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

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

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

Regency Meadows

17 REGENCY CIR, TRUMBULL, CT, 06611, Trumbull, CT 06611

$765,000

3 beds

4 baths

2,597 sq ft

Condo

17 REGENCY CIR, TRUMBULL, CT, 06611

Community: Regency Meadows

Oronoque Village

71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$600,000

1 beds

2 baths

1,375 sq ft

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$215,000

2 beds

2 baths

1,000 sq ft

Condo

751 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Prospect

112 CHERRY CIR 112, PROSPECT, CT, 06712, Prospect, CT 06712

$338,903

3 beds

2 baths

1,500 sq ft

Condo

112 CHERRY CIR 112, PROSPECT, CT, 06712

Community: Regency at Prospect

Meadow Brook Estates

107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478

$595,000

3 beds

3 baths

1,922 sq ft

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...

Community: Meadow Brook Estates

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

Questions? Call us: (959) 991-1020

Heritage Village

40 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$270,000

2 beds

2 baths

1,308 sq ft

Condo

40 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478

$710,000

3 beds

3 baths

2,008 sq ft

Condo

84 LINKS WAY 84, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

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

$310,000

2 beds

2 baths

1,432 sq ft

Condo

722 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$427,500

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$305,000

2 beds

2 baths

1,432 sq ft

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478

$624,900

2 beds

3 baths

1,673 sq ft

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Heritage Village

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

$225,000

1 beds

1 baths

928 sq ft

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$264,900

2 beds

2 baths

1,032 sq ft

Condo

23 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$465,000

2 beds

2 baths

1,398 sq ft

Condo

4 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$305,000

2 beds

2 baths

1,032 sq ft

Condo

569 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Meadow Brook Estates

188 EASTWOOD DR 188, SEYMOUR, CT, 06483, Seymour, CT 06483

$589,900

2 beds

3 baths

2,358 sq ft

Condo

188 EASTWOOD DR 188, SEYMOUR, CT, 06483

Community: Meadow Brook Estates

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

Questions? Call us: (959) 991-1020

Oronoque Village

315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$475,000

2 beds

3 baths

1,434 sq ft

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$308,000

2 beds

2 baths

1,432 sq ft

Condo

774 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

28 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$232,000

1 beds

1 baths

928 sq ft

Condo

28 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$220,000

2 beds

2 baths

1,000 sq ft

Condo

732 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$335,000

2 beds

2 baths

1,432 sq ft

Condo

783 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,900

2 beds

2 baths

1,398 sq ft

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Granite Woods

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$219,900

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762

Community: Granite Woods

Heritage Village

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

$199,900

2 beds

2 baths

1,071 sq ft

Condo

857 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$275,000

2 beds

2 baths

1,071 sq ft

Condo

9 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,900

2 beds

2 baths

1,432 sq ft

Condo

559 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

521 PUTTING GREEN LN 521, OXFORD, CT, 06..., Oxford, CT 06478

$675,000

3 beds

3 baths

2,735 sq ft

Condo

521 PUTTING GREEN LN 521, 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

Oronoque Village

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

$495,000

2 beds

3 baths

1,434 sq ft

Condo

546 N TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$219,900

1 beds

1 baths

928 sq ft

Condo

65 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

261B HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$254,000

2 beds

2 baths

1,032 sq ft

Condo

261B HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

1016 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$245,000

1 beds

1 baths

928 sq ft

Condo

1016 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Spring Lake Village

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489

$320,000

2 beds

2 baths

1,313 sq ft

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

The Village at Oxford Greens

171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478

$715,000

3 beds

3 baths

2,750 sq ft

Condo

171 COUNTRY CLUB DR 171, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Oronoque Village

621 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

2,325 sq ft

Condo

621 ONONDAGA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$374,500

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Woodbridge

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

$599,900

3 beds

3 baths

2,006 sq ft

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Heritage Village

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

$370,000

3 beds

2 baths

1,716 sq ft

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairview 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: Fairview at Oxford Greens

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

Questions? Call us: (959) 991-1020

The Village at Oxford Greens

$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

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

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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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Answers from local 55+ experts

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

Want to learn more about 55+ communities in 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 - Page 2

22 communities near Waterbury Area

105 homes near Waterbury Area

3 beds

4 baths

2,597 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

1,922 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

3 beds

3 baths

2,008 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

1,432 sq ft

Condo

2 beds

3 baths

1,673 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

3 baths

2,358 sq ft

Condo

2 beds

3 baths

1,434 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds