Osprey Florida Real Estate Listings

Osprey, Florida is a historic city on Florida’s southwest coast. Osprey is a diverse community featuring multi-million dollar homes among the intercostal highway. 

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View all real estate for sale in Osprey, Florida below with RoseBay International Realty. Contact us if you have questions or would like to schedule a showing. 

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232 Hidden Bay Drive Osprey FL 34229

MLS Number A4488011

  • Condo
  • Mls Status Active
  • Square Feet 2,241
  • Bathroom 3
  • Area Osprey

WATERVIEWS of BEAUTIFUL LITTLE SARASOTA BAY FROM THIS FANTASTIC CONDO located in the gated community of HIDDEN BAY!! The open floor plan is spacious and well laid out - offering plenty of living space. The north facing patio/ lanai is glass incased with sliding doors to provide for either a weather tight or open screened in option to enjoy the breezes off of the water. This end unit is a rare find in the Hidden Bay community where you'll have lots of natural light in that gives a warm happy glow in this wonderfully positioned unit. The kitchen is well designed with plenty of built in storage cabinets and brand new appliances. Master bedroom also has an impeccable water view, 2 walk-in closets, and a large tub. This unit also comes with a large 2 car garage on the second floor. This breathtaking 3 bedroom/3 bathroom corner unit is located on a 12 acre resort style community with an undated clubhouse, tennis courts, fitness center, library, a kayak launch area for paddling around on the Bay and a heated pool. There's even a Tiki Bar also shown in our photos. This community is a must see. Your Dream Condo awaits- Pack your bags and schedule your showing appointment today. ** One or more photos have been virtually staged**

Listed by KELLER WILLIAMS ON THE WATER

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2259 Jessie Harbor Drive Osprey FL 34229

MLS Number A4488472

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,006
  • Bathroom 3

Enjoy the Florida Lifestyle, Boats, Beaches and Sunshine! You'll feel right at home in this newer, gated, waterfront villa with spectacular water views and easy access to Bay & Gulf. Blackburn Harbor Waterfront Villas were designed to be a boating community, where you're just steps from your boat and a fun day boating on the Bay. This spacious, two story, attached villa, where the living area, 3 bedrooms and 2 1/2 baths are all located on the second floor. This unit has vaulted ceilings, granite counters in kitchen and both baths, wood cabinetry and your private oversized garage. This beautifully landscaped community offers boat docks on a first come basis and at a low monthly fee, large heated community pool, tennis/pickle ball courts, kayak/paddleboard launch, kayak storage, covered barbeque grill area and clubhouse with fitness center. This ideal central location, just South of Sarasota and North of Venice, is close to Nokomis and Siesta Key Beaches, Restaurants, Shopping and Sarasota/Bradenton Airport. Make an appointment today!

Listed by MICHAEL SAUNDERS & COMPANY

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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413 Sorrento Drive Osprey FL 34229

Osprey, FL413 Sorrento Drive

Price$1,599,000

Est. Mortgage: $/month

MLS Number N6112636

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 4,414
  • Bathroom 6

FULLY RENOVATED WATER VIEW MANSION. Make wonderful memories in this gorgeous Sorrento Shores estate with stunning Intracoastal Waterway views. A private gate and country manor-style driveway greets you as you enter the Estate. The owners have fully renovated the house inside out with a brand new state of the art kitchen, new plumbing, new flooring, new air conditioning units, new water heaters and fresh paint. The home is surrounded by mature landscaping and majestic trees that give plenty of shade on the spacious .82 acre lot. The rooms have been designed to allow tons of natural light to flood through the windows. Thoughtful owners also provided added parking space for an RV or Boat. The oversized 3 car garage has plenty of room for extra storage, bikes, golf carts, etc. An extra large lanai surrounds the sparkling heated pool and spa, a great place to host family gatherings or just catch the evening sunsets over the Bay. The first floor boasts a Master Suite as well as an office/den, two walk-in pantries, laundry room and a second en-suite bedroom perfect for overnight guests or in-laws. The open concept family room has a gas fireplace for cozy evenings on cool nights. Two more bedrooms, each with their own en suite bathrooms and walk-in closets, are located upstairs. There is also a Bonus room, perfect for game nights or just quiet lounging. The Bonus room opens onto a large Terrace offering beautiful views of the water. Great for evening cocktails or late-night stargazing over the Bay. Sorrento Shores is centrally located between Sarasota and Venice, close to shopping, excellent schools, great restaurants, lively entertainment and great beaches that are just minutes away! The community's MARINA also has boat slip rentals! LOW OPTIONAL HOA and NO CDD fees! Bring your family to Sorrento Shores, you'll be glad you did.

Listed by WEST COAST REALTY OF VENICE

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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376 Renoir Drive Osprey FL 34229

Osprey, FL376 Renoir Drive

Price$619,000

Est. Mortgage: $/month

MLS Number A4487767

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 1,900
  • Bathroom 3

Remarkable opportunity for a canal front home with no bridges to bay. Within minutes you can be cruising in the warm waters of the Gulf of Mexico. This 3-bedroom 2 ½ bath home has been lovingly maintained. The living room features a full wall of sliding glass doors overlooking the heated pool and spa to the canal beyond. Convenient pool bath is accessed from the screened lanai. Split bedroom design offers privacy for family and guests. Huge master bedroom with ensuite bath and walk-in closet. The kitchen is partially open to the dining and living areas and has newer stainless appliances. Spacious walk-in pantry and inside laundry. Oversized side load garage with ample parking space for additional vehicles or motorhome. Enjoy peace of mind with the newer metal roof, AC and hot water heater. Exterior recently painted. There is a well for irrigation of the generous 1/3-acre lot. Boat dock with 15,000 lb. lift. With a few cosmetic updates you could be the proud new owner of your waterfront dream home!

Listed by COLDWELL BANKER REALTY

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1841 Highland Road Osprey FL 34229
For Rent

MLS Number A4488199

  • Rental
  • Mls Status Active
  • Area Osprey
  • Square Feet 1,066
  • Bathroom 2

Charming 2 bedroom 2 bathroom villa in GREAT location just minutes from Nokomis beach and Sarasota! Light and Bright with open floor plan, ceiling fans ,spacious eat-in kitchen, plenty of cabinet space, and large kitchen island. Laundry closet inside with washer & dryer. Tile flooring in main living space, carpet in both the bedrooms. Plenty of off street parking, enjoy morning and evenings on the quaint patio just off the living room. Walk just steps to the heated community pool. Pets welcome with owner approval and $350 non refundable pet fee. Just minutes to downtown Sarasota, Venice and Gulf Beaches. Lovely neighborhood, launch your Kayak from Shoreline Park just at the end of the street. Call for a showing today!

Listed by JENNETTE PROPERTIES, INC.

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%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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268 Saratoga Court Osprey FL 34229

Osprey, FL268 Saratoga Court

Price$935,000

Est. Mortgage: $/month

MLS Number A4487178

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 3,815
  • Bathroom 4

Behind the gates of The Oaks, this beautiful custom built 3 bedroom plus office/den, 3.5 bath gem enjoys an idyllic, peaceful setting. The cul-de-sac location gives this home a gentle feeling of quiet privacy. Surrounded by mature oak trees, and with a long, pavered circular drive, you will be drawn to it, and want to see all it has to offer. Enter through the leaded glass double front doors and you will find a wonderful combination of elegance and comfort. An impressive marble foyer welcomes you home. Enjoy dinner in the ample formal dining room, then relax in the cozy formal living area with fireplace overlooking the pool and spa. The master bedroom suite is incredible! Spacious and bright, it had a luxurious master bathroom. There are two other nicely sized bedroom and a large office suite. AND A NEW KITCHEN IS BEING INSTALLED. There is so much to love about this house, you may never want to go outside. But when you do your breath will be taken away. The huge lanai that houses with free form pool is the perfect place to spend Florida afternoons in the sun, or lounge or dine under the large, covered area. The view, over the 3rd fairway of the Heron and beyond to the lake is as pretty as a picture. You truly must see this home to appreciate all it has to offer. The Oaks, Sarasota's premier golf and country club, has two championship golf courses, a junior Olympic community pool, tennis, state-of-the-art fitness center and a wide variety of dining, recreational and social offerings. Club membership is available and required.

Listed by COLDWELL BANKER REALTY

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$
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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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470 E Macewen Drive Osprey FL 34229

Osprey, FL470 E Macewen Drive

Price$1,870,000

Est. Mortgage: $/month

MLS Number A4486412

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 5,267
  • Bathroom 4

Escape to your very own private paradise set within the gated community of The Oaks. This stunning residence blends classic architectural elements, a sense of openness, comfort, and function to provide a near-perfect setting for a vacation retreat or a year-round home. Exquisitely finished, this home is truly one-of-a-kind and a must-see. Vaulted silver leaf ceilings, travertine marble floors, walls of glass and pocketing sliding doors to the lanai and pool area come together to create a seamless flow inside and out that allows for the perfect Florida lifestyle. The main kitchen, open to the adjacent family room, boasts custom rich wood cabinetry, granite countertops, top-of-the-line appliances and a large breakfast area, forming one large casual entertaining space. The master suite is an oasis and the separate guest/children's wing is ideal for visiting guests or family and features three bedrooms, a separate family room and a second kitchen. The home theater, an exercise room, an office, two laundry rooms, a dog spa with a dedicated dog run, a hobby/craft room, an outdoor kitchen, a stunning saltwater pool and spa and an air-conditioned three-car garage complete this incredible home. The Oaks Club, one of the area's most exclusive private country club communities, is located minutes from nationally acclaimed Pine View School, the Legacy Bike Trail, Siesta Key beaches and all that living in the Sarasota area has to offer.

Listed by PREMIER SOTHEBYS INTL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Bayview Lane Osprey FL 34229

Osprey, FL33 Bayview Lane

Price$425,000

Est. Mortgage: $/month

MLS Number A4488003

  • Land
  • Area Osprey
  • Mls Status Active
  • Acreage 0.6
  • Subdivision Sarabay Acres

This .6 acre lot is just down the street from a Sarasota County park right on Sarasota Bay. All three lots just east of the park, including this one, have an easement on the south side allowing access to the water to launch kayaks, canoes and paddleboards. Just a short stroll north is the Point restaurant and Evie's Spanish Point Pub/Tiki Bar. Several other restaurants, bars and shops are also nearby. Its Zoning description is Residential Multi-Family (6un-RMF1) and there is a potential to be zoned RMF-3 (13 units/acre). Housing on and near the water is in high demand, especially with the exponential growth this area is experiencing. Call today to schedule your showing.

Listed by RE/MAX ALLIANCE GROUP

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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233 Willow Bend Way Osprey FL 34229

Osprey, FL233 Willow Bend Way

Price$525,000

Est. Mortgage: $/month

MLS Number A4487448

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,559
  • Bathroom 3

This beautiful Park Trace home features lush palm trees surrounding a coveted southern pool exposure. Centrally located between Sarasota and Venice, it is close to shopping, Siesta Key Beach (rated #1 in the US), the Pine View School, and the Legacy Trail. The impressive entry features transom windows, a coffered twelve-foot ceiling, and extensive crown mouldings. The clever floor plan provides plenty of space between the four bedrooms as well as a very practical den / office / Zoom room. The master suite and family room both open onto the screened lanai that surrounds the heated pool. The kitchen is spacious but practical, with newer stainless appliances and ample cabinet and counter space.

Listed by RE/MAX ALLIANCE GROUP

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5100 Jessie Harbor Drive Osprey FL 34229

MLS Number A4487755

  • Condo
  • Mls Status Active
  • Square Feet 2,143
  • Bathroom 2
  • High School Venice Senior High

In todays World, along the acclaimed Gulf Coast of Sarasota, Fl - most every buyer looks for a pristine place to call home. You want it now and you want high-end finishes. You want to be WOWED when you walk in the front door. Privacy, security and sensational views is what you have been searching for. Do not pause, someone else will snap this up. Situated on the 4th floor of a 7 story mid-rise condominium this Blackburn Harbor Residence opens the door and raises your eyebrows. A wide foyer invites you to a spacious, bright and light floor plan with a defined dining area that is open to the kitchen. Appliances recently installed, you will LOVE being the center of attention in this kitchen! Exquisite. The Master suite is pure luxury with custom closets that you dream about, beautifully appointed dressing and bath area. Large walk-in shower and a separate jetted tub. Sumptuous carpet where it matters most and the rest is neutral tile throughout. Large laundry room with utility sink. Open the sliding glass doors (high impact) and slip out onto the screened lanai and be swept away night-after-night watching the sunset over the Intercoastal Waterway and the Gulf of Mexico beyond. Birds, boats and beautiful surroundings. Quiet. Park your cars in (2) designated secured covered garage spaces. Blackburn Harbor is private with gated entrance, security and conveniently located by shopping, restaurants, and Nokomis, Venice and Siesta Key Beaches. Boat docks are available (first come). Updated and fun clubhouse; heated pool; walking trails, fitness room and kayak storage provides a nice mix for enjoying the Florida lifestyle. Pickleball, freshly surfaced (and lighted for evening) tennis courts or Girls Night Out! Few properties leave such a lasting impression. This is one of them.

Listed by MICHAEL SAUNDERS & COMPANY

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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300 N Tamiami Trail Osprey FL 34229

Osprey, FL300 N Tamiami Trail

Price$2,750,000

Est. Mortgage: $/month

MLS Number A4487739

  • Land
  • Area Osprey
  • Mls Status Active
  • Acreage 2.42
  • Subdivision Osprey Park 2

VACANT ENTIRE COMMERCIAL BLOCK - STREET TO STREET This property has a distinctive singular presence in Osprey, Florida with 42,000 plus cars per day. It is an entire city block. It is bordered on all 4-sides by streets. There are 2 access median cuts on its Tamiami Trial frontage. Plenty of reaction time (even 2nd-chance access). It is planned for either a 23,000 sf strip center or a 110,000 sf self-storage facility (drafts available). There is a paying bill-board on the property. Several enterprises in the area: Walmart, Mad Mole's, New waterfront restaurant. Property is flat and ready for construction. No improvements on the property accept for some old foundations which can be considered for future impact credits.

Listed by KELLER WILLIAMS REALTY SELECT

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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318 Osprey Point Drive Osprey FL 34229

Osprey, FL318 Osprey Point Drive

Price$1,728,000

Est. Mortgage: $/month

MLS Number A4487690

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 6,981
  • Bathroom 6

Behind the gates of the highly exclusive Oaks Club and nestled on a lush private preserve lot that backs to a creek, this home is evidence of discerning ownership. Crafted by the one of the most decorated builders in our area, John Cannon Homes delivered a vision of timeless functionality, quality of workmanship, and thoughtful solid construction. This floorplan allows for unbelievable privacy and nature views from almost every room with each of the 5 en-suite bedrooms having private access to an outdoor terrace. No detail was overlooked when accommodating every need one could have in a home. Beautiful Low E Andersen windows and doors throughout offer both serenity and peace of mind. Refinement in all areas means every window is dressed with plantation shutters, every closet is clad with custom built ins, every room merging convenience and luxury seamlessly. An incredible master suite, a guest bedroom, and an additional large guest suite are found on the first floor as well as an office, home theater, a beautifully equipped kitchen with catering/service room, a salt water pool, spa, summer kitchen, and oversized 3 car garage. The second floor is an oasis with 2 en-suite bedrooms, additional guest laundry, a grand gathering room, and a flex room to accommodate a home gym or almost any hobby. This residence is fully wired with cat 5 and control 4 compatibility. 4 NEW Trane AC units were installed Dec 2020 and 2 NEW tankless hot water heaters for good measure. As a member of The Oaks Club you will enjoy access to 12 har tru tennis courts, 2 championship golf courses, a gym, croquet and bocce lawns, indoor and outdoor dining among 3 venues, fabulous schools and 24/7 security. As a resident, you will enjoy a vibrant Gulf Coast community bursting with arts and culture, beach coastline, and the lifestyle of your dreams.

Listed by MICHAEL SAUNDERS & COMPANY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to MFRMLS as of January 16, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MFRMLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.