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

113 homes near Waterbury Area

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3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

No reviews yet

The Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

No reviews yet

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

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

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

Questions? Call us: (959) 991-1020

No reviews yet

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

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

No reviews yet

Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

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

No reviews yet

The Bridges at Oxford Gre...

$600Ks - $600Ks

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

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

No reviews yet

Pond Spring Village

$300Ks - $300Ks

Pond Spring Village, Beacon Falls, CT

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

5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

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

No reviews yet

Boulder Brook

$200Ks - $200Ks

Boulder Brook, Prospect, CT

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

No reviews yet

RiverBend Estates

$400Ks - $400Ks

RiverBend Estates, Oxford, CT

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

No reviews yet

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

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

No reviews yet

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

Spring Lake Village

$200Ks - $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

No reviews yet

Applegate Estates

$500Ks - $400Ks

Applegate Estates, Southington, CT

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

No reviews yet

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

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

No reviews yet

Baldwin Station

$400Ks - $400Ks

Baldwin Station, Milford, CT

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

No reviews yet

Long Hill Village

$300Ks - $400Ks

Long Hill Village, Trumbull, CT

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

No reviews yet

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

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

No reviews yet

Regency Meadows

$500Ks - $500Ks

Regency Meadows, Trumbull, CT

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

No reviews yet

Gloria Commons

$400Ks - $400Ks

Gloria Commons, Milford, CT

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

Regency at Woodbridge

6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT..., Woodbridge, CT 06525

$619,000

3 beds

3 baths

Condo

6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT...

Community: Regency at Woodbridge

Regency at Woodbridge

12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C..., Woodbridge, CT 06525

$679,000

3 beds

3 baths

Condo

12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C...

Community: Regency at Woodbridge

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

890 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$300,000

2 beds

2 baths

1,432 sq ft

Condo

133 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$259,900

2 beds

2 baths

1,044 sq ft

Condo

73 HERITAGE VLG D, 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

568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$429,900

2 beds

2 baths

1,432 sq ft

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$415,000

2 beds

2 baths

1,432 sq ft

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$544,999

3 beds

3 baths

1,438 sq ft

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$415,000

2 beds

2 baths

1,432 sq ft

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairview at Oxford Greens

1132 ST ANDREWS DR 93, OXFORD, CT, 06478, Oxford, CT 06478

$719,900

2 beds

3 baths

2,536 sq ft

Condo

1132 ST ANDREWS DR 93, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village 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: The Village at Oxford Greens

The Village at Oxford Greens

1130 ST ANDREWS DR 94, OXFORD, CT, 06478, Oxford, CT 06478

$729,900

2 beds

3 baths

1,955 sq ft

Condo

1130 ST ANDREWS DR 94, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$773,625

2 beds

3 baths

2,536 sq ft

Condo

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

Community: Fairview at Oxford Greens

Heritage Village

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

$289,900

2 beds

2 baths

1,365 sq ft

Condo

825 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairview at Oxford Greens

$729,900

2 beds

3 baths

1,955 sq ft

Condo

1130 ST ANDREWS DR 94, 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

$719,900

2 beds

3 baths

2,536 sq ft

Condo

1132 ST ANDREWS DR 93, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Village

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

$239,000

2 beds

2 baths

1,308 sq ft

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$399,900

2 beds

2 baths

1,398 sq ft

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Long Hill Village

17 RAINBOW DR, TRUMBULL, CT, 06611, Trumbull, CT 06611

$484,900

2 beds

2 baths

1,370 sq ft

Condo

17 RAINBOW DR, TRUMBULL, CT, 06611

Community: Long Hill Village

Chatfield Farms

18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403

$599,000

2 beds

3 baths

2,719 sq ft

18 FIELDSTONE LN # 18, BEACON FALLS, CT,...

Community: Chatfield Farms

Spring Lake Village

8 VILLAGE RD # 8, SOUTHINGTON, CT, 06489, Southington, CT 06489

$224,900

2 beds

2 baths

1,314 sq ft

Condo

8 VILLAGE RD # 8, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Fairview at Oxford Greens

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0..., Oxford, CT 06478

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Fairview at Oxford Greens

1117 ST ANDREWS DR 43, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

3 baths

2,536 sq ft

Condo

1117 ST ANDREWS DR 43, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

1121 ST ANDREWS DR 45, OXFORD, CT, 06478, Oxford, CT 06478

$709,900

2 beds

3 baths

1,955 sq ft

Condo

1121 ST ANDREWS DR 45, OXFORD, CT, 06478

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

543 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

2 beds

3 baths

1,426 sq ft

Condo

543 NORTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

The Village at Oxford Greens

$699,900

2 beds

3 baths

2,536 sq ft

Condo

1117 ST ANDREWS DR 43, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Chatfield Farms

81 FIELDSTONE LN # 81, BEACON FALLS, CT,..., Beacon Falls, CT 06403

$639,900

2 beds

2 baths

1,988 sq ft

Condo

81 FIELDSTONE LN # 81, BEACON FALLS, CT,...

Community: Chatfield Farms

Heritage Village

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

$265,000

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$265,000

2 beds

2 baths

1,365 sq ft

Condo

93 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

18 COACH DR # 18, SOUTHINGTON, CT, 06489, Southington, CT 06489

$239,900

2 beds

2 baths

1,178 sq ft

Condo

18 COACH DR # 18, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Village

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

$185,000

2 beds

2 baths

1,044 sq ft

Condo

103 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$369,900

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, 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

Regency at Prospect

11 POPLAR DR # 11, PROSPECT, CT, 06712, Prospect, CT 06712

$549,000

3 beds

3 baths

2,058 sq ft

Condo

11 POPLAR DR # 11, PROSPECT, CT, 06712

Community: Regency at Prospect

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

Questions? Call us: (959) 991-1020

Heritage Village

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

$234,900

2 beds

2 baths

1,365 sq ft

Condo

793 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$409,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$359,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$379,000

3 beds

2 baths

1,716 sq ft

Condo

132 HERITAGE VLG B, 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

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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

113 homes near Waterbury Area

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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.
© 2025 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: Nov 03, 2025.
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

113 homes near Waterbury Area

3 beds

3 baths

Condo

3 beds

3 baths

Condo

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

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

2,536 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,370 sq ft

Condo

2 beds

3 baths

2,719 sq ft