons at Hunningdon...
$200Ks - $400Ks
The Commons at Hunningdon..., Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2004 - present | 87 homes
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
The Retreat at Western Br...
$400Ks - $500Ks
The Retreat at Western Br..., Chesapeake, VA
New Construction | 55+ age-restricted | Built 2021 - present | 84 homes
Quarterpath at Tutter's P...
$500Ks
Quarterpath at Tutter's P..., Williamsburg, VA
New Construction | Age-targeted | Built 2024 - present | 81 homes
5 rating (1 reviews) Retreat at Kemps River
$300Ks - $400Ks
Retreat at Kemps River, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2017 - 2021 | 80 homes
Liberty Trace
$300Ks
Liberty Trace, Mechanicsville, VA
Resale Only | 55+ age-restricted | Built 2008 - 2016 | 75 homes
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.
Walnut Farm
$400Ks - $700Ks
Walnut Farm, Williamsburg, VA
New Construction | Age-targeted | Built 2019 - present | 75 homes
Monarch Walk
$100Ks - $200Ks
Monarch Walk, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 62 homes
CoolWell
$400Ks
CoolWell, Mechanicsville, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 60 homes
5 rating (1 reviews) Rock Creek Villas
$300Ks - $400Ks
Rock Creek Villas, Quinton, VA
New and Resale | 55+ age-restricted | Built 2009 - present | 60 homes
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
Twin Rivers at Meadowvill...
$500Ks
Twin Rivers at Meadowvill..., Chester, VA
New Construction | Age-targeted | Built 2020 - present | 48 homes
Oak Crest Townhomes
$400Ks - $500Ks
Oak Crest Townhomes, Mechanicsville, VA
New Construction | 55+ age-restricted | Built 2024 - present | 40 homes
1...2
Legacy at Burbage Lake 2002 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$299,900

2 beds

|

2 baths

|

1,052 sq ft

|

Townhome

2002 ASHWORTH WAY, SUFFOLK, VA, 23435
New Colonial Heritage 7120 PINEBROOK RD, WILLIAMSBURG, VA, 231..., Williamsburg, VA 23188
$495,000

3 beds

|

3 baths

|

2,831 sq ft

|

Detached

7120 PINEBROOK RD, WILLIAMSBURG, VA, 231...
Community: Colonial Heritage
Kingsmill 139 GEORGE SANDYS, WILLIAMSBURG, VA, 231..., Williamsburg, VA 23185
$1,450,000

3 beds

|

5 baths

|

5,479 sq ft

|

Detached

139 GEORGE SANDYS, WILLIAMSBURG, VA, 231...
Community: Kingsmill
Ford's Colony 305 PAR DR, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$727,000

4 beds

|

4 baths

|

3,000 sq ft

|

Detached

305 PAR DR, WILLIAMSBURG, VA, 23188
Community: Ford's Colony
Cobblestone 116 COBBLESTONE DR, HOPEWELL, VA, 23860, Hopewell, VA 23860
$339,500

2 beds

|

2 baths

|

1,530 sq ft

|

House

116 COBBLESTONE DR, HOPEWELL, VA, 23860
Community: Cobblestone
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
Ford's Colony 104 KILLINGTON, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$769,900

4 beds

|

2 baths

|

2,922 sq ft

|

Detached

104 KILLINGTON, WILLIAMSBURG, VA, 23188
Community: Ford's Colony
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
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
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 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
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
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
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
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 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
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.
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
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
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
Eagle Pointe at Cahoon Plantation 1030 EAGLE POINTE WAY, CHESAPEAKE, VA, 2..., Chesapeake, VA 23322
$454,900

3 beds

|

2 baths

|

1,935 sq ft

|

Detached

1030 EAGLE POINTE WAY, CHESAPEAKE, VA, 2...
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
Kingsmill 412 RIVERS EDGE, WILLIAMSBURG, VA, 23185, Williamsburg, VA 23185
$1,050,000

3 beds

|

4 baths

|

3,478 sq ft

|

Townhome

412 RIVERS EDGE, WILLIAMSBURG, VA, 23185
Community: Kingsmill
Sommerton 1072 CRANBERRY DR, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320
$519,900

3 beds

|

2 baths

|

2,467 sq ft

|

Townhome

1072 CRANBERRY DR, CHESAPEAKE, VA, 23320
Community: Sommerton
Ford's Colony 208 WESTERN GAILES, WILLIAMSBURG, VA, 23..., Williamsburg, VA 23188
$899,000

4 beds

|

3 baths

|

4,754 sq ft

|

Detached

208 WESTERN GAILES, WILLIAMSBURG, VA, 23...
Community: Ford's Colony
The Retreat at Western Branch 4644 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$409,000

3 beds

|

2 baths

|

2,481 sq ft

|

Townhome

4644 LONGLEAF PL, CHESAPEAKE, VA, 23321
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 24 MILE CRSE, WILLIAMSBURG, VA, 23185, Williamsburg, VA 23185
$650,000

3 beds

|

3 baths

|

2,989 sq ft

|

Detached

24 MILE CRSE, WILLIAMSBURG, VA, 23185
Community: Kingsmill
Rock Creek Villas 3280 ROCK CREEK VILLA DR, QUINTON, VA, 2..., Quinton, VA 23141
$420,000

3 beds

|

2 baths

|

1,625 sq ft

|

House

3280 ROCK CREEK VILLA DR, QUINTON, VA, 2...
Community: Rock Creek Villas
Kingsmill 42 YEARDLEYS GRANT, WILLIAMSBURG, VA, 23..., Williamsburg, VA 23185
$675,000

3 beds

|

3 baths

|

3,484 sq ft

|

Detached

42 YEARDLEYS GRANT, WILLIAMSBURG, VA, 23...
Community: Kingsmill
New Town 6063 SETTLERS MARKET BLVD, WILLIAMSBURG,..., Williamsburg, VA 23188
$899,000

5 beds

|

4 baths

|

3,894 sq ft

|

Detached

6063 SETTLERS MARKET BLVD, WILLIAMSBURG,...
Community: New Town
The Landings at Bennett's Creek 201 COVE REACH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$680,000

4 beds

|

3 baths

|

2,698 sq ft

|

Detached

201 COVE REACH, SUFFOLK, VA, 23435
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 3008 LOOKING GLASS CT, VIRGINIA BEACH, V..., Virginia Beach, VA 23456
$565,000

4 beds

|

2 baths

|

2,453 sq ft

|

Detached

3008 LOOKING GLASS CT, VIRGINIA BEACH, V...
The Governor's Land at Two Rivers 2809 MIDDLE WOODLAND CLOSE, WILLIAMSBURG..., Williamsburg, VA 23185
$999,000

4 beds

|

5 baths

|

4,496 sq ft

|

Detached

2809 MIDDLE WOODLAND CLOSE, WILLIAMSBURG...
The Governor's Land at Two Rivers 3005 RIVER REACH, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23185
$1,074,000

4 beds

|

4 baths

|

4,930 sq ft

|

Detached

3005 RIVER REACH, WILLIAMSBURG, VA, 2318...
The Governor's Land at Two Rivers 2805 ANN JOHNSON LN, WILLIAMSBURG, VA, 2..., Williamsburg, VA 23185
$850,000

4 beds

|

4 baths

|

3,777 sq ft

|

Detached

2805 ANN JOHNSON LN, WILLIAMSBURG, VA, 2...
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.
Ford's Colony 147 BLACKHEATH, WILLIAMSBURG, VA, 23188, Williamsburg, VA 23188
$549,000

3 beds

|

3 baths

|

2,378 sq ft

|

Detached

147 BLACKHEATH, WILLIAMSBURG, VA, 23188
Community: Ford's Colony
Ford's Colony 115 W LANCASHIRE, WILLIAMSBURG, VA, 2318..., Williamsburg, VA 23188
$1,079,000

5 beds

|

4 baths

|

4,490 sq ft

|

Detached

115 W LANCASHIRE, WILLIAMSBURG, VA, 2318...
Community: Ford's Colony
The Governor's Land at Two Rivers 2801 ANN JOHNSON LN, WILLIAMSBURG, VA, 2..., Williamsburg, VA 23185
$709,000

4 beds

|

3 baths

|

2,846 sq ft

|

Detached

2801 ANN JOHNSON LN, WILLIAMSBURG, VA, 2...
Kingsmill 110 HARROPS GLN, WILLIAMSBURG, VA, 23185, Williamsburg, VA 23185
$437,000

3 beds

|

3 baths

|

1,700 sq ft

|

Townhome

110 HARROPS GLN, WILLIAMSBURG, VA, 23185
Community: Kingsmill
Want to learn more about 55+ communities in Isle of Wight? 55places can help!
Questions? Call us: (888) 625-4885
Retreat at Kemps River 936 BILTMORE WAY # 37, CHESAPEAKE, VA, 2..., Chesapeake, VA 23320
$495,000

3 beds

|

3 baths

|

2,112 sq ft

|

Townhome

936 BILTMORE WAY # 37, CHESAPEAKE, VA, 2...
The Retreat at Harbour Cove 2059 ASHER DR LOT 5, SUFFOLK, VA, 23435, Suffolk, VA 23435
$584,299

3 beds

|

2 baths

|

2,614 sq ft

|

Townhome

2059 ASHER DR LOT 5, SUFFOLK, VA, 23435
123456…7

Want more information about active adult communities around Isle of Wight?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Isle of Wight?

Call us: (888) 625-4885
269 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

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.
© 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: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top