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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393 N Point Road Osprey FL 34229

MLS Number A4522272

  • Condo
  • Mls Status Active
  • Square Feet 2,203
  • Bathroom 3
  • High School Riverview High

Situated in the popular 2nd building of Meridian, which allows two pets of any size, is this 3 bedroom, 3 bath condo. From the moment you drive through the gates of The Oaks Preserve you can feel how special this place is. Enter the building through the secure lobby and take the private elevator to a unit you will love! Once you walk into the foyer with tray ceiling, and you will be delighted with the interior. Light filled, this bright space is perfect for living the carefree, luxury condo lifestyle. A winter retreat, or a full-time residence, this unit offers plenty of room for you and guests. There is a master suite, and a guest suite, and a dining area to big enough to accommodate a large formal dining set, and a third bedroom, which can be utilized as an office, sitting room or den. Nestled amongst the trees, the private screened balcony offers the perfect place to take in the sights and sounds of the abundant local nature. Take advantage of the nearby Meridian residents-only pool, spa and gym, or enjoy all the amenities, recreational, dining and social offerings of The Oaks Clubside. Club membership is required.

Listed by COLDWELL BANKER REALTY

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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218 Willow Bend Way Osprey FL 34229

Osprey, FL218 Willow Bend Way

Price$825,000

Est. Mortgage: $/month

MLS Number A4522655

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,509
  • Bathroom 3

Welcome to this beautifully built Vision home. This elegant and spacious home offers a gourmet kitchen with stainless appliances, quartz counters & farm sink, double sided pantry, stone back splash, wood cabinetry with glass accents. A large island plus separate eat in area with aquarium glass. The private office has many custom built-ins. A luxurious Master Suite. A glistening heated pool with fiber optic colored lighting & paver decking. Additional dusk lighting adds to the ambiance of the park-like setting with new and mature landscaping. A large fenced yard for pets and play area and even room for an herb garden. Additional fine features include, plantation shutters, coffered ceilings, columns, high ceilings, 8 ft doorways, central vac, & new paint, new A/C. A 3-car garage with paver drive. This is truly a special place to call home in a prime location, minutes to Pineview school, the beaches, the Legacy trail, close to downtown Venice & Sarasota, and the new Sarasota Memorial Hospital.

Listed by MICHAEL SAUNDERS & COMPANY

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$
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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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1201 Lost Creek Drive Osprey FL 34229

Osprey, FL1201 Lost Creek Drive

Price$925,000

Est. Mortgage: $/month

Pending

MLS Number A4522821

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 3,400
  • Bathroom 4

Easy living - 5 bedrooms, 4 baths, Executive Home. Master suite and guest quarters/office on main level - three family bedrooms upstairs - Open floor plan with natural light. Specious Lanai with pool and spa. Over looking lake and nature preserve - This 16,600 square foot lot is located in the sought after community of The Woodlands at Rivendell next to Pine View School and Oscar Scherer State Park. Near Nokomis Beach and Marina facilities on Casey Key.

Listed by ILENE MIRMAN REALTY INC

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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503 Velasquez Drive Osprey FL 34229

Osprey, FL503 Velasquez Drive

Price$3,195,000

Est. Mortgage: $/month

MLS Number A4522764

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,862
  • Bathroom 4

Tucked away amongst lush landscaping, offering stunning, far-reaching views of the Intracoastal Waterway and sunsets over the exclusive barrier island of Casey Key, this hidden gem on Blackburn Bay is a boater's dream come true. Enjoy the Florida lifestyle to the fullest with private dock, boat lift, jet ski lifts and sandy beach area for launching paddle boards and kayaks. The pool and patio areas offer abundant space for entertaining while enjoying the excitement of sailboats and yachts passing by. Plenty of room for your toys as well in the oversized two car garage and additional detached garage with adjoining studio. This move in ready, single level home provides ample privacy and space for family and friends. Well sited with great elevation, the .58-acre property delivers seclusion and views that are sure to please. Located in the heart of Osprey, with easy access to downtown Sarasota, Venice, area beaches and interstate 75. Nearby Pine View School and ample choices for dining out combine to create a location with something to offer for all.

Listed by COLDWELL BANKER REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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128 Villa Drive Osprey FL 34229

Osprey, FL128 Villa Drive, Unit 128

Price$595,000

Est. Mortgage: $/month

MLS Number A4522849

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 1,404
  • Bathroom 2

Boaters dream come true! Canal front home with no bridges to the intercostal west of the trail in quiet Osprey Florida. In your private backyard you have a brand new dock and new electric boat lift to keep your boat high and dry. Dock has water, electric, ambient lighting and snook lights in the water. This 2 bed/2 bath Villa has been completely remodeled with tasteful coastal modern colors and materials. It includes a brand new A/C with new ductwork, newer roof, updated electric and new panel, all new PGT double pane impact windows and doors, beautiful new tile throughout, new custom solid wood cabinets, exotic quartzite countertops, new appliances, large baseboards and shiplap accent walls, indoor washer and dryer, new open concept living area, freshly painted inside and out. The Villa has a one car garage and driveway, beautiful new paver walkway that leads to the large backyard and paver patio with outside kayak storage. There is additional community parking spaces for your guests. This unique enclave of villas inside of Sorrento Shores has 28 units which share a community dock and pool and had no age or pet restrictions. This Villa is one of only 12 units that backs directly up to the canal and has its own private dock. This small community has an HOA that costs only $275 per month and it includes cable, lawn maintenance and community pool. From your backyard dock you have a 10 minute scenic boat drive that takes you directly to the intercoastal, turn north and head to Sarasota and siesta key and beyond or turn south and hit the popular Venice Jetties and either way leads you to the Gulf of Mexico. In the evening you can jump on your boat and go for sunset cruise, see dolphins and stop at one of the numerous waterfront restaurants or tiki bars that have boat parking. Mornings you can have coffee at your dock and enjoy the manatees and abundant wildlife. This Villa is a mile to 681 which connects you quickly to I-75 so no frustrating traffic to contend with. With an Osprey zip code you get the best of Venice Island, Casey key, Sarasota, Siesta Key and enjoy this from both on and off the water. These waterfront Villas are unique, rarely available and go fast!

Listed by FINE PROPERTIES

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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50 W Bay Street Osprey FL 34229

Osprey, FL50 W Bay Street

Price$500,000

Est. Mortgage: $/month

MLS Number A4522380

  • Land
  • Area Osprey
  • Mls Status Active
  • Subdivision Saunders V A Resub

Welcome to Parrot Bay, a custom waterfront community. Build your dream home on a 1/4-acre lot. Boat slips available to accommodate up to a 40 ft boat. Boating, canoeing, kayaking, fishing steps from your door. Use the builder of your choice, subject to architectural review. This property is part of a 9 lot community. NO timeline to build. Elevation is approximately 14 feet (NO FLOOD INSURANCE REQUIRED) Enjoy amazing sunsets, take a walk or golf cart to Spanish Point, The Point restaurant and Tiki. Close to beaches and shopping. THIS IS FLORIDA LIVING, WELCOME HOME!

Listed by BRIGHT REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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75 Osprey Point Drive Osprey FL 34229

Osprey, FL75 Osprey Point Drive

Price$2,445,000

Est. Mortgage: $/month

MLS Number A4521509

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 4,001
  • Bathroom 4

**STUNNING ESTATE** just steps away from Sarasota Bay waters… situated on TWO LOTS with Pool and separate Guest House; this former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks' Clubhouse, boasts an impressive frontage along the highly sought-after Osprey Point Drive in the exclusive Bayside neighborhood of The Oaks Country Club. A gorgeous new 4x4 “Celini Agento Italian” tile accentuates the fresh color scheme throughout this well-appointed home complete with impressive fireplace, 14-inch crown moldings, wainscoting, palladium windows and much more! The Oaks is a truly distinguished country club community, with accolades including: 2019-2020 Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid tennis courts, 4 Pickleball Courts, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area beaches and all that Gulf Coast living has to offer. Membership is required.

Listed by GENEROUS PROPERTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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55 Osprey Point Drive Osprey FL 34229

Osprey, FL55 Osprey Point Drive

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS Number A4521507

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 3,339
  • Bathroom 3

**A WONDERFUL OPPORTUNITY** to own this Move-In Ready, completely Renovated and Updated Architectural Gem in the Exclusive Bayside neighborhood of The Oaks Country Club. Designed by renowned architect “Bo MacEwen,” this Regency style estate offers an Exceptional Water View throughout this open and split floorplan, Italian “panda marble” porcelain tile flooring, brushed gold hardware and fixtures, high-end kitchen featuring Viking and Subzero appliances, New Roof, Large circular driveway on a nearly half-acre lot only steps away from Sarasota Bay waters accessible via a welcoming and covered community dock. The Oaks is a truly distinguished country club community, with accolades including: 2019-2020 Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid tennis courts, 4 Pickleball Courts, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area beaches and all that Gulf Coast living has to offer. Membership is required.

Listed by GENEROUS PROPERTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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1321 Southbay Dr Osprey FL 34229

Osprey, FL1321 Southbay Dr

Price$949,000

Est. Mortgage: $/month

Pending

MLS Number A4522235

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 2,968
  • Bathroom 3

Your search is over! Welcome home to the highly sought after Southbay Yacht and Raquet Club. This large 2 story 4 bedrooms, 2 full bathrooms, 1 half bathroom, 2 car garage POOL home is ideally situated on an oversized corner lot. The home features a first floor owners suite! Inside you are greeted by a living room that is bathed in bright natural light that overlooks the large screened in patio with the pool that is perfect for entertaining! The kitchen has tons of storage and prep space, and upstairs features 2 bedrooms plus and extra bonus/3rd bedroom with a balcony with stunning views of the marina! Enjoy all the amenities Southbay Yacht and Raquet Club has to offer, including a marina, fitness center, tennis courts, playground, and a beautiful swimming pool that will delightfully refresh you after a day of fun in the Florida sun. This home is conveniently located within a short drive to shopping, restaurants, parks and more! Whether you've been looking for a home away from home or a place to raise your family, you'll find it here!

Listed by EXIT KING REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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207 Woodland Drive Osprey FL 34229
For Rent

MLS Number R4905591

  • Rental
  • Mls Status Active
  • Area Osprey
  • Square Feet 1,325
  • Bathroom 2

Pine Run Vacation Rental. This 2 BR 2 Bath upstairs turnkey furnished includes comfortable living room, formal dining room, shaded and screened porch and 1 car carport. Stackable washer/dryer located in kitchen closet. Community amenities: 2 heated pools (one geothermal), tennis, jogging trails, saunas and fitness room. Pine Run is walking distance to the new Publix grocery, the Bay and Blackburn Point Park where one can launch boats, Casey Key Fish House and Tiki Bar and beaches.. A kayak is provided, along with two bikes and tennis rackets. Turnkey furnished with everything you need to enjoy a fun filled vacation. Sorry no pets. $3500 (Jan-Apr) $2500 (all other months). 12% sales and tourism taxes apply. Property is available May 1, 2022. Three month minimum.

Listed by LINDSAY LEASING LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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669 Trenton Way Osprey FL 34229

Osprey, FL669 Trenton Way

Price$3,250,000

Est. Mortgage: $/month

Pending

MLS Number A4521842

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 5,806
  • Bathroom 6

A combination of old-world charm and the tropics gives this lovely home its unique appeal. Idyllically situated on a lovely cul-de-sac lot in The Oaks Clubside, this large abode has everything you need to live an interesting, active country club lifestyle. With 4 bedrooms, a media room, an office and 5.5 baths there is room for every way you want to live, work and play in Florida! Enter through the 10 foot solid wood double doors and you will immediately know that quality awaits in every room. High ceilings and transom windows bring in the natural light, highlighting the warm wood you will find throughout. The open kitchen is so pretty you may think it is just for show, but it is well equipped with high-end appliances that would be the envy of any gourmet chef. The master suite features a huge walk-in closet, and a large luxurious bathroom. With crown moldings, 2 fireplaces, large wrap-around bar with a view of the pool, and so much more, you absolutely must see this home to appreciate all the interior has to offer. Outside is just as amazing with an oversized screened lanai that features large, covered areas for relaxing or dining in the shade, a gorgeous pool with spa/waterfall, and a view of local plantings, palm trees and the lake and golf course beyond. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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325 Tropical Drive Osprey FL 34229

Osprey, FL325 Tropical Drive

Price$185,000

Est. Mortgage: $/month

Pending

MLS Number A4522008

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 1,500
  • Bathroom 2

This large, bight, super clean, manufactured home is in a 55 + active community. Lots of upgrades and was lovingly maintained by the owners. The 2 bedroom 2 full bath home can easily be converted to have a 3 bedroom for the occasional seasonal guest. A big eat in kitchen and dinning area flows into the over sized living space! Bright window with classic Bahama Shutters for the tropical style with sun protection. Luxury vinyl floor planking that seamlessly flows through out with rich wood tones to welcome you home. W/D inside the home. Large master bedroom with large attached private bath and walk in closet. The best location in the park with great views due to unobstructed community lots on N & S sides. Easy walk to the pool and clubhouse. A 10 x 10 storage for all your toys and tools. A patio for sunning and entertaining. Entire outside painted in 2020. Extra parking for company near by and over sized carport. Pictures do not do this home justice; It's a must see!

Listed by EXIT KING REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 24, 2022 . 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.