17

Osprey, FL Homes for Sale under $500,000

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  • /39

    $289,900

    $60K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,165 Sq Ft

    1801 Highland Rd, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Welcome to this light-filled, beautifully maintained 2-bedroom, 2-bath townhome in the highly desirable Town-End Shores community of Osprey. With LOW HOA FEES $150.00 PER MONTH and GROUND MAINTENANCE INCLUDED IN FEE this townhouse is designed for comfortable living and easy entertaining, the open-concept main level features a spacious living room,

    Agent Photo

    Kimberly Werla

    RE/MAX ALLIANCE GROUP

    1801 Highland Rd, Osprey, FL 34229
  • /44

    $235,000

    $65K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 595 Sq Ft

    51 MacEwen Dr Unit 5, Osprey, FL 34229

    Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental.Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly

    Sabine Spycher 342 REAL ESTATE

    51 MacEwen Dr Unit 5, Osprey, FL 34229
  • /16

    $305,950

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,593 Sq Ft

    108 Villa Dr Unit 108, Osprey, FL 34229

    Come for the investment, stay for the lifestyle! Discover an exceptional waterfront opportunity in Sorrento Shores, a quiet, pet-friendly community of just 28 homes, ideally located minutes from Nokomis Beach, I-75, and the nationally recognized Pine View School.Whether you're looking for a Florida retreat, investment property, or your own year-round coastal home, this spacious, detached

    Dr. Richard Gaspar LOKATION

    108 Villa Dr Unit 108, Osprey, FL 34229
  • /45

    $249,900

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    116 Woodland Place Unit 116, Osprey, FL 34229

    Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such

    Pat Williams PAT WILLIAMS REALTY, LLC

    116 Woodland Place Unit 116, Osprey, FL 34229
  • /36

    $299,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft

    4226 Frontier Ln Unit 103, Osprey, FL 34229

    Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage

    Kate Kwiecinski COLDWELL BANKER REALTY

    4226 Frontier Ln Unit 103, Osprey, FL 34229
  • /54

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    780 Sarabay Rd Unit 16, Osprey, FL 34229

    Waterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! NEW DOCK & PIER Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. Enjoy carefree coastal living with

    Mark Segreto RMS ELITE PROPERTIES

    780 Sarabay Rd Unit 16, Osprey, FL 34229
  • /57

    $319,000

    • 2 Beds
    • 2.5 Baths
    • 1,240 Sq Ft

    1819 Highland Rd, Osprey, FL 34229

    This beautifully appointed 2-bedroom, 2-bath townhome offers a wonderful blend of comfort, privacy, and Florida living in "The Osprey", a community of just 12 residences. The open-concept floor plan features high ceilings, generous living spaces, and large windows that fill the home with an abundance of natural light. The spacious owner’s retreat provides a peaceful setting for relaxation, while

    Jennifer Linehan MICHAEL SAUNDERS & COMPANY

    1819 Highland Rd, Osprey, FL 34229
  • /7

    $289,999

    $30K PRICE INCREASE
    • Land
    • 5,662 Sq Ft
    • $2,230,762 per Acre

    456 Washington Ave, Osprey, FL 34229

    Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens. Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and the

    Mike Vo FLOTACAL

    456 Washington Ave, Osprey, FL 34229
  • /19

    $417,000

    $26K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,725 Sq Ft

    1811 Highland Rd, Osprey, FL 34229

    PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef Rolfs),

    Stephen Hachey REALTY OF RIVERVIEW LLC

    1811 Highland Rd, Osprey, FL 34229
  • /30

    $284,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,244 Sq Ft

    184 Explorer Dr, Osprey, FL 34229

    Luxury Corner Residence in Osprey | Top-Rated Pine View School District.Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities.This FULLY FURNISHED 2-bedroom, 2-bathroom

    Claudia Dybala DALTON WADE INC

    184 Explorer Dr, Osprey, FL 34229
  • /19

    $285,000

    • 1 Bed
    • 1 Bath
    • 595 Sq Ft

    51 MacEwen Dr Unit 14, Osprey, FL 34229

    This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area

    Steve Abbe COLDWELL BANKER REALTY

    51 MacEwen Dr Unit 14, Osprey, FL 34229
  • /91

    $459,900

    $215K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,594 Sq Ft

    401 N Point Rd Unit 301, Osprey, FL 34229

    Virtually Staged. Short Sale. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and

    Steve Abbe COLDWELL BANKER REALTY

    401 N Point Rd Unit 301, Osprey, FL 34229
  • /85

    $497,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 2,006 Sq Ft

    2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229

    West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass

    Christine Pope MICHAEL SAUNDERS & COMPANY

    2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229
  • /71

    $275,000

    • 1 Bed
    • 1 Bath
    • 623 Sq Ft

    51 MacEwen Dr Unit 12, Osprey, FL 34229

    Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is

    Steve Abbe COLDWELL BANKER REALTY

    51 MacEwen Dr Unit 12, Osprey, FL 34229
  • /43

    $395,000

    • 2 Beds
    • 2 Baths
    • 1,255 Sq Ft

    7204 Jessie Harbor Dr, Osprey, FL 34229

    **BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates.

    Mark Lyda GENEROUS PROPERTY

    7204 Jessie Harbor Dr, Osprey, FL 34229
  • /49

    $299,990

    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft

    4296 Expedition Way Unit 104, Osprey, FL 34229

    Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining

    Pamela Kurpiewski EXP REALTY LLC

    4296 Expedition Way Unit 104, Osprey, FL 34229
  • /41

    $419,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft

    524 Sarabay Rd, Osprey, FL 34229

    Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the

    Ibetta Giannone SUN N SAND REAL ESTATE LLC

    524 Sarabay Rd, Osprey, FL 34229

Home Price Trends

Median Sale Price
$650,000
Median Single Family Sale Price
$794,000
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$200,000
Average Price Per Sq Ft
$356
Number of Homes for Sale
77
Last 12 months Home Sales
205
Months of Supply
4.50
Median List Price
$742,900
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-13%
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