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

158 communities near New Fairfield

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

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

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Bald Eagle Commons

$100ks - $300ks

Bald Eagle Commons, West Milford, NJ

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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

Questions? Call us: (959) 214-2391

3 rating (2 reviews)

Heritage Hills

- $900ks

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

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 Waterways at Moriches

$300ks - $600ks

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.

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 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 (1 reviews)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

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

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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 (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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 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 (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

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

Questions? Call us: (959) 214-2391

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

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

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

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

Questions? Call us: (959) 214-2391

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

1 2 3...4

New Oronoque Village

619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

1 beds

3 baths

1,583 sq ft

Condo

619 ERIE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New The Hollows at Blue Hill

4105 FRED ILL JR CT, ORANGETOWN, NY, 109..., Orangetown, NY 10965

$769,900

2 beds

2 baths

1,420 sq ft

Condo

4105 FRED ILL JR CT, ORANGETOWN, NY, 109...

Community: The Hollows at Blue Hill

New The Village at Oxford Greens

1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New Bald Eagle Commons

6412 RICHMOND RD 412, WEST MILFORD, NJ, ..., West Milford, NJ 07480

$240,000

2 beds

2 baths

Condo

6412 RICHMOND RD 412, WEST MILFORD, NJ, ...

Community: Bald Eagle Commons

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

Questions? Call us: (959) 214-2391

New Oronoque Village

765 NYACK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,900

2 beds

3 baths

1,642 sq ft

Condo

765 NYACK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Jefferson Village

157 CARRIAGE CT E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$324,000

1 beds

1 baths

850 sq ft

Condo

157 CARRIAGE CT E, YORKTOWN, NY, 10598

Community: Jefferson Village

New Leisure Glen

289 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$585,000

2 beds

2 baths

1,666 sq ft

Condo

289 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Leisure Village

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$475,000

2 beds

2 baths

1,278 sq ft

Condo

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Bald Eagle Commons

6412 RICHMOND RD, WEST MILFORD TWP., NJ,..., West Milford Twp., NJ 07480

$240,000

2 beds

2 baths

985 sq ft

6412 RICHMOND RD, WEST MILFORD TWP., NJ,...

Community: Bald Eagle Commons

New Heritage Village

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

$265,000

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Retreat at Carmel

2 BLAIR HEIGHTS 3331, CARMEL, NY, 10512, Carmel, NY 10512

$500,000

2 beds

2 baths

1,733 sq ft

Condo

2 BLAIR HEIGHTS 3331, CARMEL, NY, 10512

Community: The Retreat at Carmel

New Sunrise Village

168 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$450,000

2 beds

1 baths

871 sq ft

Condo

168 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

New Heritage Hills

177A HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$395,000

1 beds

1 baths

900 sq ft

Condo

177A HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Regency at Fishkill

734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$559,000

2 beds

2 baths

1,499 sq ft

Condo

734 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

New Country Pointe Preserve

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$965,000

2 beds

3 baths

2,389 sq ft

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

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

Questions? Call us: (959) 214-2391

New Warwick Grove

6 COWDREY ST, WARWICK (TOWN), NY, 10990, Warwick (town), NY 10990

$799,000

2 beds

4 baths

1,920 sq ft

House

6 COWDREY ST, WARWICK (TOWN), NY, 10990

Community: Warwick Grove

New The Woods at Dunham Pond

30 HERON VIEW RD, NEW FAIRFIELD, CT, 068..., New Fairfield, CT 06812

$559,900

1 beds

3 baths

3,230 sq ft

Condo

30 HERON VIEW RD, NEW FAIRFIELD, CT, 068...

Community: The Woods at Dunham Pond

New Heritage Hills

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

$485,000

1 beds

2 baths

967 sq ft

Condo

955 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Sunrise Village

109 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$525,000

2 beds

2 baths

1,273 sq ft

Condo

109 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

New Bald Eagle Commons

5301 RICHMOND RD 301, WEST MILFORD, NJ, ..., West Milford, NJ 07480

2 beds

2 baths

1,456 sq ft

Condo

155 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (959) 214-2391

New Overlook

2075 SUMMIT LOOP 101, CARMEL, NY, 10512, Carmel, NY 10512

$960,000

2 beds

2 baths

1,948 sq ft

Condo

2075 SUMMIT LOOP 101, CARMEL, NY, 10512

Community: Overlook

New Overlook

2052 SUMMIT LOOP 62, CARMEL, NY, 10512, Carmel, NY 10512

$954,000

2 beds

2 baths

2,102 sq ft

Condo

2052 SUMMIT LOOP 62, CARMEL, NY, 10512

Community: Overlook

New Oronoque Village

564 PEQUOT LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$599,900

2 beds

2 baths

1,438 sq ft

Condo

564 PEQUOT LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Hopmeadow Place

1 W ST 223, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 223, SIMSBURY, CT, 06070

Community: Hopmeadow Place

Oronoque Village

638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614

$539,000

1 beds

3 baths

1,175 sq ft

Condo

638A ONONDAGA LN, STRATFORD, CT, 06614

Community: Oronoque Village

Encore Atlantic Shores

11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$925,000

2 beds

3 baths

3,037 sq ft

House

11 OVATION PL, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Stoneleigh Woods at Carmel

807 EGRETS LNDG, CARMEL, NY, 10512, Carmel, NY 10512

$575,000

3 beds

3 baths

2,788 sq ft

Condo

807 EGRETS LNDG, CARMEL, NY, 10512

Community: Stoneleigh Woods at Carmel

Bald Eagle Commons

1314 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480

$259,900

2 beds

1 baths

Condo

80 WINDING RIDGE WAY 80, DANBURY, CT, 06...

Community: Rivington

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

Questions? Call us: (959) 214-2391

Bald Eagle Commons

1314 RICHMOND RD 314, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480

$259,900

2 beds

1 baths

957 sq ft

1314 RICHMOND RD 314, WEST MILFORD TWP.,...

Community: Bald Eagle Commons

The Greens at Half Hollow

870 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$749,888

2 beds

2 baths

1,262 sq ft

Condo

870 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

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 84 days. The average price of homes for sale in this community is approximately $457,774, 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 $457,774.

Want more information about active adult communities around New Fairfield?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

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

Call us: (959) 214-2391

158 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Apr 27, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

158 communities near New Fairfield

346 homes near New Fairfield

1 beds

3 baths

1,583 sq ft

Condo

2 beds

2 baths

1,420 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

2 baths

Condo

2 beds

3 baths

1,642 sq ft

Condo

1 beds

1 baths

850 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,278 sq ft

Condo

2 beds

2 baths

985 sq ft

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,733 sq ft

Condo

2 beds

1 baths

871 sq ft

Condo

1 beds

1 baths

900 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Condo

2 beds

3 baths

2,389 sq ft

Condo

2 beds

4 baths

1,920 sq ft

House

1 beds

3 baths

3,230 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths

1,273 sq ft