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

186 homes 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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

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

Questions? Call us: (959) 265-7852

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

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.

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 (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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

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

Questions? Call us: (959) 265-7852

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

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

Questions? Call us: (959) 265-7852

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

Forest Glen

$400ks - $500ks

Forest Glen, Uxbridge, MA

New Construction | 55+ age-restricted | Built 2018 - present | 44 homes

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes

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

Questions? Call us: (959) 265-7852

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

1 2...3

O'Meara Farm

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032

$480,000

2 beds

2 baths

1,416 sq ft

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032

279 BERWICK CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (959) 265-7852

Country Village Estates

45 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$452,000

2 beds

2 baths

1,305 sq ft

Condo

45 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

The Villages at Mount Sinai Park

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$675,000

2 beds

3 baths

1,736 sq ft

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Regency at Prospect

104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712

$328,417

3 beds

2 baths

1,500 sq ft

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712

Community: Regency at Prospect

Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ...

Condo

177 THISTLE POND DR 177, BLOOMFIELD, CT,...

Community: South Pond Village

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

Questions? Call us: (959) 265-7852

The Village at Oxford Greens

523 PUTTING GREEN LN 523, OXFORD, CT, 06..., Oxford, CT 06478

$625,000

2 beds

2 baths

2,008 sq ft

Condo

523 PUTTING GREEN LN 523, OXFORD, CT, 06...

Community: The Village at Oxford Greens

Greenwood Village

2 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$192,500

2 beds

2 baths

1,064 sq ft

Condo

2 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Heritage Village

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$225,000

1 beds

1 baths

928 sq ft

Condo

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

Oronoque Village

72 DAKOTA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$539,500

1 beds

3 baths

1,118 sq ft

Condo

72 DAKOTA LN B, STRATFORD, CT, 06614

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

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

Questions? Call us: (959) 265-7852

Heritage Village

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

$214,900

2 beds

2 baths

1,032 sq ft

Condo

151 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$229,000

1 beds

1 baths

928 sq ft

Condo

79 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

75 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$135,000

2 beds

2 baths

1,110 sq ft

Condo

75 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Greenwood Village

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

$264,999

2 beds

2 baths

1,164 sq ft

Condo

43 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,308 sq ft

Condo

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

Leisure Village

395 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$289,000

2 beds

1 baths

874 sq ft

Condo

395 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...

Community: Leisure Village

Leisure Village

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$380,000

2 beds

2 baths

972 sq ft

Condo

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Fairfield at St. James

506 DREW DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$599,999

3 beds

3 baths

1,716 sq ft

Condo

506 DREW DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (959) 265-7852

Heritage Village

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

$509,000

3 beds

2 baths

1,716 sq ft

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

86 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$535,000

2 beds

3 baths

2,734 sq ft

Condo

86 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

1 2 3 4…5

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

186 homes

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 11, 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 - Page 2

106 communities near Essex

186 homes near Essex

2 beds

2 baths

1,416 sq ft

Condo

2 beds

2 baths

1,532 sq ft

House

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,360 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,305 sq ft

Condo

2 beds

3 baths

1,736 sq ft

House

3 beds

2 baths

1,500 sq ft

Condo

3 beds

3 baths

Condo

2 beds

4 baths

2,843 sq ft

Condo

2 beds

2 baths

1,261 sq ft

Condo

2 beds

2 baths

2,100 sq ft

Condo

2 beds

1 baths

720 sq ft

Manufactured Home

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

2 baths

1,341 sq ft

House

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,312 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

2 baths