Trumbull, CT 55+ active adult communities & homes for sale - Page 3

151 communities near Trumbull

Sort by:

Relevance

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

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

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

1 rating (1 reviews)

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

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

Questions? Call us: (475) 231-4869

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

Meadowbrooke Pointe East ...

$500ks - $600ks

Meadowbrooke Pointe East ..., East Meadow, NY

New Construction | 62+ age-restricted | Built 2019 - present | 104 homes

Eastport Meadows

$400ks

Eastport Meadows, Eastport, NY

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

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

The Club at Melville

$500ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 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.

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

The Seasons at Plainview

$500ks - $600ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

5 rating (1 reviews)

Regency at Trotters Point...

$700ks - $800ks

Regency at Trotters Point..., Tinton Falls, NJ

Resale Only | 55+ age-restricted | Built 2014 - 2021 | 181 homes

Stratford Park

$600ks - $800ks

Stratford Park, Melville, NY

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 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

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

Questions? Call us: (475) 231-4869

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

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

Knickerbocker Bay Club

$700ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

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

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

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

5 rating (1 reviews)

Shady Oaks

$200ks - $400ks

Shady Oaks, Red Bank, NJ

Resale Only | 55+ age-restricted | Built 1982 - 1983 | 366 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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

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

Questions? Call us: (475) 231-4869

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

Wolfe Landing

$500ks - $600ks

Wolfe Landing, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes

Eden Park

$500ks - $600ks

Eden Park, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes

Regency at Pearl River

$800ks - $1Ms

Regency at Pearl River, Pearl River, NY

New Construction | 55+ age-restricted | Built 2026 - present | 36 homes

The Hollows at Blue Hill

$500ks - $700ks

The Hollows at Blue Hill, Pearl River, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Four Seasons at Ridgemont

$800ks - $1Ms

Four Seasons at Ridgemont, Montvale, NJ

Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes

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

Questions? Call us: (475) 231-4869

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

The Residences at Butterf...

$500ks - $600ks

The Residences at Butterf..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes

1 2 3...4

Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$369,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Paris Square

1206 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647

$649,900

2 beds

2 baths

Condo

1206 RIO VISTA LN, NORTHVALE, NJ, 07647

Community: Paris Square

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

Questions? Call us: (475) 231-4869

New The Seasons at Seaford

41 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$875,000

2 beds

2 baths

1,408 sq ft

Condo

41 SPRING DR, HEMPSTEAD, NY, 11783

Community: The Seasons at Seaford

New Overlook

2006 SUMMIT LOOP 39, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

2 baths

1,948 sq ft

Condo

2006 SUMMIT LOOP 39, CARMEL, NY, 10512

Community: Overlook

New Heritage Hills

590 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$875,000

3 beds

2 baths

1,793 sq ft

Condo

590 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Rivington

714 CENTER MEADOW LN 714, DANBURY, CT, 0..., Danbury, CT 06810

$497,000

2 beds

2 baths

1,258 sq ft

Condo

714 CENTER MEADOW LN 714, DANBURY, CT, 0...

Community: Rivington

New Vineyards at Blue Point

132 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$879,999

2 beds

4 baths

2,290 sq ft

Condo

132 HALLEY DR, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

New Eagles Walk at East Quogue

1401 AERIE WAY, SOUTHAMPTON, NY, 11942, Southampton, NY 11942

$565,000

2 beds

2 baths

1,271 sq ft

Condo

1401 AERIE WAY, SOUTHAMPTON, NY, 11942

Community: Eagles Walk at East Quogue

New Heritage Village

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

$424,900

2 beds

2 baths

1,432 sq ft

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New HarborView

100 HARBOR VIEW DR 117, NORTH HEMPSTEAD,..., North Hempstead, NY 11050

$699,000

1 beds

2 baths

1,262 sq ft

Condo

100 HARBOR VIEW DR 117, NORTH HEMPSTEAD,...

Community: HarborView

New Shaker Heights

12 COPLEY CIR 12, ENFIELD, CT, 06082, Enfield, CT 06082

$589,900

2 beds

2 baths

1,897 sq ft

Condo

12 COPLEY CIR 12, ENFIELD, CT, 06082

Community: Shaker Heights

New Founders Village

2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971, Southold, NY 11971

$550,000

2 beds

2 baths

1,100 sq ft

Condo

2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971

Community: Founders Village

New The Greens at Half Hollow

559 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,299,000

3 beds

3 baths

2,396 sq ft

Condo

559 BARDINI DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (475) 231-4869

New Leisure Knoll

185 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$405,000

2 beds

1 baths

1,014 sq ft

Condo

185 KINGSTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Jefferson Village

3 HAMPTON CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$199,000

1 baths

550 sq ft

Condo

3 HAMPTON CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Village

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

$164,900

2 beds

2 baths

1,044 sq ft

Condo

549 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Snug Harbor

158 HARBOR S, BABYLON, NY, 11701, Babylon, NY 11701

$719,000

2 beds

3 baths

1,334 sq ft

Condo

158 HARBOR S, BABYLON, NY, 11701

Community: Snug Harbor

Kensington Estates

44 PLAINVIEW RD, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797

$1,999,888

6 beds

5 baths

4,333 sq ft

House

44 PLAINVIEW RD, OYSTER BAY, NY, 11797

Community: Kensington Estates

Encore Atlantic Shores

101 MOZART CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$779,000

2 beds

2 baths

2,044 sq ft

House

101 MOZART CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Heritage Village

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

$244,000

2 beds

2 baths

1,000 sq ft

Condo

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

Community: Heritage Village

Rivington

12 OLD PASTURE DR 12, DANBURY, CT, 06810, Danbury, CT 06810

$839,000

3 beds

4 baths

1,794 sq ft

Condo

12 OLD PASTURE DR 12, DANBURY, CT, 06810

Community: Rivington

Jefferson Village

43 JEFFERSON OVAL A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$465,000

2 beds

2 baths

1,051 sq ft

Condo

43 JEFFERSON OVAL A, YORKTOWN, NY, 10598

Community: Jefferson Village

Greenwood Village

205 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$125,000

2 beds

2 baths

1,138 sq ft

House

205 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Regency at Fishkill

734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$539,500

2 beds

2 baths

1,499 sq ft

Condo

734 REGENCY DR, FISHKILL, NY, 12524

Condo

272 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (475) 231-4869

Shadow Lake Village

52 EASTPORT CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$669,000

2 beds

2 baths

Ranch

52 EASTPORT CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Heritage Hills

790 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$649,999

2 beds

2 baths

1,296 sq ft

Condo

790 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Frequently Asked Questions

What size 55+ communities are there in Trumbull?

In Trumbull, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

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

The smallest 55+ communities in Trumbull has 51 homes, the largest has 71 homes, and the average communities consists of 61 homes.

Are there gated 55+ communities in Trumbull?

No, there are no gated 55+ communities in Trumbull.

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

On average, listings in 55+ communities in Trumbull stay on the market for around 643 days. The average price of homes for sale in these communities is approximately $660,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Regency Meadows average around $660,000.

Want more information about active adult communities around Trumbull?

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 optout@55places.com. 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 Trumbull?

Call us: (475) 231-4869

151 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: Aug 25, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Trumbull, CT 55+ active adult communities & homes for sale - Page 3

151 communities near Trumbull

315 homes near Trumbull

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

Condo

2 beds

2 baths

1,408 sq ft

Condo

2 beds

2 baths

1,948 sq ft

Condo

3 beds

2 baths

1,793 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

4 baths

2,290 sq ft

Condo

2 beds

2 baths

1,271 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,262 sq ft

Condo

2 beds

2 baths

1,897 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

3 beds

3 baths

2,396 sq ft

Condo

2 beds

1 baths

1,014 sq ft

Condo

1 baths

550 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

1,334 sq ft