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

169 communities near Westport

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Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

The Club at Melville

$500ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

The Seasons at East Meado...

$400ks - $600ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

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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

The Views at Pomona

$200ks - $400ks

The Views at Pomona, Pomona, NY

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

Eden Park

$500ks - $600ks

Eden Park, Clarkstown, NY

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

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 Seasons at Plainview

$500ks - $600ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

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

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

Whitney Glen

$500ks - $600ks

Whitney Glen, Westport, CT

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

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

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Questions? Call us: (475) 471-1908

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 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 Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

4 rating (1 reviews)

Vineyards at Blue Point

$500ks - $700ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Harbor View Estates

$400ks - $600ks

Harbor View Estates, Copiague, NY

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

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

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

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

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

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

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

Questions? Call us: (475) 471-1908

The Vineyards at Mount Si...

$800ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 20 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

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?

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169 communities

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

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