New Fairfield, CT 55+ active adult communities & homes for sale

159 communities near New Fairfield

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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

Bald Eagle Commons

$100ks - $300ks

Bald Eagle Commons, West Milford, NJ

Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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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Questions? Call us: (959) 214-2391

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

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

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

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

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Questions? Call us: (959) 214-2391

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 (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)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

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

Questions? Call us: (959) 214-2391

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Apple Ridge

$500ks - $1Ms

Apple Ridge, Mahwah, NJ

Resale Only | Age-targeted | Built 1977 - 1991 | 276 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

HarborView

$800ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 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 New Fairfield? 55places can help!

Questions? Call us: (959) 214-2391

The Views at Pomona

$200ks - $400ks

The Views at Pomona, Pomona, NY

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes

1 2 3...4

Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$379,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$386,000

3 beds

2 baths

1,716 sq ft

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949

$245,000

2 beds

2 baths

1,130 sq ft

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...

Community: Greenwood Village

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Heritage Village

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

$219,900

1 beds

1 baths

928 sq ft

Condo

65 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (959) 214-2391

New Heritage Village

261B HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$240,000

2 beds

2 baths

1,032 sq ft

Condo

261B HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

New Westhampton Pines

179 CARLY LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$899,000

2 beds

2 baths

2,000 sq ft

Condo

179 CARLY LN, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

New Heritage Village

1016 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$245,000

1 beds

1 baths

928 sq ft

Condo

1016 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

New Bald Eagle Commons

162 RICHMOND RD, WEST MILFORD, NJ, 07480, West Milford, NJ 07480

$529,000

3 beds

4 baths

Townhouse

162 RICHMOND RD, WEST MILFORD, NJ, 07480

Community: Bald Eagle Commons

New Spring Lake Village

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489

$330,000

2 beds

2 baths

1,313 sq ft

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

New Oronoque Village

522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,900

3 baths

2,375 sq ft

Condo

522 IROQUOIS LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Bald Eagle Commons

162 RICHMOND RD, WEST MILFORD TWP., NJ, ..., West Milford Twp., NJ 07480

$529,000

3 beds

4 baths

162 RICHMOND RD, WEST MILFORD TWP., NJ, ...

Community: Bald Eagle Commons

New The Savannah

111 PROSPECT ST 4A, WESTFIELD TOWN, NJ, ..., Westfield Town, NJ 07090

$1,599,000

2 beds

3 baths

111 PROSPECT ST 4A, WESTFIELD TOWN, NJ, ...

Community: The Savannah

New Stoneleigh Woods at Riverhead

158 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$699,000

2 beds

3 baths

2,071 sq ft

Condo

158 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

New Heritage Hills

220 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$699,000

3 beds

2 baths

1,689 sq ft

Condo

220 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New The Seasons at East Meadow

421 AUTUMN DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$635,000

2 beds

2 baths

1,272 sq ft

Condo

421 AUTUMN DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

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

Questions? Call us: (959) 214-2391

New Country Pointe Preserve

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$875,000

2 beds

3 baths

1,998 sq ft

Condo

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

New Apple Ridge

239 WESTERVELT LN, MAHWAH TWP., NJ, 0743..., Mahwah Twp., NJ 07430

$950,000

3 beds

4 baths

2,966 sq ft

239 WESTERVELT LN, MAHWAH TWP., NJ, 0743...

Community: Apple Ridge

New Rivington

424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810

$479,900

2 beds

2 baths

1,258 sq ft

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

New Windmill Gate

18 KATHLEEN DR, ISLIP, NY, 11769, Islip, NY 11769

$600,000

2 beds

2 baths

1,413 sq ft

Condo

18 KATHLEEN DR, ISLIP, NY, 11769

Community: Windmill Gate

New Country Pointe Plainview

52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803

$1,669,990

2 beds

3 baths

1,750 sq ft

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...

Community: Country Pointe Plainview

New Glenwood Village

1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ..., Riverhead, NY 11901

$329,000

2 beds

2 baths

1,152 sq ft

Manufactured Home

1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ...

Community: Glenwood Village

New The Seasons at Elwood

63 WINTER PL, HUNTINGTON, NY, 11731, Huntington, NY 11731

$427,767

2 beds

2 baths

1,108 sq ft

Condo

63 WINTER PL, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Stone Ridge Estates

110 JOSEPH LN, HUNTINGTON, NY, 11746, Huntington, NY 11746

$779,000

2 beds

2 baths

1,695 sq ft

Condo

110 JOSEPH LN, HUNTINGTON, NY, 11746

Community: Stone Ridge Estates

New Encore Atlantic Shores

140 CHOPIN PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$865,000

2 beds

3 baths

2,236 sq ft

Condo

140 CHOPIN PL, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

New Leisure Village

89 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$469,000

2 beds

2 baths

1,308 sq ft

Condo

89 ENFIELD CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Apple Ridge

239 WESTERVELT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$950,000

3 beds

4 baths

Townhouse

239 WESTERVELT LN, MAHWAH, NJ, 07430

Community: Apple Ridge

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

Questions? Call us: (959) 214-2391

New Village Vistas

35 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777

$1,300,000

3 beds

4 baths

3,000 sq ft

Condo

35 THERESA LN, BROOKHAVEN, NY, 11777

Community: Village Vistas

New Wildflowers at Wallkill

25 SUNFLOWER ST, MIDDLETOWN, NY, 10940, Middletown, NY 10940

$535,500

2 beds

2 baths

1,868 sq ft

Condo

25 SUNFLOWER ST, MIDDLETOWN, NY, 10940

Community: Wildflowers at Wallkill

New The Village at Oxford Greens

171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478

$775,000

3 beds

3 baths

2,750 sq ft

Condo

171 COUNTRY CLUB DR 171, OXFORD, CT, 064...

Community: The Village at Oxford Greens

New Oronoque Village

621 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$499,000

1 beds

3 baths

2,325 sq ft

Condo

621 ONONDAGA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Westhampton Pines

79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977

$1,295,000

2 beds

3 baths

2,440 sq ft

Condo

79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977

Community: Westhampton Pines

New Heritage Hills

88 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$699,000

2 beds

3 baths

1,585 sq ft

Condo

88 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Glen

19 SAYVILLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$615,000

2 beds

2 baths

1,666 sq ft

Condo

19 SAYVILLE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Jefferson Village

196 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$675,000

2 beds

2 baths

1,550 sq ft

Condo

196 LONG HILL DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Hopmeadow Place

1 W ST 215, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 215, SIMSBURY, CT, 06070

Community: Hopmeadow Place

New Glenwood Village

1661 OLD COUNTRY RD 258, RIVERHEAD, NY, ..., Riverhead, NY 11901

$389,999

2 beds

2 baths

1,310 sq ft

House

1661 OLD COUNTRY RD 258, RIVERHEAD, NY, ...

Community: Glenwood Village

New Leisure Village

344 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$365,000

2 beds

2 baths

1,168 sq ft

Condo

344 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

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

Questions? Call us: (959) 214-2391

New Leisure Village

275 BERWICK CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$355,000

2 beds

1 baths

875 sq ft

Condo

275 BERWICK CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New The Summit at Bethel

78 GREAT HILL DR 78, BETHEL, CT, 06801, Bethel, CT 06801

$700,000

3 beds

4 baths

Condo

78 GREAT HILL DR 78, BETHEL, CT, 06801

Community: The Summit at Bethel

Frequently Asked Questions

What size 55+ communities are there in New Fairfield?

In New Fairfield, there is 1 small community with less than 500 homes.

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

The smallest 55+ community in New Fairfield has 33 homes, the largest has 33 homes, and the average community consists of 33 homes.

Are there gated 55+ communities in New Fairfield?

No, there are no gated 55+ communities in New Fairfield.

How long do listings in 55+ communities in New Fairfield typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in New Fairfield stay on the market for around 421 days. The average price of homes for sale in this community is approximately $482,355, though prices can range widely based on the size, location, and amenities of the community. For example, homes in The Woods at Dunham Pond average around $482,355.

Want more information about active adult communities around New Fairfield?

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Want to learn more about 55+ communities in New Fairfield?

Call us: (959) 214-2391

159 communities

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REIN updates its listings on a daily basis. Data last updated: Aug 13, 2026.
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New Fairfield, CT 55+ active adult communities & homes for sale

159 communities near New Fairfield

375 homes near New Fairfield

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

2,000 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

3 beds

4 baths

Townhouse

2 beds

2 baths

1,313 sq ft

Condo

3 baths

2,375 sq ft

Condo

3 beds

4 baths

2 beds

3 baths

2 beds

3 baths

2,071 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

2 beds

3 baths

1,998 sq ft

Condo

3 beds

4 baths

2,966 sq ft

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,413 sq ft

Condo

2 beds

3 baths

1,750 sq ft

Condo