Southold, NY 55+ active adult communities & homes for sale - Page 2

149 homes near Southold

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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 Southold? 55places can help!

Questions? Call us: (631) 407-2675

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 Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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.

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 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

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

Questions? Call us: (631) 407-2675

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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 Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

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

Questions? Call us: (631) 407-2675

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Newington Ridge Preserve

$300ks - $400ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

The Seasons at East North...

$700ks

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

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

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

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

Questions? Call us: (631) 407-2675

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

The Village at Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes

Autumn Estates

$500ks - $600ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

The Powder Forest Homes

$500ks - $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 Southold? 55places can help!

Questions? Call us: (631) 407-2675

Sonoma Woods

$300ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

1 2...3

Heritage Village

419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$500,000

3 beds

2 baths

1,716 sq ft

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$167,000

2 beds

2 baths

1,164 sq ft

Condo

16 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

230 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961

$289,900

2 beds

1 baths

836 sq ft

Condo

230 BLACKPOOL CT A, RIDGE, NY, 11961

Community: Leisure Village

Meadow Brook Estates

215 MEADOW BROOK RD 215, OXFORD, CT, 064..., Oxford, CT 06478

$589,000

3 beds

3 baths

2,207 sq ft

Condo

215 MEADOW BROOK RD 215, OXFORD, CT, 064...

Community: Meadow Brook Estates

Leisure Knoll

190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$479,999

2 beds

1 baths

913 sq ft

House

190 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (631) 407-2675

Heritage Village

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

$275,000

2 beds

2 baths

1,432 sq ft

Condo

915 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Encore at Lake Grove

171 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$799,000

2 beds

3 baths

2,189 sq ft

Condo

171 SYMPHONY DR, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

Oronoque Village

445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$644,900

1 beds

3 baths

1,620 sq ft

Condo

445 NORTH TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$249,000

2 beds

2 baths

1,071 sq ft

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Encore Atlantic Shores

236 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$790,000

2 beds

2 baths

2,215 sq ft

Condo

236 ENCORE BLVD, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Leisure Knoll

475 STRATFORD LN, RIDGE, NY, 11961, Ridge, NY 11961

$519,000

3 beds

2 baths

1,592 sq ft

House

475 STRATFORD LN, RIDGE, NY, 11961

Community: Leisure Knoll

South Pond Village

162 THISTLE POND DR 162, BLOOMFIELD, CT,..., Bloomfield, CT 06002

$395,000

2 beds

2 baths

1,341 sq ft

Condo

162 THISTLE POND DR 162, BLOOMFIELD, CT,...

Community: South Pond Village

The Village at Oxford Greens

117 COUNTRY CLUB DR 117, OXFORD, CT, 064..., Oxford, CT 06478

$639,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR 117, OXFORD, CT, 064...

Community: The Village at Oxford Greens

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

Questions? Call us: (631) 407-2675

The Seasons at East Northport

142 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$790,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, HUNTINGTON, NY, 11731

Community: The Seasons at East Northport

The Village at Oxford Greens

301 FAIRWAY DR 301, OXFORD, CT, 06478, Oxford, CT 06478

$619,000

2 beds

2 baths

2,080 sq ft

Condo

301 FAIRWAY DR 301, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Westhampton Pines

39 KIMBERLY DR 39, SOUTHAMPTON, NY, 1197..., Southampton, NY 11977

$1,495,000

3 beds

3 baths

2,500 sq ft

Condo

39 KIMBERLY DR 39, SOUTHAMPTON, NY, 1197...

Community: Westhampton Pines

Granite Woods

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$229,000

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762

Community: Granite Woods

Oronoque Village

635 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

3 baths

1,454 sq ft

Condo

635 N TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$195,000

2 beds

2 baths

1,032 sq ft

Condo

73 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0..., Oxford, CT 06478

$650,000

3 beds

3 baths

2,731 sq ft

Condo

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Greenwood Village

54 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$130,000

2 beds

2 baths

1,134 sq ft

Condo

54 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (631) 407-2675

Oronoque Village

13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

1 beds

2 baths

1,330 sq ft

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614

Community: Oronoque Village

The Village at Oxford Greens

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478

$645,000

3 beds

3 baths

2,595 sq ft

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...

Community: The Village at Oxford Greens

The Village at Oxford Greens

185 COUNTRY CLUB DR 185, OXFORD, CT, 064..., Oxford, CT 06478

$645,000

3 beds

3 baths

2,595 sq ft

185 COUNTRY CLUB DR 185, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Heritage Village

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

$320,000

2 beds

2 baths

1,365 sq ft

Condo

423 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961

$359,900

2 beds

1 baths

875 sq ft

Condo

278 BERWICK CT UNIT B B, RIDGE, NY, 1196...

Community: Leisure Village

Regency at Woodbridge

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525

$629,000

3 beds

3 baths

Condo

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...

Community: Regency at Woodbridge

Regency at Woodbridge

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ..., Woodbridge, CT 06525

$749,000

3 beds

3 baths

Condo

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ...

Community: Regency at Woodbridge

Heritage Village

405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$199,900

2 beds

2 baths

1,044 sq ft

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,036 sq ft

Condo

418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (631) 407-2675

The Waterways at Moriches

554 MIRROR POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$499,000

2 beds

2 baths

1,497 sq ft

Condo

554 MIRROR POND CT, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

Oronoque Village

446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$635,000

3 beds

3 baths

1,426 sq ft

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

Oronoque Village

151 S TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$460,000

1 beds

3 baths

1,426 sq ft

Condo

151 S TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$339,900

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Fairfield at St. James

901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780

$499,000

2 beds

2 baths

1,230 sq ft

Condo

901 FENWAY RD, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

Leisure Glen

10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961

$599,900

2 beds

2 baths

1,666 sq ft

Condo

10 OAKDALE CT, RIDGE, NY, 11961

Community: Leisure Glen

Heritage Village

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

$310,000

2 beds

2 baths

1,432 sq ft

Condo

891 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Encore Atlantic Shores

6 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$795,000

2 beds

2 baths

2,150 sq ft

Condo

6 OVATION PL, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

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

Questions? Call us: (631) 407-2675

Stone Ridge Estates

153 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746

$775,000

2 beds

2 baths

1,415 sq ft

Condo

153 CHRISTINE DR, DIX HILLS, NY, 11746

Community: Stone Ridge Estates

Leisure Village

186 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$289,000

2 beds

1 baths

900 sq ft

Condo

186 VENTRY CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

1 2 3…4

Frequently Asked Questions

What size 55+ communities are there in Southold?

In Southold, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Southold?

The smallest 55+ community in Southold has 92 homes, the largest has 92 homes, and the average community consists of 92 homes.

Are there gated 55+ communities in Southold?

No, there are no gated 55+ communities in Southold.

How long do listings in 55+ communities in Southold typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in Southold stay on the market for around 169 days. The average price of homes for sale in this community is approximately $527,500, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Founders Village average around $527,500.

Want more information about active adult communities around Southold?

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 Southold?

Call us: (631) 407-2675

149 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: Feb 27, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Southold, NY 55+ active adult communities & homes for sale - Page 2

94 communities near Southold

149 homes near Southold

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,164 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

3 beds

3 baths

2,207 sq ft

Condo

2 beds

1 baths

913 sq ft

House

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

2,189 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

2 baths

2,215 sq ft

Condo

3 beds

2 baths

1,592 sq ft

House

2 beds

2 baths

1,341 sq ft

Condo

3 beds

3 baths

2,666 sq ft

2 beds

2 baths

1,536 sq ft

Condo

2 beds

2 baths

2,080 sq ft

Condo

3 beds

3 baths

2,500 sq ft

Condo

1 beds

1 baths

889 sq ft

Condo

1 beds

3 baths

1,454 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

3 beds

3 baths