Connecticut 55+ active adult communities & homes for sale - Page 2

Living in Connecticut

Connecticut offers a classic New England retirement lifestyle coupled with unparalleled regional access — New York City and Boston are each under two hours away, the scenic Long…

Connecticut offers a classic New England retirement lifestyle coupled with unparalleled regional access — New York City and Boston are each under two hours away, the scenic Long Island Sound shoreline runs the length of the state, and the Litchfield Hills provide a peaceful, rural alternative. The state boasts an exceptional healthcare network, anchored by Yale New Haven Health and Hartford HealthCare, alongside four distinct seasons featuring world-renowned autumn foliage.Connecticut is home to 62 active adult communities, with properties ranging from the mid-$100Ks to over $1M and averaging around $547K. Heritage Village in Southbury (2,580 homes) is the crown jewel of the state — ranking as one of the largest and most established 55+ communities in all of New England. Active adults seeking mid-sized options gravitate toward Oronoque Village in Stratford (929 homes) and Spring Lake Village in Southington (640 homes), while those prioritizing modern layouts favor new construction neighborhoods like Chatfield Farms in Beacon Falls and The Village at Oxford Greens in Oxford. 55places has thoroughly profiled every local development with verified pricing tiers, honest resident reviews, and direct local agent connections.

Quick Facts About Retiring in Connecticut

Does Connecticut tax Social Security, IRAs, or 401(k) retirement income?

Retirement income is 100% tax-exempt for a large portion of Connecticut residents. For single filers with an AGI under $75,000 and married joint filers under $100,000, Connecticut exempts all Social Security benefits, qualifying pensions, and 401(k) distributions. Furthermore, traditional IRA distributions are 100% tax-exempt under these same income limits. For taxpayers above these thresholds, a partial step-down exemption still applies

What are the main retirement areas for 55+ buyers in Connecticut?

The primary development corridors include the Fairfield County/Stamford Area (ideal for New York commuters), the New Haven Shoreline (for coastal access), and the Central Connecticut Valley towns surrounding Hartford and Waterbury, which host the state's largest master-planned lifestyle communities.

What size 55+ communities are there in Connecticut?

In Connecticut, there are 2 large communities with over 1000 homes, 3 medium communities with 500-1000 homes, and 56 small communities with less than 500 homes.

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

The smallest 55+ communities in Connecticut has 8 homes, the largest has 2580 homes, and the average communities consists of 175 homes.

Are there new 55+ homes available in Connecticut?

Yes, there are new 55+ homes available in Connecticut. The most recent communities started in Connecticut include The Bridges at Oxford Greens, Rivington Landing, Regency at Woodbridge. There are also 27 communities in Connecticut that offer new construction homes, including Applegate Estates, Beckley Farms, North Woods of Colchester.

Are there gated 55+ communities in Connecticut?

Yes, there are gated 55+ communities in Connecticut. Approximately 14.8% of 55+ communities in the area are gated. For instance, The Village at Buckingham is a gated communities with 56 homes, and Liberty at Newtown is another gated communities with 96 homes.

How long do listings in 55+ communities in Connecticut typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Connecticut stay on the market for around 443 days. The average price of homes for sale in these communities is approximately $550,800, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Fieldstone Village average around $1,195,000, while homes in Oronoque Village average around $532,863.

62 communities near Connecticut

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The Village at Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes

O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

The Coach Homes at Ridgef...

$300ks - $400ks

The Coach Homes at Ridgef..., Ridgefield, CT

New Construction | 55+ age-restricted | Built 2019 - present | 30 homes

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

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

Questions? Call us: (888) 625-4885

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 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.

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 homes

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

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Questions? Call us: (888) 625-4885

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 homes

1 2

New Heritage Village

16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$389,900

2 beds

2 baths

1,432 sq ft

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Spring Lake Village

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489

$350,000

2 beds

2 baths

1,230 sq ft

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...

Community: Spring Lake Village

New Bartlett Hill

19 PLUMROSE CT 19, PORTLAND, CT, 06480, Portland, CT 06480

$500,000

2 beds

3 baths

1,503 sq ft

19 PLUMROSE CT 19, PORTLAND, CT, 06480

Community: Bartlett Hill

New Heritage Village

38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$299,900

2 beds

2 baths

1,032 sq ft

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$450,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (888) 625-4885

New Baldwin Station

15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461

$599,000

2 beds

3 baths

2,331 sq ft

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461

Community: Baldwin Station

New Fairview at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

$310,000

2 beds

2 baths

1,398 sq ft

Condo

233 HERITAGE VLG A, SOUTHBURY, CT, 06488

2 beds

4 baths

1,572 sq ft

11 MERCY ST 11, DANBURY, CT, 06810

Community: Rivington

Heritage Village

701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$589,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

157 COUNTRY CLUB DR 157, OXFORD, CT, 064..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,008 sq ft

Condo

157 COUNTRY CLUB DR 157, OXFORD, CT, 064...

Community: The Village at Oxford Greens

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Heritage Village

24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488

$419,900

2 beds

2 baths

1,217 sq ft

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...

Community: Heritage Village

Heritage Village

593 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$205,000

2 beds

2 baths

1,044 sq ft

Condo

593 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

147 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$235,000

2 beds

2 baths

1,076 sq ft

Condo

147 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

22 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$204,000

2 beds

2 baths

1,032 sq ft

Condo

22 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Liberty at Newtown

76 SUZIE DR 76, NEWTOWN, CT, 06470, Newtown, CT 06470

$648,000

2 beds

3 baths

2,341 sq ft

Condo

76 SUZIE DR 76, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Heritage Village

804 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$259,000

2 beds

2 baths

1,432 sq ft

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Oak Meadow Estates

197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790

$399,000

2 beds

2 baths

1,419 sq ft

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...

Community: Oak Meadow Estates

Billingsgate

$750,000

2 beds

3 baths

2,729 sq ft

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...

Community: Billingsgate

Heritage Village

184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$209,000

1 beds

1 baths

928 sq ft

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

333 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$335,000

2 beds

2 baths

1,432 sq ft

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (888) 625-4885

The Village at Oxford Greens

443 TEE SHOT DR 443, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

3 beds

3 baths

2,759 sq ft

Condo

443 TEE SHOT DR 443, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Hopmeadow Place

1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,430 sq ft

Condo

1 W ST 310, SIMSBURY, CT, 06070

Community: Hopmeadow Place

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62 communities

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Connecticut 55+ active adult communities & homes for sale - Page 2

Living in Connecticut

Quick Facts About Retiring in Connecticut

62 communities near Connecticut

120 homes near Connecticut

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

3 baths

1,503 sq ft

2 beds

2 baths

1,032 sq ft

Condo

1 beds

2 baths

1,360 sq ft

Condo

2 beds

3 baths

2,331 sq ft

Condo

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,682 sq ft

3 beds

3 baths

1,600 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

2 baths

1,747 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,328 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

2,008 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

2,152 sq ft

2 beds

2 baths

1,044 sq ft