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

125 communities near Middletown

Sort by:

Relevance

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

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

Questions? Call us: (860) 854-8527

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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.

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 125 homes

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 homes

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes

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

Questions? Call us: (860) 854-8527

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

Eastport Meadows

$400ks

Eastport Meadows, Eastport, NY

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

Country Village Estates

$300ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

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

Questions? Call us: (860) 854-8527

4 rating (1 reviews)

Vineyards at Blue Point

$500ks - $700ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 20 homes

The Polo Club at Islandia

$600ks - $700ks

The Polo Club at Islandia, Islandia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

The Bridges at Oxford Gre...

$600ks

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

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

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

Questions? Call us: (860) 854-8527

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

1 2 3...4

New Heritage Village

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

$229,000

1 beds

1 baths

928 sq ft

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Meadowbrook Pointe Links & Spa

48 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763

$749,990

2 beds

4 baths

1,553 sq ft

Condo

48 AUGUSTA DR, BROOKHAVEN, NY, 11763

Community: Meadowbrook Pointe Links & Spa

New Fairfield at St. James

209 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$419,000

1 beds

2 baths

900 sq ft

Condo

209 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Heritage Village

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

$219,900

2 beds

2 baths

1,308 sq ft

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

1 beds

3 baths

1,583 sq ft

Condo

619 ERIE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (860) 854-8527

New Fairview at Oxford Greens

1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Oronoque Village

765 NYACK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,900

2 beds

3 baths

1,642 sq ft

Condo

765 NYACK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Glen

289 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$585,000

2 beds

2 baths

1,666 sq ft

Condo

289 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Leisure Village

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$475,000

2 beds

2 baths

1,278 sq ft

Condo

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Heritage Village

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

$265,000

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Sunrise Village

168 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$450,000

2 beds

1 baths

871 sq ft

Condo

168 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

New Country Pointe Preserve

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$965,000

2 beds

3 baths

2,389 sq ft

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

New The Woods at Dunham Pond

30 HERON VIEW RD, NEW FAIRFIELD, CT, 068..., New Fairfield, CT 06812

$559,900

1 beds

3 baths

3,230 sq ft

Condo

30 HERON VIEW RD, NEW FAIRFIELD, CT, 068...

Community: The Woods at Dunham Pond

New Sunrise Village

109 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$525,000

2 beds

2 baths

1,273 sq ft

Condo

109 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

New Stoneleigh Woods at Riverhead

156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$659,000

2 beds

3 baths

1,942 sq ft

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

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

Questions? Call us: (860) 854-8527

New Leisure Glen

155 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$495,000

2 beds

2 baths

1,456 sq ft

Condo

155 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Oronoque Village

564 PEQUOT LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,900

2 beds

2 baths

1,438 sq ft

Condo

564 PEQUOT LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Hopmeadow Place

1 W ST 223, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 223, SIMSBURY, CT, 06070

Community: Hopmeadow Place

Oronoque Village

638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614

$539,000

1 beds

3 baths

1,175 sq ft

Condo

638A ONONDAGA LN, STRATFORD, CT, 06614

Community: Oronoque Village

Encore Atlantic Shores

11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$925,000

2 beds

3 baths

3,037 sq ft

House

11 OVATION PL, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Country Pointe Plainview

21105 ASPENWOOD DR 275, OYSTER BAY, NY, ..., Oyster Bay, NY 11803

$1,245,000

2 beds

2 baths

1,475 sq ft

Condo

21105 ASPENWOOD DR 275, OYSTER BAY, NY, ...

Community: Country Pointe Plainview

Heritage Village

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

$205,000

2 beds

2 baths

1,308 sq ft

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

80 WINDING RIDGE WAY 80, DANBURY, CT, 06..., Danbury, CT 06810

$775,000

3 beds

3 baths

2,204 sq ft

Condo

80 WINDING RIDGE WAY 80, DANBURY, CT, 06...

Community: Rivington

The Greens at Half Hollow

870 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$749,888

2 beds

2 baths

1,262 sq ft

Condo

870 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Heritage Village

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

$289,000

2 beds

2 baths

1,432 sq ft

Condo

69 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

The Waterways at Moriches

248 RIVER DR 248, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$629,000

2 beds

2 baths

1,544 sq ft

Condo

248 RIVER DR 248, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

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

Questions? Call us: (860) 854-8527

The Greens at Half Hollow

381 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,499,999

2 beds

2 baths

2,575 sq ft

Condo

381 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Heritage Village

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

$399,999

3 beds

2 baths

1,716 sq ft

Condo

110 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Greens at Half Hollow

259 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,399,999

3 beds

3 baths

3,200 sq ft

Condo

259 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Setauket Meadows

113 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$779,000

2 beds

3 baths

1,842 sq ft

Condo

113 BRIANNA DR, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Regency at Prospect

28 TAMARACK CT 28, PROSPECT, CT, 06712, Prospect, CT 06712

$635,000

2 beds

3 baths

2,005 sq ft

Condo

28 TAMARACK CT 28, PROSPECT, CT, 06712

Community: Regency at Prospect

Setauket Meadows

58 BLAIR RD 58, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$849,999

2 beds

4 baths

1,773 sq ft

House

58 BLAIR RD 58, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Newbury Village

46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804

$725,000

2 beds

4 baths

2,560 sq ft

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...

Community: Newbury Village

Leisure Village

150 EASTBOURNE CT B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$419,000

2 beds

2 baths

1,515 sq ft

Condo

150 EASTBOURNE CT B, BROOKHAVEN, NY, 119...

Community: Leisure Village

Heritage Village

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

$289,900

2 beds

2 baths

1,032 sq ft

Condo

32 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$239,900

1 beds

1 baths

928 sq ft

Condo

12 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Foxwood Village

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$469,000

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933

Community: Foxwood Village

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

Questions? Call us: (860) 854-8527

The Coves at Melville

80 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$589,999

2 beds

2 baths

1,169 sq ft

Condo

80 MORLEY CIR, HUNTINGTON, NY, 11747

Community: The Coves at Melville

Rivington

524 CENTER MEADOW LN 524, DANBURY, CT, 0..., Danbury, CT 06810

$519,000

2 beds

2 baths

1,258 sq ft

Condo

524 CENTER MEADOW LN 524, DANBURY, CT, 0...

Community: Rivington

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there are no large communities, no medium communities, and 3 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middletown?

The smallest 55+ communities in Middletown has 25 homes, the largest has 75 homes, and the average communities consists of 56 homes.

Are there new 55+ homes available in Middletown?

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.

Are there gated 55+ communities in Middletown?

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.

How long do listings in 55+ communities in Middletown typically stay on the market, and what is the average price of homes for sale?

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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Middletown?

Call us: (860) 854-8527

125 communities

Remove Boundaries ×

Map Satellite

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 28, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

125 communities near Middletown

226 homes near Middletown

1 beds

1 baths

928 sq ft

Condo

2 beds

4 baths

1,553 sq ft

Condo

1 beds

2 baths

900 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

1 beds

3 baths

1,583 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,642 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,278 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

1 baths

871 sq ft

Condo

2 beds

3 baths

2,389 sq ft

Condo

1 beds

3 baths

3,230 sq ft

Condo

2 beds

2 baths

1,273 sq ft

Condo

2 beds

3 baths

1,942 sq ft

Condo

2 beds

2 baths

1,456 sq ft

Condo

2 beds

2 baths

1,438 sq ft

Condo

2 beds

2 baths

1,477 sq ft

Condo

1 beds