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

123 communities near Portland

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3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

3.7 rating (3 reviews)

Greenwood Village

<$100k - $200Ks

Greenwood Village, Manorville, NY

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

The Village at Oxford Gre...

$600Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

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Harmony Place

$400Ks

Harmony Place, Rutland, MA

New Construction | 55+ age-restricted | Built 2023 - present | 142 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

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

The Waterways at Moriches

$400Ks - $500Ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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

$400Ks - $800Ks

Rivington, Danbury, CT

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

4 rating (8 reviews)

Glenwood Village

$100Ks - $200Ks

Glenwood Village, Riverhead, NY

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

Country Pointe Plainview

$1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 homes

5 rating (1 reviews)

Encore Atlantic Shores

$700Ks

Encore Atlantic Shores, Eastport, NY

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

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Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

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

Leisure Knoll

$400Ks - $500Ks

Leisure Knoll, Ridge, NY

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

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Questions? Call us: (860) 854-7490

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Village Estates

$500Ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes

5 rating (1 reviews)

Westhampton Pines

$1Ms

Westhampton Pines, Westhampton, NY

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

The Villas at Narraganset...

$500Ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

Stoneleigh Woods at River...

$500Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

The Manors at The Colony ...

$500Ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

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Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

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

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

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

Kensington Estates

$2Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

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

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The Vineyards at Miller P...

$600Ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Stone Ridge Estates

$700Ks

Stone Ridge Estates, Dix Hills, NY

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

Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

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

Country Village Estates

$400Ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

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Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

Baldwin Station

$400Ks

Baldwin Station, Milford, CT

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

5 rating (1 reviews)

The Villages at Mount Sin...

$500Ks - $700Ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

The Seasons at Plainview

$600Ks - $700Ks

The Seasons at Plainview, Plainview, NY

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

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

Questions? Call us: (860) 854-7490

Strathmore Gate East

$300Ks - $400Ks

Strathmore Gate East, Coram, NY

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks - $600Ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

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Questions? Call us: (860) 854-7490

The Seasons at East North...

$700Ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 homes

4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$300Ks - $700Ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes

1 2 3...4

New Encore at Lake Grove

17 SONATA CT, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$635,000

2 beds

3 baths

1,486 sq ft

Condo

17 SONATA CT, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

New Meadow Brook Estates

215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478

$589,000

3 beds

3 baths

2,207 sq ft

Condo

215 MEADOW BROOK RD # 215, OXFORD, CT, 0...

Community: Meadow Brook Estates

New Leisure Village

406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$245,000

1 beds

1 baths

704 sq ft

Condo

406 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

New Long Hill Village

71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$539,900

1 beds

3 baths

1,370 sq ft

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

New Leisure Knoll

190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$479,999

2 beds

1 baths

913 sq ft

House

190 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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Questions? Call us: (860) 854-7490

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New Village Estates

34 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701

$569,999

2 beds

2 baths

1,251 sq ft

Condo

34 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

New Heritage Village

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

$295,000

2 beds

2 baths

1,432 sq ft

Condo

915 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Greenwood Village

126 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$225,000

2 beds

2 baths

1,032 sq ft

Condo

126 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

New Encore at Lake Grove

171 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$799,000

2 beds

3 baths

2,189 sq ft

Condo

171 SYMPHONY DR, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

New Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$644,900

1 beds

3 baths

1,620 sq ft

Condo

445 NORTH TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Rivington

1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681..., Danbury, CT 06810

$899,900

3 beds

4 baths

2,596 sq ft

Condo

1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681...

Community: Rivington

New Fairview at Oxford Greens

909 TILLINGHAST DR # 909, OXFORD, CT, 06..., Oxford, CT 06478

$699,000

2 beds

3 baths

2,239 sq ft

Condo

909 TILLINGHAST DR # 909, OXFORD, CT, 06...

Community: Fairview at Oxford Greens

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

Questions? Call us: (860) 854-7490

New The Village at Oxford Greens

$699,000

2 beds

3 baths

2,239 sq ft

Condo

909 TILLINGHAST DR # 909, OXFORD, CT, 06...

Community: The Village at Oxford Greens

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+ rental communities in Portland? 55places can help!

Questions? Call us: (860) 854-7490

Encore Atlantic Shores

236 ENCORE BLVD, EASTPORT, NY, 11941, Eastport, NY 11941

$790,000

2 beds

2 baths

2,215 sq ft

Condo

236 ENCORE BLVD, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Leisure Knoll

475 STRATFORD LN, RIDGE, NY, 11961, Ridge, NY 11961

$519,000

3 beds

2 baths

1,592 sq ft

House

475 STRATFORD LN, RIDGE, NY, 11961

Community: Leisure Knoll

Glenwood Village

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901

$245,000

2 beds

2 baths

1,156 sq ft

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...

Community: Glenwood Village

Chatfield Farms

9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403

$515,000

2 beds

3 baths

1,700 sq ft

Condo

9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0...

Community: Chatfield Farms

Sonoma Woods

60 SONOMA LN # 60, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$549,900

2 beds

3 baths

2,054 sq ft

Condo

60 SONOMA LN # 60, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

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

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South Pond Village

162 THISTLE POND DR # 162, BLOOMFIELD, C..., Bloomfield, CT 06002

$395,000

2 beds

2 baths

1,341 sq ft

Condo

162 THISTLE POND DR # 162, BLOOMFIELD, C...

Community: South Pond Village

The Village at Oxford Greens

117 COUNTRY CLUB DR 117, OXFORD, CT, 064..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR 117, OXFORD, CT, 064...

Community: The Village at Oxford Greens

The Seasons at East Northport

142 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$790,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, HUNTINGTON, NY, 11731

Community: The Seasons at East Northport

Leisure Glen

77 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,699 sq ft

House

77 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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The Manors at The Colony Preserve

34 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967

$515,000

2 beds

2 baths

1,357 sq ft

Condo

34 GREENTREE CT, SHIRLEY, NY, 11967

Community: The Manors at The Colony Preserve

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

Community: The Village at Oxford Greens

Meadowbrook Pointe Links & Spa

146 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763

$749,990

2 beds

3 baths

2,047 sq ft

Condo

146 AUGUSTA DR, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Westhampton Pines

39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11..., Westhampton, NY 11977

$1,495,000

3 beds

2 baths

2,500 sq ft

Condo

39 KIMBERLY DR # 39, WESTHAMPTON, NY, 11...

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

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Oronoque Village

635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

3 baths

1,454 sq ft

Condo

635 NORTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$195,000

2 beds

2 baths

1,032 sq ft

Condo

73 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0..., Oxford, CT 06478

$650,000

3 beds

3 baths

2,731 sq ft

Condo

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Country Pointe Plainview

28301 SPRUCE POND CIR, PLAINVIEW, NY, 11..., Plainview, NY 11803

$1,150,000

2 beds

2 baths

1,379 sq ft

Condo

28301 SPRUCE POND CIR, PLAINVIEW, NY, 11...

Community: Country Pointe Plainview

Fairfield at St. James

101 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$449,000

1 beds

2 baths

900 sq ft

Condo

101 FLAIR CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

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Snug Harbor

170 HARBOR, AMITYVILLE, NY, 11701, Amityville, NY 11701

$550,000

2 beds

3 baths

1,334 sq ft

Condo

170 HARBOR, AMITYVILLE, NY, 11701

Community: Snug Harbor

Greenwood Village

54 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$130,000

2 beds

2 baths

1,134 sq ft

Condo

54 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

Fairfield at St. James

1107 CABOT CT N, SAINT JAMES, NY, 11780, Saint James, NY 11780

$439,990

1 beds

2 baths

929 sq ft

Condo

1107 CABOT CT N, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (860) 854-7490

Heritage Village

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

$299,900

2 beds

2 baths

1,365 sq ft

Condo

198 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Summit at Bethel

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680..., Bethel, CT 06801

$619,900

2 beds

3 baths

2,023 sq ft

Condo

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680...

Community: The Summit at Bethel

Frequently Asked Questions

What size 55+ communities are there in Portland?

In Portland, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Portland?

The smallest 55+ communities in Portland has 56 homes, the largest has 82 homes, and the average communities consists of 69 homes.

Are there gated 55+ communities in Portland?

Yes, there is gated 55+ communities in Portland. Approximately 50.0% of 55+ communities in the area are gated. For instance, Bartlett Hill is a gated communities with 82 homes.

Want more information about active adult communities around Portland?

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123 communities

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

123 communities near Portland

191 homes near Portland

2 beds

3 baths

1,486 sq ft

Condo

3 beds

3 baths

2,207 sq ft

Condo

1 beds

1 baths

704 sq ft

Condo

1 beds

3 baths

1,370 sq ft

Condo

2 beds

1 baths

913 sq ft

House

2 beds

2 baths

1,251 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

3 baths

2,189 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

3 beds

4 baths

2,596 sq ft

Condo

2 beds

3 baths

2,239 sq ft

Condo

2 beds

3 baths

2,239 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

2 baths

2,215 sq ft

Condo

3 beds

2 baths

1,592 sq ft

House

2 beds

2 baths

1,156 sq ft

Manufactured Home

2 beds

3 baths

1,700 sq ft

Condo

2 beds