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

105 homes 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

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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

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

Questions? Call us: (959) 991-1020

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

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

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

The Bridges at Oxford Gre...

$600ks

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

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762

Community: Granite Woods

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

Questions? Call us: (959) 991-1020

Long Hill Village

48 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$499,900

2 beds

2 baths

1,070 sq ft

Condo

48 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

Meadow Brook Estates

130 MEADOW BROOK RD 130, OXFORD, CT, 064..., Oxford, CT 06478

$599,000

2 beds

3 baths

1,920 sq ft

Condo

130 MEADOW BROOK RD 130, OXFORD, CT, 064...

Community: Meadow Brook Estates

Long Hill Village

36 LONG HILL PL, TRUMBULL, CT, 06611, Trumbull, CT 06611

$550,000

2 beds

3 baths

1,370 sq ft

Condo

36 LONG HILL PL, TRUMBULL, CT, 06611

Community: Long Hill Village

Regency at Woodbridge

18 HILLCREST DR 18, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525

$829,900

3 beds

3 baths

2,412 sq ft

Condo

18 HILLCREST DR 18, WOODBRIDGE, CT, 0652...

Community: Regency at Woodbridge

Heritage Village

2 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$469,900

2 beds

2 baths

1,420 sq ft

Condo

2 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

19 HICKORY HL 19, SOUTHINGTON, CT, 06489, Southington, CT 06489

$256,000

2 beds

2 baths

1,285 sq ft

Condo

19 HICKORY HL 19, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Village

4 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,000

2 beds

2 baths

1,306 sq ft

Condo

4 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$350,000

3 beds

2 baths

1,716 sq ft

Condo

682 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$415,000

2 beds

2 baths

1,432 sq ft

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$324,900

2 beds

2 baths

1,000 sq ft

Condo

883 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Pond Spring Village

111 PONDVIEW CIR 111, BEACON FALLS, CT, ..., Beacon Falls, CT 06403

$435,000

2 beds

2 baths

1,328 sq ft

Condo

111 PONDVIEW CIR 111, BEACON FALLS, CT, ...

Community: Pond Spring Village

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

Questions? Call us: (959) 991-1020

Meadow Brook Estates

132 MEADOW BROOK RD 132, OXFORD, CT, 064..., Oxford, CT 06478

$599,900

2 beds

3 baths

1,931 sq ft

Condo

132 MEADOW BROOK RD 132, OXFORD, CT, 064...

Community: Meadow Brook Estates

Oronoque Village

88 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$356,000

1 beds

2 baths

1,175 sq ft

Condo

88 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$245,000

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

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

$389,000

1 beds

2 baths

1,480 sq ft

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$279,000

2 beds

2 baths

1,432 sq ft

Condo

991 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Meadow Brook Estates

207 WOODLAWN DR 207, SEYMOUR, CT, 06483, Seymour, CT 06483

$625,000

3 beds

3 baths

2,484 sq ft

Condo

207 WOODLAWN DR 207, SEYMOUR, CT, 06483

Community: Meadow Brook Estates

Spring Lake Village

1 HICKORY HL 1, SOUTHINGTON, CT, 06489, Southington, CT 06489

$239,000

2 beds

2 baths

1,285 sq ft

Condo

1 HICKORY HL 1, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Village

226A S DURKEE HILL RD 226A, SOUTHBURY, C..., Southbury, CT 06488

$338,500

2 beds

2 baths

1,398 sq ft

Condo

226A S DURKEE HILL RD 226A, SOUTHBURY, C...

Community: Heritage Village

Heritage Village

162 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$249,000

2 beds

2 baths

1,076 sq ft

Condo

162 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

397 KRUEGER CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$439,700

3 beds

2 baths

1,716 sq ft

Condo

397 KRUEGER CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478

$629,900

2 beds

3 baths

2,232 sq ft

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478

28 COACH DR 28, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

The Village at Oxford Greens

155 COUNTRY CLUB DR 155, OXFORD, CT, 064..., Oxford, CT 06478

$659,000

3 beds

3 baths

2,908 sq ft

155 COUNTRY CLUB DR 155, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Heritage Village

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

$375,000

2 beds

2 baths

1,398 sq ft

Condo

616 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

Spring Lake Village

102 TIMBER RDG 102, SOUTHINGTON, CT, 064..., Southington, CT 06489

$210,000

1 beds

1 baths

920 sq ft

Condo

102 TIMBER RDG 102, SOUTHINGTON, CT, 064...

Community: Spring Lake Village

Heritage Village

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

$414,900

2 beds

2 baths

1,398 sq ft

Condo

886 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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Waterbury Area

Frequently Asked Questions

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

Of the 13 55+ communities in the Waterbury Area, 13 are for sale and none are rentals. By size, 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 RiverBend Estates, Granite Woods, Fairview at Oxford Greens.

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, Regency at Prospect is a gated communities with 379 homes, and Chatfield Farms is another gated communities with 231 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 584 days. The average price of homes for sale in these communities is approximately $553,292, 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 Chatfield Farms average around $580,396.

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

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105 homes

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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: Oct 13, 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

105 homes near Waterbury Area

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

2,258 sq ft

Condo

2 beds

1 baths

890 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

2 beds

3 baths

1,920 sq ft

Condo

2 beds

3 baths

1,370 sq ft

Condo

3 beds

3 baths

2,412 sq ft

Condo

2 beds

2 baths

1,420 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

2 baths

1,306 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,328 sq ft

Condo

2 beds

3 baths

1,931 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

1 beds