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

77 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

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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

Questions? Call us: (959) 991-1020

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

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

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

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

Questions? Call us: (959) 991-1020

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

The Bridges at Oxford Gre...

$600ks

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

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

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

The Village at Oxford Greens

520 TRADITIONS CT N # 520, OXFORD, CT, 0..., Oxford, CT 06478

$629,000

2 beds

2 baths

1,590 sq ft

Condo

520 TRADITIONS CT N # 520, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Spring Lake Village

621 OVERLOOK PATH # 621, SOUTHINGTON, CT..., Southington, CT 06489

$340,000

2 beds

3 baths

1,133 sq ft

Condo

621 OVERLOOK PATH # 621, SOUTHINGTON, CT...

Community: Spring Lake Village

Heritage Village

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

$319,000

2 beds

2 baths

1,432 sq ft

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$364,900

2 beds

2 baths

1,398 sq ft

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Baldwin Station

7 FIRE THORN LN # 7, MILFORD, CT, 06461, Milford, CT 06461

$679,950

2 beds

3 baths

2,331 sq ft

Condo

7 FIRE THORN LN # 7, MILFORD, CT, 06461

Community: Baldwin Station

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

Questions? Call us: (959) 991-1020

Oronoque Village

766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

766 NYACK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$449,000

2 beds

2 baths

1,447 sq ft

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$259,900

2 beds

2 baths

1,365 sq ft

Condo

723 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

35 ALGONQUIN LN D, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

2 beds

2 baths

1,300 sq ft

Condo

35 ALGONQUIN LN D, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$465,000

1 beds

2 baths

1,175 sq ft

Condo

164 BISON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$356,000

2 beds

2 baths

1,398 sq ft

Condo

876 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$499,900

3 beds

2 baths

1,716 sq ft

Condo

929 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$329,000

3 beds

2 baths

1,716 sq ft

Condo

701 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

Heritage Village

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

$374,500

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$298,000

2 beds

2 baths

1,044 sq ft

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

930 TILLINGHAST DR 930, OXFORD, CT, 0647..., Oxford, CT 06478

$699,900

2 beds

3 baths

2,365 sq ft

930 TILLINGHAST DR 930, OXFORD, CT, 0647...

Community: The Village at Oxford Greens

Heritage Village

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

$214,900

2 beds

2 baths

1,044 sq ft

Condo

73 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$385,000

2 beds

2 baths

1,432 sq ft

Condo

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

Community: Heritage Village

Heritage Village

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

$499,900

3 beds

2 baths

1,716 sq ft

Condo

862 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

712 CHAMPIONSHIP DR 712, OXFORD, CT, 064..., Oxford, CT 06478

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR 712, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR 712, OXFORD, CT, 064...

Community: Fairview at Oxford Greens

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

Questions? Call us: (959) 991-1020

Heritage Village

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

$249,900

2 beds

2 baths

1,032 sq ft

Condo

176 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

69 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,900

1 beds

3 baths

1,438 sq ft

Condo

664 OSAGE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$249,900

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614

$465,000

1 beds

3 baths

1,426 sq ft

Condo

736 QUINNIPIAC LN B, STRATFORD, CT, 0661...

Community: Oronoque Village

Heritage Village

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

$298,000

2 beds

2 baths

1,032 sq ft

Condo

114 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$515,000

3 beds

2 baths

1,716 sq ft

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$389,900

2 beds

2 baths

1,398 sq ft

Condo

902 HERITAGE VLG A, 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

Heritage Village

626 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$319,900

2 beds

2 baths

1,432 sq ft

Condo

626 HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$524,900

3 beds

2 baths

1,716 sq ft

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$279,900

2 beds

2 baths

1,365 sq ft

Condo

825 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$339,980

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$285,000

2 beds

2 baths

1,432 sq ft

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$409,000

2 beds

2 baths

1,432 sq ft

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairview at Oxford Greens

1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478

$773,625

2 beds

3 baths

2,536 sq ft

Condo

1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$773,625

2 beds

3 baths

2,536 sq ft

Condo

1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...

Community: The Village at Oxford Greens

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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 10 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 399 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 Granite Woods, Fairview at Oxford Greens, Chatfield Farms. There are also 7 communities in the Waterbury Area that offer new construction homes, including Fairview at Oxford Greens, Pond Spring Village, Chatfield Farms.

Are there gated 55+ communities in the Waterbury Area?

Yes, there are gated 55+ communities in the Waterbury Area. Approximately 16.7% 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 316 days. The average price of homes for sale in these communities is approximately $557,765, 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 Benson Woods average around $534,900.

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

77 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: Feb 26, 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 - Page 2

22 communities near Waterbury Area

77 homes near Waterbury Area

2 beds

2 baths

1,590 sq ft

Condo

2 beds

3 baths

1,133 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

2,331 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

2,365 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths