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

22 communities near Waterbury 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

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

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

Questions? Call us: (959) 991-1020

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

The Bridges at Oxford Gre...

$600ks

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

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

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

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

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

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

139 HERITAGE VLG B, SOUTHBURY, CT, 06488

Condo

926 HERITAGE VLG B, 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

The Village at Oxford Greens

505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478

$775,000

3 beds

3 baths

2,652 sq ft

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Oronoque Village

543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$585,000

1 beds

3 baths

1,426 sq ft

Condo

543 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Regency at Prospect

196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712

$307,127

3 beds

2 baths

1,500 sq ft

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712

Community: Regency at Prospect

Heritage Village

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

$390,000

2 beds

2 baths

1,432 sq ft

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

96 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$469,000

2 beds

3 baths

1,438 sq ft

Condo

96 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

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

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

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

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

Questions? Call us: (959) 991-1020

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

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

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

$229,000

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

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

Community: Oronoque Village

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

Questions? Call us: (959) 991-1020

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

Home
Connecticut
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 The Bridges at Oxford Greens, Granite Woods, 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 493 days. The average price of homes for sale in these communities is approximately $558,023, 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 $573,142.

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

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: May 21, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

22 communities near Waterbury Area

94 homes near Waterbury Area

2 beds

2 baths

1,350 sq ft

Condo

2 beds

2 baths

1,590 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

2,891 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

1,044 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

1,398 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,572 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

3 baths

2,652 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

3 beds

2 baths

1,500 sq ft

Condo

2 beds