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

169 communities 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

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.

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

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.

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

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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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

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

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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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

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Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Four Seasons at Cedar Gro...

$400ks - $600ks

Four Seasons at Cedar Gro..., Cedar Grove, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

Parker Village Estates

$500ks - $600ks

Parker Village Estates, Eatontown, NJ

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

3.7 rating (3 reviews)

Rosemont Estates

$500ks - $700ks

Rosemont Estates, Marlboro, NJ

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

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Questions? Call us: (475) 471-1908

Regency at Holmdel

$900ks - $1Ms

Regency at Holmdel, Holmdel, NJ

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

Chelsea Square

$300ks - $400ks

Chelsea Square, Morganville, NJ

New and Resale | 55+ age-restricted | Built 2007 - present | 225 homes

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Questions? Call us: (475) 471-1908

Equestra at Colts Neck Cr...

$600ks - $700ks

Equestra at Colts Neck Cr..., Farmingdale, NJ

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 483 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

1 2 3 4...5

New Winthrop Court

9210 RAVENSCROFT RD, CLIFTON CITY, NJ, 0..., Clifton City, NJ 07013

$585,000

2 beds

2 baths

1,871 sq ft

9210 RAVENSCROFT RD, CLIFTON CITY, NJ, 0...

Community: Winthrop Court

New Country Pointe Preserve

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$865,000

2 beds

3 baths

1,998 sq ft

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

New Heritage Hills

29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589

$495,000

2 beds

3 baths

1,340 sq ft

Condo

29 HERITAGE HLS 29D, SOMERS, NY, 10589

Community: Heritage Hills

New Oronoque Village

99 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,426 sq ft

Condo

99 SEMINOLE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Shady Oaks

56 PRIVET PL, RED BANK, NJ, 07701, Red Bank, NJ 07701

$600,000

2 beds

2 baths

1,788 sq ft

House

56 PRIVET PL, RED BANK, NJ, 07701

Community: Shady Oaks

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Questions? Call us: (475) 471-1908

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New Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$340,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New The Waterways at Moriches

290 W MIDLAND POND CT 290, BROOKHAVEN, N..., Brookhaven, NY 11955

$629,000

2 beds

2 baths

1,440 sq ft

Condo

290 W MIDLAND POND CT 290, BROOKHAVEN, N...

Community: The Waterways at Moriches

New The Seasons at Seaford

56 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$820,000

2 beds

3 baths

1,034 sq ft

Condo

56 SPRING DR, HEMPSTEAD, NY, 11783

Community: The Seasons at Seaford

New Country Pointe Plainview

31201 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,150,000

2 beds

2 baths

1,379 sq ft

Condo

31201 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

New Heritage Village

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

$279,000

2 beds

2 baths

1,432 sq ft

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

196 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$365,000

1 beds

2 baths

1,175 sq ft

Condo

196 APACHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Breton Hills

401 BRETON WAY 401, GLEN COVE, NY, 11542, Glen Cove, NY 11542

$699,999

2 beds

2 baths

1,300 sq ft

Condo

401 BRETON WAY 401, GLEN COVE, NY, 11542

Community: Breton Hills

New Equestra at Colts Neck Crossing

21 W BACCIO LN, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727

$679,000

2 beds

2 baths

1,632 sq ft

House

21 W BACCIO LN, FARMINGDALE, NJ, 07727

Community: Equestra at Colts Neck Crossing

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Questions? Call us: (475) 471-1908

New Enclave at Shrewsbury

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

$1,249,000

3 beds

3 baths

2,777 sq ft

House

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

Community: Enclave at Shrewsbury

New Nobility Crest at Ocean

7 CENTRE ST 2101, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712

$449,000

1 beds

1 baths

1,058 sq ft

Adult Community

7 CENTRE ST 2101, OCEAN TWP, NJ, 07712

Community: Nobility Crest at Ocean

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New Autumn Fields

5 QUAIL HOLW 5, ENFIELD, CT, 06082, Enfield, CT 06082

$399,900

2 beds

3 baths

1,679 sq ft

Condo

5 QUAIL HOLW 5, ENFIELD, CT, 06082

Community: Autumn Fields

New Shadow Lake Village

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

$465,000

2 beds

2 baths

952 sq ft

Ranch

122 MANCHESTER CT, RED BANK, NJ, 07701

Community: Shadow Lake Village

New Jefferson Village

158 CARRIAGE CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$686,000

2 beds

2 baths

1,555 sq ft

Condo

158 CARRIAGE CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Sunrise Village

93 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$525,000

2 beds

2 baths

1,230 sq ft

Condo

93 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

New The Villages at Mount Sinai Park

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$899,000

3 beds

3 baths

2,455 sq ft

House

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Surrey Downs

53 FARNWORTH CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$379,900

2 beds

2 baths

Ranch

53 FARNWORTH CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

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Jefferson Village

10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$240,000

1 baths

550 sq ft

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598

Community: Jefferson Village

O'Meara Farm

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032

$480,000

2 beds

2 baths

1,416 sq ft

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032

Community: O'Meara Farm

The Greens at Half Hollow

625 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$980,000

2 beds

3 baths

1,940 sq ft

Condo

625 MADEIRA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Surrey Downs

19 JAFFREYTON CLOSE, HOWELL, NJ, 07731, Howell, NJ 07731

$429,000

2 beds

2 baths

1,261 sq ft

Adult Community

19 JAFFREYTON CLOSE, HOWELL, NJ, 07731

Community: Surrey Downs

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Chelsea Square

112 REGENCY CT 112, MORGANVILLE, NJ, 077..., Morganville, NJ 07751

$500,000

2 beds

2 baths

Ranch

112 REGENCY CT 112, MORGANVILLE, NJ, 077...

Community: Chelsea Square

Meadowbrooke Pointe East Meadow

137 EMANUEL WAY, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$839,000

2 beds

3 baths

1,390 sq ft

Condo

137 EMANUEL WAY, HEMPSTEAD, NY, 11554

Community: Meadowbrooke Pointe East Meadow

Foxwood Village

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$364,000

2 beds

2 baths

1,532 sq ft

House

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933

Community: Foxwood Village

Heritage Village

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

$360,000

2 beds

2 baths

1,432 sq ft

Condo

640 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Fishkill

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

$555,000

2 beds

2 baths

1,803 sq ft

Condo

145 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

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Oronoque Village

47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$409,000

2 beds

2 baths

1,360 sq ft

Condo

47 HURON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$299,999

2 beds

1 baths

875 sq ft

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

Country Village Estates

45 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$475,000

2 beds

2 baths

1,305 sq ft

Condo

45 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

Surrey Downs

45 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728

$395,000

2 beds

1 baths

1,012 sq ft

Ranch

45 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728

Community: Surrey Downs

The Villages at Mount Sinai Park

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$675,000

2 beds

3 baths

1,736 sq ft

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

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Four Seasons at Colts Farm

2 PASTURE DR, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727

$999,900

3 beds

3 baths

2,793 sq ft

House

2 PASTURE DR, FARMINGDALE, NJ, 07727

Community: Four Seasons at Colts Farm

Regency at Prospect

104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712

$328,417

3 beds

2 baths

1,500 sq ft

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712

Community: Regency at Prospect

Rivington

131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810

$770,000

3 beds

3 baths

1,592 sq ft

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...

Community: Rivington

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Regency at Woodbridge

27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525

$599,900

3 beds

3 baths

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525

Community: Regency at Woodbridge

Castle Heights of Cheshire

151 VICTORIA DR, CHESHIRE, CT, 06410, Cheshire, CT 06410

$769,900

2 beds

4 baths

2,843 sq ft

Condo

151 VICTORIA DR, CHESHIRE, CT, 06410

Community: Castle Heights of Cheshire

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.

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169 communities

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

169 communities near Westport

321 homes near Westport

2 beds

2 baths

1,871 sq ft

2 beds

3 baths

1,998 sq ft

Condo

2 beds

3 baths

1,340 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,788 sq ft

House

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,440 sq ft

Condo

2 beds

3 baths

1,034 sq ft

Condo

2 beds

2 baths

1,379 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds

2 baths

1,632 sq ft

House

3 beds

3 baths

2,777 sq ft

House

1 beds

1 baths

1,058 sq ft

Adult Community

2 beds

3 baths

1,679 sq ft

Condo

2 beds

2 baths

952 sq ft

Ranch

2 beds

2 baths

1,555 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

3 beds

3 baths