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

142 homes near New Haven Area

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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

Questions? Call us: (959) 991-1879

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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.

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

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

Questions? Call us: (959) 991-1879

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

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

Questions? Call us: (959) 991-1879

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 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

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

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

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

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

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

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

Questions? Call us: (959) 991-1879

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

1...2

Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Fairfield at St. James

708 W CABOT CT 708, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$515,000

1 beds

1 baths

886 sq ft

Condo

708 W CABOT CT 708, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

The Village at Oxford Greens

1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478

$799,900

2 beds

3 baths

1,955 sq ft

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$799,900

2 beds

3 baths

1,955 sq ft

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fieldstone Village

101 SUNRISE HILL CIR 101, ORANGE, CT, 06..., Orange, CT 06477

$875,000

2 beds

3 baths

2,350 sq ft

Condo

101 SUNRISE HILL CIR 101, ORANGE, CT, 06...

Community: Fieldstone Village

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

Questions? Call us: (959) 991-1879

Glenwood Village

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901

$375,000

3 beds

2 baths

1,317 sq ft

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Village

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$349,000

2 beds

1 baths

875 sq ft

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Leisure Glen

29 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,900

2 beds

2 baths

1,314 sq ft

Condo

29 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Spring Lake Village

142 TIMBER RDG 142, SOUTHINGTON, CT, 064..., Southington, CT 06489

$359,900

2 beds

3 baths

1,601 sq ft

Condo

142 TIMBER RDG 142, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

Heritage Village

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

$165,000

2 beds

2 baths

1,076 sq ft

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Chatfield Farms

6 WOODLAND PATH 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$799,000

3 beds

4 baths

2,600 sq ft

Condo

6 WOODLAND PATH 6, BEACON FALLS, CT, 064...

Community: Chatfield Farms

Leisure Village

179 VENTRY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$319,000

2 beds

1 baths

1,085 sq ft

Condo

179 VENTRY CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ..., Riverhead, NY 11901

$205,000

2 beds

2 baths

1,036 sq ft

Manufactured Home

1661 OLD COUNTRY RD 189, RIVERHEAD, NY, ...

Community: Glenwood Village

Heritage Village

1003 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$325,000

2 beds

2 baths

1,398 sq ft

Condo

1003 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

Spring Lake Village

253 CARRIAGE DR 253, SOUTHINGTON, CT, 06..., Southington, CT 06489

$309,900

2 beds

2 baths

1,152 sq ft

Condo

253 CARRIAGE DR 253, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

The Village at Oxford Greens

1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (959) 991-1879

Fairview at Oxford Greens

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fairview at Oxford Greens

1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478

$778,585

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$778,585

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478

$754,150

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$754,150

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairfield at St. James

302 BENTLEY CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

2 beds

2 baths

1,067 sq ft

Condo

302 BENTLEY CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Oronoque Village

372 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$384,900

1 beds

2 baths

1,375 sq ft

Condo

372 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Eagles Walk at East Quogue

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11..., Southampton, NY 11942

$565,000

2 beds

2 baths

1,341 sq ft

Condo

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11...

Community: Eagles Walk at East Quogue

Heritage Village

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

$342,500

2 beds

2 baths

1,398 sq ft

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Windcrest East

5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$775,000

3 beds

3 baths

2,449 sq ft

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933

Community: Windcrest East

Oronoque Village

383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,360 sq ft

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614

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

Community: Leisure Village

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

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

The Village at Oxford Greens

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Glenwood Village

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901

$469,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...

Community: Glenwood Village

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

Questions? Call us: (959) 991-1879

Heritage Village

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$518,000

3 beds

2 baths

1,716 sq ft

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Leisure Village

66 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,085 sq ft

Condo

66 ENFIELD CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

1 2 3…4

Home
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

Thanks! A local 55+ expert will be in touch shortly.

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

Call us: (959) 991-1879

142 homes

Remove Boundaries ×

Map Satellite

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

Call Us Call Us

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

54 communities near New Haven Area

142 homes near New Haven Area

3 beds

3 baths

Condo

1 beds

1 baths

886 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

2,350 sq ft

Condo

3 beds

2 baths

1,317 sq ft

Manufactured Home

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,314 sq ft

Condo

2 beds

3 baths

1,601 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

3 beds

4 baths

2,600 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,036 sq ft

Manufactured Home

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,152 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths