Homes in ZIP Code 34229

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  $329,000 Sold Jan 14, 2026

  85 Navigation Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $230/SF
  • 8 Days On Market

  Current Estimated Value $329,550

  Last Listing Agent Kate Kwiecinski COLDWELL BANKER REALTY

  85 Navigation Cir, Osprey, FL 34229
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  /48

  Est $597,781 Not Listed For Sale

  522 Meadow Sweet Cir, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 2,424 Sq Ft
  • Built 1998

  522 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 13% Below List Price
  • $284/SF
  • 145 Days On Market

  Last Sold Price $687,500

  Last Listing Agent Sandi Tresh RE/MAX
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  /94

  $990,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  401 N Point Rd Unit 504, Osprey, FL 34229

  FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION From the moment the private elevator opens into your foyer, this residence reveals itself as a home crafted with intention, artistry, and a deep appreciation for its natural surroundings. Sunlight fills the space as water and preserve views stretch out beyond the generous lanai—an ever-changing backdrop that greets you

  Mary Elizabeth Mock COLDWELL BANKER REALTY

  401 N Point Rd Unit 504, Osprey, FL 34229
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  $155,000 Sold Nov 26, 2025

  170 Edgewood Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $162/SF
  • 132 Days On Market

  Last Listing Agent Roberta Burish KW SUNCOAST

  170 Edgewood Dr, Osprey, FL 34229
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  /38

  Est $591,652 Not Listed For Sale

  574 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,325 Sq Ft
  • Built 1999

  574 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 5% Below List Price
  • $269/SF
  • 7 Days On Market

  Last Sold Price $625,000

  Last Listing Agent Frank Zeckel COLDWELL BANKER REALTY
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  /66

  $674,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  1303 Thornapple Dr, Osprey, FL 34229

  Under contract-accepting backup offers. INCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appointed FURNISHED Lee Wetherington residence with NEW $54,000 Barrel Tile ROOF (Nov 2025) in Sought After Willowbend---- A MAINTENANCE-FREE (lawn/landscaping/irrigation) Boutique Community ideally located near the Fitness Center and Community Pool, Pickleball Courts &

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  1303 Thornapple Dr, Osprey, FL 34229
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  $3,900,000 Sold Aug 27, 2025

  426 N Casey Key Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1992

  Last Sold Summary

  • 20% Below List Price
  • $2,079/SF
  • 657 Days On Market

  Current Estimated Value $3,584,278

  Last Listing Agent Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  426 N Casey Key Rd, Osprey, FL 34229
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  /48

  Est $745,553 Not Listed For Sale

  763 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,093 Sq Ft
  • Built 1998

  763 Shadow Bay Way, Osprey, FL 34229

  Last Sold Summary

  • 13% Below List Price
  • $278/SF
  • 22 Days On Market

  Last Sold Price $860,000

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  /36

  $569,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft

  1337 Copperwood Dr, Osprey, FL 34229

  This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings,

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1337 Copperwood Dr, Osprey, FL 34229
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  $3,500,000 Sold Dec 17, 2025

  431 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,006 Sq Ft
  • Built 1979

  Last Sold Summary

  • 19% Below List Price
  • $1,164/SF
  • 11 Days On Market

  Current Estimated Value $3,594,396

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  431 Yacht Harbor Dr, Osprey, FL 34229
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  /39

  Est $688,811 Not Listed For Sale

  1096 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,492 Sq Ft
  • Built 2000

  1096 Mallard Marsh Dr, Osprey, FL 34229

  Last Sold Summary

  • 9% Below List Price
  • $305/SF
  • 39 Days On Market

  Last Sold Price $760,000

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  $599,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  51 Webb St, Osprey, FL 34229

  Under contract-accepting backup offers. Location, location, location. Nestled west of the Trail in the heart of Osprey, this beautifully updated three-bedroom, two-bath home with a den offers a rare opportunity just moments from Sarasota Bay. Set on a spacious, private lot framed by mature oak trees and lush tropical landscaping, the property features no HOA or CDD restrictions. Inside, the home

  Marina Myers FINE PROPERTIES

  51 Webb St, Osprey, FL 34229
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  $2,400,000 Sold Jan 09, 2026

  432 Sorrento Dr, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 3,640 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $659/SF
  • 7 Days On Market

  Current Estimated Value $2,371,739

  Last Listing Agent Tanya Waxler UKEEPCOMMISSION REAL ESTATE

  432 Sorrento Dr, Osprey, FL 34229
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  Est $723,628 Not Listed For Sale

  1000 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,441 Sq Ft
  • Built 2003

  1000 Scherer Way, Osprey, FL 34229

  Last Sold Summary

  • 4% Below List Price
  • $309/SF
  • 54 Days On Market

  Last Sold Price $755,000

  Last Listing Agent Jody Callan PREMIER SOTHEBYS INTL REALTY
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  /55

  $515,000

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  120 Villa Dr Unit 120, Osprey, FL 34229

  Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel

  Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  120 Villa Dr Unit 120, Osprey, FL 34229
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  $470,000 Sold Feb 10, 2026

  1363 New Forest Ln, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 2002

  Last Sold Summary

  • 14% Below List Price
  • $270/SF
  • 260 Days On Market

  Current Estimated Value $562,292

  Last Listing Agent Pamela Strom RE/MAX PALM

  1363 New Forest Ln, Osprey, FL 34229
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  /55

  Est $565,226 Not Listed For Sale

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 2,143 Sq Ft
  • Built 2004

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  Last Sold Summary

  • 11% Below List Price
  • $298/SF
  • 363 Days On Market

  Last Sold Price $638,000

  Last Listing Agent Jeremy Myers COMPASS PROPERTY MANAGEMENT LLC
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  /42

  $200,000

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft

  211 Woodland Dr Unit 211, Osprey, FL 34229

  Tucked away in the charming community of Pine Run, this uniquely designed two-story condo offers the perfect blend of privacy, comfort, and Florida lifestyle living in the heart of Osprey. This spacious 2-bedroom, 2-bath residence features a layout offering the primary suite on the first floor—ideal for ease of living and added privacy. The main level offers an inviting living and dining area

  Samantha Campbell BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  211 Woodland Dr Unit 211, Osprey, FL 34229
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  $649,000 Sold Aug 26, 2025

  0 Four Knot Ln, Osprey, FL 34229

  • Land
  • 0.26 Acre
  • $2,496,154 per Acre

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Gregory Wood CERUS REALTY

  0 Four Knot Ln, Osprey, FL 34229
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  Est $541,188 Not Listed For Sale

  590 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft
  • Built 1999

  590 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 11% Below List Price
  • $322/SF
  • 53 Days On Market

  Last Sold Price $609,000

  Last Listing Agent Kathy White PREFERRED SHORE LLC
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  /37

  $1,499,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,798 Sq Ft

  1471 Shoal Way, Osprey, FL 34229

  One or more photo(s) has been virtually staged. This exceptional residence truly checks every box.Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the

  Lauren Doyle DALTON WADE INC

  1471 Shoal Way, Osprey, FL 34229
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  $43,000 Sold Nov 04, 2025

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229

  Last Sold Summary

  • 2% Below List Price
  • 98 Days On Market

  Last Listing Agent Rick Bumbaca NORTHGROUP REAL ESTATE, INC

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229
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  /46

  Est $599,867 Not Listed For Sale

  730 Fordingbridge Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft
  • Built 2002

  730 Fordingbridge Way, Osprey, FL 34229

  Last Sold Summary

  • 11% Below List Price
  • $309/SF
  • 128 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE
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  /35

  $175,000 Pending

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft

  200 Woodland Dr Unit 200, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to Pine Run in Osprey! Half-way between Sarasota and Venice, convenient to both with ample shopping and dining close by. Your 1 bedroom one and a half bath oasis is nestled on 20+ acres of lush native Florida landscape. This popular ground floor unit features large glass sliders and your own private courtyard in the front of the unit where

  Kathleen Griffin MICHAEL SAUNDERS & COMPANY

  200 Woodland Dr Unit 200, Osprey, FL 34229
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  $220,000 Sold Oct 23, 2025

  216 Woodland Dr Unit 216, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $166/SF
  • 55 Days On Market

  Current Estimated Value $217,594

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  216 Woodland Dr Unit 216, Osprey, FL 34229
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  Est $741,725 Not Listed For Sale

  356 S Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,369 Sq Ft
  • Built 1990

  356 S Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 2% Above List Price
  • $308/SF
  • 36 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Christiana Kopetzky Michael Saunders
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  $599,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,162 Sq Ft

  767 Fordingbridge Way, Osprey, FL 34229

  Set on a quiet cul-de-sac in The Woodlands at Rivendell, this furnished and thoughtfully maintained residence offers a peaceful setting surrounded by mature landscaping and wooded views. The extended foyer welcomes you into an open great-room layout spanning nearly 2,200 square feet, where high tray ceilings, plantation shutters, and hardwood flooring create a cohesive flow throughout the main

  Roger Pettingell COLDWELL BANKER REALTY

  767 Fordingbridge Way, Osprey, FL 34229
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  $660,000 Sold Mar 10, 2026

  471 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,267 Sq Ft
  • Built 2001

  Last Sold Summary

  • 12% Below List Price
  • $291/SF
  • 197 Days On Market

  Current Estimated Value $684,120

  Last Listing Agent Bill Cantrell WILLIAM RAVEIS REAL ESTATE

  471 Park Trace Blvd, Osprey, FL 34229
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  /81

  Est $1,105,709 Not Listed For Sale

  385 N Point Rd Unit 604, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2000

  385 N Point Rd Unit 604, Osprey, FL 34229

  Last Sold Summary

  • 18% Below List Price
  • $486/SF
  • 48 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Rosalie Phillips Michael Saunders
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  $445,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  288 Woods Point Rd, Osprey, FL 34229

  Under contract-accepting backup offers. Perfectly positioned West of the Trail near Blackburn Point and Casey Key, this turnkey furnished 3 bedroom, 2 bathroom attached single family residence offers nearly 1,800 square feet of vaulted, light-filled interiors framed by lush preserve views. Set within an exclusive enclave of just 44 homes, this residence delivers the privacy and proportions of

  Toni Zarghami KW COASTAL LIVING III

  288 Woods Point Rd, Osprey, FL 34229
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  $1,015,000 Sold Aug 01, 2025

  678 Clear Creek Dr, Osprey, FL 34229

  • 5 Beds
  • 3 Baths
  • 3,912 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $259/SF
  • 11 Days On Market

  Current Estimated Value $957,714

  Last Listing Agent Dena Dominiczak EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
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  /40

  Est $766,300 Not Listed For Sale

  672 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,830 Sq Ft
  • Built 2003

  672 Crane Prairie Way, Osprey, FL 34229

  Last Sold Summary

  • 19% Below List Price
  • $336/SF
  • 4 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $489,249 New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 102, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 102, Osprey, FL 34229
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  $1,200,000 Sold Oct 24, 2025

  1484 Seafarer Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,479 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $345/SF
  • 82 Days On Market

  Current Estimated Value $1,173,298

  Last Listing Agent Seth Westerberg EXP REALTY LLC

  1484 Seafarer Dr, Osprey, FL 34229
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  /21

  Est $1,207,480 Not Listed For Sale

  1108 Bayhead Ln, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 3,541 Sq Ft
  • Built 1997

  1108 Bayhead Ln, Osprey, FL 34229

  Last Sold Summary

  • 51% Above List Price
  • $226/SF
  • 99 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Rosalie Phillips Michael Saunders
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  /99

  $1,350,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,679 Sq Ft

  133 Osprey Point Dr, Osprey, FL 34229

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Custom Home located in the exclusive gated community of The Oaks Bayside with a private pool and spa. Just across the street from Sarasota Bay. Recent improvements include updated bathrooms and a newer kitchen (with Thermador appliances) and all freshly painted. This 4 bedroom, 3 bathroom plus bonus room house

  Lisa Warren OWN SRQ LLC

  133 Osprey Point Dr, Osprey, FL 34229
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  $1,275,000 Sold Sep 30, 2025

  364 Renoir Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,241 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $393/SF
  • 7 Days On Market

  Current Estimated Value $1,260,850

  Last Listing Agent Lore Miller RESULTS REALTY GROUP LLC

  364 Renoir Dr, Osprey, FL 34229
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  Est $1,799,911 Not Listed For Sale

  280 Saratoga Ct, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,970 Sq Ft
  • Built 1994

  280 Saratoga Ct, Osprey, FL 34229

  Last Sold Summary

  • 1% Above List Price
  • $450/SF
  • 41 Days On Market

  Last Sold Price $1,787,500

  Last Listing Agent Mark Lyda GENEROUS PROPERTY
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  /74

  $385,000

  • 3 Beds
  • 3 Baths
  • 1,879 Sq Ft

  1795 Highland Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in

  Rachel Tritschler RE/MAX ALLIANCE GROUP

  1795 Highland Rd, Osprey, FL 34229
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  $945,000 Sold Apr 15, 2025

  128 Sea Anchor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,677 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $353/SF
  • 4 Days On Market

  Current Estimated Value $906,302

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  128 Sea Anchor Dr, Osprey, FL 34229

Showing Results 361 - 400, Page 10 of 18