Waterbury Area, CT 55+ active adult communities & homes for sale

22 communities near Waterbury 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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

Questions? Call us: (959) 991-1020

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

The Bridges at Oxford Gre...

$600ks

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

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

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

Questions? Call us: (959) 991-1020

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

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

593 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (959) 991-1020

New 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

New 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

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

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

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

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

Heritage Village

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

$414,900

2 beds

2 baths

1,432 sq ft

Condo

945 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

The Village at Oxford Greens

567 INVERNESS CT 567, OXFORD, CT, 06478, Oxford, CT 06478

$665,000

2 beds

2 baths

2,008 sq ft

567 INVERNESS CT 567, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (959) 991-1020

Oronoque Village

283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$625,000

2 beds

3 baths

1,415 sq ft

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Meadow Brook Estates

211 MEADOW BROOK RD 211, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

2,201 sq ft

Condo

211 MEADOW BROOK RD 211, OXFORD, CT, 064...

Community: Meadow Brook Estates

Heritage Village

10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$364,000

3 beds

2 baths

1,716 sq ft

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

342 SONGBIRD LN 342, SOUTHINGTON, CT, 06..., Southington, CT 06489

$259,900

2 beds

1 baths

912 sq ft

Condo

342 SONGBIRD LN 342, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

Heritage Village

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

$238,000

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$237,000

2 beds

2 baths

1,076 sq ft

Condo

24 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$245,000

2 beds

2 baths

1,076 sq ft

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$559,000

2 beds

3 baths

2,542 sq ft

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

196 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$229,900

2 beds

2 baths

1,044 sq ft

Condo

196 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Prospect

6 LILAC LN 6, PROSPECT, CT, 06712, Prospect, CT 06712

$474,900

2 beds

3 baths

1,552 sq ft

Condo

6 LILAC LN 6, PROSPECT, CT, 06712

Community: Regency at Prospect

The Village at Oxford Greens

527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478

$685,000

3 beds

3 baths

2,008 sq ft

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...

Community: The Village at Oxford Greens

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

Questions? Call us: (959) 991-1020

Regency at Prospect

10 ASH LN 10, PROSPECT, CT, 06712, Prospect, CT 06712

$539,000

2 beds

3 baths

1,928 sq ft

Condo

10 ASH LN 10, PROSPECT, CT, 06712

Community: Regency at Prospect

Heritage Village

18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$434,981

3 beds

2 baths

1,735 sq ft

Condo

18 HERITAGE CRST D, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairview at Oxford Greens

1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478

$713,775

2 beds

3 baths

2,536 sq ft

Condo

Community: Heritage Village

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

Questions? Call us: (959) 991-1020

Heritage Village

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

$424,900

2 beds

2 baths

1,432 sq ft

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$396,000

1 beds

2 baths

1,480 sq ft

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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Waterbury Area

Frequently Asked Questions

What size 55+ communities are there in the Waterbury Area?

In the Waterbury Area, there are 1 large community with over 1000 homes, 1 medium community with 500-1000 homes, and 11 small communities with less than 500 homes.

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

The smallest 55+ communities in the Waterbury Area has 24 homes, the largest has 2580 homes, and the average communities consists of 376 homes.

Are there new 55+ homes available in the Waterbury Area?

Yes, there are new 55+ homes available in the Waterbury Area. The most recent communities started in the Waterbury Area include The Bridges at Oxford Greens, Granite Woods, Fairview at Oxford Greens. There are also 8 communities in the Waterbury Area that offer new construction homes, including Granite Woods, RiverBend Estates, Chatfield Farms.

Are there gated 55+ communities in the Waterbury Area?

Yes, there are gated 55+ communities in the Waterbury Area. Approximately 15.4% of 55+ communities in the area are gated. For instance, Chatfield Farms is a gated communities with 231 homes, and Regency at Prospect is another gated communities with 379 homes.

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

On average, listings in 55+ communities in the Waterbury Area stay on the market for around 522 days. The average price of homes for sale in these communities is approximately $563,832, 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 Meadow Brook Estates average around $569,400.

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

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

Want to learn more about 55+ communities in Waterbury Area?

Call us: (959) 991-1020

22 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 04, 2026.
This application does not include information on all of the properties available for sale at this time.

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Waterbury Area, CT 55+ active adult communities & homes for sale

22 communities near Waterbury Area

91 homes near Waterbury Area

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

1,032 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

2,759 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

2,008 sq ft

2 beds

3 baths

1,415 sq ft

Condo

3 beds

3 baths

2,201 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

1 baths