Chesapeake, VA 55+ active adult communities & homes for sale

62 homes near Chesapeake

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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

The Retreat at Greenbrier

$400Ks

The Retreat at Greenbrier, Chesapeake, VA

Resale Only | 55+ age-restricted | Built 2003 - 2015 | 184 homes

Retreat at Edinburgh Farm...

$500Ks

Retreat at Edinburgh Farm..., Chesapeake, VA

New Construction | 55+ age-restricted | Built 2023 - present | 102 homes

Sommerton

$500Ks

Sommerton, Chesapeake, VA

Resale Only | 55+ age-restricted | Built 2006 - 2017 | 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 Chesapeake? 55places can help!

Questions? Call us: (804) 568-8917

The Retreat at Western Br...

$400Ks - $500Ks

The Retreat at Western Br..., Chesapeake, VA

New Construction | 55+ age-restricted | Built 2021 - present | 84 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

Monarch Walk

$100Ks - $200Ks

Monarch Walk, Chesapeake, VA

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 62 homes

The Retreat at Harbour Co...

$500Ks

The Retreat at Harbour Co..., Suffolk, VA

New Construction | 55+ age-restricted | Built 2022 - present | 101 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.

Legacy at Burbage Lake

$200Ks - $400Ks

Legacy at Burbage Lake, Suffolk, VA

New Construction | 55+ age-restricted | 90 homes

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

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

2024 MUNRO LN, CHESAPEAKE, VA, 23322

Community: Retreat at Edinburgh Farms

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The Retreat at Harbour Cove

2051 ASHER DR LOT 1, SUFFOLK, VA, 23435, Suffolk, VA 23435

$572,766

4 beds

2 baths

2,553 sq ft

Townhome

2051 ASHER DR LOT 1, SUFFOLK, VA, 23435

Community: The Retreat at Harbour Cove

New Retreat at Edinburgh Farms

2009 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322

$590,990

4 beds

2 baths

2,614 sq ft

Townhome

2009 MUNRO LN, CHESAPEAKE, VA, 23322

Community: Retreat at Edinburgh Farms

The Retreat at Harbour Cove

2005 ASHER DR LOT 74, SUFFOLK, VA, 23435, Suffolk, VA 23435

$550,973

3 beds

2 baths

2,136 sq ft

Townhome

2005 ASHER DR LOT 74, SUFFOLK, VA, 23435

Community: The Retreat at Harbour Cove

The Commons at Hunningdon Lakes

800 MONROE CT, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320

$398,000

3 beds

2 baths

2,225 sq ft

Townhome

800 MONROE CT, CHESAPEAKE, VA, 23320

Community: The Commons at Hunningdon Lakes

The Retreat at Western Branch

4646 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321

$515,000

4 beds

3 baths

2,842 sq ft

Townhome

4646 LONGLEAF PL, CHESAPEAKE, VA, 23321

Community: The Retreat at Western Branch

The Commons at Hunningdon Lakes

809 MASON CT, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320

$430,000

3 beds

2 baths

2,225 sq ft

Detached

809 MASON CT, CHESAPEAKE, VA, 23320

Community: The Commons at Hunningdon Lakes

The Retreat at Western Branch

4639 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321

$455,000

3 beds

2 baths

2,555 sq ft

Townhome

4639 LONGLEAF PL, CHESAPEAKE, VA, 23321

Community: The Retreat at Western Branch

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

Community: Legacy at Burbage Lake

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Questions? Call us: (804) 568-8917

Sommerton

1000 LIL WALNUT LN, CHESAPEAKE, VA, 2332..., Chesapeake, VA 23320

$529,900

4 beds

2 baths

2,900 sq ft

Townhome

1000 LIL WALNUT LN, CHESAPEAKE, VA, 2332...

Community: Sommerton

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

Community: Eagle Pointe at Cahoon Plantation

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

Community: Retreat at Edinburgh Farms

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

Community: Retreat at Edinburgh Farms

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

Community: Retreat at Edinburgh Farms

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

Community: Retreat at Edinburgh Farms

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

Community: Retreat at Edinburgh Farms

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

Community: The Retreat at Western Branch

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

Questions? Call us: (804) 568-8917

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

Community: Retreat at Edinburgh Farms

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

Community: Retreat at Edinburgh Farms

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

Community: Retreat at Edinburgh Farms

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...

Community: Eagle Pointe at Cahoon Plantation

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

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

Community: The Retreat at Western Branch

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

Community: The Landings at Bennett's Creek

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...

Community: Retreat at Kemps River

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

Community: The Retreat at Harbour Cove

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

Questions? Call us: (804) 568-8917

Legacy at Burbage Lake

2018 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435

$330,184

2 beds

2 baths

1,563 sq ft

Townhome

2018 ASHWORTH WAY, SUFFOLK, VA, 23435

Community: Legacy at Burbage Lake

Retreat at Edinburgh Farms

2028 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322

$578,740

3 beds

2 baths

2,557 sq ft

Townhome

2028 MUNRO LN, CHESAPEAKE, VA, 23322

Community: Retreat at Edinburgh Farms

Retreat at Edinburgh Farms

2150 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322

$530,740

2 beds

3 baths

1,986 sq ft

Townhome

2150 EDWIN DR, CHESAPEAKE, VA, 23322

Community: Retreat at Edinburgh Farms

Legacy at Burbage Lake

1018 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435

$387,678

2 beds

2 baths

1,489 sq ft

Townhome

1018 ASHWORTH WAY, SUFFOLK, VA, 23435

Community: Legacy at Burbage Lake

The Retreat at Greenbrier

1439 THISTLEWOOD LN, CHESAPEAKE, VA, 233..., Chesapeake, VA 23320

$425,000

2 beds

2 baths

1,727 sq ft

Townhome

1439 THISTLEWOOD LN, CHESAPEAKE, VA, 233...

Community: The Retreat at Greenbrier

The Landings at Bennett's Creek

100 CREEK LN, SUFFOLK, VA, 23435, Suffolk, VA 23435

$729,900

3 beds

2 baths

2,170 sq ft

Detached

100 CREEK LN, SUFFOLK, VA, 23435

Community: The Landings at Bennett's Creek

The Retreat at Western Branch

3505 ELAINA WAY, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321

$533,793

4 beds

2 baths

2,433 sq ft

Townhome

3505 ELAINA WAY, CHESAPEAKE, VA, 23321

Community: The Retreat at Western Branch

The Retreat at Western Branch

4728 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321

$516,909

4 beds

3 baths

2,880 sq ft

Townhome

4728 MAHOGANY RUN, CHESAPEAKE, VA, 23321

Community: The Retreat at Western Branch

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

Questions? Call us: (804) 568-8917

Retreat at Edinburgh Farms

2012 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322

$584,990

4 beds

2 baths

2,614 sq ft

Townhome

2012 MUNRO LN, CHESAPEAKE, VA, 23322

Community: Retreat at Edinburgh Farms

Legacy at Burbage Lake

1016 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435

$439,923

4 beds

3 baths

1,978 sq ft

Townhome

1016 ASHWORTH WAY, SUFFOLK, VA, 23435

Community: Legacy at Burbage Lake

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Frequently Asked Questions

What size 55+ communities are there in Chesapeake?

In Chesapeake, there are no large communities, 1 medium community with 500-1000 homes, and 7 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Chesapeake?

The smallest 55+ communities in Chesapeake has 62 homes, the largest has 501 homes, and the average communities consists of 148 homes.

Are there new 55+ homes available in Chesapeake?

Yes, there are new 55+ homes available in Chesapeake. The most recent communities started in Chesapeake include Retreat at Edinburgh Farms, The Retreat at Western Branch, Retreat at Kemps River. There are also 2 communities in Chesapeake that offer new construction homes, including The Retreat at Western Branch, Retreat at Edinburgh Farms.

Are there gated 55+ communities in Chesapeake?

Yes, there are gated 55+ communities in Chesapeake. Approximately 25.0% of 55+ communities in the area are gated. For instance, Monarch Walk is a gated communities with 62 homes, and Eagle Pointe at Cahoon Plantation is another gated communities with 501 homes.

Want more information about active adult communities around Chesapeake?

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Chesapeake, VA 55+ active adult communities & homes for sale

11 communities near Chesapeake

62 homes near Chesapeake

4 beds

3 baths

2,880 sq ft

Townhome

4 beds

2 baths

2,584 sq ft

Townhome

4 beds

2 baths

2,584 sq ft

Townhome

3 beds

3 baths

2,687 sq ft

Townhome

4 beds

2 baths

2,614 sq ft

Townhome

4 beds

2 baths

2,553 sq ft

Townhome

4 beds

2 baths

2,614 sq ft

Townhome

3 beds

2 baths

2,136 sq ft

Townhome

3 beds

2 baths

2,225 sq ft

Townhome

4 beds

3 baths

2,842 sq ft

Townhome

3 beds

2 baths

2,225 sq ft

Detached

3 beds

2 baths

2,555 sq ft

Townhome

2 beds

2 baths

1,052 sq ft

Townhome

4 beds

2 baths

2,900 sq ft

Townhome

3 beds

2 baths

1,760 sq ft

Townhome

2 beds

3 baths

1,986 sq ft

Townhome

4 beds

2 baths

2,614 sq ft

Townhome

4 beds

3 baths

2,781 sq ft

Townhome

3 beds

3 baths

2,314 sq ft

Townhome

2 beds