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

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

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

Questions? Call us: (959) 214-2391

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

5 rating (1 reviews)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

New and Resale | 55+ age-restricted | Built 2004 - present | 215 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 Manors at The Colony ...

$300ks - $400ks

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

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

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

Questions? Call us: (959) 214-2391

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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

Questions? Call us: (959) 214-2391

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

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

Questions? Call us: (959) 214-2391

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

102 WINGED FOOT WAY, RIVERHEAD, NY, 1190...

Community: Sunken Pond Estates

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

Questions? Call us: (959) 214-2391

New Heritage Hills

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

$780,000

3 beds

2 baths

1,780 sq ft

Condo

103 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Country Pointe Plainview

33204 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,735,000

2 beds

2 baths

1,976 sq ft

Condo

33204 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

New Woodcrest at Jacobs Hill

2306 JACOBS HILL RD 306, CORTLANDT, NY, ..., Cortlandt, NY 10567

$425,000

2 beds

2 baths

1,145 sq ft

Condo

2306 JACOBS HILL RD 306, CORTLANDT, NY, ...

Community: Woodcrest at Jacobs Hill

New Warwick Grove

50 CROPSEY ST, WARWICK (TOWN), NY, 10990, Warwick (town), NY 10990

$750,000

3 beds

3 baths

2,482 sq ft

Condo

50 CROPSEY ST, WARWICK (TOWN), NY, 10990

Community: Warwick Grove

New Leisure Village

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$228,888

2 beds

1 baths

836 sq ft

Condo

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961

50 MERRICK AVE 415, HEMPSTEAD, NY, 11554

Community: The Bel Aire at East Meadow

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

Questions? Call us: (959) 214-2391

New HarborView

100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,..., North Hempstead, NY 11050

$829,000

2 beds

3 baths

Condo

100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,...

Community: HarborView

New Oronoque Village

448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$525,000

1 beds

3 baths

1,438 sq ft

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

New The Powder Forest Homes

6 RONAN WAY 6, SIMSBURY, CT, 06070, Simsbury, CT 06070

$739,900

2 beds

3 baths

1,864 sq ft

6 RONAN WAY 6, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Saddle Lakes

174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$675,000

2 beds

2 baths

1,631 sq ft

Condo

174 ADELE CT, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Wanaque Reserve

8208 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$419,000

2 beds

2 baths

8208 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

Wanaque Reserve

8208 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465

2 beds

2 baths

1,379 sq ft

Condo

115 AUTUMN DR, OYSTER BAY, NY, 11803

160 CHRISTINE DR, HUNTINGTON, NY, 11746

Community: Stone Ridge Estates

Heritage Village

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

$424,900

2 beds

2 baths

1,398 sq ft

Condo

892 HERITAGE VLG A, 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

Country Village Estates

110 THEODORE DR 110, BROOKHAVEN, NY, 117..., Brookhaven, NY 11727

$475,000

2 beds

2 baths

1,261 sq ft

Condo

110 THEODORE DR 110, BROOKHAVEN, NY, 117...

Community: Country Village Estates

Heritage Village

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

$335,000

2 beds

2 baths

1,398 sq ft

Condo

339 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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.

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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: Jun 26, 2026.
This application does not include information on all of the properties available for sale at this time.

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

159 communities near New Fairfield

350 homes near New Fairfield

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,428 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

3 beds

2 baths

1,780 sq ft

Condo

2 beds

2 baths

1,976 sq ft

Condo

2 beds

2 baths

1,145 sq ft

Condo

3 beds

3 baths

2,482 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

3 beds

3 baths

2,759 sq ft

Condo

2 beds

3 baths

1,340 sq ft

Condo

3 beds

2 baths

1,905 sq ft

Condo

2 beds

2 baths

1,430 sq ft

Condo

1 beds

1 baths

530 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

3 baths

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

3 baths

1,864 sq ft

2 beds

2 baths

1,631 sq ft