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

157 communities near New Fairfield

Sort by:

Relevance

Four Seasons at Wayne

$500Ks

Four Seasons at Wayne, Wayne, NJ

Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

Woodridge Strathmore Terr...

$400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

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

5 rating (1 reviews)

Warwick Grove

$600Ks - $800Ks

Warwick Grove, Warwick, NY

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

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

Questions? Call us: (959) 214-2391

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

Questions? Call us: (959) 214-2391

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

Sunrise Village, Sayville, NY

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

Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

Country Village Estates

$400Ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $500Ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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 Seasons at East North...

$700Ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

5 rating (1 reviews)

Westhampton Pines

$900Ks - $1Ms

Westhampton Pines, Westhampton, NY

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

5 rating (1 reviews)

The Villages at Mount Sin...

$500Ks - $700Ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

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

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

Questions? Call us: (959) 214-2391

The Pointe

$500Ks

The Pointe, Livingston, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

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

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

Questions? Call us: (959) 214-2391

Snug Harbor

$600Ks - $700Ks

Snug Harbor, Amityville, NY

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

Stoneleigh Woods at River...

$600Ks

Stoneleigh Woods at River..., Riverhead, NY

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

The Coves at Melville

$500Ks

The Coves at Melville, Melville, NY

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

Strathmore Gate East

$300Ks - $400Ks

Strathmore Gate East, Coram, NY

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

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Regency at Fishkill

$400Ks - $500Ks

Regency at Fishkill, Fishkill, NY

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

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

Questions? Call us: (959) 214-2391

Four Seasons at Cedar Gro...

$700Ks

Four Seasons at Cedar Gro..., Cedar Grove, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes

South Pond Village

$100Ks - $200Ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

The Manors at The Colony ...

$400Ks - $500Ks

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

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

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

Questions? Call us: (959) 214-2391

Vineyards at Brookfield

$700Ks

Vineyards at Brookfield, Center Moriches, NY

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

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

Village Estates

$500Ks

Village Estates, Amityville, NY

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

The Villas at Narraganset...

$500Ks - $600Ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

Campagna

$300Ks

Campagna, Montville Township, NJ

Resale Only | 55+ age-restricted | Built 1980 - 1986 | 136 homes

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

Questions? Call us: (959) 214-2391

The Seasons at Plainview

$600Ks - $700Ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

The Hollows at Blue Hill

$1Ms

The Hollows at Blue Hill, Pearl River, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes

Windcrest East

$600Ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Fairview at Oxford Greens

$600Ks

Fairview at Oxford Greens, Oxford, CT

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

Newbury Village

$500Ks - $600Ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

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

Questions? Call us: (959) 214-2391

The Seasons at Seaford

$700Ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

Windmill Gate

$300Ks - $400Ks

Windmill Gate, Oakdale, NY

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

Four Seasons at Ridgemont

$800Ks - $1Ms

Four Seasons at Ridgemont, Montvale, NJ

Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes

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

Questions? Call us: (959) 214-2391

5 rating (1 reviews)

Four Seasons at North Cal...

$700Ks - $800Ks

Four Seasons at North Cal..., North Caldwell, NJ

Resale Only | 55+ age-restricted | Built 2011 - 2015 | 108 homes

Bear's Cove

$1Ms

Bear's Cove, Ramsey, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 104 homes

59 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Wanaque Reserve

9116 WARRENS WAY # 116, WANAQUE, NJ, 074..., Wanaque, NJ 07465

$449,000

2 beds

2 baths

9116 WARRENS WAY # 116, WANAQUE, NJ, 074...

Community: Wanaque Reserve

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

Questions? Call us: (959) 214-2391

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

Questions? Call us: (959) 214-2391

Wanaque Reserve

10203 WARRENS WAY # 203, WANAQUE, NJ, 07..., Wanaque, NJ 07465

$439,900

2 beds

2 baths

1,768 sq ft

10203 WARRENS WAY # 203, WANAQUE, NJ, 07...

Community: Wanaque Reserve

Overlook

1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512

$879,000

2 beds

3 baths

2,496 sq ft

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512

Community: Overlook

Overlook

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512

$665,000

3 beds

3 baths

1,914 sq ft

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...

Community: Overlook

Fairfield at St. James

304 GOTHAM WAY, SAINT JAMES, NY, 11780, Saint James, NY 11780

$449,803

1 beds

2 baths

Condo

304 GOTHAM WAY, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

The Waterways at Moriches

477 WOODSCREEK CT, MORICHES, NY, 11955, Moriches, NY 11955

$565,000

3 beds

2 baths

1,839 sq ft

Condo

477 WOODSCREEK CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Plymouth Estates at Mount Sinai

166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$579,999

2 beds

2 baths

1,820 sq ft

House

166 IRA RD, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Encore Atlantic Shores

113 OVERTURE PL, EASTPORT, NY, 11941, Eastport, NY 11941

$885,000

2 beds

3 baths

3,037 sq ft

Condo

113 OVERTURE PL, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Leisure Village

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$342,000

2 beds

1 baths

1,278 sq ft

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...

Community: Leisure Village

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

Questions? Call us: (959) 214-2391

Leisure Knoll

190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$434,999

2 beds

1 baths

787 sq ft

Condo

190 CANTERBURY DR, RIDGE, NY, 11961

Community: Leisure Knoll

Heritage Hills

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

$675,000

2 beds

2 baths

1,500 sq ft

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...

Condo

66 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

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

Questions? Call us: (959) 214-2391

The Villages at Mount Sinai Park

4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$799,999

3 beds

3 baths

2,850 sq ft

Condo

4 OAKHURST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Heritage Hills

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

$625,000

2 beds

2 baths

1,559 sq ft

Condo

443 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New The Vineyards at Miller Place

45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$650,000

2 beds

3 baths

1,853 sq ft

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

Glenwood Village

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,..., Riverhead, NY 11901

$205,000

2 beds

2 baths

1,008 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,...

Community: Glenwood Village

New Leisure Village

475 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961

$437,500

2 beds

2 baths

1,423 sq ft

Condo

475 DARWEN DR B, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (959) 214-2391

Saddle Lakes

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$749,990

3 beds

3 baths

1,837 sq ft

Condo

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Blackburne Farm Townhomes

32 OTTAWAY LN, CAMPBELL HALL, NY, 10916, Campbell Hall, NY 10916

$700,000

2 beds

4 baths

3,600 sq ft

House

32 OTTAWAY LN, CAMPBELL HALL, NY, 10916

Community: Blackburne Farm Townhomes

Breton Hills

704 BRETON WAY # 704, GLEN COVE, NY, 115..., Glen Cove, NY 11542

$629,000

2 beds

2 baths

1,440 sq ft

Condo

704 BRETON WAY # 704, GLEN COVE, NY, 115...

Community: Breton Hills

The Seasons at East Northport

142 AUGUST CIR, EAST NORTHPORT, NY, 1173..., East Northport, NY 11731

$780,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, EAST NORTHPORT, NY, 1173...

Community: The Seasons at East Northport

Leisure Glen

10 SAGAPONACK CT # 10, RIDGE, NY, 11961, Ridge, NY 11961

$649,000

2 beds

2 baths

1,867 sq ft

Condo

10 SAGAPONACK CT # 10, RIDGE, NY, 11961

Condo

42 TRENT CT D, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (959) 214-2391

Glenwood Village

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901

$139,999

2 beds

1 baths

816 sq ft

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Village

474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961

$400,000

2 beds

2 baths

1,200 sq ft

Condo

474 DARWEN DR B, RIDGE, NY, 11961

Community: Leisure 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 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

157 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.
© 2025 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: Dec 27, 2025.
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

157 communities near New Fairfield

244 homes near New Fairfield

2 beds

2 baths

1,663 sq ft

Condo

2 beds

4 baths

3,500 sq ft

Condo

2 beds

2 baths

1,434 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

2 baths

2 beds

2 baths

1,768 sq ft

2 beds

3 baths

2,496 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

1 beds

2 baths

Condo

3 beds

2 baths

1,839 sq ft

Condo

2 beds

2 baths

1,820 sq ft

House

2 beds

3 baths

3,037 sq ft

Condo

2 beds

1 baths

1,278 sq ft

Condo

2 beds

1 baths

787 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

938 sq ft

Condo

2 beds

2 baths

1,147 sq ft

Condo

2 beds

2 baths

1,144 sq ft

Mobile Home

2 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

1,803 sq ft

Condo

2 beds