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

106 communities near Essex

Sort by:

Relevance

The Villages at Walker Me...

$600ks - $700ks

The Villages at Walker Me..., Westborough, MA

Resale Only | 55+ age-restricted | Built 1999 - 2000 | 100 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

Hopmeadow Place

$200ks - $300ks

Hopmeadow Place, Simsbury, CT

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

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

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

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

Questions? Call us: (959) 265-7852

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

Bidwell Village

$300ks - $400ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 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 (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

The Seasons at East North...

$700ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 homes

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

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

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

Questions? Call us: (959) 265-7852

The Polo Club at Islandia

$600ks - $700ks

The Polo Club at Islandia, Islandia, NY

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

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

1 rating (1 reviews)

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

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

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

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

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

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

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes

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

Questions? Call us: (959) 265-7852

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

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

Questions? Call us: (959) 265-7852

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

Cobblestone Court

$400ks - $500ks

Cobblestone Court, Essex, CT

New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes

1 2...3

Greenwood Village

201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$250,000

2 beds

2 baths

1,078 sq ft

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Strathmore Gate East

46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$429,999

2 beds

2 baths

1,112 sq ft

House

46 FORGE LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New Foxwood Village

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$465,000

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Upton Ridge

87 SHANNON WAY 1, UPTON, MA, 01568, Upton, MA 01568

$669,900

2 beds

3 baths

1,950 sq ft

Condo

87 SHANNON WAY 1, UPTON, MA, 01568

Community: Upton Ridge

New Granite Woods

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$250,000

2 beds

1 baths

890 sq ft

Condo

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762

Community: Granite Woods

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

Questions? Call us: (959) 265-7852

New Greenwood Village

33 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$225,000

2 beds

2 baths

1,134 sq ft

House

33 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Windcrest East

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933

$799,000

3 beds

3 baths

2,620 sq ft

Condo

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...

Community: Windcrest East

New Windcrest East

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933

$799,990

3 beds

3 baths

2,531 sq ft

Condo

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...

Community: Windcrest East

New Leisure Glen

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$519,900

2 beds

2 baths

1,476 sq ft

Condo

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Long Hill Village

48 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$499,900

2 beds

2 baths

1,070 sq ft

Condo

48 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

New Meadow Brook Estates

130 MEADOW BROOK RD 130, OXFORD, CT, 064..., Oxford, CT 06478

$599,000

2 beds

3 baths

1,920 sq ft

Condo

130 MEADOW BROOK RD 130, OXFORD, CT, 064...

Community: Meadow Brook Estates

New Greenwood Village

10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$179,999

2 beds

1 baths

938 sq ft

Condo

10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Leisure Knoll

148 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,096 sq ft

Condo

148 LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Fairfield at St. James

1406 GOTHAM CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$579,803

2 beds

2 baths

1,321 sq ft

Condo

1406 GOTHAM CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Long Hill Village

36 LONG HILL PL, TRUMBULL, CT, 06611, Trumbull, CT 06611

$550,000

2 beds

3 baths

1,370 sq ft

Condo

36 LONG HILL PL, TRUMBULL, CT, 06611

Community: Long Hill Village

New Regency Meadows

17 REGENCY CIR, TRUMBULL, CT, 06611, Trumbull, CT 06611

$765,000

3 beds

4 baths

2,597 sq ft

17 REGENCY CIR, TRUMBULL, CT, 06611

Community: Regency Meadows

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

Questions? Call us: (959) 265-7852

New Greenwood Village

1 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$268,833

2 beds

2 baths

1,027 sq ft

Condo

1 LIMETREE DR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Foxwood Village

1407 MIDDLE RD 245, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$349,000

3 beds

2 baths

1,368 sq ft

House

1407 MIDDLE RD 245, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Setauket Meadows

33 BLAIR RD, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$849,999

2 beds

3 baths

1,700 sq ft

Condo

33 BLAIR RD, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

New Encore at Lake Grove

163 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$645,000

2 beds

3 baths

1,378 sq ft

Condo

163 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

New Regency at Woodbridge

18 HILLCREST DR 18, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525

$829,900

3 beds

3 baths

2,412 sq ft

Condo

18 HILLCREST DR 18, WOODBRIDGE, CT, 0652...

Community: Regency at Woodbridge

Heritage Village

2 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$469,900

2 beds

2 baths

1,420 sq ft

Condo

2 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

19 HICKORY HL 19, SOUTHINGTON, CT, 06489, Southington, CT 06489

$256,000

2 beds

2 baths

1,285 sq ft

Condo

19 HICKORY HL 19, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Leisure Village

38 TRENT CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$339,000

2 beds

1 baths

836 sq ft

Condo

38 TRENT CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

Heritage Village

4 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,000

2 beds

2 baths

1,306 sq ft

Condo

4 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$350,000

3 beds

2 baths

1,716 sq ft

Condo

682 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

5 HOLLY DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$99,990

2 beds

2 baths

960 sq ft

Condo

5 HOLLY DR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (959) 265-7852

Heritage Village

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

$415,000

2 beds

2 baths

1,432 sq ft

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$324,900

2 beds

2 baths

1,000 sq ft

Condo

883 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Pond Spring Village

111 PONDVIEW CIR 111, BEACON FALLS, CT, ..., Beacon Falls, CT 06403

$435,000

2 beds

2 baths

1,328 sq ft

Condo

111 PONDVIEW CIR 111, BEACON FALLS, CT, ...

Community: Pond Spring Village

Encore at Lake Grove

35 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$598,000

2 beds

2 baths

1,390 sq ft

Condo

35 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

Meadow Brook Estates

132 MEADOW BROOK RD 132, OXFORD, CT, 064..., Oxford, CT 06478

$599,900

2 beds

3 baths

1,931 sq ft

Condo

132 MEADOW BROOK RD 132, OXFORD, CT, 064...

Community: Meadow Brook Estates

Oronoque Village

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

$356,000

1 beds

2 baths

1,175 sq ft

Condo

88 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$245,000

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$389,000

1 beds

2 baths

1,480 sq ft

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Saddle Lakes

120 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$549,000

2 beds

2 baths

1,386 sq ft

Condo

120 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Eastport Meadows

15 MEADOW WAY, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$650,000

2 beds

3 baths

1,855 sq ft

Condo

15 MEADOW WAY, BROOKHAVEN, NY, 11941

Community: Eastport Meadows

Westhampton Pines

30 KIMBERLY DR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,395,000

2 beds

3 baths

2,400 sq ft

Condo

30 KIMBERLY DR, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

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

Questions? Call us: (959) 265-7852

Heritage Village

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

$279,000

2 beds

2 baths

1,432 sq ft

Condo

991 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Meadow Brook Estates

207 WOODLAWN DR 207, SEYMOUR, CT, 06483, Seymour, CT 06483

$625,000

3 beds

3 baths

2,484 sq ft

Condo

207 WOODLAWN DR 207, SEYMOUR, CT, 06483

Community: Meadow Brook Estates

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 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 Essex?

Call us: (959) 265-7852

106 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: Oct 09, 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

238 homes near Essex

2 beds

2 baths

1,078 sq ft

Condo

2 beds

2 baths

1,112 sq ft

House

3 beds

2 baths

1,792 sq ft

Manufactured Home

2 beds

3 baths

1,950 sq ft

Condo

2 beds

1 baths

890 sq ft

Condo

2 beds

2 baths

1,134 sq ft

House

3 beds

3 baths

2,620 sq ft

Condo

3 beds

3 baths

2,531 sq ft

Condo

2 beds

2 baths

1,476 sq ft

Condo

2 beds

2 baths

1,070 sq ft

Condo

2 beds

3 baths

1,920 sq ft

Condo

2 beds

1 baths

938 sq ft

Condo

2 beds

2 baths

1,096 sq ft

Condo

2 beds

2 baths

1,321 sq ft

Condo

2 beds

3 baths

1,370 sq ft

Condo

3 beds

4 baths

2,597 sq ft

2 beds

2 baths

1,027 sq ft

Condo

3 beds

2 baths

1,368 sq ft

House

2 beds

3 baths

1,700 sq ft

Condo

2 beds

3 baths