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

54 communities near New Haven Area

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Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

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

Questions? Call us: (959) 991-1879

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

The Bridges at Oxford Gre...

$600ks

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

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

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

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

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

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

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

1 2

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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Questions? Call us: (959) 991-1879

New The Village at Oxford Greens

349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478

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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Questions? Call us: (959) 991-1879

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

Leisure Village

258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$299,000

2 beds

1 baths

875 sq ft

Condo

258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196...

Community: Leisure Village

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

Strathmore Gate East

4 FLAIR WAY, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$495,000

2 beds

2 baths

1,112 sq ft

House

4 FLAIR WAY, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

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

Strathmore Gate East

9 FREEDOM LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$289,000

1 beds

1 baths

728 sq ft

Condo

9 FREEDOM LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

Leisure Knoll

338 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$419,990

2 beds

1 baths

960 sq ft

Condo

338 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Leisure Village

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$239,000

1 beds

1 baths

684 sq ft

Condo

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

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

Questions? Call us: (959) 991-1879

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

Sunken Pond Estates

102 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$515,000

2 beds

3 baths

1,350 sq ft

Condo

102 WINGED FOOT WAY, RIVERHEAD, NY, 1190...

Community: Sunken Pond Estates

Leisure Village

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$228,888

2 beds

1 baths

836 sq ft

Condo

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Leisure Knoll

152B LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$374,000

1 beds

1 baths

530 sq ft

Condo

152B LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Oronoque Village

448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$525,000

1 beds

3 baths

1,438 sq ft

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

Saddle Lakes

174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$675,000

2 beds

2 baths

1,631 sq ft

Condo

174 ADELE CT, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Leisure Village

133 EASTBOURNE CT F, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$349,000

2 beds

1 baths

836 sq ft

Condo

133 EASTBOURNE CT F, BROOKHAVEN, NY, 119...

Community: Leisure Village

Sunken Pond Estates

2803 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$499,000

2 beds

3 baths

1,350 sq ft

Condo

2803 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

Heritage Village

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

$398,900

2 beds

2 baths

1,432 sq ft

Condo

945 HERITAGE VLG A, 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

Country Village Estates

110 THEODORE DR 110, BROOKHAVEN, NY, 117..., Brookhaven, NY 11727

$475,000

2 beds

2 baths

1,261 sq ft

Condo

110 THEODORE DR 110, BROOKHAVEN, NY, 117...

Community: Country Village Estates

Heritage Village

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

$335,000

2 beds

2 baths

1,398 sq ft

Condo

339 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage 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 RiverWalk, Cobblestone Court, Regency at Woodbridge.

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 349 days. The average price of homes for sale in these communities is approximately $620,649, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Baldwin Station average around $820,000, while homes in Regency at Woodbridge average around $640,382.

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

54 communities

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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: Jul 10, 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

133 homes near New Haven Area

2 beds

2 baths

1,624 sq ft

Manufactured Home

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

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

2 baths

948 sq ft

Condo

1 beds

1 baths

752 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

2 baths

1,451 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

3 baths

2,008 sq ft

Condo

2 beds

2 baths

1,217 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths