25

Osprey, FL Homes for Sale with Acreage

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  • /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
  • /52

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,799 Sq Ft

    14041 Bellagio Way Unit 214, Osprey, FL 34229

    Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village-3 Bedrooms | 2 Bathrooms | Direct Intracoastal FrontageRare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and

    Agent Photo

    Veronica Lee

    COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 214, 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
  • /4

    $36,000

    570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229

    This slip will house a boat with the maximum dimensions of 35.5' length, 10' width and 6' height 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

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit Siesta 26, 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
  • /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
  • /74

    $1,200,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,474 Sq Ft

    700 Faith Ave, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools in the state and country. The peace and tranquility of the outdoor space is highlighted by a resort

    steve mularky LACEY REALTY INC

    700 Faith Ave, Osprey, FL 34229
  • /39

    $749,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft

    280 Hidden Bay Dr Unit 302, Osprey, FL 34229

    Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity.The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant

    Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

    280 Hidden Bay Dr Unit 302, 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
  • /46

    $949,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,086 Sq Ft

    14041 Bellagio Way Unit 318, Osprey, FL 34229

    Virtually Staged. Newly priced at $949,000. Boaters, sunset lovers, and buyers seeking a true Gulf Coast lifestyle will appreciate this spacious waterfront condominium in The Villas at Bellagio Harbor Village, complete with a 37 foot wet slip included in the sale. This 3 bedroom plus den, 2 bath residence offers 2,086 square feet of living space, plus large lanai, private elevator entry, and

    Margot Vigar (Leonard) COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 318, 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
  • /4

    $39,500

    $3K PRICE DROP

    570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

    Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 9.5W x 6.5H. With valet boat service,

    Daniel Treiman MICHAEL SAUNDERS & COMPANY

    570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
  • /62

    $1,100,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,778 Sq Ft

    385 N Point Rd Unit 304, Osprey, FL 34229

    **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled

    Mark Lyda GENEROUS PROPERTY

    385 N Point Rd Unit 304, 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
  • /16

    $1,400,000

    • Land
    • 2.51 Acres
    • $557,769 per Acre

    2099 S Tamiami Trail, Osprey, FL 34229

    2.51 Acre Lot directly on South Tamiami Trail in Osprey - where Sarasota is growing and expanding! This property is zoned OPI and would be a good fit for an office/medical center or retail with residential above. Great exposure with consistently heavy traffic from Sarasota to Ft. Myers on S. Tamiami Trail just minutes from Sarasota Bay, Oscar Scherer State Park, Legacy Trail and all that Sarasota

    Susan Repp COLDWELL BANKER REALTY

    2099 S Tamiami Trail, 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
  • /48

    $599,000

    $86K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,055 Sq Ft

    409 N Point Rd Unit 502, Osprey, FL 34229

    **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

    Mark Lyda GENEROUS PROPERTY

    409 N Point Rd Unit 502, Osprey, FL 34229
  • /38

    $899,995

    • 3 Beds
    • 2.5 Baths
    • 2,199 Sq Ft

    14021 Bellagio Way Unit 309, Osprey, FL 34229

    Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy

    Tristin Hopler COMPASS FLORIDA, LLC

    14021 Bellagio Way Unit 309, Osprey, FL 34229
  • /70

    $694,000

    $5K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    260 Hidden Bay Dr Unit B-304, Osprey, FL 34229

    The Boca Residence: Spacious Living & Resort StyleDiscover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal

    Jamie Styers ENGEL + VOELKERS SARASOTA

    260 Hidden Bay Dr Unit B-304, Osprey, FL 34229
  • /99

    $1,095,000

    $102K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,770 Sq Ft

    403 Longbow Trail, Osprey, FL 34229

    Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort,

    Edward Bieker DALTON WADE INC

    403 Longbow Trail, 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
  • /50

    $4,795,000

    • 5 Beds
    • 3.5 Baths
    • 4,914 Sq Ft

    4678 Silent Creek Way, Nokomis, FL 34275

    Tucked away at the end of a quiet road on a breathtakingly private one-acre homesite, this extraordinary luxury gated estate overlooks the serene waters of South Creek with the untouched natural beauty of Oscar Scherer State Park creating an incomparable backdrop. Completely reimagined with a sophisticated contemporary aesthetic, this custom-built residence blends timeless architecture with

    Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4678 Silent Creek Way, Nokomis, FL 34275

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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