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

362 homes near Westport

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

2.8 rating (4 reviews)

Cheesequake Village

$100ks - $200ks

Cheesequake Village, Old Bridge, NJ

Resale Only | 55+ age-restricted | Built 1965 - 1971 | 713 homes

3 rating (2 reviews)

Heritage Hills

- $900ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

5 rating (2 reviews)

Shadow Lake Village

$200ks - $500ks

Shadow Lake Village, Red Bank, NJ

Resale Only | 55+ age-restricted | Built 1972 - 1980 | 952 homes

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

Questions? Call us: (475) 471-1908

2.8 rating (5 reviews)

The Villages NJ

$200ks - $300ks

The Villages NJ, Howell, NJ

Resale Only | 55+ age-restricted | Built 1967 - 1975 | 670 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

3.7 rating (3 reviews)

Rosemont Estates

$500ks - $700ks

Rosemont Estates, Marlboro, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 homes

4.2 rating (12 reviews)

Surrey Downs

$200ks - $300ks

Surrey Downs, Freehold, NJ

Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 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

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 Westport? 55places can help!

Questions? Call us: (475) 471-1908

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Equestra at Colts Neck Cr...

$600ks - $700ks

Equestra at Colts Neck Cr..., Farmingdale, NJ

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 483 homes

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

The Greens at Half Hollow

$600ks - $1Ms

The Greens at Half Hollow, Melville, NY

Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 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 Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

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

Questions? Call us: (475) 471-1908

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

3.7 rating (3 reviews)

Nobility Crest at Ocean

$300ks - $500ks

Nobility Crest at Ocean, Ocean Township, NJ

New and Resale | 55+ age-restricted | Built 2006 - present | 198 homes

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

Winthrop Court

$400ks - $600ks

Winthrop Court, Clifton, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes

Glassbury Court at Cold S...

$500ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

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

Questions? Call us: (475) 471-1908

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

1 2 3 4...5

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 The Retreat at Carmel

2 BLAIR HEIGHTS 3331, CARMEL, NY, 10512, Carmel, NY 10512

$500,000

2 beds

2 baths

1,733 sq ft

Condo

2 BLAIR HEIGHTS 3331, CARMEL, NY, 10512

Community: The Retreat at Carmel

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 Heritage Hills

177A HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$395,000

1 beds

1 baths

900 sq ft

Condo

177A HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New The Villages NJ

71 PATRICK HENRY SQ A, FREEHOLD, NJ, 077..., Freehold, NJ 07728

$389,900

2 beds

1 baths

1,144 sq ft

Ranch

71 PATRICK HENRY SQ A, FREEHOLD, NJ, 077...

Community: The Villages NJ

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

Questions? Call us: (475) 471-1908

New Regency at Fishkill

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

$559,000

2 beds

2 baths

1,499 sq ft

Condo

734 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

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 Cheesequake Village

5 MISSOURI CT 217, MATAWAN, NJ, 07747, Matawan, NJ 07747

$330,000

2 beds

1 baths

875 sq ft

Ranch

5 MISSOURI CT 217, MATAWAN, NJ, 07747

Community: Cheesequake Village

New Cheesequake Village

5 MISSOURI CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747

$330,000

2 beds

1 baths

Condo

5 MISSOURI CT, OLD BRIDGE, NJ, 07747

Community: Cheesequake Village

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 Heritage Hills

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

$485,000

1 beds

2 baths

967 sq ft

Condo

955 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

New Shadow Lake Village

7 HAMPTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$730,000

2 beds

2 baths

1,448 sq ft

Ranch

7 HAMPTON CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

New Cheesequake Village

52 GALEWOOD DR 52, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747

$359,000

2 beds

2 baths

Condo

52 GALEWOOD DR 52, OLD BRIDGE, NJ, 07747

Community: Cheesequake Village

New Jefferson Village

78 INDEPENDENCE CT I, YORKTOWN, NY, 1059..., Yorktown, NY 10598

$360,000

1 beds

1 baths

800 sq ft

Condo

78 INDEPENDENCE CT I, YORKTOWN, NY, 1059...

Community: Jefferson Village

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

Questions? Call us: (475) 471-1908

New HarborView

100 HARBOR VIEW DR 241, NORTH HEMPSTEAD,..., North Hempstead, NY 11050

$875,000

2 beds

3 baths

1,493 sq ft

Condo

100 HARBOR VIEW DR 241, NORTH HEMPSTEAD,...

Community: HarborView

New Jefferson Village

67 INDEPENDENCE CT B, YORKTOWN, NY, 1059..., Yorktown, NY 10598

$539,900

2 beds

2 baths

1,000 sq ft

Condo

67 INDEPENDENCE CT B, YORKTOWN, NY, 1059...

Community: Jefferson Village

New Meadowbrook Pointe Athletic Club & Spa

923 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ..., North Hempstead, NY 11590

$899,000

2 beds

2 baths

1,328 sq ft

Condo

923 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ...

Community: Meadowbrook Pointe Athletic Club & Spa

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 Overlook

2075 SUMMIT LOOP 101, CARMEL, NY, 10512, Carmel, NY 10512

$960,000

2 beds

2 baths

1,948 sq ft

Condo

2075 SUMMIT LOOP 101, CARMEL, NY, 10512

Community: Overlook

New Overlook

2052 SUMMIT LOOP 62, CARMEL, NY, 10512, Carmel, NY 10512

$954,000

2 beds

2 baths

2,102 sq ft

Condo

2052 SUMMIT LOOP 62, CARMEL, NY, 10512

Community: Overlook

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

New 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

New 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

New Stoneleigh Woods at Carmel

807 EGRETS LNDG, CARMEL, NY, 10512, Carmel, NY 10512

$575,000

3 beds

3 baths

2,788 sq ft

Condo

807 EGRETS LNDG, CARMEL, NY, 10512

Community: Stoneleigh Woods at Carmel

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

Questions? Call us: (475) 471-1908

New 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

New 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

New 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

New 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

New Equestra at Colts Neck Crossing

56 E BOSWORTH BLVD, FARMINGDALE, NJ, 077..., Farmingdale, NJ 07727

$889,000

2 beds

2 baths

2,184 sq ft

Ranch

56 E BOSWORTH BLVD, FARMINGDALE, NJ, 077...

Community: Equestra at Colts Neck Crossing

New 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

New The Waterways at Moriches

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

$649,000

2 beds

2 baths

1,544 sq ft

Condo

248 RIVER DR 248, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New 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

New Heritage Hills

371 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$650,000

2 beds

2 baths

1,470 sq ft

Condo

371 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New 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

Shadow Lake Village

18 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$279,900

1 beds

1 baths

1,021 sq ft

Adult Community

18 LEXINGTON CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

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

Questions? Call us: (475) 471-1908

Shadow Lake Village

42 MEDFORD CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$400,000

2 beds

2 baths

1,210 sq ft

Adult Community

42 MEDFORD CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Glassbury Court at Hunterbrook

2272 DALTON DR, CORTLANDT, NY, 10567, Cortlandt, NY 10567

$944,500

2 beds

3 baths

2,265 sq ft

Condo

2272 DALTON DR, CORTLANDT, NY, 10567

Community: Glassbury Court at Hunterbrook

1 2 3 4 5 6 7 8 9…10

Frequently Asked Questions

What size 55+ communities are there in Westport?

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

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

The smallest 55+ community in Westport has 62 homes, the largest has 62 homes, and the average community consists of 62 homes.

Are there gated 55+ communities in Westport?

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

Want more information about active adult communities around Westport?

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 Westport?

Call us: (475) 471-1908

362 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 26, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

169 communities near Westport

362 homes near Westport

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,733 sq ft

Condo

2 beds

1 baths

871 sq ft

Condo

1 beds

1 baths

900 sq ft

Condo

2 beds

1 baths

1,144 sq ft

Ranch

2 beds

2 baths

1,499 sq ft

Condo

2 beds

3 baths

2,389 sq ft

Condo

2 beds

1 baths

875 sq ft

Ranch

2 beds

1 baths

Condo

1 beds

3 baths

3,230 sq ft

Condo

1 beds

2 baths

967 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

1,448 sq ft

Ranch

2 beds

2 baths

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

3 baths

1,493 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,328 sq ft

Condo

2 beds

2 baths

1,456 sq ft