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

163 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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

4 rating (1 review)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

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

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

Questions? Call us: (959) 214-2391

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

5 rating (2 reviews)

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

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

Questions? Call us: (959) 214-2391

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

1 rating (1 review)

Plymouth Estates at Mount...

$400ks - $500ks

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

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

5 rating (1 review)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

5 rating (1 review)

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

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

Parkview Crossings at Woo...

$300ks - $400ks

Parkview Crossings at Woo..., Woodbridge, NJ

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 85 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

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

Questions? Call us: (959) 214-2391

5 rating (1 review)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

5 rating (1 review)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

5 rating (1 review)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

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

The Vineyards at Miller P...

$500ks

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

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

5 rating (1 review)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 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 review)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

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

Questions? Call us: (959) 214-2391

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Glassbury Court at Cold S...

$600ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 90 homes

201 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (959) 214-2391

Jefferson Village

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

$333,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

New Wanaque Reserve

2217 WARRENS WAY 217, WANAQUE BORO, NJ, ..., Wanaque Boro, NJ 07465

$439,900

2 beds

2 baths

1,768 sq ft

2217 WARRENS WAY 217, WANAQUE BORO, NJ, ...

Community: Wanaque Reserve

New Glenwood Village

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$289,000

2 beds

2 baths

1,248 sq ft

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...

Community: Glenwood Village

New Leisure Glen

8 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$559,000

2 beds

2 baths

1,212 sq ft

Condo

8 FLANDERS CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Jefferson Village

36 SUSSEX DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$350,000

1 beds

1 baths

725 sq ft

Condo

36 SUSSEX DR A, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Hills

343 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$520,000

2 beds

2 baths

1,435 sq ft

Condo

343 HERITAGE HLS C, SOMERS, NY, 10589

39 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (959) 214-2391

New Greenwood Village

33A LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$144,999

2 beds

1 baths

800 sq ft

House

33A LIMETREE DR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Glenwood Village

1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ..., Riverhead, NY 11901

$259,000

2 beds

2 baths

1,200 sq ft

Mobile Home

1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ...

Community: Glenwood Village

New Woodridge Strathmore Terrace

74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$549,990

2 beds

2 baths

1,240 sq ft

Condo

74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Woodridge Strathmore Terrace

9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$439,000

2 beds

2 baths

1,240 sq ft

Condo

9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Rivington

79 WINDING RIDGE WAY 79, DANBURY, CT, 06..., Danbury, CT 06810

$1,112,000

3 beds

4 baths

2,596 sq ft

Condo

79 WINDING RIDGE WAY 79, DANBURY, CT, 06...

Community: Rivington

New Heritage Hills

254 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$829,000

3 beds

2 baths

1,780 sq ft

Condo

254 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Spring Lake Village

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06..., Southington, CT 06489

$375,000

2 beds

2 baths

1,207 sq ft

Condo

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06...

Community: Spring Lake Village

New Heritage Hills

314 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$490,000

2 beds

2 baths

1,138 sq ft

Condo

314 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New The Bel Aire at East Meadow

50 MERRICK AVE 216, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$479,000

2 beds

2 baths

920 sq ft

Condo

50 MERRICK AVE 216, HEMPSTEAD, NY, 11554

Community: The Bel Aire at East Meadow

New The Powder Forest Homes

4 ASHTON CIR 4, SIMSBURY, CT, 06070, Simsbury, CT 06070

$729,000

2 beds

4 baths

2,381 sq ft

4 ASHTON CIR 4, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Leisure Knoll

259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,000

2 beds

2 baths

1,135 sq ft

Condo

259 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (959) 214-2391

New Stoneleigh Woods at Riverhead

47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$599,999

2 beds

3 baths

1,942 sq ft

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

New Plymouth Estates at Mount Sinai

262 POND CIR 262, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$599,000

2 beds

2 baths

1,820 sq ft

Condo

262 POND CIR 262, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

New Foxwood Village

1407 MIDDLE RD 103, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$449,000

2 beds

2 baths

1,586 sq ft

Manufactured Home

1407 MIDDLE RD 103, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Foxwood Village

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$405,000

3 beds

2 baths

3,133 sq ft

Manufactured Home

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933

Community: Foxwood Village

New Greenwood Village

402 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$250,000

2 beds

2 baths

1,122 sq ft

Condo

402 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Leisure Village

449 ARLINGTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$310,000

2 beds

1 baths

1,074 sq ft

Condo

449 ARLINGTON DR, BROOKHAVEN, NY, 11961

Community: Leisure Village

New The Greens at Half Hollow

849 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$738,888

2 beds

2 baths

1,150 sq ft

Condo

849 MADEIRA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Heritage Village

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

$275,000

2 beds

2 baths

1,076 sq ft

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Hills

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

$749,900

2 beds

2 baths

1,764 sq ft

Condo

788 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Vineyards at Blue Point

103 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$699,000

2 beds

2 baths

1,652 sq ft

Condo

103 HALLEY DR, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

New Woodridge Strathmore Terrace

41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$599,000

2 beds

2 baths

1,501 sq ft

Condo

41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

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

Questions? Call us: (959) 214-2391

New The Vineyards at Miller Place

48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764

$619,996

2 beds

3 baths

1,486 sq ft

Condo

48 AVERY LN, BROOKHAVEN, NY, 11764

Community: The Vineyards at Miller Place

New Village Estates

20 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701

$589,000

2 beds

2 baths

1,243 sq ft

Condo

20 SARAH CT, BABYLON, NY, 11701

Community: Village Estates

Frequently Asked Questions

What size 55+ communities are there in New Fairfield?

Of the 1 55+ community in New Fairfield, it is for sale. By size, 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 548 days. The average price of homes for sale in this community is approximately $488,500, 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 $488,500.

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163 communities

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REIN updates its listings on a daily basis. Data last updated: Nov 07, 2026.
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New Fairfield, CT 55+ active adult communities & homes for sale

163 communities near New Fairfield

375 homes near New Fairfield

2 beds

2 baths

1,123 sq ft

Condo

2 beds

2 baths

1,592 sq ft

Condo

2 beds

3 baths

2,168 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,078 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,768 sq ft

2 beds

2 baths

1,248 sq ft

Manufactured Home

2 beds

2 baths

1,212 sq ft

Condo

1 beds

1 baths

725 sq ft

Condo

2 beds

2 baths

1,435 sq ft

Condo

2 beds

2 baths

1,370 sq ft

Condo

2 beds

2 baths

1,685 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

1 baths

800 sq ft

House

2 beds

2 baths

1,200 sq ft

Mobile Home

2 beds

2 baths

1,240 sq ft

Condo

2 beds

2 baths