32

Homes for Sale in Osprey, FL with 2-Bedrooms

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  • /41

    $299,900

    • 2 Beds
    • 2 Baths
    • 1,165 Sq Ft

    1801 Highland Rd, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and

    Agent Photo

    Kimberly Werla

    RE/MAX ALLIANCE GROUP

    (941) 757-8192

    1801 Highland Rd, Osprey, FL 34229
  • /62

    $850,000

    • 2 Beds
    • 2 Baths
    • 2,310 Sq Ft

    13 Bayhead Ln, Osprey, FL 34229

    **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

    Mark Lyda GENEROUS PROPERTY

    13 Bayhead Ln, Osprey, FL 34229
  • /72

    $550,000

    • 2 Beds
    • 2 Baths
    • 1,932 Sq Ft

    242 Hidden Bay Dr Unit 603, Osprey, FL 34229

    Stunning, unobstructed views of the Intracoastal Waterway, Little Sarasota Bay, and the Gulf await from this beautiful Penthouse residence in Baypoint Vista, Osprey. Located within Hidden Bay, a gated and amenity rich community, this exceptional condo features 2 Bedrooms, 2 Bathrooms plus a versatile Den, an open floor plan, high ceilings, recessed lighting, a spacious kitchen, morning room,

    Susan Retzke RE/MAX PALM

    242 Hidden Bay Dr Unit 603, Osprey, FL 34229
  • /71

    $379,900

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

    4235 Expedition Way Unit 102, Osprey, FL 34229

    This well-maintained first-floor condominium offers an ideal opportunity for full-time living or a seasonal Florida retreat. Featuring the desirable Osprey floor plan, this open-concept residence includes two bedrooms, two bathrooms both with granite vanity tops, and a bonus room/office. The unit is conveniently located on the first floor with no stairs and provides easy access to the community’s

    Tim Weller EXIT KING REALTY

    4235 Expedition Way Unit 102, Osprey, FL 34229
  • /65

    $545,000

    • 2 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    1116 Beachcomber Ct Unit 3, Osprey, FL 34229

    LOCATION, LOCATION, LOCATION! Nestled within the highly desirable gated enclave of Blackburn Point Marina Village, this beautifully maintained 3-bed, 2.5 bath residence is ready to welcome its new owners. This bright and airy two-story unit features soaring ceilings and a spacious open floor plan, creating an inviting and comfortable living environment. The main living areas are enhanced with

    Christine Green COLDWELL BANKER REALTY

    1116 Beachcomber Ct Unit 3, Osprey, FL 34229
  • /76

    $167,000

    • 2 Beds
    • 2 Baths
    • 959 Sq Ft

    166 Edgewood Dr, Osprey, FL 34229

    Welcome to easy Florida living in The Arbors of Osprey! This charming 2-bedroom, 2-bath manufactured home offers comfort, updates, and plenty of space to relax and entertain. Step inside to a spacious living room filled with natural light, perfect for gathering with family and friends. The updated kitchen features warm wood cabinetry and a brand-new refrigerator (2025), making meal prep both

    Karen Geiger COLDWELL BANKER SARASOTA CENT.

    166 Edgewood Dr, Osprey, FL 34229
  • /81

    $269,000

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft

    135 Woodland Place, Osprey, FL 34229

    Ideally located in the heart of Osprey, this private corner, first floor condo offers effortless Florida living just minutes from pristine Gulf beaches and less than half a mile from the Intracoastal Waterway. The sought after community at the entrance to Casey Key was designed to live in harmony with nature by Frank Folsum Smith of the Sarasota School of Architecture. This unit features a garden

    Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

    135 Woodland Place, Osprey, FL 34229
  • /40

    $120,000

    • 2 Beds
    • 2 Baths
    • 987 Sq Ft

    234 Palm Air Dr, Osprey, FL 34229

    Welcome to The Arbors, a highly sought-after 55+ resident-owned community in Osprey known for its active lifestyle, friendly atmosphere, and prime location. This well-maintained 2 bedroom, 2 bathroom double-wide mobile home is being offered completely turn-key, with furnishings included if desired, making for an easy, move-in ready experience from day one. Inside, you’ll find a bright and

    Toni Zarghami KW COASTAL LIVING III

    234 Palm Air Dr, Osprey, FL 34229
  • /51

    $449,000

    • 2 Beds
    • 2 Baths
    • 1,284 Sq Ft

    107 Sorrento Dr, Osprey, FL 34229

    This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from

    Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

    107 Sorrento 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
  • /64

    $450,000

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft

    764 Sarabay Rd Unit 8, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10

    Michael Christo PREMIER SOTHEBYS INTL REALTY

    764 Sarabay Rd Unit 8, Osprey, FL 34229
  • /86

    $225,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    252 Sun Air Cir, Osprey, FL 34229

    Welcome to easy Florida living in The Arbors of Osprey! This beautifully updated 2-bedroom, 2-bath manufactured home offers modern finishes, thoughtful upgrades, and a spacious open layout designed for comfort and entertaining. Step inside to discover newer tile and laminate flooring flowing throughout the home. The remodeled kitchen is a true showstopper, featuring raised-panel cabinetry, quartz

    Karen Geiger COLDWELL BANKER SARASOTA CENT.

    252 Sun Air Cir, Osprey, FL 34229
  • /70

    $699,000

    • 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

    Janice Martin ENGEL & VOELKERS VENICE DOWNTOWN

    260 Hidden Bay Dr Unit B-304, Osprey, FL 34229
  • /86

    $655,000

    • 2 Beds
    • 2.5 Baths
    • 1,890 Sq Ft

    57 Bishops Court Rd Unit 121, Osprey, FL 34229

    Enjoy the perfect maintenance free country club lifestyle in the charming and quaint Bishopscourt Townhomes located in The Oaks Preserve. Architecturally designed, this classic Georgian style townhouse features two bedrooms, two full ensuite baths, one half bath, a spacious great room, and a large terrace overlooking a lake. A welcoming foyer leads to the expansive great room where high ceilings,

    Rosalie Phillips MICHAEL SAUNDERS & COMPANY

    57 Bishops Court Rd Unit 121, Osprey, FL 34229
  • /58

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,479 Sq Ft

    291 Hidden Bay Dr Unit 102, Osprey, FL 34229

    In the lush and serene grounds of this private and peaceful community is a best-kept secret with a name that says it all. Within Hidden Bay, this condominium gem resides in a spot on the community lake with a stunning view and soothing sound of waterfalls from your own enclosed lanai. Fully furnished with mostly all new furniture in the owners’ suite, including a new king-size mattress, living

    Pat McMillan PREMIER SOTHEBY'S INTERNATIONAL REALTY

    291 Hidden Bay Dr Unit 102, Osprey, FL 34229
  • /93

    $885,000

    • 2 Beds
    • 2 Baths
    • 2,071 Sq Ft

    227 Saint James Park, Osprey, FL 34229

    Experience the charm and wonderful location of this golf course home on Saint James Park, the leafy and quiet cul-de-sac where you can walk to tennis, golf, pickleball, croquet, heated pool and state of the art fitness center all within The Oaks Country Club, where the luxury lifestyle awaits! This 2 bedroom, 2 bath traditional home overlooks the first hole of the Eagle Golf course, and is being

    Rosalie Phillips MICHAEL SAUNDERS & COMPANY

    227 Saint James Park, Osprey, FL 34229
  • /41

    $719,000

    • 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
  • /69

    $697,500

    • 2 Beds
    • 2.5 Baths
    • 1,890 Sq Ft

    33 Bishops Court Rd Unit 118, Osprey, FL 34229

    **EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living

    Mark Lyda GENEROUS PROPERTY

    33 Bishops Court Rd Unit 118, Osprey, FL 34229
  • /60

    $519,000

    • 2 Beds
    • 2 Baths
    • 1,555 Sq Ft

    786 Sarabay Rd Unit 19, Osprey, FL 34229

    Boat Slips included, Insurance included, Ground maintenance included!!Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is

    Michael Christo PREMIER SOTHEBYS INTL REALTY

    786 Sarabay Rd Unit 19, Osprey, FL 34229
  • /52

    $675,000

    • 2 Beds
    • 2 Baths
    • 1,943 Sq Ft

    232 Hidden Bay Dr Unit 303, Osprey, FL 34229

    Waterfront resort-style living is behind the gates of Hidden Bay, set along the shores of the Intracoastal Waterway, Little Sarasota Bay, and a tranquil preserve and park in the heart of Osprey. This third-floor residence, accessible by elevator, has been tastefully remodeled and offers two full bedrooms, each with en-suite baths. The lanai’s exterior sliders open to an all-season, tiled living

    Tom Hedge, Jr PREMIER SOTHEBY'S INTERNATIONAL REALTY

    232 Hidden Bay Dr Unit 303, Osprey, FL 34229
  • /44

    $679,900 Open Sun 2PM - 4PM

    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

    This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid

    Cindy Migone PREMIER SOTHEBY'S INTERNATIONAL REALTY

    5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229
  • /47

    $264,900

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

    232 Woodland Dr, Osprey, FL 34229

    This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within

    Pat Williams PAT WILLIAMS REALTY, LLC

    232 Woodland Dr, Osprey, FL 34229
  • /19

    $422,000

    • 2 Beds
    • 2 Baths
    • 1,725 Sq Ft

    1811 Highland Rd, Osprey, FL 34229

    PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef Rolfs),

    Stephen Hachey REALTY OF RIVERVIEW LLC

    1811 Highland Rd, Osprey, FL 34229
  • /41

    $200,000

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

    244 Woodland Dr Unit 244, Osprey, FL 34229

    Best value in Pine Run now priced at $200,000 after a $25,000 price improvement. This updated 2-bedroom, 2-bath condo offers 1,325 square feet of bright, open living with vaulted ceilings, a spacious layout, and a screened lanai overlooking lush, private greenery. The kitchen features stainless steel appliances, glass backsplash, and a functional breakfast nook with natural light. The primary

    Derek Edwards KELLER WILLIAMS ON THE WATER S

    244 Woodland Dr Unit 244, Osprey, FL 34229
  • /25

    $109,000

    • 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
  • /51

    $415,000

    • 2 Beds
    • 2 Baths
    • 2,148 Sq Ft

    32 Bay Ave, Osprey, FL 34229

    Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless

    Jennifer Pereira LOKATION

    32 Bay Ave, Osprey, FL 34229
  • /41

    $179,900 Open Sun 2PM - 4PM

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    238 Palm Air Dr, Osprey, FL 34229

    AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais add more

    John Alexander FINE PROPERTIES

    238 Palm Air Dr, Osprey, FL 34229
  • /55

    $510,000

    • 2 Beds
    • 2 Baths
    • 1,404 Sq Ft

    120 Villa Dr Unit 120, Osprey, FL 34229

    Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel

    Hansel Pitts COLDWELL BANKER SARASOTA CENT.

    120 Villa Dr Unit 120, Osprey, FL 34229
  • /62

    $349,000

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

    2251 Jessie Harbor Dr, Osprey, FL 34229

    **1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

    Mark Lyda GENEROUS PROPERTY

    2251 Jessie Harbor Dr, Osprey, FL 34229
  • /2

    $540,749 New Construction

    • 2 Beds
    • 2 Baths
    • 952 Sq Ft

    791 S Tamiami Trail Unit 302, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. 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 302, Osprey, FL 34229
  • /2

    $514,999 New Construction

    • 2 Beds
    • 2 Baths
    • 952 Sq Ft

    791 S Tamiami Trail Unit 202, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. 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 202, Osprey, FL 34229
  • /2

    $489,249 New Construction

    • 2 Beds
    • 2 Baths
    • 952 Sq Ft

    791 S Tamiami Trail Unit 102, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. 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
$670,000
Median Single Family Sale Price
$850,000
Median Townhouse Sale Price
$489,000
Median 2 Bedroom Sale Price
$315,000
Median 1 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$375
Number of Homes for Sale
136
Last 12 months Home Sales
193
Months of Supply
8.50
Median List Price
$750,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-13%
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