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

89 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

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

The Bridges at Oxford Gre...

$600ks

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

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

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

Questions? Call us: (959) 991-1020

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

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

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

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

Questions? Call us: (959) 991-1020

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

Meadow Brook Estates

312 SPRUCE HILL DR 312, OXFORD, CT, 0647..., Oxford, CT 06478

$509,900

2 beds

3 baths

1,564 sq ft

Condo

312 SPRUCE HILL DR 312, OXFORD, CT, 0647...

Community: Meadow Brook Estates

Heritage Village

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

$509,000

3 beds

2 baths

1,716 sq ft

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

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

$600,000

2 beds

3 baths

1,620 sq ft

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

The Village at Oxford Greens

1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1125 ST ANDREWS DR 47, 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

1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fairview at Oxford Greens

1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478

$739,900

2 beds

3 baths

2,536 sq ft

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$739,900

2 beds

3 baths

2,536 sq ft

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

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

$289,900

2 beds

2 baths

1,044 sq ft

Condo

103 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

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

$679,000

2 beds

3 baths

1,434 sq ft

Condo

546 N TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$635,000

1 beds

2 baths

1,360 sq ft

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$599,900

3 beds

2 baths

1,716 sq ft

Condo

191 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

Spring Lake Village

41 COACH DR 41, SOUTHINGTON, CT, 06489, Southington, CT 06489

$249,900

2 beds

2 baths

1,232 sq ft

Condo

41 COACH DR 41, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$279,900

2 beds

2 baths

1,000 sq ft

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Spring Lake Village

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489

$315,000

3 beds

3 baths

1,471 sq ft

Condo

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Oronoque Village

488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

1 beds

3 baths

2,199 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$349,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$399,000

3 beds

2 baths

1,716 sq ft

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$635,000

2 beds

3 baths

2,038 sq ft

Condo

133 BANNOCK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (959) 991-1020

Heritage Village

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

$289,900

2 beds

2 baths

1,144 sq ft

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Chatfield Farms

8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$699,900

3 beds

4 baths

2,610 sq ft

Condo

8 WOODLAND PATH 8, BEACON FALLS, CT, 064...

Community: Chatfield Farms

Heritage Village

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

$500,000

3 beds

2 baths

1,716 sq ft

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,000

2 beds

2 baths

1,432 sq ft

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$249,000

2 beds

2 baths

1,071 sq ft

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

301 FAIRWAY DR 301, OXFORD, CT, 06478, Oxford, CT 06478

$584,900

2 beds

2 baths

2,080 sq ft

Condo

301 FAIRWAY DR 301, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Granite Woods

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$229,000

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762

Community: Granite Woods

Oronoque Village

635 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

1 beds

3 baths

1,454 sq ft

Condo

635 N TRL B, STRATFORD, CT, 06614

Community: Oronoque 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

607 CHAMPIONSHIP DR 607, OXFORD, CT, 064..., Oxford, CT 06478

$650,000

3 beds

3 baths

2,731 sq ft

Condo

607 CHAMPIONSHIP DR 607, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Oronoque Village

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

$399,000

1 beds

2 baths

1,330 sq ft

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$299,000

2 beds

2 baths

1,365 sq ft

Condo

423 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$635,000

3 beds

3 baths

1,426 sq ft

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

Oronoque Village

151 S TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$449,000

1 beds

3 baths

1,426 sq ft

Condo

151 S TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$324,900

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

1 COACH DR 1, SOUTHINGTON, CT, 06489, Southington, CT 06489

$279,900

2 beds

2 baths

1,323 sq ft

Condo

1 COACH DR 1, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Spring Lake Village

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

$330,000

2 beds

3 baths

1,133 sq ft

Condo

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

Community: Spring Lake 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

Heritage Village

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

$289,900

2 beds

2 baths

1,044 sq ft

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

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

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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

89 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: Apr 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

89 homes near Waterbury Area

2 beds

3 baths

1,564 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

3 baths

1,620 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

1,434 sq ft

Condo

1 beds

2 baths

1,360 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,232 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

3 baths

1,471 sq ft

Condo

1 beds

3 baths

2,199 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds