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

167 communities near Westport

Sort by:

Relevance

Stoneleigh Woods at Carme...

$400Ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

Eagles Walk at East Quogu...

$500Ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

Hopmeadow Place

$200Ks - $300Ks

Hopmeadow Place, Simsbury, CT

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

Parker Village Estates

$700Ks

Parker Village Estates, Eatontown, NJ

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

Enclave at Shrewsbury

$600Ks - $800Ks

Enclave at Shrewsbury, Shrewsbury, NJ

Resale Only | 55+ age-restricted | Built 2011 - 2014 | 66 homes

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

Questions? Call us: (475) 471-1908

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

Questions? Call us: (475) 471-1908

Glassbury Court at Hunter...

$500Ks - $700Ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

RiverWalk

$500Ks - $600Ks

RiverWalk, Branford, CT

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

Woodcrest at Jacobs Hill

$300Ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

The Village at Buckingham

$500Ks - $600Ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 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 Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Autumn Fields

$200Ks - $300Ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

The Views at Pomona

$200Ks - $400Ks

The Views at Pomona, Pomona, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 homes

77 Sunset Lane

$400Ks - $700Ks

77 Sunset Lane, Ridgefield, CT

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

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

Questions? Call us: (475) 471-1908

Evergreen

$500Ks

Evergreen, Cromwell, CT

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

Regency Meadows

$500Ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

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

Questions? Call us: (475) 471-1908

Gloria Commons

$400Ks

Gloria Commons, Milford, CT

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

Villas at Seminary Hill

$400Ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Eastport Meadows

$400Ks

Eastport Meadows, Eastport, NY

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

The Residences at Butterf...

$500Ks - $600Ks

The Residences at Butterf..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes

Bramble Ridge

$400Ks - $500Ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 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 Westport? 55places can help!

Questions? Call us: (475) 471-1908

Enclave at Shark River

$500Ks

Enclave at Shark River, Tinton Falls, NJ

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

Cheshire Square

$600Ks - $700Ks

Cheshire Square, Little Silver, NJ

Resale Only | 55+ age-restricted | Built 1974 - 1974 | 44 homes

Wolfe Landing

$500Ks - $600Ks

Wolfe Landing, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes

Village Vistas

$800Ks - $1Ms

Village Vistas, Port Jefferson, NY

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

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

Questions? Call us: (475) 471-1908

West End Crossing

$800Ks

West End Crossing, Long Branch, NJ

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

Harbor View Estates

$400Ks - $600Ks

Harbor View Estates, Copiague, NY

New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes

Forest Mews

$300Ks - $400Ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes

Hidden Harbor Estates

$500Ks - $600Ks

Hidden Harbor Estates, Copiague, NY

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

Clockmaker's Hill

$100Ks

Clockmaker's Hill, Winsted, CT

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

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

Questions? Call us: (475) 471-1908

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Stratford Park

$900Ks

Stratford Park, Melville, NY

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes

Boulder Brook

$200Ks

Boulder Brook, Prospect, CT

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

Eden Park

$500Ks - $600Ks

Eden Park, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes

The Woods at Dunham Pond

$400Ks - $500Ks

The Woods at Dunham Pond, New Fairfield, CT

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

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

Questions? Call us: (475) 471-1908

Knickerbocker Bay Club

$700Ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

Oak Meadow Estates

$400Ks

Oak Meadow Estates, Torrington, CT

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

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

Questions? Call us: (475) 471-1908

Autumn Estates

$500Ks - $600Ks

Autumn Estates, Farmington, CT

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

The Coach Homes at Ridgef...

$200Ks - $500Ks

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

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

1 2 3 4...5

New The Villages NJ

112 PILATUS PLATZ D, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$410,000

2 beds

1 baths

1,144 sq ft

112 PILATUS PLATZ D, FREEHOLD, NJ, 07728

Community: The Villages NJ

New Paris Square

5309 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647

$479,000

1 beds

1 baths

Condo

5309 RIO VISTA LN, NORTHVALE, NJ, 07647

Community: Paris Square

Surrey Downs

1 CARNABY CLOSE # 1000, FREEHOLD, NJ, 07..., Freehold, NJ 07728

$409,900

2 beds

2 baths

1,261 sq ft

Ranch

1 CARNABY CLOSE # 1000, FREEHOLD, NJ, 07...

Community: Surrey Downs

The Villages NJ

24 CALLE DE ELVIRA B, FREEHOLD, NJ, 0772..., Freehold, NJ 07728

$430,000

2 beds

2 baths

1,144 sq ft

Ranch

24 CALLE DE ELVIRA B, FREEHOLD, NJ, 0772...

Community: The Villages NJ

New Surrey Downs

5 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$469,999

2 beds

2 baths

1,144 sq ft

Ranch

5 JAFFREYTON 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

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

Questions? Call us: (475) 471-1908

New The Villages NJ

166 COURS DE LORRAINE D, FREEHOLD, NJ, 0..., Freehold, NJ 07728

$295,000

2 beds

1 baths

1,144 sq ft

Ranch

166 COURS DE LORRAINE D, FREEHOLD, NJ, 0...

Community: The Villages NJ

Cheesequake Village

4 HAWAII CT B, MATAWAN, NJ, 07747, Matawan, NJ 07747

$279,500

1 beds

1 baths

Condo

4 HAWAII CT B, MATAWAN, NJ, 07747

Community: Cheesequake Village

New Shadow Lake Village

29 DICKINSON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$629,900

2 beds

2 baths

1,288 sq ft

House

29 DICKINSON CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Enclave at Ocean

1218 W PARK AVE, OCEAN, NJ, 07712, Ocean, NJ 07712

$1,400,000

5 beds

7 baths

3,953 sq ft

House

1218 W PARK AVE, OCEAN, NJ, 07712

Community: Enclave at Ocean

New Shadow Lake Village

41 WESTERN REACH, RED BANK, NJ, 07701, Red Bank, NJ 07701

$325,000

2 beds

1 baths

999 sq ft

Adult Community

41 WESTERN REACH, RED BANK, NJ, 07701

Community: Shadow Lake Village

New Shadow Lake Village

3 AUBURN CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$619,000

2 beds

2 baths

1,179 sq ft

House

3 AUBURN CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Rosemont Estates

160 SCARBOROUGH WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746

$835,000

3 beds

4 baths

2,706 sq ft

House

160 SCARBOROUGH WAY, MARLBORO, NJ, 07746

Community: Rosemont Estates

Surrey Downs

23 DATCHET CLOSE # 1000, FREEHOLD, NJ, 0..., Freehold, NJ 07728

$310,000

2 beds

1 baths

896 sq ft

Ranch

23 DATCHET CLOSE # 1000, FREEHOLD, NJ, 0...

Community: Surrey Downs

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

Questions? Call us: (475) 471-1908

Rosemont Estates

142 SCARBOROUGH WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746

$850,000

3 beds

3 baths

2,790 sq ft

Adult Community

142 SCARBOROUGH WAY, MARLBORO, NJ, 07746

Community: Rosemont Estates

Cheesequake Village

4 HAWAII CT # 1003, MATAWAN, NJ, 07747, Matawan, NJ 07747

$279,500

1 beds

1 baths

708 sq ft

Adult Community

4 HAWAII CT # 1003, MATAWAN, NJ, 07747

Community: Cheesequake Village

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

Questions? Call us: (475) 471-1908

Surrey Downs

47 CARNABY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$389,999

2 beds

2 baths

1,074 sq ft

Ranch

47 CARNABY CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

Shadow Lake Village

4 DICKINSON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$620,000

2 beds

2 baths

1,288 sq ft

House

4 DICKINSON CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Four Seasons at Wayne

511 FOUR SEASONS DR # 511, WAYNE, NJ, 07..., Wayne, NJ 07470

$545,000

2 beds

2 baths

Condo

511 FOUR SEASONS DR # 511, WAYNE, NJ, 07...

Community: Four Seasons at Wayne

Four Seasons at Wayne

511 FOUR SEASONS DR, WAYNE, NJ, 07470, Wayne, NJ 07470

$545,000

2 beds

2 baths

511 FOUR SEASONS DR, WAYNE, NJ, 07470

Community: Four Seasons at Wayne

The Villages NJ

161A PARKWAY DR A, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$335,000

2 beds

2 baths

1,262 sq ft

Adult Community

161A PARKWAY DR A, FREEHOLD, NJ, 07728

Community: The Villages NJ

Rosemont Estates

211 BRADWICK WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746

$784,900

2 beds

3 baths

2,452 sq ft

House

211 BRADWICK WAY, MARLBORO, NJ, 07746

Community: Rosemont Estates

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

Questions? Call us: (475) 471-1908

Shadow Lake Village

126 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$375,000

1 beds

1 baths

999 sq ft

Adult Community

126 MANCHESTER CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Surrey Downs

3 GATLEY CLOSE # 1000, FREEHOLD, NJ, 077..., Freehold, NJ 07728

$469,900

2 beds

2 baths

1,261 sq ft

Ranch

3 GATLEY CLOSE # 1000, FREEHOLD, NJ, 077...

Community: Surrey Downs

Cheesequake Village

26 GALEWOOD DR, MATAWAN, NJ, 07747, Matawan, NJ 07747

$215,000

1 beds

1 baths

708 sq ft

Condo

26 GALEWOOD DR, MATAWAN, NJ, 07747

Community: Cheesequake Village

Surrey Downs

38 MORDEN CLOSE # 1000, FREEHOLD, NJ, 07..., Freehold, NJ 07728

$419,000

2 beds

2 baths

1,261 sq ft

Ranch

38 MORDEN CLOSE # 1000, FREEHOLD, NJ, 07...

Community: Surrey Downs

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

Questions? Call us: (475) 471-1908

Surrey Downs

35 IVY RIDGE CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$314,900

2 beds

1 baths

1,113 sq ft

House

35 IVY RIDGE CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

The Villages NJ

82 PARKWAY DR B, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$459,900

2 beds

2 baths

1,168 sq ft

Ranch

82 PARKWAY DR B, FREEHOLD, NJ, 07728

Community: The Villages NJ

The Villages NJ

84 PARKWAY DR B, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$337,000

2 beds

1 baths

1,008 sq ft

84 PARKWAY DR B, FREEHOLD, NJ, 07728

Community: The Villages NJ

Shadow Lake Village

11 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$385,000

2 beds

1 baths

999 sq ft

Adult Community

11 MANCHESTER CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

The Villages NJ

93 HALLS CROFT RD D, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$329,000

2 beds

2 baths

1,008 sq ft

Ranch

93 HALLS CROFT RD D, 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

Shadow Lake Village

20 DANBURY CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$599,000

2 beds

2 baths

1,272 sq ft

House

20 DANBURY CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Shadow Lake Village

50 HANCOCK CT, RED BANK, NJ, 07701, Red Bank, NJ 07701

$419,999

2 beds

2 baths

1,235 sq ft

Adult Community

50 HANCOCK CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Rolling Meadows at Wayside

68 ROLLING MEADOWS BLVD, ASBURY PARK, NJ..., Asbury Park, NJ 07712

$749,900

2 beds

2 baths

Ranch

68 ROLLING MEADOWS BLVD, ASBURY PARK, NJ...

Community: Rolling Meadows at Wayside

Cheesequake Village

9 VALERY RD # 651, MATAWAN, NJ, 07747, Matawan, NJ 07747

$259,900

1 beds

1 baths

758 sq ft

Adult Community

9 VALERY RD # 651, MATAWAN, NJ, 07747

Community: Cheesequake Village

Surrey Downs

7 MORDEN CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$460,000

2 beds

2 baths

1,261 sq ft

Ranch

7 MORDEN CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

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

Questions? Call us: (475) 471-1908

The Villages NJ

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

$365,000

2 beds

1 baths

1,144 sq ft

Ranch

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

Community: The Villages NJ

Shadow Lake Village

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

$325,000

2 beds

1 baths

1,021 sq ft

Adult Community

143 LEXINGTON CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

Cheesequake Village

9 VALERY RD, MATAWAN, NJ, 07747, Matawan, NJ 07747

$259,900

1 beds

1 baths

758 sq ft

House

9 VALERY RD, MATAWAN, NJ, 07747

Community: Cheesequake Village

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

Questions? Call us: (475) 471-1908

Cheesequake Village

7 NEBRASKA DR # 153, MATAWAN, NJ, 07747, Matawan, NJ 07747

$295,000

2 beds

1 baths

875 sq ft

Ranch

7 NEBRASKA DR # 153, MATAWAN, NJ, 07747

Community: Cheesequake Village

Cheesequake Village

14 CONNECTICUT CT # 869, MATAWAN, NJ, 07..., Matawan, NJ 07747

$249,999

2 beds

1 baths

914 sq ft

Duplex

14 CONNECTICUT CT # 869, MATAWAN, NJ, 07...

Community: Cheesequake 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.

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

167 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: Jan 25, 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

167 communities near Westport

262 homes near Westport

2 beds

1 baths

1,144 sq ft

1 beds

1 baths

Condo

2 beds

2 baths

1,261 sq ft

Ranch

2 beds

2 baths

1,144 sq ft

Ranch

2 beds

2 baths

1,144 sq ft

Ranch

2 beds

1 baths

1,144 sq ft

Ranch

1 beds

1 baths

Condo

2 beds

2 baths

1,288 sq ft

House

5 beds

7 baths

3,953 sq ft

House

2 beds

1 baths

999 sq ft

Adult Community

2 beds

2 baths

1,179 sq ft

House

3 beds

4 baths

2,706 sq ft

House

2 beds

1 baths

896 sq ft

Ranch

3 beds

3 baths

2,790 sq ft

Adult Community

1 beds

1 baths

708 sq ft

Adult Community

2 beds

2 baths

1,074 sq ft

Ranch

2 beds

2 baths

1,288 sq ft

House

2 beds

2 baths

Condo

2 beds

2 baths

2 beds

2 baths

1,262 sq ft

Adult Community

2 beds

3 baths

2,452 sq ft