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Osprey, FL Homes for Sale with Acreage

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  • /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

    $1,495,000 Open Sun 12PM - 4PM

    • 5 Beds
    • 3.5 Baths
    • 3,354 Sq Ft

    296 Pine Ranch Trail, Osprey, FL 34229

    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 a nearby golf course, offering tranquil views and peaceful surroundings. With no rear neighbors, you'll enjoy the privacy and serenity that your 1 acre+ lot affords. Have a boat or RV? This community is deed restricted but

    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
  • /89

    $1,275,000

    • 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
  • /37

    $853,000 Open Sun 1PM - 4PM

    • 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, impact-rated

    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 2199

    Tristin Hopler EXP REALTY LLC

    14021 Bellagio Way Unit 309, 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
  • /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 canal

    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
  • /75

    $190,000

    • 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
  • /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
  • /40

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    4236 Expedition Way Unit 106, Osprey, FL 34229

    FABULOUS, MODERN, FURNISHED 3 BEDROOM/2 BATHROOM/1 CAR GARAGE CONDO in desirable Bay Street Village. This second story (walk-up) is impressive! The OPEN CONCEPT offers a spacious feel, yet the split bedroom design allows for privacy when your guests are visiting. Quality features include a designer kitchen with cherry cabinets, crown molding, granite countertops, IMPACT WINDOWS, tile roof, paver

    Susan Honsberger RE/MAX ALLIANCE GROUP

    4236 Expedition Way Unit 106, 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
  • /72

    $244,950

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    362 Pine Run Dr Unit 362, Osprey, FL 34229

    Welcome to 362 Pine Run Drive, a modern retreat nestled in the heart of Osprey, FL. This stunning 2-bedroom, 2-bathroom home offers 1,224 square feet of thoughtfully designed living space, set on an expansive 20-acre property. Revel in the tranquility of garden views and the glow of sunsets in the distance off the rear facing deck. Looking for a little more privacy? Access a large, private

    Priscilla Adams COMPASS FLORIDA LLC

    362 Pine Run Dr Unit 362, 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
  • /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

Home Trends in Osprey, FL

Housing Trends

Median Sale Price
$752,500
Median Single Family Sale Price
$845,000
Median Townhouse Sale Price
$590,000
Median 2 Bedroom Sale Price
$284,500
Median 1 Bedroom Sale Price
$217,000
Average Price Per Sq Ft
$383
Number of Homes for Sale
104
Last 12 months Home Sales
188
Months of Supply
6.60
Median List Price
$815,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-6%
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