Westport, CT 55+ active adult communities & homes for sale - Page 3

348 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

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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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

Questions? Call us: (475) 471-1908

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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 Greens at Half Hollow

$600ks - $1Ms

The Greens at Half Hollow, Melville, NY

Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 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.

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Apple Ridge

$500ks - $1Ms

Apple Ridge, Mahwah, NJ

Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes

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

Questions? Call us: (475) 471-1908

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

5 rating (1 reviews)

Four Seasons at Great Not...

$400ks - $700ks

Four Seasons at Great Not..., Woodland Park, NJ

Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 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

3.7 rating (3 reviews)

Rosemont Estates

$500ks - $700ks

Rosemont Estates, Marlboro, NJ

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

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

Questions? Call us: (475) 471-1908

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Regency at Holmdel

$900ks - $1Ms

Regency at Holmdel, Holmdel, NJ

Resale Only | 55+ age-restricted | Built 2016 - 2019 | 181 homes

The Hollows at Blue Hill

$500ks - $700ks

The Hollows at Blue Hill, Pearl River, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes

5 rating (1 reviews)

Shady Oaks

$200ks - $400ks

Shady Oaks, Red Bank, NJ

Resale Only | 55+ age-restricted | Built 1982 - 1983 | 366 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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

Questions? Call us: (475) 471-1908

Four Seasons at Colts Far...

$600ks - $800ks

Four Seasons at Colts Far..., Farmingdale, NJ

New Construction | 55+ age-restricted | Built 2021 - present | 111 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

1 2 3 4...5

Shady Oaks

1 BOXWOOD TER 243, RED BANK, NJ, 07701, Red Bank, NJ 07701

$485,000

2 beds

2 baths

1,147 sq ft

Ranch

1 BOXWOOD TER 243, RED BANK, NJ, 07701

Community: Shady Oaks

Leisure Knoll

379 LARCHMONT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,000

2 beds

2 baths

1,070 sq ft

Condo

379 LARCHMONT CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Surrey Downs

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

$325,000

2 beds

1 baths

942 sq ft

Ranch

1 LINTON CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

Surrey Downs

51 LINTON, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$329,900

2 beds

1 baths

Ranch

51 LINTON, FREEHOLD, NJ, 07728

Community: Surrey Downs

The Greens at Half Hollow

562 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$949,888

2 beds

3 baths

1,941 sq ft

Condo

562 BARDINI DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (475) 471-1908

Chatfield Farms

24 BAYBERRY CT 24, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$725,000

3 beds

3 baths

1,981 sq ft

Condo

24 BAYBERRY CT 24, BEACON FALLS, CT, 064...

Community: Chatfield Farms

The Seasons at Elwood

53 WINTER PL 53, HUNTINGTON, NY, 11731, Huntington, NY 11731

$979,900

2 beds

3 baths

1,500 sq ft

Condo

53 WINTER PL 53, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

Regency at Fishkill

541 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$529,000

2 beds

2 baths

1,499 sq ft

Condo

541 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

The Seasons at Elwood

240 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,299,999

2 beds

3 baths

2,329 sq ft

Condo

240 FALL CT, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

Leisure Knoll

220 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,999

2 beds

2 baths

1,445 sq ft

Condo

220 BELFAST LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Leisure Glen

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

$560,000

2 beds

2 baths

1,434 sq ft

House

515 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Meadowbrook Pointe Athletic Club & Spa

246 ROOSEVELT WAY 11103, HEMPSTEAD, NY, ..., Hempstead, NY 11590

$1,150,000

2 beds

3 baths

1,620 sq ft

Condo

246 ROOSEVELT WAY 11103, HEMPSTEAD, NY, ...

Community: Meadowbrook Pointe Athletic Club & Spa

Jefferson Village

131 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$399,000

2 beds

2 baths

1,141 sq ft

Condo

131 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

Regency at Wappinger

2 AVONDALE LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$799,000

2 beds

4 baths

2,941 sq ft

Condo

2 AVONDALE LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

Heritage Hills

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

$679,999

2 beds

2 baths

1,416 sq ft

Condo

386 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Villages NJ

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

$350,000

2 beds

1 baths

1,144 sq ft

Ranch

56 LARGO SAN NICOLA 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

Jefferson Village

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

$339,000

1 beds

1 baths

700 sq ft

Condo

23 DORSET CT C, YORKTOWN, NY, 10598

Community: Jefferson Village

Shady Oaks

90 CRANBERRY CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$379,000

2 beds

2 baths

1,124 sq ft

House

90 CRANBERRY CT, RED BANK, NJ, 07701

Community: Shady Oaks

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...

Community: Meadow Brook Estates

Greenwood Village

40 WILLOW CT, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$249,999

2 beds

2 baths

1,151 sq ft

Manufactured On Land

40 WILLOW CT, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Oronoque Village

261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$550,000

2 beds

3 baths

1,620 sq ft

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

Chelsea Square

103 BECKET WAY, MORGANVILLE, NJ, 07751, Morganville, NJ 07751

$499,000

2 beds

2 baths

1,648 sq ft

Adult Community

103 BECKET WAY, MORGANVILLE, NJ, 07751

Community: Chelsea Square

Heritage Village

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

$479,000

2 beds

2 baths

1,432 sq ft

Condo

899 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$599,000

1 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

The Villages NJ

6 PLAZA DE LAS FLORES C, FREEHOLD, NJ, 0..., Freehold, NJ 07728

$419,900

2 beds

2 baths

1,082 sq ft

Townhouse

6 PLAZA DE LAS FLORES C, FREEHOLD, NJ, 0...

Community: The Villages NJ

Surrey Downs

81 FARNWORTH CLOSE 1000, FREEHOLD, NJ, 0..., Freehold, NJ 07728

$469,900

2 beds

2 baths

1,397 sq ft

House

81 FARNWORTH CLOSE 1000, FREEHOLD, NJ, 0...

Community: Surrey Downs

The Powder Forest Homes

9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070

$700,000

2 beds

2 baths

1,809 sq ft

Condo

9 ASHTON CIR, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

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

Questions? Call us: (475) 471-1908

Applegate Estates

90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489

$450,000

2 beds

2 baths

1,350 sq ft

Condo

90 APPLE GATE 190, SOUTHINGTON, CT, 0648...

Community: Applegate Estates

The Village at Oxford Greens

71 LINKS WAY 71, OXFORD, CT, 06478, Oxford, CT 06478

$598,000

2 beds

2 baths

1,590 sq ft

Condo

71 LINKS WAY 71, OXFORD, CT, 06478

Community: The Village at Oxford Greens

The Greens at Half Hollow

1153 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$750,000

2 beds

2 baths

1,100 sq ft

Condo

1153 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Cheesequake Village

2 UTAH DR, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747

$350,000

2 beds

1 baths

875 sq ft

Condo

2 UTAH DR, OLD BRIDGE, NJ, 07747

Community: Cheesequake Village

Regency at Fishkill

145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$539,999

2 beds

2 baths

1,803 sq ft

Condo

145 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Cheesequake Village

4 MICHIGAN DR, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747

$325,000

2 beds

1 baths

Condo

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

$350,000

2 beds

1 baths

875 sq ft

Ranch

2 UTAH DR 143, MATAWAN, NJ, 07747

Community: Cheesequake Village

Woodridge Strathmore Terrace

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$435,000

2 beds

2 baths

1,025 sq ft

Condo

58 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Greenwood Village

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

$165,000

2 beds

2 baths

1,062 sq ft

Manufactured Home

131 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Cheesequake Village

72 HAVEN DR 500, MATAWAN, NJ, 07747, Matawan, NJ 07747

$325,000

2 beds

1 baths

949 sq ft

Adult Community

72 HAVEN DR 500, MATAWAN, NJ, 07747

Community: Cheesequake Village

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

Questions? Call us: (475) 471-1908

Regency at Holmdel

1 LENNOX CT, HOLMDEL, NJ, 07733, Holmdel, NJ 07733

$1,550,000

3 beds

4 baths

3,395 sq ft

Adult Community

1 LENNOX CT, HOLMDEL, NJ, 07733

Community: Regency at Holmdel

The Waterways at Moriches

629 WATER WAY 29, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$715,000

2 beds

3 baths

1,611 sq ft

Condo

629 WATER WAY 29, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

1 2 3 4 5 6 7 8…9

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 13 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 [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

348 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: Jun 10, 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 3

170 communities near Westport

348 homes near Westport

2 beds

2 baths

1,147 sq ft

Ranch

2 beds

2 baths

1,070 sq ft

Condo

2 beds

1 baths

942 sq ft

Ranch

2 beds

1 baths

Ranch

2 beds

3 baths

1,941 sq ft

Condo

3 beds

3 baths

1,981 sq ft

Condo

2 beds

3 baths

1,500 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Condo

2 beds

3 baths

2,329 sq ft

Condo

2 beds

2 baths

1,445 sq ft

Condo

2 beds

2 baths

1,434 sq ft

House

2 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,141 sq ft

Condo

2 beds

4 baths

2,941 sq ft

Condo

2 beds

2 baths

1,416 sq ft

Condo

2 beds

1 baths

1,144 sq ft

Ranch

1 beds

1 baths

700 sq ft

Condo

2 beds

2 baths

1,124 sq ft

House

2 beds

2 baths

1,480 sq ft

Condo

2 beds

2 baths