26

Osprey, FL Homes for Sale under $400,000

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  • /41

    $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
  • /50

    $215,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    110 Woodland Place, Osprey, FL 34229

    FURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beauty and modern living. This two-bedroom, two-bath condo is nestled within the serene 20+ acres of lush native Florida landscape. As you step inside, you'll be greeted by a spacious and inviting living area, thoughtfully designed to maximize comfort and functionality. The condo offers two well-appointed

    Agent Photo

    Echo Belser PA

    COLDWELL BANKER REALTY

    110 Woodland Place, Osprey, FL 34229
  • /20

    $175,000

    $15K PRICE DROP
    • Land
    • 20,908 Sq Ft
    • $364,583 per Acre

    14 Old Venice Rd, Osprey, FL 34229

    **Pine View School** NO HOA** Custom House-Separate Guest House- Separate RV/Boat** Discover an exceptional opportunity to create your custom dream home in the heart of Osprey — one of Sarasota County’s most desirable coastal communities. This buildable vacant homesite offers the perfect canvas to design a private retreat tailored to your lifestyle, all while enjoying the charm, convenience, and

    Agent Photo

    Mousa Wakileh

    COLDWELL BANKER REALTY

    14 Old Venice Rd, Osprey, FL 34229
  • /35

    $265,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft

    4271 Expedition Way Unit 103, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar

    Agent Photo

    Toni Zarghami

    KW COASTAL LIVING III

    4271 Expedition Way Unit 103, 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
  • /4

    $115,000

    570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229

    This slip will house a boat with the maximum dimensions of 27.5'L x 11'W x 11.5'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric.

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229
  • /39

    $320,000

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

    4213 Expedition Way Unit 107, Osprey, FL 34229

    "Location, Location, Location" The luxury Florida lifestyle you’ve been dreaming. Welcome to this beautifully appointed 3-bed, 2-bath walk-up condo in a highly desirable location in a pet-friendly gated community. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability. The attached ground-level garage beneath

    Yunfei Liu DALTON WADE INC

    4213 Expedition Way Unit 107, Osprey, FL 34229
  • /45

    $254,900

    $15K 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
  • /4

    $109,000

    570 Blackburn Point Rd Unit 13, Osprey, FL 34229

    The slip can hold a boat with the maximum dimensions of 32.5L x 9'W x 9'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit 13, 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
  • /45

    $259,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,379 Sq Ft

    754 Pine Run Dr Unit 754, Osprey, FL 34229

    Virtually Staged. Rarely available and truly one-of-a-kind, this beautifully updated ground-floor 2-bedroom, 2-bath residence offers an exceptional combination of privacy, architectural character, and an unbeatable location. Designed around a stunning private open-air atrium, the home features 8-foot glass doors on three sides, flooding the interior with natural light and creating a seamless

    Sasha Volosevych CALL IT CLOSED INTL REALTY

    754 Pine Run Dr Unit 754, Osprey, FL 34229
  • /37

    $195,000

    • 2 Beds
    • 2 Baths
    • 1,199 Sq Ft

    320 Tropic Dr, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an

    Susan Retzke RE/MAX PALM

    320 Tropic Dr, 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
  • /34

    $109,900

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    348 Tropic Dr, Osprey, FL 34229

    Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in

    John Alexander FINE PROPERTIES

    348 Tropic Dr, Osprey, FL 34229
  • /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
  • /22

    $139,900

    • Land
    • 8,712 Sq Ft
    • $699,500 per Acre

    0 Westview Dr, Osprey, FL 34229

    Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile lot offers an exceptional opportunity to enjoy the Florida lifestyle. A perfect opportunity to build a new home on a lot that totals 8,800 square feet (80-by-110-feet) along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with

    Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

    0 Westview Dr, Osprey, FL 34229
  • /2

    $172,000

    Coming Soon
    • 1 Bed
    • 1 Bath
    • 586 Sq Ft

    701 Pine Run Dr, Osprey, FL 34229

    Rare Treehouse Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a

    Pat Williams PAT WILLIAMS REALTY, LLC

    701 Pine Run Dr, Osprey, FL 34229
  • /30

    $294,900

    • 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 Mac Ewen 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 Mac Ewen Dr Unit 14, Osprey, FL 34229
  • /61

    $320,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,449 Sq Ft

    89 Navigation Cir, Osprey, FL 34229

    Virtually Staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of

    Jozefina Polimirova KW COASTAL LIVING II

    89 Navigation Cir, Osprey, FL 34229
  • /50

    $285,000

    Open Sun 1PM - 3PM $100K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft

    108 Woodland Place Unit 108, Osprey, FL 34229

    Bring your furniture and move right in to this popular Pine Run neighborhood. No need to worry about remodeling this condo! New coastal look ceramic tile throughout the entire home! New kitchen and appliances, new guest bathroom, new doors throughout, new light fixtures, and newly painted. Wow! First floor condo offers more outdoor living space. The patio off the main entry offers privacy and has

    Pat Williams PAT WILLIAMS REALTY, LLC

    108 Woodland Place Unit 108, 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 CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO** Featuring 2 Beds and 2 Full Baths, this FULLY RENOVATED, 2ND FLOOR unit features an Impressive Kitchen with quartz counters, stainless steel appliances, new solid wood cabinets while the Spacious Owner’s Suite boasts custom built-in cabinets/closets and an equally

    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
  • /71

    $319,500

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    173 Navigation Cir Unit 107, Osprey, FL 34229

    Immaculate and lightly lived-in 3BR/2BA condo in the gated community of Bay Street Village, offering beautiful water views with a fountain from the main living areas, the primary suite, and the screened lanai. The popular Ibis floor plan features an open-concept kitchen, dining, and great room with 42" upper cabinets, granite countertops, a custom tile backsplash, and stainless-steel appliances.

    Tim Weller EXIT KING REALTY

    173 Navigation Cir Unit 107, Osprey, FL 34229
  • /10

    $269,000

    • Land
    • 13,939 Sq Ft
    • $840,625 per Acre

    0 Sarabay Rd, Osprey, FL 34229

    RARE OPPORTUNITY – WEST OF TRAIL -- OVERSIZED 0.32-ACRE CORNER HOMESITE in the sought-after Waterfront Community of Bay Acres in Osprey. Zoned RSF-2, the property offers the flexibility to build a custom home of approximately 4,500 square feet with a pool or design a smaller residence with a detached guest house or ADU. The lot is served by public water and sewer and includes a private well for a

    Mark Lyda GENEROUS PROPERTY

    0 Sarabay Rd, Osprey, FL 34229

Home Price Trends

Median Sale Price
$657,000
Median Single Family Sale Price
$817,000
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$342,500
Median 1 Bedroom Sale Price
$186,000
Average Price Per Sq Ft
$363
Number of Homes for Sale
96
Last 12 months Home Sales
192
Months of Supply
6.00
Median List Price
$739,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-13%
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