New Haven Area, CT 55+ active adult communities & homes for sale - Page 2

161 homes near New Haven Area

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

The Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

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

Questions? Call us: (959) 991-1879

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 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.

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

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

Questions? Call us: (959) 991-1879

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

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

Questions? Call us: (959) 991-1879

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

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

Questions? Call us: (959) 991-1879

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

1...2

Leisure Village

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$349,000

2 beds

1 baths

1,085 sq ft

Condo

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Setauket Meadows

100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$769,000

2 beds

3 baths

1,820 sq ft

Condo

100 COVE LN 100, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Oronoque Village

315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,000

2 beds

3 baths

1,434 sq ft

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$299,000

2 beds

1 baths

875 sq ft

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...

Community: Leisure Village

Heritage Village

14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$269,000

2 beds

2 baths

1,000 sq ft

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (959) 991-1879

Leisure Knoll

541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$519,000

3 beds

2 baths

1,412 sq ft

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Village

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

$309,000

3 beds

2 baths

1,716 sq ft

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$470,000

1 beds

3 baths

1,426 sq ft

Condo

132 BISON LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$405,000

2 beds

2 baths

1,432 sq ft

Condo

648 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairfield at St. James

309 FLAIR DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$454,000

1 beds

2 baths

983 sq ft

Condo

309 FLAIR DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Foxwood Village

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$449,000

3 beds

2 baths

1,753 sq ft

House

1407 MIDDLE RD 253, RIVERHEAD, NY, 11933

Community: Foxwood Village

Leisure Village

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$335,000

2 beds

1 baths

875 sq ft

Condo

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Fairfield at St. James

604 CABOT CT 604, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

2 beds

2 baths

10 sq ft

Condo

604 CABOT CT 604, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Encore at Lake Grove

58 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$599,990

2 beds

3 baths

Condo

58 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

Pond Spring Village

35 OCTOBER LN 35, BEACON FALLS, CT, 0646..., Beacon Falls, CT 06468

$420,000

2 beds

3 baths

1,328 sq ft

Condo

35 OCTOBER LN 35, BEACON FALLS, CT, 0646...

Community: Pond Spring Village

Leisure Knoll

520 CRANSTON LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,999

2 beds

2 baths

1,574 sq ft

Condo

520 CRANSTON LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (959) 991-1879

Heritage Village

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

$239,000

1 beds

1 baths

928 sq ft

Condo

551 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

298 BATON LN 298 A, STRATFORD, CT, 06614, Stratford, CT 06614

$435,000

1 beds

2 baths

1,175 sq ft

Condo

298 BATON LN 298 A, STRATFORD, CT, 06614

Community: Oronoque Village

Fairfield at St. James

604 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$449,999

1 beds

2 baths

954 sq ft

Condo

604 GOTHAM DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Leisure Glen

104 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$589,900

2 beds

2 baths

1,635 sq ft

Condo

104 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Oronoque Village

209 ACORN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$574,900

2 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$389,990

2 beds

1 baths

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...

Community: Leisure Village

Leisure Village

110 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$389,900

2 beds

1 baths

1,085 sq ft

Condo

110 EXMORE CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Regency at Prospect

156 SYCAMORE DR 156, PROSPECT, CT, 06712, Prospect, CT 06712

$559,000

2 beds

3 baths

2,067 sq ft

Condo

156 SYCAMORE DR 156, PROSPECT, CT, 06712

Community: Regency at Prospect

Heritage Village

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

$219,000

1 beds

1 baths

928 sq ft

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$219,900

2 beds

2 baths

1,308 sq ft

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

1 beds

3 baths

1,583 sq ft

Condo

619 ERIE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (959) 991-1879

Fairview at Oxford Greens

1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478

$761,150

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$761,150

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Leisure Village

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$450,000

2 beds

2 baths

1,278 sq ft

Condo

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119...

Community: Leisure Village

Heritage Village

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

$265,000

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Stoneleigh Woods at Riverhead

156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$659,000

2 beds

3 baths

1,942 sq ft

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Leisure Glen

155 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$495,000

2 beds

2 baths

1,456 sq ft

Condo

155 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Oronoque Village

564 PEQUOT LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,900

2 beds

2 baths

1,438 sq ft

Condo

564 PEQUOT LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614

$539,000

1 beds

3 baths

1,175 sq ft

Condo

638A ONONDAGA LN, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$205,000

2 beds

2 baths

1,308 sq ft

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$399,999

3 beds

2 baths

1,716 sq ft

Condo

110 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

32 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$289,900

2 beds

2 baths

1,032 sq ft

Condo

32 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (959) 991-1879

Heritage Village

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

$239,900

1 beds

1 baths

928 sq ft

Condo

12 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Foxwood Village

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$469,000

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933

Community: Foxwood Village

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Connecticut
New Haven Area

Frequently Asked Questions

What size 55+ communities are there in the New Haven Area?

In the New Haven Area, there are no large communities, 1 medium community with 500-1000 homes, and 8 small communities with less than 500 homes.

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

The smallest 55+ communities in the New Haven Area has 8 homes, the largest has 929 homes, and the average communities consists of 148 homes.

Are there new 55+ homes available in the New Haven Area?

Yes, there are new 55+ homes available in the New Haven Area. The most recent communities started in the New Haven Area include Regency at Woodbridge, Cobblestone Court, Summer Wind Estates. There are also 4 communities in the New Haven Area that offer new construction homes, including Summer Wind Estates, Regency at Woodbridge, Cobblestone Court.

Are there gated 55+ communities in the New Haven Area?

No, there are no gated 55+ communities in the New Haven Area.

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

On average, listings in 55+ communities in the New Haven Area stay on the market for around 343 days. The average price of homes for sale in these communities is approximately $604,435, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Baldwin Station average around $743,609, while homes in Regency at Woodbridge average around $639,995.

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

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

Want to learn more about 55+ communities in New Haven Area?

Call us: (959) 991-1879

161 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: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.

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New Haven Area, CT 55+ active adult communities & homes for sale - Page 2

54 communities near New Haven Area

161 homes near New Haven Area

2 beds

1 baths

1,085 sq ft

Condo

2 beds

3 baths

1,820 sq ft

Condo

2 beds

3 baths

1,434 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,412 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

983 sq ft

Condo

3 beds

2 baths

1,753 sq ft

House

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

10 sq ft

Condo

2 beds

3 baths

Condo

2 beds

3 baths

1,328 sq ft

Condo

2 beds

2 baths

1,574 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

1 beds

2 baths

954 sq ft

Condo

2 beds

2 baths