Westport, CT 55+ active adult communities & homes for sale - Page 7

369 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

2.8 rating (4 reviews)

Cheesequake Village

$100ks - $200ks

Cheesequake Village, Old Bridge, NJ

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

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

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

Questions? Call us: (475) 471-1908

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 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 (2 reviews)

Shadow Lake Village

$200ks - $500ks

Shadow Lake Village, Red Bank, NJ

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

4.2 rating (12 reviews)

Surrey Downs

$200ks - $300ks

Surrey Downs, Freehold, NJ

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

Questions? Call us: (475) 471-1908

The Manors at The Colony ...

$300ks - $400ks

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

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Rolling Meadows at Waysid...

$500ks - $600ks

Rolling Meadows at Waysid..., Ocean Township, NJ

Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

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

Questions? Call us: (475) 471-1908

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

5 rating (1 reviews)

The Villas at Jumping Bro...

$300ks - $500ks

The Villas at Jumping Bro..., Neptune Township, NJ

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 168 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

$800ks - $1Ms

HarborView, Port Washington, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Winthrop Court

$400ks - $600ks

Winthrop Court, Clifton, NJ

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

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

Questions? Call us: (475) 471-1908

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

1 2 3 4...5

Apple Ridge

143 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$975,000

3 beds

4 baths

Townhouse

143 FISHER RD, MAHWAH, NJ, 07430

Community: Apple Ridge

Harbor View Estates

206 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726

$599,000

2 beds

2 baths

1,200 sq ft

Condo

206 ANCHOR CT, BABYLON, NY, 11726

Community: Harbor View Estates

Oronoque Village

778 QUINNIPIAC LN A, STRATFORD, CT, 0661..., Stratford, CT 06614

Condo

40 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

Surrey Downs

1 LINTON CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$325,000

2 beds

1 baths

942 sq ft

House

1 LINTON CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

Leisure Glen

515 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$524,999

2 beds

2 baths

1,434 sq ft

House

515 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

The Villages NJ

56 LARGO SAN NICOLA A, FREEHOLD, NJ, 077..., Freehold, NJ 07728

$335,000

2 beds

1 baths

1,144 sq ft

Ranch

56 LARGO SAN NICOLA A, FREEHOLD, NJ, 077...

Community: The Villages NJ

Meadow Brook Estates

223 MEADOW BROOK RD 223, OXFORD, CT, 064..., Oxford, CT 06478

$589,900

2 beds

2 baths

1,480 sq ft

Condo

223 MEADOW BROOK RD 223, OXFORD, CT, 064...

4 MICHIGAN DR, OLD BRIDGE, NJ, 07747

Community: Cheesequake Village

The Waterways at Moriches

377 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$599,999

3 beds

2 baths

2,141 sq ft

Condo

377 QUARRY POND CT, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

Cheesequake Village

2 UTAH DR 143, MATAWAN, NJ, 07747, Matawan, NJ 07747

$335,000

2 beds

1 baths

875 sq ft

Ranch

2 UTAH DR 143, MATAWAN, NJ, 07747

Community: Cheesequake Village

Greenwood Village

131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$159,000

2 beds

2 baths

1,062 sq ft

Manufactured Home

131 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Regency Meadows

108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611

$719,000

2 beds

3 baths

2,891 sq ft

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611

Community: Regency Meadows

Four Seasons at Ridgemont

602 FOUR SEASONS LN, MONTVALE, NJ, 07645, Montvale, NJ 07645

$915,000

2 beds

2 baths

Condo

602 FOUR SEASONS LN, MONTVALE, NJ, 07645

224 WESTERVELT LN, MAHWAH, NJ, 07430

Community: Apple Ridge

Jefferson Village

23 DORSET CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$315,000

2 beds

1 baths

925 sq ft

Condo

23 DORSET CT F, YORKTOWN, NY, 10598

Community: Jefferson Village

Four Seasons at Colts Farm

49 PASTURE DR, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727

$1,225,000

4 beds

3 baths

3,090 sq ft

House

49 PASTURE DR, FARMINGDALE, NJ, 07727

Community: Four Seasons at Colts Farm

Heritage Village

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

$349,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$575,000

2 beds

3 baths

1,438 sq ft

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (475) 471-1908

Plymouth Estates at Mount Sinai

26 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$555,000

2 beds

2 baths

1,563 sq ft

Condo

26 ROSE LN, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

Heritage Village

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

$350,000

2 beds

2 baths

1,572 sq ft

Condo

2 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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.

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

On average, listings in 55+ community in Westport stay on the market for around 19 days. The average price of homes for sale in this community is approximately $459,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Whitney Glen average around $459,000.

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 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 Westport?

Call us: (475) 471-1908

369 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: Jul 27, 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 - Page 7

170 communities near Westport

369 homes near Westport

3 beds

4 baths

Townhouse

2 beds

2 baths

1,200 sq ft

Condo

1 beds

3 baths

1,175 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

1 beds

2 baths

1,480 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

3 beds

3 baths

1,771 sq ft

Condo

2 beds

2 baths

1,360 sq ft

Condo

2 beds

1 baths

942 sq ft

House

2 beds

2 baths

1,434 sq ft

House

2 beds

1 baths

1,144 sq ft

Ranch

2 beds

2 baths

1,480 sq ft

Condo

2 beds

3 baths

1,620 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,809 sq ft

Condo

2 beds

2 baths

1,350 sq ft