23

Osprey, FL Homes for Sale with Acreage

Section Image Section Image
  • /88

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,379 Sq Ft

    201 Eaglenook Way, Osprey, FL 34229

    Nestled in the exclusive Pine Ranch community of Osprey, Florida, this 4-bedroom, 3-bath estate offers a rare opportunity for those seeking privacy, tranquility, and a healthier way of living. Situated on just over two acres of lush, tree-canopied land, this meticulously maintained home is designed for comfort, sustainability, and connection to nature. From the moment you enter the long private

    Agent Photo

    Dawn Bear

    WILLIAM RAVEIS REAL ESTATE

    (941) 757-8209

    201 Eaglenook Way, Osprey, FL 34229
  • /34

    $1,450,000

    • 5 Beds
    • 3.5 Baths
    • 3,481 Sq Ft

    296 Pine Ranch Trail, Osprey, FL 34229

    **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of

    Deborah Frederick ASHTON LAKES REALTY INC

    296 Pine Ranch Trail, Osprey, FL 34229
  • /43

    $780,250 New Construction

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

    280 Hidden Bay Dr Unit 202, Osprey, FL 34229

    READY FOR IMMEDIATE OCCUPANCY!Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota BayStep into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space for your

    Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    280 Hidden Bay Dr Unit 202, Osprey, FL 34229
  • /65

    $710,000 Open Sat 12PM - 3PM

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

    250 Hidden Bay Dr Unit A302, Osprey, FL 34229

    WHAT A VIEW and the pictures don't do it justice!! Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offering unobstructed vistas across Little Sarasota Bay to the peaceful barrier island of Casey Key. Welcome to Edgewater at Hidden Bay — a gated, 12-acre resort-style community perfectly positioned between the charm of historic Venice and the

    Merryl Koven COLDWELL BANKER REALTY

    250 Hidden Bay Dr Unit A302, Osprey, FL 34229
  • /37

    $820,000

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft

    260 Hidden Bay Dr Unit B 305, Osprey, FL 34229

    Move-in Ready | Turnkey Furnished | Gulf & Intracoastal Views + Glorious Sunsets3 Bed | 2.5 Bath | Den w/ Custom Queen Murphy Bed | 2,168 Sq Ft | End UnitBright, breezy, and beautifully maintained, this move-in ready End Unit at Edgewater at Hidden Bay is offered fully Turnkey Furnished by the original owners and designed for effortless coastal living. Plantation shutters throughout,

    Cathy Rustin FIRST LIGHT REAL ESTATE

    260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
  • /51

    $950,000

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

    14021 Bellagio Way Unit 309, Osprey, FL 34229

    A boaters paradise. Discover the epitome of coastal living in this stunning 3-bedroom, 2.5-bathroom condo located in the highly desired, Bellagio Harbor Village. Nestled in between Sarasota Big Pass and the Venice Jetty, just minutes from Midnight pass and the gulf, this property offers prompt access to Sarasota County’s pristine beaches, fine dining, and boutique shopping.With a generous

    Tristin Hopler EXP REALTY LLC

    14021 Bellagio Way Unit 309, Osprey, FL 34229
  • /46

    $675,000

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

    14041 Bellagio Way Unit 214, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Massive Price Reduction! Original Listing Price was $810,000. Reduced by $135,000 to $675,000. Seller is motivated! Step into this luxurious, meticulously maintained 3-bedroom, 2-bath condo featuring high ceilings, granite countertops, updated appliances, and a separate laundry room. Enjoy magnificent views of Little Sarasota Bay and a lively

    Veronica Lee FINE PROPERTIES

    14041 Bellagio Way Unit 214, Osprey, FL 34229
  • /48

    $685,000

    • 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
  • /4

    $575,904 New Construction

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    791 S Tamiami Trail Unit 103, Osprey, FL 34229

    Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $575,904. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

    Laurie Eshleman PRO GROUP REALTY & PROP MGT

    791 S Tamiami Trail Unit 103, Osprey, FL 34229
  • /4

    $527,904 New Construction

    • 2 Beds
    • 2 Baths
    • 952 Sq Ft

    791 S Tamiami Trail Unit 102, Osprey, FL 34229

    Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $527,904. 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
  • /7

    $115,000

    570 Blackburn Point Rd Unit 13, Osprey, FL 34229

    Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! This rarely available slip can fit boats up to 9 ft in height and offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing

    Daniel Treiman MICHAEL SAUNDERS & COMPANY

    570 Blackburn Point Rd Unit 13, Osprey, FL 34229
  • /61

    $319,000

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

    116 Navigation Cir Unit 106, Osprey, FL 34229

    Location, Lifestyle, and Peace of Mind — All in One!Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low

    Pan Steele, GRI COLDWELL BANKER REALTY

    116 Navigation Cir Unit 106, Osprey, FL 34229
  • /4

    $42,500

    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 10.5W x 6.5H. With valet boat service,

    Daniel Treiman MICHAEL SAUNDERS & COMPANY

    570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
  • /8

    $44,000

    570 Blackburn Point Rd Unit 6, Osprey, FL 34229

    Dry Boat Slip for Sale – Osprey Harbor Village, Sarasota CountySecure your spot in one of Sarasota County’s premier boating destinations with this hurricane-protected dry boat slip at Osprey Harbor Village. Designed to offer both protection and convenience, this indoor slip ensures your boat is shielded from Florida’s unpredictable weather — potentially reducing your insurance premiums by

    Rick Bumbaca AZZURRO REALTY

    570 Blackburn Point Rd Unit 6, Osprey, FL 34229
  • /53

    $499,900

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

    780 Sarabay Rd Unit 16, Osprey, FL 34229

    Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay. This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry and granite

    Mark Segreto RMS ELITE PROPERTIES

    780 Sarabay Rd Unit 16, Osprey, FL 34229
  • /35

    $310,000

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

    4267 Expedition Way, Osprey, FL 34229

    Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minutes to the pristine shoreline of Nokomis Beach. This desirable gated community features a resort style heated pool, clubhouse and a fitness center designed to enhance your Florida life style. Enjoy local dining, shopping, and many arts and cultural attractions. This

    Judi Cipollina COLDWELL BANKER REALTY

    4267 Expedition Way, Osprey, FL 34229
  • /75

    $188,000

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

    137 Woodland Place, Osprey, FL 34229

    Unbelievable!!! A 2-bedroom/2-bathroom, West of Trail condo for under $200,000! Come home to this warm, cozy and charming unit and enjoy a cup of tea on your tranquil and private outside deck, nestled in a wooded, West of Trail paradise! The condo is surrounded by a backdrop of nature and you can enjoy the outdoors on three balconies which is wonderfully unique! The unit features generous room

    Priscilla Adams COMPASS FLORIDA LLC

    137 Woodland Place, Osprey, FL 34229
  • /89

    $1,150,000

    • 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 ~ The eye of an artist and perfected skill of a craftsman created this spacious, expertly designed residence. From the moment the elevator doors open to the private foyer, you'll notice every fine detail in this home was carefully thought out and executed, while the splendor of nature and water creates the backdrop

    Mary Elizabeth Mock COLDWELL BANKER REALTY

    401 N Point Rd Unit 504, Osprey, FL 34229
  • /28

    $299,500

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

    232 Explorer Dr Unit 15, Osprey, FL 34229

    Charming 2 Bedroom 2 Bath corner end unit( which provides extra natural light) condominium with attached 1 car Garage. Open floor plan, Kitchen features granite counter tops and stainless steel appliances, master bedroom suite has walk-in closet private bath with double vanity. Dining Room opens to enclosed balcony. Quality construction concrete block building with impact resistant glass windows,

    Gary Hoskins COLDWELL BANKER REALTY

    232 Explorer Dr Unit 15, Osprey, FL 34229
  • /64

    $4,750,000

    • 3 Beds
    • 3 Baths
    • 2,582 Sq Ft

    1049 N Casey Key Rd, Osprey, FL 34229

    Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies the timeless beauty of Old Florida

    Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

    1049 N Casey Key Rd, Osprey, FL 34229
  • /60

    $11,750,000

    • 5 Beds
    • 8 Baths
    • 8,050 Sq Ft

    1216 N Casey Key Rd, Osprey, FL 34229

    This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

    Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1216 N Casey Key Rd, Osprey, FL 34229
  • /92

    $1,300,000

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

    393 N Point Rd Unit 604, Osprey, FL 34229

    Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room. Experience the epitome

    Debbie Baraona ROBERT SLACK LLC

    393 N Point Rd Unit 604, Osprey, FL 34229
  • /91

    $399,900

    • 3 Beds
    • 3 Baths
    • 2,594 Sq Ft

    401 N Point Rd Unit 301, Osprey, FL 34229

    One or more photo(s) has been virtually staged. 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

    Steve Abbe COLDWELL BANKER REALTY

    401 N Point Rd Unit 301, Osprey, FL 34229

Home Trends in Osprey, FL

Housing Trends

Median Sale Price
$832,750
Median Single Family Sale Price
$560,000
Median 2 Bedroom Sale Price
$400,000
Average Price Per Sq Ft
$427
Number of Homes for Sale
4
Last 12 months Home Sales
33
Months of Supply
1.50
Median List Price
$710,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
59%
How to Buy a Home How to Finance a Home How to Sell a Home