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

218 homes near Portland

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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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
Want to learn more about 55+ communities in Portland? 55places can help!
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The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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
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
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
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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
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
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
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.
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 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
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.
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
The Villas at Narraganset...
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
The Seasons at Seaford
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
Eagles Walk at East Quogu...
$300ks - $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 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 Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
123...4
Heritage Village 103 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

103 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 546 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$679,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

546 N TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
The Manors at The Colony Preserve 41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$525,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

41 GREENTREE CT, BROOKHAVEN, NY, 11967
Harmony Place 15 FIDELITY DR 70, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

15 FIDELITY DR 70, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Harmony Place 4 FIDELITY DR 2, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

4 FIDELITY DR 2, RUTLAND, MA, 01543
Community: Harmony Place
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$599,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 21 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$499,999

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

21 GREENTREE CT, BROOKHAVEN, NY, 11967
Spring Lake Village 41 COACH DR 41, SOUTHINGTON, CT, 06489, Southington, CT 06489
$249,900

2 beds

|

2 baths

|

1,232 sq ft

|

Condo

41 COACH DR 41, SOUTHINGTON, CT, 06489
Community: Spring Lake 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 865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
The Seasons at Seaford 28 SPRING DR, SEAFORD, NY, 11783, Seaford, NY 11783
$829,000

2 beds

|

2 baths

|

1,034 sq ft

|

Condo

28 SPRING DR, SEAFORD, NY, 11783
Rivington 13 MERCY ST 13, DANBURY, CT, 06810, Danbury, CT 06810
$630,000

3 beds

|

3 baths

|

1,572 sq ft

|

Condo

13 MERCY ST 13, DANBURY, CT, 06810
Community: Rivington
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Village at Orchard Meadows 47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,..., Shrewsbury, MA 01545
$499,900

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,...
Spring Lake Village 6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489
$315,000

3 beds

|

3 baths

|

1,471 sq ft

|

Condo

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$599,000

1 beds

|

3 baths

|

2,199 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, 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.
Leisure Glen 530 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$579,000

2 beds

|

2 baths

|

1,434 sq ft

|

Condo

530 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
The Greens at Half Hollow 833 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$728,000

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

833 MADEIRA BLVD, HUNTINGTON, NY, 11747
Heritage Village 575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
South Pond Village 81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$259,999

2 beds

|

2 baths

|

1,204 sq ft

|

Condo

81 SILO WAY 81, BLOOMFIELD, CT, 06002
Community: South Pond Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Coves at Melville 54 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$549,000

2 beds

|

2 baths

|

1,162 sq ft

|

Condo

54 MORLEY CIR, HUNTINGTON, NY, 11747
Oronoque Village 133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

2 beds

|

3 baths

|

2,038 sq ft

|

Condo

133 BANNOCK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
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
Chatfield Farms 8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403
$699,900

3 beds

|

4 baths

|

2,610 sq ft

|

Condo

8 WOODLAND PATH 8, BEACON FALLS, CT, 064...
Community: Chatfield Farms
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 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
$167,000

2 beds

|

2 baths

|

1,164 sq ft

|

Condo

16 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
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
Village Vistas 11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,325,000

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
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
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
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
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$624,900

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
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 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
$619,000

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
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
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Oronoque Village 635 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$399,000

1 beds

|

3 baths

|

1,454 sq ft

|

Condo

635 N TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
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...
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