13

Condos for Sale in Osprey, FL with 2-Bedrooms

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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
  • /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
  • /71

    $725,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229

    Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining

    Suki Scollo COLDWELL BANKER REALTY

    5100 Jessie Harbor Dr Unit 304, 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
  • /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
  • /68

    $359,000

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    2251 Jessie Harbor Dr Unit 2101, Osprey, FL 34229

    INCREDIBLE VIEWS!....INCREDIBLE LOCATION!...You Will be Wowed by the LONG WATER & SUNSET VIEWS in this Bright and Spacious (2) Bedroom (2) Bath Corner Unit with PRIVATE GARAGE located in Blackburn Harbor Waterfront Villas, a PET FRIENDLY Gated 11 acre Waterfront Resort-Style Community with: HeatedPool; Fitness Center; Kayak Storage & Launch; BBQ Gazebo; Dog Park; Walking Trails; Pickleball/Tennis

    Michael A Martino KELLER WILLIAMS ON THE WATER S

    2251 Jessie Harbor Dr Unit 2101, 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
  • /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

    $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
  • /41

    $700,000

    $19K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,932 Sq Ft

    242 Hidden Bay Dr Unit 602, Osprey, FL 34229

    Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features

    Cathy Rustin FIRST LIGHT REAL ESTATE

    242 Hidden Bay Dr Unit 602, 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
  • /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

Home Price Trends

Median Sale Price
$657,000
Median Single Family Sale Price
$828,500
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$350,000
Median 1 Bedroom Sale Price
$217,500
Average Price Per Sq Ft
$363
Number of Homes for Sale
100
Last 12 months Home Sales
192
Months of Supply
6.30
Median List Price
$739,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-13%
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