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Newest Homes for Sale in Osprey, FL

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  • /60

    $1,995,000

    • 3 Beds
    • 3 Baths
    • 3,029 Sq Ft

    401 N Point Rd Unit 1001, Osprey, FL 34229

    **Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. The open-concept floor plan is

    Mark Lyda GENEROUS PROPERTY

    401 N Point Rd Unit 1001, Osprey, FL 34229
  • /38

    $619,000

    • 4 Beds
    • 2 Baths
    • 2,217 Sq Ft

    472 Park Trace Blvd, Osprey, FL 34229

    Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for

    Damon Zuchelli SUNDANCE REAL ESTATE SERVICES

    472 Park Trace Blvd, Osprey, FL 34229
  • /51

    $1,800,000

    • 4 Beds
    • 3.5 Baths
    • 4,387 Sq Ft

    401 Walls Way, Osprey, FL 34229

    Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, and

    Agent Photo

    Andrea Stultz

    ENGEL + VOELKERS SARASOTA

    (941) 231-5436

    401 Walls Way, Osprey, FL 34229
  • /73

    $2,850,000

    • 4 Beds
    • 4 Baths
    • 4,359 Sq Ft

    662 Fernwalk Ln, Osprey, FL 34229

    **EXCEPTIONAL, FULLY RENOVATED, COUNTRY CLUB ESTATE HOME OFFERING TRANQUIL LAKE AND GARDEN VIEWS** ideally positioned on a serene interior cul-de-sac lot in Flood Zone X (no flood insurance required). Located behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. This expansive residence features 4 Bedrooms and 4

    Mark Lyda GENEROUS PROPERTY

    662 Fernwalk Ln, Osprey, FL 34229
  • /93

    $885,000 Open Sun 1PM - 3PM

    • 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
  • /42

    $275,000

    • 1 Bed
    • 1 Bath
    • 623 Sq Ft

    51 MacEwen Dr Unit 11, Osprey, FL 34229

    Rarely available Windsor Lodge efficiency condominium located within The Oaks Club. This second-floor, maintenance-free, lakeside unit features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted. Enjoy the country club lifestyle at The Oaks Club, a private, member-owned club in Osprey, Florida. Mandatory membership

    Sabine Spycher 342 REAL ESTATE

    51 MacEwen Dr Unit 11, Osprey, FL 34229
  • /41

    $719,000 Open Sun 1PM - 4PM

    • 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
  • /2

    $699,000

    • Land
    • 0.55 Acre
    • $1,270,909 per Acre

    410 Blue Garden Ln, Osprey, FL 34229

    Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-de-sac lot, this generous parcel offers privacy, mature landscaping, and an ideal canvas for a custom residence. Enjoy convenient access to world-class amenities including championship golf, tennis and pickleball facilities, a

    Mark Grigoli ELITE PROPERTIES LLC

    410 Blue Garden Ln, Osprey, FL 34229
  • /50

    $899,000

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

    260 Hidden Bay Dr Unit B 405, Osprey, FL 34229

    Built in 2019 and perfectly positioned on the fourth floor, this waterfront residence offers sweeping views across the Intracoastal Waterway, tranquil mangroves, and surrounding waterways from nearly every room. Designed with comfort and functionality in mind, the three-bedroom plus office layout spans nearly 2,200 square feet of interior living space and captures the essence of relaxed coastal

    Roger Pettingell COLDWELL BANKER REALTY

    260 Hidden Bay Dr Unit B 405, Osprey, FL 34229
  • /58

    $725,000 Open Sun 1PM - 4PM

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

    250 Hidden Bay Dr Unit A-301, Osprey, FL 34229

    Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in Jan 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building.

    Per Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

    250 Hidden Bay Dr Unit A-301, Osprey, FL 34229
  • /74

    $1,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,066 Sq Ft

    25 Sugar Mill Dr, Osprey, FL 34229

    METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite

    Mark Lyda GENEROUS PROPERTY

    25 Sugar Mill Dr, Osprey, FL 34229
  • /4

    $1,500

    • 1 Bed
    • 1 Bath

    124 Happy Haven Dr Unit 10, Osprey, FL 34229

    Calling all Investors! Huge opportunity to make a deal on this perfect renovation project. Quick Closing, Quick Renovation and Quick Profit! This home needs significant work and is priced accordingly. Given the amount of work necessary to bring this gem up to it's fiull potential, prospective investors must be licensed and experienced renovation specialists. Call today, we are currently

    Tori Coil Happy Haven

    124 Happy Haven Dr Unit 10, Osprey, FL 34229
  • /7

    $3,000

    • 1 Bed
    • 1 Bath

    124 Happy Haven Dr Unit 28, Osprey, FL 34229

    Calling all Investors! Huge opportunity to make a deal on this perfect renovation project. Quick Closing, Quick Renovation and Quick Profit! This home needs significant work and is priced accordingly. Given the amount of work necessary to bring this gem up to it's fiull potential, prospective investors must be licensed and experienced renovation specialists. Call today, we are currently

    Tori Coil Happy Haven

    124 Happy Haven Dr Unit 28, Osprey, FL 34229
  • /63

    $799,000

    • 4 Beds
    • 3.5 Baths
    • 2,854 Sq Ft

    919 Tranquility Cir, Osprey, FL 34229

    WOW! TOTAL OF 50,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle . This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy your own "Selby Garden" like setting .So hard to

    Ann Winger TIDELINE REAL ESTATE BROKERS

    919 Tranquility Cir, 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
  • /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
  • /62

    $1,200,000

    • 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
  • /4

    $34,900

    • 1 Bed
    • 1 Bath

    124 Happy Haven Dr Unit 56, Osprey, FL 34229

    Happy Haven, a professionally managed, well-maintained manufactured home community, currently has a 418 sq. ft. home with 1 bedrooms and 1 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our current promotions!

    Tori Coil Happy Haven

    124 Happy Haven Dr Unit 56, 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
  • /48

    $699,000

    • 3 Beds
    • 2 Baths
    • 2,032 Sq Ft

    242 Hidden Bay Dr Unit 302, Osprey, FL 34229

    Enjoy breathtaking water views and unforgettable sunsets over Little Sarasota Bay from this spacious three-bedroom condominium with an office, on the third floor with convenient elevator access. This beautifully appointed residence is in the exclusive, gated Hidden Bay community, a waterfront gem. The open floor plan features soaring ceilings, PGT impact windows, sliding glass doors, new

    Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

    242 Hidden Bay Dr Unit 302, Osprey, FL 34229
  • /52

    $675,000 Open Sun 1AM - 4PM

    • 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
  • /2

    $617,999 New Construction

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

    791 S Tamiami Trail Unit 101, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION -STARTING FROM THE MID $500,000'S. 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 101, Osprey, FL 34229
  • /2

    $617,999 New Construction

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

    791 S Tamiami Trail Unit 103, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION-STARTING FROM THE MID $500,000'S. 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
  • /2

    $617,999 New Construction

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

    791 S Tamiami Trail Unit 301, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION-STARTING FROM THE MID $500,000'S. 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 301, 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

    $643,749 New Construction

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

    791 S Tamiami Trail Unit 303, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION-STARTING FROM THE MID $500,000'S. 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 303, 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

    $592,249 New Construction

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

    791 S Tamiami Trail Unit 201, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION -STARTING FROM THE MID $500,000'S. 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 201, Osprey, FL 34229
  • /55

    $2,249,000

    • 4 Beds
    • 3.5 Baths
    • 4,117 Sq Ft

    362 MacEwen Dr, Osprey, FL 34229

    Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with

    Steve Abbe COLDWELL BANKER REALTY

    362 MacEwen Dr, Osprey, FL 34229
  • /47

    $1,300,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,850 Sq Ft

    17 Bayhead Ln, Osprey, FL 34229

    Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No detail was overlooked in the renovation, resulting in a truly beautiful and thoughtfully designed home. The interior showcases high-end finishes throughout, including wood-look tile flooring, quartzite countertops, a stylish coffee bar, and a custom

    Steve Abbe COLDWELL BANKER REALTY

    17 Bayhead Ln, 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
  • /15

    $41,000

    570 Blackburn Point Rd Unit 42, Osprey, FL 34229

    Welcome to OSPREY HARBOR VILLAGE. This boat rackominium was built as a category 3 hurricane-rated building. Store your boat out of the sun and protected from the harsh Florida weather. This 3rd-level rack measures 28'L x 12'W x 8.5'H and can accommodate a boat with dimensions of 28'L x 11'W x ~6.5'H (measure height from the keel to the highest fixed point on the boat). This rackominium features

    Joe Cleary RE/MAX ALLIANCE GROUP

    570 Blackburn Point Rd Unit 42, Osprey, FL 34229
  • /59

    $995,000

    • 3 Beds
    • 3 Baths
    • 2,055 Sq Ft

    409 N Point Rd Unit 902, Osprey, FL 34229

    **A RARE OFFERING, 9TH FLOOR, UPDATED PENTHOUSE with PRIVATE 2-CAR GARAGE** Enjoy the ultimate unobstructed views of Little Sarasota Bay that includes the Gulf of Mexico & Midnight Pass with Casey Key and Siesta Key in the vista. This upper-level Penthouse condo offers a tranquil, quiet residence that transports you to another world high above the preserve and waterways where birds dance and dive

    Mark Lyda GENEROUS PROPERTY

    409 N Point Rd Unit 902, Osprey, FL 34229
  • /73

    $1,575,000 Open Sun 1AM - 4PM

    • 4 Beds
    • 3 Baths
    • 3,486 Sq Ft

    20 Bayhead Ln, Osprey, FL 34229

    A rare opportunity to own a significantly newer, custom-built residence inside the exclusive The Oaks Club Preserve, where most surrounding homes were built decades earlier. Completed in 2017 and set on a lakefront lot in a non-flood zone, this move-in-ready, hurricane-secure home offers a level of modern construction, privacy, and peace of mind seldom found in this exclusive community. In

    Lielei Wahlmann EXP REALTY LLC

    20 Bayhead Ln, Osprey, FL 34229
  • /93

    $649,500 Pending

    • 3 Beds
    • 2 Baths
    • 2,505 Sq Ft

    186 Windward Dr, Osprey, FL 34229

    Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been

    Brittany Coleman KELLER WILLIAMS ON THE WATER S

    186 Windward Dr, Osprey, FL 34229
  • /43

    $874,900

    • 3 Beds
    • 3 Baths
    • 2,630 Sq Ft

    6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229

    Enjoy sweeping Intercoastal water views with peek-a-boo Gulf glimpses from this beautifully upgraded top-floor, end-unit residence filled with natural light, privacy, and coastal elegance. The interior features Luxury vinyl plank flooring, plantation shutters, crown molding, and higher ceilings unique to the top floor. The chef’s kitchen offers Bosch and JennAir appliances, a Liebherr split

    Agent Photo

    Andrea Stultz

    ENGEL + VOELKERS SARASOTA

    (941) 883-9484

    6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229
  • /95

    $1,380,000

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    365 S Shore Dr, Osprey, FL 34229

    Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined

    Lisa Asaro EXIT KING REALTY

    365 S Shore Dr, Osprey, FL 34229
  • /44

    $679,900

    • 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
  • /72

    $2,250,000

    • 4 Beds
    • 3.5 Baths
    • 4,012 Sq Ft

    433 E MacEwen Dr, Osprey, FL 34229

    An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior

    Mark Lyda GENEROUS PROPERTY

    433 E MacEwen Dr, Osprey, FL 34229
  • /41

    $419,000

    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft

    524 Sarabay Rd, Osprey, FL 34229

    Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the

    Ibetta Giannone SUN N SAND REAL ESTATE LLC

    524 Sarabay Rd, Osprey, FL 34229

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