New Fairfield, CT 55+ active adult communities & homes for sale - Page 2

373 homes near New Fairfield

Sort by:

Relevance

Bald Eagle Commons

$100ks - $300ks

Bald Eagle Commons, West Milford, NJ

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

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 rating (1 reviews)

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 - $800ks

Heritage Hills, Somers, NY

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

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

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

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

Questions? Call us: (959) 214-2391

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

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

Questions? Call us: (959) 214-2391

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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

5 rating (1 reviews)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

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

Questions? Call us: (959) 214-2391

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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 Views at Pomona

$200ks - $400ks

The Views at Pomona, Pomona, NY

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

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

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

Questions? Call us: (959) 214-2391

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

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

1 2 3 4...5

Jefferson Village

45 JEFFERSON OVAL H, YORKTOWN, NY, 10598, Yorktown, NY 10598

$370,000

2 beds

2 baths

1,100 sq ft

Condo

45 JEFFERSON OVAL H, YORKTOWN, NY, 10598

Community: Jefferson Village

Leisure Glen

272 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$549,000

2 beds

2 baths

1,456 sq ft

Condo

272 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Wanaque Reserve

3116 WARRENS WAY 116, WANAQUE BORO, NJ, ..., Wanaque Boro, NJ 07465

$387,000

2 beds

2 baths

3116 WARRENS WAY 116, WANAQUE BORO, NJ, ...

Community: Wanaque Reserve

Heritage Hills

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

$649,999

2 beds

2 baths

1,296 sq ft

Condo

790 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Bald Eagle Commons

12 LAFAYETTE ST, WEST MILFORD, NJ, 07480, West Milford, NJ 07480

$558,000

3 beds

3 baths

Townhouse

12 LAFAYETTE ST, WEST MILFORD, NJ, 07480

Community: Bald Eagle Commons

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

Questions? Call us: (959) 214-2391

Woodridge Strathmore Terrace

62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$425,000

2 beds

2 baths

1,105 sq ft

Condo

62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

Bald Eagle Commons

12 LAFAYETTE ST, WEST MILFORD TWP., NJ, ..., West Milford Twp., NJ 07480

$558,000

3 beds

3 baths

2,372 sq ft

12 LAFAYETTE ST, WEST MILFORD TWP., NJ, ...

Community: Bald Eagle Commons

Meadow Brook Estates

107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478

$639,000

3 beds

3 baths

1,922 sq ft

107 MEADOW BROOK RD 107, OXFORD, CT, 064...

Community: Meadow Brook Estates

Bear's Cove

99 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446

$1,175,000

3 beds

3 baths

Townhouse

99 WINDSOR LN, RAMSEY, NJ, 07446

Community: Bear's Cove

The Powder Forest Homes

9 GRISWOLD PL 9, SIMSBURY, CT, 06070, Simsbury, CT 06070

$1,250,000

3 beds

5 baths

2,774 sq ft

9 GRISWOLD PL 9, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Woodcrest at Jacobs Hill

1104 JACOBS HILL RD, CORTLANDT, NY, 1056..., Cortlandt, NY 10567

$389,000

2 beds

2 baths

1,145 sq ft

House

1104 JACOBS HILL RD, CORTLANDT, NY, 1056...

Community: Woodcrest at Jacobs Hill

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

Heritage Village

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

$260,000

2 beds

2 baths

1,032 sq ft

Condo

261B HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

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

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

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

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

Questions? Call us: (959) 214-2391

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

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

The Savannah

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

1,152 sq ft

Manufactured Home

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

Community: Glenwood Village

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

Questions? Call us: (959) 214-2391

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

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

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

Apple Ridge

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

$950,000

3 beds

4 baths

Townhouse

196 LONG HILL DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (959) 214-2391

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

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

1 2 3 4 5 6 7 8 9…10

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?

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 optout@55places.com. 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

373 homes

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: Aug 25, 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 - Page 2

161 communities near New Fairfield

373 homes near New Fairfield

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,456 sq ft

Condo

2 beds

2 baths

2 beds

2 baths

1,296 sq ft

Condo

3 beds

3 baths

Townhouse

2 beds

2 baths

1,105 sq ft

Condo

3 beds

3 baths

2,372 sq ft

3 beds

3 baths

1,922 sq ft

3 beds

3 baths

Townhouse

3 beds

5 baths

2,774 sq ft

2 beds

2 baths

1,145 sq ft

House

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 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