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 North Point Road Osprey FL 34229

MLS Number A4552430

  • Condo
  • Mls Status Active
  • Square Feet 2,055
  • Bathroom 3
  • High School Riverview High

This picture-perfect 3 bedroom, 3 bath condo offers the perfect living space for those who seek luxury and comfort in a country club community. The elevator opens to your private foyer and upon entry you know you have entered a special sanctuary. Meticulously maintained, it has many custom features including an eat in kitchen with designer backsplash, granite counters, solid wood 42” upper cabinets and a Subzero refrigerator all in neutral tones. Beautiful solid wood Brazilian floors installed on the diagonal throughout, designer lighting fixtures, and custom designed silk drapes lend an air of elegance and uniqueness to this unit. This is not a cookie cutter look as many in the towers are. The Den/third bedroom has a custom designed built-in desk and lots of custom shelving. This is a perfect space for a pull-out couch for extra guests, but also be used as an office for the owner. The laundry room has an abundance of storage cabinets, and the guest bedroom and bath are situated away from the main living area for added privacy. You'll have your own climate-controlled storage area and convenient parking under the building, and be just steps away from the elevator. Your quiet and private balcony overlooks a preserve and features wonderful bay breezes as well as good views of the intracoastal waterway. Your eyes are immediately drawn to the mesmerizing views of the glorious sunsets and native birds on flight throughout the preserve. Peace of mind security with 24/7 guarded gate entry, coded building access, coded private elevators and building backup generator make for a lifestyle of easy living in the luxury and security of the Meridian II Towers at The Oaks. Spend a sunny Florida day at the Meridian residents-only pool with spa and fitness room, just steps from your building. Stroll the sidewalks through this beautiful preserve community or enjoy the lifestyle and many activities as a member of The Oaks Club. The Oaks Club membership is required, social or equity, which offers you exclusive privileges of two 18-hole championship golf courses, four pickleball courts, 12 Har-Tru tennis courts, croquet, bocce, gourmet dining in three restaurants, fitness and wellness centers and an Olympic size pool. Ready for immediate occupancy.

Listed by COLDWELL BANKER REALTY

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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134 Marys Chapel Court Osprey FL 34229

Osprey, FL134 Marys Chapel Court

Price$2,650,000

Est. Mortgage: $/month

MLS Number O6074376

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 5,521
  • Bathroom 8

Luxury coastal living in the heart of Sarasota! This gorgeous, remodeled 6 BR / 8 BA estate, with 3-car side-entry garage and upgraded luxurious pool area, is located in the exclusive Bayside neighborhood of the Oaks Club. Wide open floor plan features dual staircases, elevator, new gorgeous kitchen with hidden walk-in pantry, 2 fireplaces, and spacious family areas. Upstairs has a grand master suite and sauna. This move-in ready home has many NEW improvements from slate tile roof, HVAC, paver driveway, completely resurfaced pool with premium decking, gorgeous modern kitchen & bathrooms, luxury vinyl plank floors to upscale lighting throughout, and MUCH MORE. The second floor in-law suite contains a modern kitchen with the private bedroom and bath. Many amenities and upgrades throughout. 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, new regulation Croquet court, state-of-the-art Fitness center and junior Olympic, heated community Swimming Pool. Wind mitigation and 4-point inspection complete. This property won't last long!

Listed by BEYCOME OF FLORIDA LLC

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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599 Oak Bay Drive Osprey FL 34229

Osprey, FL599 Oak Bay Drive

Price$595,000

Est. Mortgage: $/month

MLS Number A4553355

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,037
  • Bathroom 2

Rarely available 3 bedroom 2 bath 2 car garage pool home located in the quaint neighborhood of Bay Oaks Estates convenient to Sarasota and Venice. This lovingly maintained one owner home has 2037 square feet and was built in 2002. New roof installed in 2020, granite counter tops in 2021 and pool equipment in only 2 months old. Some of the extras that this home features are wood cabinets, stainless steel appliances and tiled back splash along with new granite counter tops in the kitchen. The living room and dining room boast decorative columns and niches, crown molding, trey ceilings, recessed lighting and built in cabinets. In this split bedroom floor plan you will find ceramic tile on the diagonal through out the kitchen and living areas, laminate wood floors in the two bedrooms and carpeting in the oversized master bedroom. An aquarium window overlooks the pool area with sink and refrigerator on the lanai, perfect for entertaining. Inside laundry, walk in closets and decorative driveway and walkways complete this one-of-kind home. Hurry! This one won't last! (Professional photos coming soon)

Listed by BRIGHT REALTY

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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419 E Macewen Drive Osprey FL 34229

Osprey, FL419 E Macewen Drive

Price$2,100,000

Est. Mortgage: $/month

MLS Number A4553067

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 4,201
  • Bathroom 5

BEAUTIFUL CUSTOM-BUILT HOME situated on a Premium .72-acre direct golf course lake homesite. This 4,201 SF living home with a 3-car side garage entry offers many features that new homes don't offer today. Imagine 4-bedroom ensuite home for guests or family, plus an office/den in addition to 3 fireplaces located in the master bedroom, living room and family room. Features include a well-equipped kitchen, premium built-in wood cabinets, volume tray and coffered ceilings, crown molding, and a wet bar. Upon entering the foyer, you have an expansive view of the screened lanai with heated pool & spa, cook out area which overlooks the quiet 'Heron' golf course and lake. The Oaks has many amenities which include 2 18-hole championship golf courses, 12 Har-Tru Hydro-Grid tennis courts, 4 Pickleball courts, Fitness center, junior Olympic heated community pool plus the elegant CLUBHOUSE. Excellent location just a short distance to Gulf beaches, Legacy Bike Trail, Pine View High School, Publix, Lowes, Walgreen's/CVS and Target. MEMBERSHIP IS MANDATORY. THE OWNER HAS RELOCATED. THE HOME IS PRESENTLY VACANT AND CAN CLOSE ANYTIME. SEEING IS BELIEVING!!

Listed by RON STAHL REALTY

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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526 Latitude Lane Osprey FL 34229

Osprey, FL526 Latitude Lane

Price$760,000

Est. Mortgage: $/month

Open House

MLS Number A4552141

  • Residential
  • Next Open House: Sat 11/26 1:00 pm. to 4:00 pm.
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,165

This elegant 3 bed + den / 2 Bath / 2 car garage home with private pool and STUNNING LAKE VIEWS is just 10 minutes to Nokomis Beach. The LIGHT, BRIGHT, OPEN CONCEPT floor plan features tray ceilings with rich crown molding, elegant arches, niches, and built-ins that announce that you are in a quality-built Lee Wetherington custom home. The spacious owner's suite features 2 walk-in closets with custom cabinetry. The master bath contains his and hers sinks as well as a door which leads to the pool area and serves as a pool bath. The 13'x13' den at the front of the home is perfect for a home office or flex space and features a large bay window with plantation shutters. In the gourmet kitchen you will find Corian counters, rich 36” wood cabinets, gas range, breakfast bar perfect for entertaining, and dinette area with fabulous views of the pool and lake. The pool area features one of the largest pools built in the neighborhood and is set-back from surrounding homes which enhances privacy. Mature landscaping provides additional privacy and shade. The tropical pool area has raised planters and pleasant water features which add to the peaceful setting. The desirable SW exposure and private cul-de-sac location make this one of the best homesites in the entire community. The highly sought-after boutique enclave of Willowbend is a warm and inviting neighborhood featuring an active social calendar and active lifestyle where homes rarely become available. THERE ARE NO CDD FEES and a low HOA of just $328/month which INCLUDES YARD MAINTENANCE, IRRIGATION WATER, BASIC CABLE TV, HEATED COMMUNITY POOL AND SPA, FITNESS CENTER, 2 PICKLEBALL COURTS AND PLAYGROUND. The location is ideal due to its close proximity to Oscar Scherer State Park, The Legacy Bike Trail, and Casey Key Marina and the Intercoastal Waterway. Minutes to Publix grocery, restaurants, A rated schools including Pine View School, as well as Historic downtown areas of Venice and Sarasota. This home is an ABSOLUTE MUST SEE if you are seeking a quality built home that's close to the beach.

Listed by RE/MAX ALLIANCE GROUP

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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803 Placid Lake Drive Osprey FL 34229

Osprey, FL803 Placid Lake Drive

Price$699,000

Est. Mortgage: $/month

Open House

MLS Number A4553140

  • Residential
  • Next Open House: Sun 11/27 1:00 pm. to 4:00 pm.
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,009

Welcome home! This beautiful property in Rivendell is waiting for you. Set on almost a quarter of an acre lot, amidst a lovely vista of native Florida preserve. In this serene setting, you can enjoy your backyard, heated pool, or sit on your screened-in deck and lanai and watch the western sunset skies in the evening and/or enjoy your morning coffee in nature, with the added bonus of both a convenient pool half bath and deck outdoor shower. The 2 bedrooms plus a den/home office, could easily be converted into a 3rd bedroom or flex room with Murphy Bed, which lends itself well to modern living. Recently added, beautiful neutral flooring throughout, along with a remodeled kitchen, and updated guest bathroom really modernize the look and feel of the home which feels very in the moment. Completely move-in ready, start living your best Florida life in the less busy and quaint town of Osprey, which is a slice of Old Florida located in between Sarasota and Venice. Choose your pick of beaches, Nokomis, Venice, Caspersen, or Siesta Key, nature trails, visit Oscar Scherer State Park, and numerous, nearby waterfront restaurants and tiki bars. Located a stone's through from the state's best-rated (per Niche) elementary, middle and high school, Pine View School for the Gifted. Give your family the very best public education possible. Close to I-75, shops, downtown Sarasota and its 21 Zagat-surveyed restaurants, Saturday farmers market, theatre, opera, museums, orchestras, and ballet. What are you waiting for? Come and make this home yours and begin enjoying the good life today.

Listed by PREMIER SOTHEBYS INTL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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567 Macewen Drive Osprey FL 34229

Osprey, FL567 Macewen Drive

Price$1,650,000

Est. Mortgage: $/month

MLS Number A4552797

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 3,556
  • Bathroom 3

What's better than living on a golf course? Living on a golf course in one of the finest communities on Sarasota's beautiful Gulf Coast. Situated behind the gates of The Oaks, this spacious 4 bedroom plus office, 3 bath home offers everything you could want for luxury living. A large pavered circular driveway leads to the front of this extraordinary home. Enter through the double front doors with leaded glass and you will immediately see all the potential it has for the best country club lifestyle. The formal living room with fireplace looks out over the pool and spa. Situated on the 15th hole of the Heron Course, if offers lovely golf and lake views. The Southern exposure brings plenty of sunshine, and the many windows, doors and transoms make the interior light and bright. The master bedroom is spacious and features an amazing, updated master bath. With 3 additional bedrooms, a den, office and open kitchen with breakfast nook, formal dining room and large laundry room, there is plenty of room to live, work and play in this 3,556 square foot home. Additional features include a newer roof, oversized 3 car garage, plantation shutters, tray ceiling and ceiling fans, and art niches; this is a true MUST SEE house. The Oaks Club has two 18-hole championship golf courses, twelve HAR-TRU tennis courts (4 lighted) and an extraordinary tennis culture; 4 new pickle ball courts, WellFit, an over 7,500 square feet state-of-the-art fitness center, three onsite restaurants, and a wide array of social activities and programs. Club membership required with home ownership.

Listed by COLDWELL BANKER REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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410 N Tamiami Trail Osprey FL 34229

MLS Number A4553083

  • BusinessOpportunities
  • Square Feet 7,500

Rare opportunity to purchase a highly successful and profitable business with an excellent reputation and repeat clientele. Business is well equipped with lifts, alignment rack, etc., and all things necessary to start earning from day one. The return on investment is in the double digits with a tremendous upside for growth.

Listed by RE/MAX PLATINUM REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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14021 Bellagio Way Osprey FL 34229

Osprey, FL14021 Bellagio Way, Unit 305

Price$1,050,000

Est. Mortgage: $/month

MLS Number A4552651

  • Condo
  • Mls Status Active
  • Square Feet 2,190
  • Bathroom 3
  • High School Pine View School

This absolutely stunning 3 bedroom/2.5 bathroom condo has incredible intracoastal water views from all bedrooms and is located in a quiet & gated community that is well-equipped with everything you will need to enjoy the highly desired Florida lifestyle, including a marina!. This condo has been freshly painted inside, has brand new lighting and faucets, and has hurricane impact windows and doors throughout. The spacious and airy living and dining room area leads you to the gourmet eat-in kitchen which offers beautiful wood cabinets, stainless steel appliances, granite countertops, a large walk-in pantry, and oversized island/breakfast bar where you can prepare a nice meal and entertain guests with ease or catch up with the family over coffee in the mornings. The amazing primary suite has the best view in the house, and with a private entrance to the patio, it will become your own little sanctuary where you can retreat after long days. There is a grand walk-in closet with built-ins galore to help keep you organized and the en-suite bathroom has a luxurious stand alone shower, a garden tub and water closet. With 2 more bedrooms plus a den you will have many options to host company and also have space for an in-home office, library or whatever your heart desires. This condo also features an indoor laundry room with soaker sink, plenty of storage and 2 convenient covered, under-building parking spaces. This wonderful community is surrounded by carefully maintained landscaping and has many amenities to enjoy such as a 24/7 sparkling heated pool, spa, sauna, indoor fitness center, and a World Class Full Service Marina w/ boat slip and kayak launch. The dockmaster reported that additional wet slips will be available in the next couple of weeks. Centrally located just minutes from Nokomis Beach and only 20 minutes to Siesta Key, this convenient location allows smooth traveling to area waterfront restaurants, shopping, golfing, and cultural activities. Do not wait to make this slice of paradise your own...schedule a tour today!

Listed by FIRST LIGHT REAL ESTATE

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$
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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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104 Shoreland Drive Osprey FL 34229

Osprey, FL104 Shoreland Drive

Price$449,500

Est. Mortgage: $/month

MLS Number N6123866

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 2,363
  • Bathroom 2

Just listed WEST of the TRAIL. 3 bedroom/2 bath POOL HOME with FLEX ROOM/IN-LAW SUITE! Freshly painted and landscaped, this beautiful home is ready for you to make your own! The tranquil and inviting 2,363 sq. ft. split floor plan consists of a primary suite, 2 additional bedrooms, and a bath plus a generously sized flex room with private bath. Highlights include a Craftsmen style floor-to-ceiling tongue and groove entrance/foyer, built-in cabinetry, and wood burning fireplace in the living room. Start your morning in the bright eat-in kitchen that features a stainless appliance package, solid wood cabinetry, and tile backsplash. Enjoy entertaining in the adjacent living/dining rooms or bring the party onto the LANAI with OUTDOOR KITCHEN. A SPA STYLE POOL is just the right size to cool off and have some fun while leaving room for lounging and dining. For added convenience, a bathroom is accessible from the lanai. The nice size owner's suite includes a walk-in closet and sliders out to the pool deck. Two additional guestrooms share a bath off the hall. The in-law suite has a separate entrance and laundry room. The lovely landscaped yard features palms and native Florida plants, an irrigation system and multiple sheds for storage. Located in Towns-End Shores, a non-deed restricted neighborhood that has a park with a kayak/paddleboard launch into the canal of the intercoastal. Osprey is just minutes away from area beaches (Nokomis, Venice, Siesta Key), The Legacy Trail, and Oscar Scherer State Park. There are excellent schools like Pine View School and Sarasota's flagship regional medical center, Sarasota Memorial Hospital nearby. And a new public boat ramp is just a mile away at Blackburn Point. Close to I75 for quick access to downtown Venice and Sarasota cultural activities and nightlife. Don't miss out, call now to schedule your private tour today!

Listed by KELLER WILLIAMS ON THE WATER

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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608 N Casey Key Road Osprey FL 34229

Osprey, FL608 N Casey Key Road

Price$7,750,000

Est. Mortgage: $/month

MLS Number A4552859

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 3,086
  • Bathroom 3

Opportunities are endless with this extremely unique 1.5 acre property situated on North Casey Key Road. Watch the sunrise from your private 175' frontage on Little Sarasota Bay (with permits for docks) and watch the sunset from your private 175' beach on the Gulf of Mexico. The 1.5 acres of this unique property allow its future owner to have utmost privacy. The property currently still has the original 1916 4,375 SqFt homestead, along with 2 additional footprints; a detached garage, and small guest quarters. Whether your choose to restore the original homestead or simply bring your architect and your imagination to build your dream property... The opportunities are endless! Come discover the hidden paradise of Casey Key, nestled between Sarasota and Venice.

Listed by AVENUE REAL ESTATE GROUP INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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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409 North Point Road Osprey FL 34229
Pending

MLS Number A4552340

  • Condo
  • Mls Status Pending
  • Square Feet 2,055
  • Bathroom 3
  • High School Riverview High

This 3 bedroom, 3 bath 9th floor penthouse with PRIVATE 2 CAR GARAGE in Meridian at The Oaks Preserve offers the perfect living space for those who seek luxury and comfort in a country club community. Updated and meticulously maintained, this residence's open, spacious floor plan features a beautiful new kitchen with new stainless steel appliances and quartz countertops. Freshly painted, and with new oak wood floors, the interior is pristine. Each room is light-filled and most offer lovely water views during the day, and spectacular sunsets as the day turns to dusk. Spend a sunny Florida day at the Meridian residents-only pool with spa and fitness room, just steps from the building. Or take advantage of everything else The Oaks, Sarasota's premier golf and country club, has to offer, 2 championship golf courses, 12 Har-Tru tennis courts (4 lighted), pickleball and croquet courts, a state-of-art WellFit center, incredible dining options and a celebrated social calendar. Club membership is required with homeownership.

Listed by COLDWELL BANKER REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to StellarMLS as of November 26, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or StellarMLS. 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.