Essex, CT 55+ active adult communities & homes for sale

105 communities near Essex

Sort by:

Relevance

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

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

Questions? Call us: (959) 265-7852

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

Questions? Call us: (959) 265-7852

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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

Questions? Call us: (959) 265-7852

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

New Construction | 55+ age-restricted | Built 2017 - present | 170 homes

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

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

Questions? Call us: (959) 265-7852

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

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

Questions? Call us: (959) 265-7852

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

The Village at Orchard Me...

$400ks - $500ks

The Village at Orchard Me..., Shrewsbury, MA

Resale Only | 55+ age-restricted | Built 2002 - 2007 | 114 homes

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

Questions? Call us: (959) 265-7852

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

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

Questions? Call us: (959) 265-7852

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

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

Questions? Call us: (959) 265-7852

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

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

Questions? Call us: (959) 265-7852

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

252 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

New Fairfield at St. James

909 FENWAY RD, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$489,000

2 beds

2 baths

1,230 sq ft

Condo

909 FENWAY RD, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Sunrise Village

4 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$499,000

2 beds

2 baths

1,230 sq ft

Condo

4 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

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

Questions? Call us: (959) 265-7852

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

Questions? Call us: (959) 265-7852

New Heritage Village

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

$280,000

2 beds

2 baths

1,032 sq ft

Condo

78 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Villages at Mount Sinai Park

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$799,000

3 beds

3 baths

2,455 sq ft

Condo

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

New Bartlett Hill

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480

$479,900

2 beds

3 baths

1,404 sq ft

415 LEISURE DR 415, BROOKHAVEN, NY, 1196...

Community: Leisure Glen

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

Questions? Call us: (959) 265-7852

New Oronoque Village

639 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

2 beds

3 baths

1,438 sq ft

Condo

639 ONONDAGA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Fairfield at St. James

908 DREW LN, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$609,000

2 beds

2 baths

1,050 sq ft

Condo

908 DREW LN, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (959) 265-7852

New The Villages at Mount Sinai Park

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$789,000

3 beds

3 baths

2,455 sq ft

Condo

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Greenwood Village

43 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$264,999

2 beds

2 baths

1,164 sq ft

House

43 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Sunken Pond Estates

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$489,000

2 beds

3 baths

1,350 sq ft

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

Leisure Knoll

506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,000

2 beds

2 baths

1,394 sq ft

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Heritage Village

41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

3 baths

1,479 sq ft

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

65A VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$134,900

1 beds

1 baths

672 sq ft

Condo

65A VILLAGE CIR, BROOKHAVEN, NY, 11949

Condo

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (959) 265-7852

Leisure Village

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$259,990

1 beds

1 baths

684 sq ft

Condo

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Meadow Brook Estates

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

$529,900

2 beds

3 baths

1,564 sq ft

Condo

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

Community: Meadow Brook Estates

Leisure Knoll

151 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,000

2 beds

1 baths

1,000 sq ft

Condo

151 LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Fairfield at St. James

1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$449,990

1 beds

2 baths

948 sq ft

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Heritage Village

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

$524,900

3 beds

2 baths

1,716 sq ft

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (959) 265-7852

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

Fairview 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: Fairview at Oxford Greens

The Village at Oxford Greens

$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

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

Questions? Call us: (959) 265-7852

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

Frequently Asked Questions

What size 55+ communities are there in Essex?

In Essex, there is 1 small community with less than 500 homes.

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

The smallest 55+ community in Essex has 8 homes, the largest has 8 homes, and the average community consists of 8 homes.

Are there new 55+ homes available in Essex?

Yes, there is new 55+ home available in Essex. The most recent community started in Essex include Cobblestone Court. There is also 1 community in Essex that offers new construction homes, including Cobblestone Court.

Are there gated 55+ communities in Essex?

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

Want more information about active adult communities around Essex?

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 Essex?

Call us: (959) 265-7852

105 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: Mar 16, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Essex, CT 55+ active adult communities & homes for sale

105 communities near Essex

170 homes near Essex

3 beds

2 baths

1,716 sq ft

Condo

2 beds

3 baths

2,734 sq ft

Condo

2 beds

3 baths

2,823 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

3 beds

3 baths

2,455 sq ft

Condo

2 beds

3 baths

1,404 sq ft

3 beds

3 baths

2,047 sq ft

Condo

2 beds

2 baths

1,315 sq ft

Condo

3 beds

3 baths

2,107 sq ft

Condo

1 beds

1 baths

750 sq ft

Condo

2 beds

2 baths

1,867 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

3 beds

3 baths

2,455 sq ft

Condo

2 beds

2 baths

1,164 sq ft

House

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,394 sq ft

House

2 beds

3 baths