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Westport, CT 55+ active adult communities & homes for sale - Page 8

363 homes near Westport

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3.6 rating (7 reviews) Heritage Village
$200ks - $500ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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
3 rating (2 reviews) Heritage Hills
- $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
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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
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
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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 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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
3.7 rating (3 reviews) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 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
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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
5 rating (1 reviews) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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
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.
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Parker Village Estates
$500ks - $600ks
Parker Village Estates, Eatontown, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2002 | 66 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 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.
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Heritage Village 914 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$500,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$162,000

2 beds

|

2 baths

|

1,164 sq ft

|

Condo

16 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Four Seasons at Wayne 109 FOUR SEASONS DR 109, WAYNE, NJ, 0747..., Wayne, NJ 07470
$525,000

2 beds

|

2 baths

|

Condo

109 FOUR SEASONS DR 109, WAYNE, NJ, 0747...
Cheesequake Village 23 HAVEN DR, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$285,000

1 beds

|

1 baths

|

708 sq ft

|

Condo

23 HAVEN DR, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 745 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rosemont Estates 407 EDINBURGH PL, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$899,000

2 beds

|

3 baths

|

2,547 sq ft

|

House

407 EDINBURGH PL, MARLBORO, NJ, 07746
Community: Rosemont Estates
Village Vistas 11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,299,000

2 beds

|

4 baths

|

3,000 sq ft

|

Condo

11 THERESA LN, BROOKHAVEN, NY, 11777
Community: Village Vistas
Heritage Village 968 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Encore Atlantic Shores 236 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$790,000

2 beds

|

2 baths

|

2,215 sq ft

|

Condo

236 ENCORE BLVD, BROOKHAVEN, NY, 11941
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 Villages NJ 80 PARKWAY DR D, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$419,000

2 beds

|

2 baths

|

1,262 sq ft

|

Ranch

80 PARKWAY DR D, FREEHOLD, NJ, 07728
Community: The Villages NJ
Leisure Knoll 475 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$499,900

3 beds

|

2 baths

|

1,592 sq ft

|

House

475 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Kensington Estates 48 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797
$2,349,999

6 beds

|

5 baths

|

4,333 sq ft

|

House

48 PLAINVIEW RD, WOODBURY, NY, 11797
Community: Kensington Estates
Parker Village Estates 3 CARRINGTON DR, EATONTOWN, NJ, 07724, Eatontown, NJ 07724
$719,900

2 beds

|

4 baths

|

2,308 sq ft

|

Townhouse

3 CARRINGTON DR, EATONTOWN, NJ, 07724
The Retreat at Carmel 18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512
$725,000

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

18 WHEELER CT, CARMEL, NY, 10512
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$610,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Cheesequake Village 72 HAVEN DR D, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$325,000

2 beds

|

1 baths

|

949 sq ft

|

Condo

72 HAVEN DR D, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
The Manors at The Colony Preserve 34 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$515,000

2 beds

|

2 baths

|

1,357 sq ft

|

Condo

34 GREENTREE CT, BROOKHAVEN, NY, 11967
The Village at Oxford Greens 301 FAIRWAY DR 301, OXFORD, CT, 06478, Oxford, CT 06478
$584,900

2 beds

|

2 baths

|

2,080 sq ft

|

Condo

301 FAIRWAY DR 301, OXFORD, CT, 06478
Westhampton Pines 39 KIMBERLY DR 39, SOUTHAMPTON, NY, 1197..., Southampton, NY 11977
$1,495,000

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

39 KIMBERLY DR 39, SOUTHAMPTON, NY, 1197...
Community: Westhampton Pines
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 Villages NJ 139 WEIN MARKET F, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$352,000

2 beds

|

2 baths

|

1,244 sq ft

|

Ranch

139 WEIN MARKET F, FREEHOLD, NJ, 07728
Community: The Villages NJ
The Villages NJ 139 WEIN MARKET C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$395,000

2 beds

|

2 baths

|

1,132 sq ft

|

Ranch

139 WEIN MARKET C, FREEHOLD, NJ, 07728
Community: The Villages NJ
Granite Woods 35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$229,000

1 beds

|

1 baths

|

889 sq ft

|

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762
Community: Granite Woods
The Village at Oxford Greens 607 CHAMPIONSHIP DR 607, OXFORD, CT, 064..., Oxford, CT 06478
$650,000

3 beds

|

3 baths

|

2,731 sq ft

|

Condo

607 CHAMPIONSHIP DR 607, OXFORD, CT, 064...
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
Greenwood Village 54 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$120,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

54 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
The Summit at Bethel 12 BRIAR RIDGE DR 12, BETHEL, CT, 06801, Bethel, CT 06801
$619,900

2 beds

|

3 baths

|

2,023 sq ft

|

Condo

12 BRIAR RIDGE DR 12, BETHEL, CT, 06801
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Oronoque Village 13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614
$389,000

1 beds

|

2 baths

|

1,330 sq ft

|

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614
Community: Oronoque Village
Rosemont Estates 211 BRADWICK WAY, MARLBORO TWP., NJ, 077..., Marlboro Twp., NJ 07746
$774,900

2 beds

|

3 baths

211 BRADWICK WAY, MARLBORO TWP., NJ, 077...
Community: Rosemont Estates
Heritage Village 423 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

423 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
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.
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$189,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$635,000

3 beds

|

3 baths

|

1,426 sq ft

|

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$324,900

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 79 SUZIE DR 79, NEWTOWN, CT, 06470, Newtown, CT 06470
$575,000

2 beds

|

3 baths

|

2,317 sq ft

|

Condo

79 SUZIE DR 79, NEWTOWN, CT, 06470
Community: Liberty at Newtown
The Coves at Melville 6 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747
$530,000

2 beds

|

2 baths

|

Condo

6 MORLEY CIR, MELVILLE, NY, 11747
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
Leisure Village 116 B EXMORE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$285,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

116 B EXMORE CT, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Retreat at Carmel 2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512, Carmel, NY 10512
$449,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Village 373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$415,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 164 FALMOUTH CT E, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$279,000

2 beds

|

1 baths

|

819 sq ft

|

Condo

164 FALMOUTH CT E, BROOKHAVEN, NY, 11961
Community: Leisure Village
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.

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