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Sarasota Retirement Communities Real Estate Search

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Home  >  Sarasota  >  55+

Sarasota Retirement CommunitiesBiking on Siesta Key

Florida has long been known as a magnet for attracting retirees from the north.  Today's lifestyle is not your parent's retirement home.  Many of the retirement communities place emphasis on community for those of a similar era.  There are activities, events, and just plain friendships that endure for years.  Of course, some communities do offer graduated levels of assistance for those who require a little more help.

Search for Maintenance Free Homes in Sarasot and OspreyBelow are the listings newest to the market from Sarasota, Osprey, and Venice.  The list is updated daily with new listings or price changes.  Bookmark this link and check back often for the newest listings.   The complete list  is available and can be customized to meet your homebuying needs.  We'll email updates to you daily with only the homes you want to see.  It costs you nothing, and you are never under any obligation to buy!

Here are some other Southwest Florida communities that may be of interest:

Venice Retirement Communities

The Newest Sarasota Retirement Home Listings

3626 Medford Lane Unit 1537, Sarasota image
3626 Medford Lane Unit 1537, Sarasota — 1537 $254,000

Welcome to carefree Florida living in the highly desirable Village Green, a well-established 55+ maintenance-free community in the heart of Sarasota. This spacious and FU...

  • 2 Beds
  • 2 Baths
  • Village Green SubDv.
  • 34232 Zip Code
4312 Rum Cay Place Unit 11, Sarasota image
4312 Rum Cay Place Unit 11, Sarasota — 11 $216,500

CENTER GATE ESTATES VILLAGE IS A DESIRABLE 55+ COMMUNITY IDEALLY LOCATED NEAR SHOPPING, DINING, AND EVERYDAY CONVENIENCES. THIS SPACIOUS 2 BEDROOM HOME OFFERS BOTH COMFO...

  • 2 Beds
  • 2 Baths
  • Center Gate Estates SubDv.
  • 34233 Zip Code
4438 Narraganset Trail Unit 98A, Sarasota image
4438 Narraganset Trail Unit 98A, Sarasota — 4438 $157,500

Lowest-priced home in Lake Tippecanoe! Don't miss this opportunity to own a spacious 2-bedroom, 2-bath condominium with 1,272 square feet and a beautiful, unobstructed la...

  • 2 Beds
  • 2 Baths
  • Lake Tippecanoe SubDv.
  • 34233 Zip Code
2260 Stickney Point Road Unit 324, Sarasota image
2260 Stickney Point Road Unit 324, Sarasota — 2260 $160,000

Welcome to 2260 Stickney Point Road, Unit #324, an inviting 2-bedroom, 2-bath condominium nestled in the desirable Tregate Manor 55+ community in Sarasota. Located on the...

  • 2 Beds
  • 2 Baths
  • Tregate Manor SubDv.
  • 34231 Zip Code
4562 Forest Wood Trail Unit 15, Sarasota image
4562 Forest Wood Trail Unit 15, Sarasota $265,000

Extremely well maintained and improved split plan 2 bedroom, 2 bath villa in active plus 55 community in gated Bent Tree Hammocks II. The property features a comfortable...

  • 2 Beds
  • 2 Baths
  • Bent Tree Condo SubDv.
  • 34241 Zip Code
5689 Evergreen Drive Unit 18, Sarasota image
5689 Evergreen Drive Unit 18, Sarasota $339,000

Welcome to this stunning 2-bedroom, 2-bathroom villa in the highly sought-after Center Gate Village! Recently and completely remodeled, this home boasts modern finishes a...

  • 2 Beds
  • 2 Baths
  • Center Gate Village SubDv.
  • 34233 Zip Code
5119 Glen Echo Avenue, Sarasota image
5119 Glen Echo Avenue, Sarasota $129,000

Don’t miss this great opportunity to own a beautifully updated 2-bedroom, 2-bath 720 sq ft furnished single-wide home—perfect as a comfortable full-time residence or an e...

  • 2 Beds
  • 2 Baths
  • Tri-Par Estates SubDv.
  • 34234 Zip Code
3983 Maceachen Boulevard Unit 434, Sarasota image
3983 Maceachen Boulevard Unit 434, Sarasota — 3983 $169,900

Welcome to this top- 3rd floor 3 Bedroom - 2 Bath condominium in the desirable 55+ affordable community of Tregate East, ideally located just minutes from the world-famou...

  • 3 Beds
  • 2 Baths
  • Tregate East SubDv.
  • 34233 Zip Code
3402 Shingle Oak Terrace, Sarasota image
3402 Shingle Oak Terrace, Sarasota $155,000

Charming, cozy, and move-in ready in the highly desirable 55+ gated community of Oakwood Manor, the ONLY resident-owned park within Sarasota city limits—meaning NO LOT RE...

  • 2 Beds
  • 2 Baths
  • Oakwood Manor SubDv.
  • 34237 Zip Code
71 Twin Shores Boulevard, Longboat Key image
71 Twin Shores Boulevard, Longboat Key $395,000

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can...

  • 2 Beds
  • 2 Baths
  • Twin Shores Mobile Home SubDv.
  • 34228 Zip Code
3981 Maceachen Boulevard Unit 330, Sarasota image
3981 Maceachen Boulevard Unit 330, Sarasota — N/A $154,900 ▼

Welcome to easy Sarasota living in this beautifully updated 3rd-floor condo, ideally located in a sought-after 55+ community just minutes from grocery stores, shopping, a...

  • 2 Beds
  • 2 Baths
  • Tregate East SubDv.
  • 34233 Zip Code
2305 Riverbluff Parkway Unit V256, Sarasota image
2305 Riverbluff Parkway Unit V256, Sarasota $249,300

NEW ROOF (installed January 2024) with SOPHISTCIATED FINISHES! This beautifully reimagined 2 bedroom, 2 bath villa has been thoughtfully redesigned with exceptional atten...

  • 2 Beds
  • 2 Baths
  • Strathmore Riverside SubDv.
  • 34231 Zip Code
208 Hourglass Way Unit V11, Sarasota image
208 Hourglass Way Unit V11, Sarasota $480,000

This rare, freestanding 3-bedroom, 2-bath villa presents an exceptional opportunity to create the coastal home you've always envisioned in the premier Gulf front communit...

  • 3 Beds
  • 2 Baths
  • Whispering Sands SubDv.
  • 34242 Zip Code
3383 Oakwood Boulevard N, Sarasota image
3383 Oakwood Boulevard N, Sarasota $145,900

OAKWOOD MANOR — WHERE FUN AND FRIENDSHIP HAPPEN TURNKEY SARASOTA RETREAT IN ONE OF THE AREA’S BEST-VALUE 55+ COMMUNITIES Don’t miss this beautifully maintained 2-bedr...

  • 2 Beds
  • 2 Baths
  • Oakwood Manor SubDv.
  • 34237 Zip Code
3324 Overcup Oak Terrace, Sarasota image
3324 Overcup Oak Terrace, Sarasota $289,000

OAKWOOD MANOR — WHERE FUN & FRIENDSHIP HAPPENS TURNKEY LIVING • FRIENDLY NEIGHBORS • UNBEATABLE VALUE Own your piece of paradise in Oakwood Manor, Sarasota's highly des...

  • 3 Beds
  • 2 Baths
  • Oakwood Manor SubDv.
  • 34237 Zip Code
3226 Sweet Bay Terrace, Sarasota image
3226 Sweet Bay Terrace, Sarasota $152,000

*Additional photos coming soon* Welcome to 3226 Sweet Bay Terrace in the highly desirable 55+ gated community of Oakwood Manor, the ONLY resident-owned manufactured home ...

  • 2 Beds
  • 2 Baths
  • Oakwood Manor SubDv.
  • 34237 Zip Code
4068 Wilshire Circle E Unit 145, Sarasota image
4068 Wilshire Circle E Unit 145, Sarasota $285,000 ▼

Welcome home to this spacious end-unit villa nestled in a peaceful, park-like setting within one of Sarasota's desirable 55+ communities. Offering 2 generously sized bedr...

  • 2 Beds
  • 2 Baths
  • Lakeshore Village SubDv.
  • 34238 Zip Code
3731 Sarasota Square Boulevard Unit 205D, Sarasota image
3731 Sarasota Square Boulevard Unit 205D, Sarasota — N/A $261,600

Enjoy all the conveniences of maintenance-free living in this spacious two-bedroom, two-and-a-half-bathroom condominium located on the 2nd floor of the Palmer Club at Pre...

  • 2 Beds
  • 3 Baths
  • Palmer Club At Prestancia SubDv.
  • 34238 Zip Code

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