Call us at (860) 854-8527 to learn more about active adult communities near Middletown
Middletown, CT 55+ active adult communities & homes for sale
123 communities near Middletown
259 homes near Middletown
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5 rating (3 reviews)
![Founders Ridge]()
$500Ks
- $600Ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 homes
No reviews yet
![Sonoma Woods]()
$300Ks
- $300Ks
Sonoma Woods, Middletown, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2015
|
68 homes
No reviews yet
![Bartlett Hollow]()
$200Ks
- $400Ks
Bartlett Hollow, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
25 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
Want to learn more about 55+ communities in Middletown?
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No reviews yet
![The Greens at Half Hollow]()
$600Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
No reviews yet
![Rivington]()
$400Ks
- $500Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 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
![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
![Leisure Knoll]()
$300Ks
- $500Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 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
![Country Pointe Plainview]()
$1Ms
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (2 reviews)
![Fairfield at St. James]()
$400Ks
- $500Ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
No reviews yet
![Leisure Glen]()
$400Ks
- $400Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(860) 854-8527
3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
No reviews yet
![The Seasons at East Meado...]()
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 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
![The Waterways at Moriches]()
$400Ks
- $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 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.
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$300Ks
- $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
280 homes
4 rating (1 reviews)
![Vineyards at Blue Point]()
$800Ks
- $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
No reviews yet
![The Club at Melville]()
$500Ks
- $500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
No reviews yet
![The Seasons at Elwood]()
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(860) 854-8527
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$600Ks
- $900Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
No reviews yet
![The Summit at Bethel]()
$600Ks
- $600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$600Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$600Ks
- $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 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
![Woodridge Strathmore Terr...]()
$400Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $500Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
No reviews yet
![Brierly Pond Village]()
$400Ks
- $400Ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
No reviews yet
![Country Village Estates]()
$300Ks
- $400Ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 homes
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(860) 854-8527
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
No reviews yet
![The Seasons at East North...]()
$700Ks
- $700Ks
The Seasons at East North..., East Northport, NY
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
190 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900Ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$600Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
No reviews yet
![The Powder Forest Homes]()
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
Glenwood Village
![1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|1 baths
|816 sq ft
|Mobile Home
1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 904992 • Patriot Real Properties Gr LLC, Jack...
Leisure Village
![195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 888315 • Integrity Core Realty, Patroy Quarry
Glenwood Village
![1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,...
Community: Glenwood Village
MLS 901006 • Signature Premier Properties, Noreen...
Greenwood Village
![164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|938 sq ft
|Manufactured Home
164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 887454 • Realty Connect USA L I Inc, Joseph I...
Leisure Glen
![12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 897659 • Homeside Realty, Frank Profeta
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(860) 854-8527
Leisure Village
![419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119..., Ridge, NY 11961]()
1 beds
|1 baths
|782 sq ft
|Condo
419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119...
Community: Leisure Village
MLS 899638 • Howard Hanna Coach, Linda Stowell
Leisure Village
![166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 895352 • Voro LLC, Lauren A. Granger
The Waterways at Moriches
![107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955]()
2 beds
|2 baths
|2,141 sq ft
|Condo
107 E MIDLAND POND CT, MORICHES, NY, 119...
Community: The Waterways at Moriches
MLS 829455 • Douglas Elliman Real Estate, Jo Ann ...
The Waterways at Moriches
![521 HIGHLAND CT # 521, MORICHES, NY, 119..., Moriches, NY 11955]()
2 beds
|2 baths
|1,839 sq ft
|Condo
521 HIGHLAND CT # 521, MORICHES, NY, 119...
Community: The Waterways at Moriches
MLS 838254 • Douglas Elliman Real Estate, Jo Ann ...
The Waterways at Moriches
![279 DOCKSIDE CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|1,480 sq ft
|Condo
279 DOCKSIDE CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 877043 • Douglas Elliman Real Estate, Jo Ann ...
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.
Plymouth Estates at Mount Sinai
![164 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,820 sq ft
|Condo
164 IRA RD, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 878455 • Aliano Real Estate, Nicholas A. Colo...
Plymouth Estates at Mount Sinai
![166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,820 sq ft
|Townhouse
166 IRA RD, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 878423 • Aliano Real Estate, Nicholas A. Colo...
The Village at Westminster Place
![8 INDIAN CIR # 8, HOLDEN, MA, 01520, Holden, MA 01520]()
3 beds
|3 baths
|1,998 sq ft
|House
8 INDIAN CIR # 8, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73444852 • Keller Williams Boston MetroWest, ...
The Gardens of Wilbraham
![116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095]()
2 beds
|2 baths
|1,634 sq ft
|Condo
116 CHERRY DR # 116, WILBRAHAM, MA, 0109...
Community: The Gardens of Wilbraham
MLS 73441478 • Coldwell Banker Realty - Western M...
Brierly Pond Village
![32 HORNE WAY # 32, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|2 baths
|1,420 sq ft
|Condo
32 HORNE WAY # 32, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73433720 • Lamacchia Realty, Inc, Diane Dabro...
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(860) 854-8527
The Village at Westminster Place
![27 TEA PARTY CIR # 27, HOLDEN, MA, 01520, Holden, MA 01520]()
3 beds
|3 baths
|1,895 sq ft
|Condo
27 TEA PARTY CIR # 27, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73430095 • BA Property & Lifestyle Advisors, ...
The Village at Westminster Place
![2 EXPLORERS WAY # 2, HOLDEN, MA, 01520, Holden, MA 01520]()
2 beds
|2 baths
|1,661 sq ft
|Condo
2 EXPLORERS WAY # 2, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73437136 • RE/MAX Partners, David Stead
Harmony Place
![6 FIDELITY DR # 3, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
6 FIDELITY DR # 3, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73399780 • Harbor Classic Realty, Karin Ander...
Harmony Place
![4 FIDELITY DR # 2, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
4 FIDELITY DR # 2, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73403315 • Harbor Classic Realty, Karin Ander...
Frequently Asked Questions
In Middletown, there are no large communities, no medium communities, and 3 small communities with less than 500 homes.
The smallest 55+ communities in Middletown has 25 homes, the largest has 75 homes, and the average communities consists of 56 homes.
Yes, there are new 55+ homes available in Middletown. The most recent communities started in Middletown include Founders Ridge, Bartlett Hollow, Sonoma Woods. There are also 2 communities in Middletown that offer new construction homes, including Bartlett Hollow, Founders Ridge.
Yes, there is gated 55+ communities in Middletown. Approximately 33.3% of 55+ communities in the area are gated. For instance, Bartlett Hollow is a gated communities with 25 homes.
On average, listings in 55+ communities in Middletown stay on the market for around 237 days. The average price of homes for sale in these communities is approximately $577,386, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Sonoma Woods average around $649,900, while homes in Bartlett Hollow average around $579,139.
Want more information about active adult communities around Middletown?
Want to learn more about 55+ communities in Middletown?
259
homes
near Middletown
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© 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: Oct 23, 2025.
This application does not include information on all of the properties available for sale at this time.
