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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161 Willow Bend Way Osprey FL 34229

Osprey, FL161 Willow Bend Way

Price$629,000

Est. Mortgage: $/month

MLS Number A4507861

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,395
  • Bathroom 3

Beautiful family home in Park Trace Estates. Enjoy the peaceful lake views from the pool deck while cooking up some dinner or grabbing a cold drink from the outdoor kitchen. Covered lanai space offers plenty of outdoor living under the newly resurfaced lanai screen. The home has an open floor plan with sliding glass doors, giving easy access to the pool area. Three bedrooms and three baths (one is a pool bath) in a split plan design with a separate office up front. The home has wonderful features; tray ceilings, a dry bar off the dining room, a built-in desk and shelving in the office, a large master bath with a garden tub and dual sinks, a side-entry two-car garage and a large laundry/mudroom. The Park Trace neighborhood is in a great location for shopping (Costco, Target, Walmart), Pine View School, the Legacy Trail and Oscar Scherer State Park.

Listed by PREMIER SOTHEBYS INTL REALTY

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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Glenwood Avenue Osprey FL 34229

Osprey, FLGlenwood Avenue

Price$110,000

Est. Mortgage: $/month

Pending

MLS Number N6116637

  • Land
  • Area Osprey
  • Mls Status Pending
  • Acreage 0.13
  • Subdivision Osprey Park 2

Perfect location to build your dream home or investment! Two vacant lots next to each other in close proximity to the best schools in the area. Make an offer before they are gone!

Listed by PELICAN REALTY CORP

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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502 Meadow Sweet Circle Osprey FL 34229

Osprey, FL502 Meadow Sweet Circle

Price$424,900

Est. Mortgage: $/month

Pending

MLS Number A4507353

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 1,776
  • Bathroom 2

Charming tranquil community at the Cottages of Rivendell. Custom home build by Merrell Brothers Custom Builders. Spacious, open living plan opening to a huge, private, screened lanai. Three bedrooms or third bedroom can be used for an office/den. The tree lined streets provide beauty and privacy. Perfect for a shaded stroll along the sidewalks to the community center and large heated community pool. The location is convenient for shopping, restaurants and midway between Venice and Sarasota. Just a short drive to the beaches of Nokomis, Venice and Siesta Key, or enjoy the natural beauty of Oscar Scheer State Park which is adjacent to the Rivendell Community.

Listed by RE/MAX PLATINUM REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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925 Blue Heron Overlook Osprey FL 34229

Osprey, FL925 Blue Heron Overlook

Price$990,700

Est. Mortgage: $/month

MLS Number A4507345

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,975
  • Bathroom 4

Located behind the gates of The Oaks, on a quiet cul-de-sac, this 3 bedroom, 3.5 bath home is situated on a lovely, private lot. From the moment you see the unique facade, you will anticipate what is behind the double front doors. As you enter you will be greeted by gleaming oversized ceramic tiles, and a great view through the living room, out over the pool to the golf course beyond. The master bedroom is spacious with a large walk-in closet and a bath with dual sinks, jetted garden tub and walk-in shower. Besides the master suite there are two additional bedrooms that share a bath, outfitted with cool bowl sinks. The kitchen features granite countertops, and newer stainless steel appliances. With a formal dining room, breakfast bar and dining nook, there are plenty of options for family meals as well as entertaining. Outside the screened lanai houses a large pool with spa, and plenty of covered space for dining al fresco or sitting in the shade taking in the pretty views of the lake and 9th hole of the Heron course. High ceilings, a newer roof (replaced in 2014), hurricane shutters on most windows, and a two car garage all add to the reasons you must see this home; neat as a pin and waiting for you to make it your own. Membership in The Oaks Club is available and required. Sarasota's finest golf and country club offers two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), 4 new pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth of recreational activities and social events.

Listed by COLDWELL BANKER REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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1308 Thornapple Drive Osprey FL 34229
For Rent

MLS Number N6116557

  • Rental
  • Mls Status Active
  • Area Osprey
  • Square Feet 2,188
  • Bathroom 2

Gorgeous turnkey 3 bed/2 bath furnished annual rental near Nokomis Beach. Professionally decorated, on an oversized lot, the home overlooks a tranquil lake in the Willowbend subdivision. The beautiful lanai features travertine marble tile, a heated pool, and spa with privacy screening. Inside you'll be wowed by many tasteful upgrades including genuine wood plank oak flooring, custom closets, quartz kitchen counters & a master bath complete with spa tower. Features also include spacious sized bedrooms, a master bedroom with two walk-in closets, an office/den with built-in cabinetry, natural fabric wall coverings and plantation shutters, an open kitchen with cherry cabinets featuring dove-tail joinery and quartz countertops, ceramic tile flooring, high ceilings, an abundance of windows, crown molding and designer millwork, laundry with storage closet with an oversized sink and custom shelving, plus a 2-car garage with air-conditioning capabilities. This maintenance-free community offers high-speed internet, cable television, yard maintenance, as well as a heated community pool, spa, fitness center, pickleball court, and playground. Outdoor enthusiasts will enjoy knowing that Oscar Scherer State Park, Casey Key, and the Legacy Trail are all nearby. Location is just minutes to area beaches, and the top-ranked school in Florida, Pine View School, as well as downtown Sarasota and Venice. Schedule your showing today!

Listed by KELLER WILLIAMS ON THE WATER

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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242 Washington Avenue Osprey FL 34229

Osprey, FL242 Washington Avenue

Price$195,000

Est. Mortgage: $/month

MLS Number A4507264

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 630
  • Bathroom 1

Wonderful location! Lots of new homes in neighborhood. Close to pineview; beaches; mall shopping; wal-mart. 2 bedroom 1 bath home is perfect for retirees, 1st time home buyers or investors.

Listed by RE/MAX TROPICAL SANDS

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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1615 Southbay Drive Osprey FL 34229

Osprey, FL1615 Southbay Drive

Price$570,000

Est. Mortgage: $/month

MLS Number T3316228

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 1,886
  • Bathroom 2

Welcome home to the premier location of Southbay Yacht Club! West of Tamiami Trail and within a short drive or bike ride to Nokomis beach, this house is perfect for entertaining family and friends with a circular floor plan, updated kitchen, indoor/outdoor living with easy access to the large screened in lanai area, circular driveway and split floor plan for privacy for you and your guests or family members. Oversized garage just off the large laundry area with plenty of storage. Southbay Yacht Club is a community with social events, a new, renovated community center with beautiful pool area, social area, kitchen, library & gym. Yacht slips are available for rent. Restaurants and shopping are a block away. Quiet location with easy access to I-75 and everything Sarasota has to offer. Don't miss this opportunity to put your personal touches on this great home and schedule a showing today!

Listed by REDFIN CORPORATION

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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232 Hidden Bay Drive Osprey FL 34229
Pending

MLS Number A4506442

  • Condo
  • Mls Status Pending
  • Square Feet 1,943
  • Bathroom 2
  • High School Venice Senior High

This 6th floor Penthouse condo is an immediate WOW from the moment you open the door. The spectacular views of the Intracoastal Waterway, Casey Key, Siesta Key, and the Gulf of Mexico are jaw-dropping. Kitchen walls have been removed for an open floorplan that allows magnificent views from all common rooms. Watch the boats from your 9-foot kitchen island while entertaining friends in your designer kitchen. Or grab a drink and curl up for a romantic sunset on your enclosed lanai. Wood flooring throughout allows a seamless integration of all rooms. The views continue as you make your way to the master bedroom with his-and-her walk-in closets. The fully updated master bath includes a doorless walk-in shower with river rock flooring. A whirlpool tub, dual sinks, and a separate water closet round out the bathroom. There are two additional bedrooms, one with a walk-in closet and attached bathroom. Interior features include impact windows, crown molding, motorized window treatments and plantation shutters. MOST FURNITURE INCLUDED. The unit comes with a private two-car garage PLUS an additional one-car garage. One small pet is happily welcome. Hidden Bay is a 12-acre gated resort community offering a 500-foot boardwalk through beautiful mangroves opening to a fishing pier on the Bay. Relax at the pool or spa, play a game of tennis, or use one of two pickleball courts. Drop in your kayak to explore the intracoastal waterway. Mingle under the tiki bar to grill up your favorite meal. Spend time in the club house, fitness center or library. Perfectly located between Sarasota and Venice you are just minutes from shopping, dining, the Legacy Trail and the beautiful beaches of Sarasota County.

Listed by COLDWELL BANKER REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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48 Osprey Point Drive Osprey FL 34229
Pending

MLS Number A4506975

  • Rental
  • Mls Status Pending
  • Area Osprey
  • Square Feet 3,881
  • Bathroom 4

This spacious three bedroom, three-and-a-half-bathroom home is built to entertain. From the grand master bedroom, bonus room with sunken bar and open fireplace in the dining room this home is in a class of its own. Home features Spanish tile throughout with laminate flooring in bedrooms and dining room. Split plan for bedrooms allows for privacy when guests come to visit. Kitchen includes walk in pantry, built in oven and two sinks. Den with built in bookcases. Wonderful view of the pool from most rooms. A wonderful community and a great place to call home.

Listed by HOME REALTY & MANAGEMENT LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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210 Old Venice Road Osprey FL 34229

Osprey, FL210 Old Venice Road

Price$554,890

Est. Mortgage: $/month

MLS Number A4506724

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,298
  • Bathroom 2

Rare find!* 1.2 acre ranch home in the center of town. Yes, in town, not east of the interstate or way down south. *NO HOA, *NO CDD, *NO FLOOD insurance needed and *NO Deed Restrictions! Build that garage you've always wanted, or even work from home. There is room for it! This is a masonry block/brick *4 bedroom, *2 bath, country style homestead on a concrete slab with vented crawlspace and access. Walking distance to Pine View school, Wal-Mart, Osprey Post Office, and Lady of Mt. Carmel Catholic church. Osprey is right between Sarasota and Venice, so just minutes from everthing including multiple beaches and the *Legacy Trail* down and around the corner. If you searching for a remodled/updated home with a fancy pool, stainless appliances, granite counters and new floors, ... keep looking, because this isn't it. But, if you like a country feel, room for your boat, RV, trailer/s and privacy, and are ok with a gravel driveway, come take a look as this could be for you! This is not a fixer upper unless you want it to be, as there is a big difference between wants and needs. You may have visions of doing a lot, but this doesn't need a lot. This is a well operating home in good shape that you can live in immediately with rebuilt sliders, new paint, fans, bedroom carpet, lighting, disposal, Hardee Plank gables, gutters, soffit, fascia, 3 exterior doors, porch screens, porch ceilings, and more. This may have the look and feel of a 70/80's home, but it's very comfortable with large rooms and 3 porches, (1 open, 1 covered, and one large screened) and lots of *room for a pool*. Lots of closets and storage space too* which you don't get with many newer homes. The bedroom/*office off the master also has it's own entrance from front porch* (great for clients), and the kitchen window has a pass through to rear lanai bartop. This home has a great split floorplan to fit many remodling ideas you may have and a family room that is 28x13!! Ping pong/billiards etc! Attached is a 20' deep 2.5 car garage with an electric opener, work bench and wash sink. Detached barn is an 18x18 unit on a concrete slab, w/electric, and barn doors on back for equipment access. This home is connected to county water, and on septic so you aren't paying for high sewer charges. 2003 A/C blows cold and roof is 2011. One Mango tree gives quite a bit of fruit once a year, and beautiful oak trees shade many parts of this easy to maintain property. If you are looking for a forever piece of homestead property in town to enjoy for many years, this will probably fit the bill. This is a great home, completely funtional. Buy today, move in tomorrow type property. If you get focused on thinking you have to update everything right away, you may talk yourself right out of a forever home opportunity! Remember, you don't have to do everything in the first week, as you can make it your own over time. Come in person to view this, because you will not find a large selection of these "in town acreage" type properties on the market, guaranteed! Thanks for looking. Room sizes are close approximates, buyer to verify. Furnishings may be different than pictured.

Listed by BRIGHT REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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410, 411, 401 N Casey Key Road Osprey FL 34229

MLS Number A4505431

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 11,132
  • Bathroom 14

Situated on the exclusive barrier island of Casey Key, Florida, and straddling the waters of the Gulf of Mexico and Sarasota Bay, this unique Gulf-to-bay compound ticks all the boxes at a time when privacy, security and space for flexible lifestyle options have never been more in demand. Encompassing over 2.55 acres with 300 feet of water frontage on the Gulf of Mexico and Sarasota Bay, respectively, this breathtaking property features three separate residences (two Gulf-side, one bayside), a park-like setting with expansive grounds including a sculpture park, a tennis court with stadium lighting that's easily relined for pickleball, two pools and two bayside docks. Gulf-side, the rare 8-foot privacy wall bookended by two electric gates creates an oasis of security and privacy within for twin residences, which bracket the tennis court, pool and spa with fountains and built-in bar stools. The main house (411) boasts an inviting and open interior with oversized rooms, marble floors, crown moldings and baseboards in exotic wood throughout, two fireplaces, multiple second-floor decks and a layout that emphasizes picture-perfect views of the Gulf from every room. A cathedral ceiling soaring to 21 feet in the great room, recently opened to the gourmet kitchen, greets visitors on their arrival with dramatic breathtaking views of the Gulf. From the 24-by-30-foot master suite, enjoy “cruise ship” views of sunsets over the turquoise Gulf waters. Luxuriate in the master bath with custom finishes ranging from glass shower doors by famed artist Erté to swan pedestal sinks, a claw foot tub, 24-karat gold-plated trim and hardware details. The remaining three bedrooms feature en-suite baths and customized walk-in closets. The twin residence/guesthouse (401) features an open floor plan on the ground level and five en-suite bedrooms, each with a balcony fronting on the Gulf. Comprising the compound's bayside portion is the third residence and sculpture park, which is divisible into two buildable lots, each with its own deeded dock. The bayside residence wraps around its own screened-in pool, and its floor plan allows for three bedrooms, including a large second-level owner's suite with a private balcony to enjoy the sunrise over the bay. Whatever your lifestyle scenario, whether work-from-home, homeschooling, multigenerational living, hosting guests and/or accommodating staff, this one-of-a-kind property fits the bill. While remote and exclusive, Casey Key offers the best of both worlds in its easy accessibility to culturally rich Sarasota, charming Venice, Legacy Bike Trail, world-class shopping and dining, international airports, jet ports and top-rated schools.

Listed by PREMIER SOTHEBYS INTL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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156 Bishops Court Road Osprey FL 34229

Osprey, FL156 Bishops Court Road

Price$825,000

Est. Mortgage: $/month

MLS Number A4506439

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 3,112
  • Bathroom 4

Enjoy the privacy of The Oaks Preserve in this mini estate, as your backyard is a pristine nature sanctuary and a deeded nature preserve. This Cape Cod style home has so much charm, is a hidden jewel, and is part the legendary Oaks Country Club. Bishops Court is a small, traditional, shaded, oak canopied neighborhood with flowering trees, a community pool and pool house, and is perfect for taking long walks. Graceful living is what you will find in this 3 bedroom, 3 ½ bath home with a heated pool and spa. The spacious study/library can easily be a 4th bedroom, and the upstairs loft is large enough for a gym, double office, or media room. Handsome wood floors throughout the home add to the ambiance. The great room's focal point is a traditional brick fireplace, and a screened, 336 square foot enclosed Florida room with French doors is the perfect place to have a quiet dinner overlooking the gardens and pool. Invite your friends over on holidays to see the fireworks from the rooftop deck! This special home was designed by noted architect Frank Folsom Smith, and is unique in it's design. The thoughtful design features a spacious kitchen with an island cooktop (gas range), granite counters, stainless appliances and built-in shelving to showcase pottery ware. There is surround sound throughout the home, a wet bar with a wine cooler, and a brick front porch to enjoy the majestic oaks and landscaping. The backyard pool and spa are very private, overlooking the preserve. In addition to the patio, pool and spa area, the home enjoys 732 square feet of outdoor deck space off the second floor and rooftop. Bishops Court is a maintenance free neighborhood, where lawn and landscape maintenance, and irrigation is included in the homeowner's association. The Oaks Preserve has a staffed, 24 hour guard gate. Membership in the Oaks Country Club, one of Sarasota's most established country clubs is required, and your key to membership is two championship 18 hole golf courses, tennis, pickleball, croquet, bocce, dining, and a full schedule of member events. Be sure to see this very special home.

Listed by MICHAEL SAUNDERS & COMPANY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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 July 29, 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.