Westport, CT 55+ active adult communities & homes for sale - Page 4

172 communities near Westport

Sort by:

Relevance

Cedar Village at Ocean

$500ks - $600ks

Cedar Village at Ocean, Ocean Township, NJ

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 295 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

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

The Woods at Dunham Pond

$200ks - $400ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

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

Questions? Call us: (475) 471-1908

The Coach Homes at Ridgef...

$300ks - $400ks

The Coach Homes at Ridgef..., Ridgefield, CT

New Construction | 55+ age-restricted | Built 2019 - present | 30 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

Regency at Pearl River

$800ks - $1Ms

Regency at Pearl River, Pearl River, NY

New Construction | 55+ age-restricted | Built 2026 - present | 36 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.

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 homes

West End Crossing

$800ks

West End Crossing, Long Branch, NJ

Resale Only | 55+ age-restricted | Built 2023 - 2023 | 41 homes

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

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

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

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

Questions? Call us: (475) 471-1908

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

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

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

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

1 rating (1 reviews)

Beckley Farms

$300ks - $400ks

Beckley Farms, Berlin, CT

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

Parker Village Estates

$500ks - $600ks

Parker Village Estates, Eatontown, NJ

Resale Only | 55+ age-restricted | Built 2002 - 2002 | 66 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

Enclave at Shark River

$500ks

Enclave at Shark River, Tinton Falls, NJ

Resale Only | 55+ age-restricted | Built 2015 - 2018 | 44 homes

Chimney Hill

$500ks - $700ks

Chimney Hill, Farmington, CT

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

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

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

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

Questions? Call us: (475) 471-1908

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Eastport Meadows

$400ks

Eastport Meadows, Eastport, NY

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

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

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes

Meadowbrooke Pointe East ...

$500ks - $600ks

Meadowbrooke Pointe East ..., East Meadow, NY

New Construction | 62+ age-restricted | Built 2019 - present | 104 homes

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

Questions? Call us: (475) 471-1908

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

1 2 3 4...5

Greenwood Village

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949

$245,000

2 beds

2 baths

1,130 sq ft

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...

Community: Greenwood Village

The Villages NJ

41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077..., Freehold, NJ 07728

$410,000

2 beds

2 baths

1,008 sq ft

Ranch

41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077...

Community: The Villages NJ

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Fairfield at St. James

704 FENWAY RD, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$519,000

2 beds

2 baths

1,292 sq ft

Condo

704 FENWAY RD, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New The Villages NJ

61C PIAZZA VITTORIA, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$349,999

2 beds

1 baths

1,082 sq ft

House

61C PIAZZA VITTORIA, FREEHOLD, NJ, 07728

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 Wappinger

5 PALMERTON DR, WAPPINGER, NY, 12590, Wappinger, NY 12590

$829,900

2 beds

3 baths

3,156 sq ft

Condo

5 PALMERTON DR, WAPPINGER, NY, 12590

Community: Regency at Wappinger

New Chelsea Square

114 BLOOMSBURY DR 114, MORGANVILLE, NJ, ..., Morganville, NJ 07751

$505,000

2 beds

2 baths

1,491 sq ft

Adult Community

114 BLOOMSBURY DR 114, MORGANVILLE, NJ, ...

Community: Chelsea Square

New The Village at Oxford Greens

84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478

$710,000

3 beds

3 baths

2,008 sq ft

Condo

84 LINKS WAY 84, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Autumn Fields

24 QUAIL HOLW 24, ENFIELD, CT, 06082, Enfield, CT 06082

$339,000

1 beds

2 baths

1,235 sq ft

Condo

24 QUAIL HOLW 24, ENFIELD, CT, 06082

Community: Autumn Fields

Heritage Village

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

$310,000

2 beds

2 baths

1,432 sq ft

Condo

722 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Country Pointe Plainview

30101 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,200,000

2 beds

2 baths

1,379 sq ft

Condo

30101 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

Enclave at Shrewsbury

114 CAMPBELL CT, SHREWSBURY BORO, NJ, 07..., Shrewsbury Boro, NJ 07702

$1,175,000

3 beds

3 baths

2,560 sq ft

House

114 CAMPBELL CT, SHREWSBURY BORO, NJ, 07...

Community: Enclave at Shrewsbury

HarborView

$1,299,000

3 beds

3 baths

2,426 sq ft

Condo

100 HARBOR VIEW DR 630, NORTH HEMPSTEAD,...

Community: HarborView

Heritage Village

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

$309,000

2 beds

2 baths

1,432 sq ft

Condo

970 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

44 WARRINGTON ROUND ST 44, DANBURY, CT, ..., Danbury, CT 06810

$628,000

3 beds

3 baths

1,600 sq ft

Condo

44 WARRINGTON ROUND ST 44, DANBURY, CT, ...

Community: Rivington

Surrey Downs

47 DATCHET CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$455,000

2 beds

2 baths

1,261 sq ft

Ranch

47 DATCHET CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

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

Questions? Call us: (475) 471-1908

Leisure Glen

477 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$589,000

2 beds

2 baths

1,434 sq ft

Condo

477 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Country Pointe Plainview

38204 WINTERBERRY DR, OYSTER BAY, NY, 11..., Oyster Bay, NY 11803

$1,585,000

2 beds

2 baths

1,989 sq ft

Condo

38204 WINTERBERRY DR, OYSTER BAY, NY, 11...

Community: Country Pointe Plainview

The Manors at The Colony Preserve

41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$485,000

2 beds

2 baths

1,557 sq ft

Condo

41 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

Heritage Village

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

$427,500

2 beds

2 baths

1,398 sq ft

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$319,000

2 beds

2 baths

1,432 sq ft

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Country Pointe Preserve

119 MIA LN 76, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$940,000

2 beds

3 baths

2,187 sq ft

Condo

119 MIA LN 76, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

Shady Oaks

64 ARROWWOOD CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$355,000

2 beds

2 baths

1,124 sq ft

House

64 ARROWWOOD CT, RED BANK, NJ, 07701

Community: Shady Oaks

The Village at Oxford Greens

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478

$624,900

2 beds

3 baths

1,673 sq ft

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Sunken Pond Estates

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$520,000

2 beds

2 baths

1,350 sq ft

Condo

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...

Community: Sunken Pond Estates

Saddle Lakes

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

$595,000

2 beds

2 baths

1,386 sq ft

Condo

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Shadow Lake Village

38 BERKSHIRE CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$699,000

2 beds

3 baths

1,408 sq ft

Townhouse

38 BERKSHIRE 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

Village Estates

30 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701

$599,000

2 beds

2 baths

1,251 sq ft

Condo

30 SARAH CT, BABYLON, NY, 11701

Community: Village Estates

Shadow Lake Village

21 CONCORD CT A, RED BANK, NJ, 07701, Red Bank, NJ 07701

$474,900

2 beds

2 baths

1,066 sq ft

House

21 CONCORD CT A, RED BANK, NJ, 07701

Community: Shadow Lake Village

The Greens at Half Hollow

643 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,299,999

3 beds

3 baths

2,500 sq ft

Condo

643 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Regency at Prospect

133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712

$550,000

2 beds

3 baths

1,850 sq ft

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712

Community: Regency at Prospect

Vineyards at Moriches

19 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$775,000

2 beds

3 baths

2,251 sq ft

Condo

19 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

Leisure Glen

279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$569,999

2 beds

2 baths

1,542 sq ft

Condo

279 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Newtown Woods

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470

$498,900

2 beds

2 baths

1,504 sq ft

Condo

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470

Community: Newtown Woods

Heritage Hills

675 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$825,000

2 beds

2 baths

1,663 sq ft

Condo

675 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$225,000

1 beds

1 baths

928 sq ft

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Retreat at Carmel

88 BLAIR HEIGHTS, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

2,695 sq ft

Condo

88 BLAIR HEIGHTS, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Hills

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

$679,000

2 beds

2 baths

1,470 sq ft

Condo

370 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (475) 471-1908

The Village at Buckingham

13 KENINGTON RD 13, AVON, CT, 06001, Avon, CT 06001

$639,900

3 beds

3 baths

2,024 sq ft

Condo

13 KENINGTON RD 13, AVON, CT, 06001

Community: The Village at Buckingham

Heritage Village

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

$269,900

2 beds

2 baths

1,032 sq ft

Condo

23 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

172 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: Sep 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 4

172 communities near Westport

393 homes near Westport

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,008 sq ft

Ranch

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,292 sq ft

Condo

2 beds

1 baths

1,082 sq ft

House

2 beds

3 baths

3,156 sq ft

Condo

2 beds

2 baths

1,491 sq ft

Adult Community

3 beds

3 baths

2,008 sq ft

Condo

1 beds

2 baths

1,235 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,379 sq ft

Condo

3 beds

3 baths

2,560 sq ft

House

3 beds

3 baths

2,426 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

1,261 sq ft

Ranch

2 beds

2 baths

1,434 sq ft

Condo

2 beds

2 baths

1,989 sq ft

Condo

2 beds

2 baths

1,557 sq ft

Condo

2 beds