New Fairfield, CT 55+ active adult communities & homes for sale - Page 3

159 communities near New Fairfield

Sort by:

Relevance

The Savannah

$600ks - $700ks

The Savannah, Westfield, NJ

Resale Only | 55+ age-restricted | Built 2009 - 2009 | 35 homes

The Pointe at Garwood

$600ks - $700ks

The Pointe at Garwood, Garwood, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 44 homes

Brooklake Park

$400ks

Brooklake Park, Florham Park, NJ

Resale Only | 55+ age-restricted | Built 2008 - 2008 | 25 homes

Eagle Ridge at East Hanov...

$200ks - $300ks

Eagle Ridge at East Hanov..., East Hanover, NJ

Resale Only | 55+ age-restricted | Built 1992 - 1993 | 50 homes

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

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

Questions? Call us: (959) 214-2391

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Eastport Meadows

$400ks

Eastport Meadows, Eastport, NY

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 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.

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

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

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

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

Questions? Call us: (959) 214-2391

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

Wolfe Landing

$500ks - $600ks

Wolfe Landing, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes

Eden Park

$500ks - $600ks

Eden Park, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes

The Views at Pomona

$200ks - $400ks

The Views at Pomona, Pomona, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Windmill Gate

$300ks - $400ks

Windmill Gate, Oakdale, NY

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

The Club at Melville

$500ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

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

4 rating (1 reviews)

Vineyards at Blue Point

$500ks - $700ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

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

Questions? Call us: (959) 214-2391

Knickerbocker Bay Club

$700ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes

5 rating (2 reviews)

Blackburne Farm Townhomes

$400ks

Blackburne Farm Townhomes, Campbell Hall, NY

New Construction | 55+ age-restricted | Built 2019 - present | 29 homes

The Residences at Butterf...

$500ks - $600ks

The Residences at Butterf..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Meadowbrooke Pointe East ...

$500ks - $600ks

Meadowbrooke Pointe East ..., East Meadow, NY

New Construction | 62+ age-restricted | Built 2019 - present | 104 homes

Hidden Harbor Estates

$500ks - $600ks

Hidden Harbor Estates, Copiague, NY

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes

The Pines at Bohemia

$400ks - $500ks

The Pines at Bohemia, Bohemia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 20 homes

The Polo Club at Islandia

$600ks - $700ks

The Polo Club at Islandia, Islandia, NY

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

Stratford Park

$600ks - $800ks

Stratford Park, Melville, NY

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 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

1 rating (2 reviews)

Knoll Edge

$600ks - $700ks

Knoll Edge, Boonton, NJ

New Construction | 55+ age-restricted | Built 2024 - present | 16 homes

17101 ASPENWOOD DR, OYSTER BAY, NY, 1180...

Community: Country Pointe Plainview

New Liberty at Newtown

76 SUZIE DR 76, NEWTOWN, CT, 06470, Newtown, CT 06470

$648,000

2 beds

3 baths

2,341 sq ft

Condo

76 SUZIE DR 76, NEWTOWN, CT, 06470

Community: Liberty at Newtown

New Wanaque Reserve

4301 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$410,000

2 beds

2 baths

4301 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

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

Questions? Call us: (959) 214-2391

New Heritage Village

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

$259,000

2 beds

2 baths

1,432 sq ft

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Strathmore Gate East

4 FLAIR WAY, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$495,000

2 beds

2 baths

1,112 sq ft

House

4 FLAIR WAY, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New The Greens at Half Hollow

1130 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$710,000

2 beds

2 baths

1,140 sq ft

Condo

1130 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Oak Meadow Estates

197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790

$399,000

2 beds

2 baths

1,419 sq ft

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...

Community: Oak Meadow Estates

New Strathmore Gate East

9 FREEDOM LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$289,000

1 beds

1 baths

728 sq ft

Condo

9 FREEDOM LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New Jefferson Village

27 WALDEN CT J, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

1 beds

1 baths

800 sq ft

Condo

27 WALDEN CT J, YORKTOWN, NY, 10598

Community: Jefferson Village

New Leisure Knoll

338 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$419,990

2 beds

1 baths

960 sq ft

Condo

338 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Greenwood Village

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$227,000

2 beds

2 baths

1,291 sq ft

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Billingsgate

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070

$750,000

2 beds

3 baths

2,729 sq ft

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...

Community: Billingsgate

New Encore Atlantic Shores

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

$925,000

2 beds

3 baths

2,900 sq ft

Condo

11 OVATION PL, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

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

Questions? Call us: (959) 214-2391

New Leisure Village

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$239,000

1 beds

1 baths

684 sq ft

Condo

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Heritage Village

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

$209,000

1 beds

1 baths

928 sq ft

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Powder Forest Homes

6 PROSPECT RDG 6, SIMSBURY, CT, 06070, Simsbury, CT 06070

$715,000

3 beds

3 baths

2,183 sq ft

6 PROSPECT RDG 6, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Bear's Cove

75 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446

2 beds

3 baths

1,350 sq ft

Condo

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

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

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

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

Community: Leisure Village

The Village at Oxford Greens

443 TEE SHOT DR 443, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

3 beds

3 baths

2,759 sq ft

Condo

443 TEE SHOT DR 443, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Heritage Hills

29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589

$495,000

2 beds

3 baths

1,340 sq ft

Condo

29 HERITAGE HLS 29D, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

$825,000

3 beds

2 baths

1,905 sq ft

Condo

606 HERITAGE HILLS DR C, SOMERS, NY, 105...

Community: Heritage Hills

Hopmeadow Place

1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,430 sq ft

Condo

1 W ST 310, SIMSBURY, CT, 06070

Community: Hopmeadow Place

Leisure Knoll

152B LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$374,000

1 beds

1 baths

530 sq ft

Condo

152B LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

The Bel Aire at East Meadow

50 MERRICK AVE 415, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$500,000

2 beds

2 baths

1,000 sq ft

Condo

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

HarborView

$829,000

2 beds

3 baths

Condo

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

Community: HarborView

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

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 [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

159 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: Jun 29, 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 3

159 communities near New Fairfield

351 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

1,400 sq ft

Condo

2 beds

3 baths

2,341 sq ft

Condo

2 beds

2 baths

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,112 sq ft

House

2 beds

2 baths

1,140 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,419 sq ft

Condo

1 beds

1 baths

728 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

1 baths

960 sq ft

Condo

2 beds

2 baths

1,291 sq ft

Condo

2 beds

3 baths

2,729 sq ft

Condo

2 beds

3 baths

2,900 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

3 beds

3 baths

2,183 sq ft

3 beds

4 baths

Condo

2 beds