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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154 Lookout Point Drive Osprey FL 34229

Osprey, FL154 Lookout Point Drive

Price$995,000

Est. Mortgage: $/month

Pending

MLS Number C7450058

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 4,578
  • Bathroom 4

Incredible Large modern home in Southbay Yacht and Racquet Club offers Five thousand plus sq ft of LUXURY! As you enter through Double Leaded Glass doors into the Foyer with Grand Staircase plus views of the oversized Dining and Living Rooms with coffered ceilings and crown molding. Features: New METAL Roof and Gutters, paint inside and out, NEW porcelain and marble floors throughout. All rooms are OVERSIZED and OPEN, the amazing Family room has a stone faced wood burning Fireplace plus boasts a second dining area. Large gatherings are easily entertained. Plus the amazing Chef's KITCHEN boasts a COPPER Farm House sink and faucet, wine cooler, double oven, built in microwave, pantry, wet bar and appliance garage. All this including two Breakfast Bars, top of the line appliances and so many extras. The massive Master Suite with pool access, double walk in closets, plus claw footed tub, bidet, and separate shower. One of a kind den / office or Fourth bedroom with TEAK Walls and Custom Floor can be private by closing the double pocket doors. Upstairs Family or Guests will enjoy two oversized bedrooms with new BATHROOM / Shower / double sinks and vanity. Large Foyer with French doors for Privacy. Plumbing system replaced and upgraded throughout excluding Master, new air conditioner plus so much more. Entertain by the oversized pool and spa. The ESTABLISHED Community of Southbay Yacht and Racquet Club with INTER COASTAL access offer: Recreational Facilities to include a deep water MARINA with over 150 boat slips, PWC docks, plus 175 vessels, up to 55 ft. Kayak facilities, Sport Courts for Tennis and Pickle ball, Bocce and Shuffleboard courts. A children's playground and miles of paths in a park-like setting. This is a once in a life time opportunity to BOAT, PLAY and live the FLORIDA DREAM!

Listed by MAXIM LLC

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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259 Osprey Point Drive Osprey FL 34229

Osprey, FL259 Osprey Point Drive

Price$1,325,000

Est. Mortgage: $/month

MLS Number A4513309

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 3,867
  • Bathroom 4

Set gracefully among lush landscaping on a large lakefront lot in the gated waterfront community of The Oaks Bayside, this stunning Bo MacEwen-designed, single-story home is welcoming from the moment one approaches the long paver driveway and courtyard entry. The soaring ceilings, panel and crown molding, 7-inch baseboards, marble and parquet floors, huge banks of windows and doors are just some of the features that make this home truly special. The expansive living room opens out onto the covered patio through multiple sets of French doors, extending the space and highlighting the impressive open pool area and lakefront setting. The dining room is perfect for a dinner party or holiday family gathering, while the adjacent kitchen and breakfast nook provide a casual, intimate and relaxed feel. The bonus room also opens to the pool area and is the perfect spot for relaxing after a day of golf or after being on the water. Positioned to maximize the tranquil lake view, the master suite is an oasis and boasts two walk-in closets, a dressing area, dual vanity, tub and shower. Each of the two guest bedrooms has its own private bath. A powder room, large laundry room and two-car garage complete this stunning residence. Some of the recent updates include new hurricane shutters, Culligan water softener system and ADT security system. Oaks Bayside is a gated bayfront community with a day dock and is part of The Oaks Club, one of the area's most beautiful clubs, featuring award-winning golf, tennis, pool, WellFit Center, croquet lawn and multiple dining options. 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.

Listed by PREMIER SOTHEBYS INTL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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720 N Macewen Drive Osprey FL 34229

Osprey, FL720 N Macewen Drive

Price$1,250,000

Est. Mortgage: $/month

Open House

MLS Number A4514781

  • Residential
  • Next Open House: Sun 10/24 10:00 am. to 1:00 pm.
  • Area Osprey
  • Mls Status Active
  • Square Feet 3,308

**DON'T MISS THIS OPPORTUNITY** Situated on an Extraordinary Lot with stunning water view while looking out toward the 13th Green of The Oaks' EAGLE Course, this Gorgeous, impeccably maintained Home offers an Ideal, Single-Story, Open Floorplan with premium features throughout including Onyx and stone countertops, solid wood cabinets, crown moldings, vaulted ceilings, circular driveway, magnificent landscape and much more! The neighboring preserve offers an ideal Private setting as you enjoy the pinnacle of outdoor living with an expansive lanai, wonderful Outdoor Kitchen and Heated Pool & Spa. Newer A/C units (2019). 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. **MUST SEE 3D VIRTUAL TOUR and AERIAL VIDEO**

Listed by GENEROUS PROPERTY

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%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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149 Puesta Del Sol Osprey FL 34229

Osprey, FL149 Puesta Del Sol

Price$1,750,000

Est. Mortgage: $/month

Pending

MLS Number A4514882

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 4,615
  • Bathroom 4

Welcome to Sunset Place. This custom built home offers a deeded boat dock and 10,000 lb. lift just steps from your front door. Direct access to Little Sarasota Bay and the Intracoastal are great for the boating enthusiast. Community gazebo and fishing pier provide the perfect setting to watch the glorious colors of the sunset. Located in a small gated community with 8 private residences conveniently located between Sarasota and Venice. The entry foyer with travertine flooring and marble insets opens to the living room overlooking the pool and features volume ceilings, clerestory windows and fireplace. The master bedroom includes a 11x13 sitting area with fireplace, large aquarium window, sliders to the pool and two walk in closets. The master bath was recently remodeled and features new jetted free standing tub, porcelain tile, quartz counters with dual sinks and make up area and large walk in shower. Office with tray ceiling, wood flooring, French doors and built ins. Throughout the home you will find tray ceilings, crown molding, built-ins and custom woodwork. The spacious kitchen includes a breakfast bar as well as an eat in area, travertine flooring, granite counters, wood cabinetry with pull-outs, built-in desk and Kitchen Aide appliances. The kitchen is open to the family room with cathedral ceilings and a third fireplace, two sets of sliders opening to the pool. All on one level for easy of living you will find 4 bedrooms, an office and 3 and ½ baths. All bedrooms have walk in closets. Guest bedroom with En suite bath. Two additional bedrooms with new wood flooring. Second bath has been remodeled with quartz counters and dual sinks. Paver decking surrounds the 13X26 pool and spa with planters, fountains and a covered area that is 18x32 with built in bar area. The side entry three-car garage has walls of custom built-ins and epoxy flooring. Wonderful, spacious home with a home for your boat. Florida lifestyle awaits you!

Listed by MICHAEL SAUNDERS & COMPANY

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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242 Washington Avenue Osprey FL 34229
For Rent

MLS Number A4514982

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

Lovely 2 Bedroom, 1 Bath Home in Osprey. Carpet and tile throughout, Window Blinds, Private Fenced Back Yard. Outside Storage with hookups for Washer and Dryer. Additional Storage Shed. Wooden Decking both front and backyard. No pets. No Smoking. Showings by appointment only. EACH prospective resident who is 18yrs old + must fill out a separate application. Make sure to upload ALL required documents. Not doing so will delay your application. You will hear back within 48 business hours of your application. Basic Qualification Criteria: GROSS income (before taxes) should be approximately 3-times rent. We conduct national, background, eviction, credit and employment checks for all prospective residents 18yrs old +. Rent: $1,300/m Base Deposit: $1,650 (with good credit) Background Checks: $75 (each person 18yrs+) Your deposit is due at lease signing. First month's rent is due the day you move in.

Listed by REAL PROPERTY MANAGEMENT

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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1287 Thornapple Drive Osprey FL 34229

Osprey, FL1287 Thornapple Drive

Price$525,000

Est. Mortgage: $/month

Pending

MLS Number A4514869

  • Residential
  • Area Osprey
  • Mls Status Pending
  • Square Feet 2,153
  • Bathroom 2

Stunning Lee Wetherington-built residence in the maintenance-free landscaping community of Willowbend. Fantastic location across the street and just steps from the large, heated community pool/spa, gym and pickleball court. Poised on a corner lot with a wide paver driveway and partial lake views from the lanai. The home was built with many high-end finishes and upgrades, central vacuum, 8-foot doorways, abundant crown and chair molding. The open great room plan also features 12-foot tray ceilings, triple sliders, plantation shutters, built-in entertainment shelving and tile on diagonal. The lanai is spacious, set on a coveted southern exposure. Master suite with tray ceiling, sitting area, walk-in closet and luxurious bath. Incredible gourmet kitchen with high-quality cabinetry, built-in oven and cooktop. Natural gas is available in the community, with a gas stub to convert the current electric cooktop to gas. On a practical note, AC was replaced in 2014. Willowbend has low monthly fees with complete landscaping care, high-speed internet and cable. Minutes to beaches, shopping, restaurants, Legacy Bike Trail, Pine View School and a short distance to the Osprey Publix.

Listed by PREMIER SOTHEBYS INTL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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Glenwood Avenue Osprey FL 34229

Osprey, FLGlenwood Avenue

Price$111,000

Est. Mortgage: $/month

MLS Number A4514713

  • Land
  • Area Osprey
  • Mls Status Active
  • Acreage 0.14
  • Subdivision Osprey Park 2

Bring your own builder to Design and Build, or let Courtyard Modern do it for you! Up to you! Many modern homes to choose from, or start from scratch! NO HOA, NO DEED RESTRICTIONS, Just Freedom to Make Your Own Decisions. Just a Short Drive to Waterfront Dining, Boating, Fishing, Nokomis Beach/Casey Key (7 Miles), and Siesta Key Beach (8 Miles)! The Legacy Bike Trail is Nearby and there is a Kayak Launch Just a Few Blocks Away. Just Around the Corner from Historic Spanish Point, Oscar Scherer State Park, and Blackburn Point Park. Convenient to Venice AND Sarasota! Looking for a Buying Opportunity to be Close to It All! 2 separate lots are available. $111,000 each.

Listed by COURTYARD MODERN

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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Glenwood Avenue Osprey FL 34229

Osprey, FLGlenwood Avenue

Price$111,000

Est. Mortgage: $/month

MLS Number A4514705

  • Land
  • Area Osprey
  • Mls Status Active
  • Acreage 0.14
  • Subdivision Osprey Park 2

Bring your own builder to Design and Build, or let Courtyard Modern do it for you! Up to you! Many modern homes to choose from, or start from scratch! NO HOA, NO DEED RESTRICTIONS, Just Freedom to Make Your Own Decisions. Just a Short Drive to Waterfront Dining, Boating, Fishing, Nokomis Beach/Casey Key (7 Miles), and Siesta Key Beach (8 Miles)! The Legacy Bike Trail is Nearby and there is a Kayak Launch Just a Few Blocks Away. Just Around the Corner from Historic Spanish Point, Oscar Scherer State Park, and Blackburn Point Park. Convenient to Venice AND Sarasota! Looking for a Buying Opportunity to be Close to It All! 2 separate lots are available. $111,000 each.

Listed by COURTYARD MODERN

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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409 N Point Road Osprey FL 34229
Pending

MLS Number A4514610

  • Condo
  • Mls Status Pending
  • Square Feet 2,594
  • Bathroom 3
  • High School Riverview High

Welcome home to Meridian IV at The Oaks Preserve. Invite family and friends through the secure lobby into a private elevator access to only your front door. This end unit boasts over 2,500 square feet, three bedrooms and bathrooms, plus a flex room which can serve as formal dining, den, or study. Your primary bedroom has direct access to the screened-in patio with beautiful preserve views and electric storm shutters. This home also features its second bedroom with additional en-suite bathroom and walk-in closet, great for house guests. This home has zoned AC and heating, eat-in kitchen, additional locked owner storage on the second floor, and two assigned parking spaces under the building with remote entry into the parking garage. The Oaks Club Membership is mandatory.

Listed by MICHAEL SAUNDERS & COMPANY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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249 Shell Midden Court Osprey FL 34229

Osprey, FL249 Shell Midden Court

Price$3,100,000

Est. Mortgage: $/month

MLS Number A4514402

  • Residential
  • Area Osprey
  • Mls Status Active
  • Square Feet 4,620
  • Bathroom 5

Beautiful country French home on two lots in a private cul-de-sac location. Designed by Bo McEwen and featuring outstanding millwork with double and triple crown moldings, solid wood doors, soaring ceilings and large open rooms with ample closets and storage. Huge kitchen with Wolf 6 burner gas stove with two ovens; two additional wall ovens, limestone island, marble counters and farmer's sink make cooking a pleasure. Adjacent dining room is filled with light from huge windows and features an octagonal vaulted ceiling. Each bedroom is en-suite and each has large walk-in closets;the storage is amazing.There is a 4th suite on the 2nd level and is an ideal bonus room, office or guest suite.French doors lead from the major rooms to a private brick pavered patio and pool. Absolute seclusion is afforded with no near neighbors, so for the person who enjoys peace and quiet this is ideal. Located on Oak's Bayside just steps from the bay, the private dock affords kayaking or a view of the colorful Florida sunsets. House was re-roofed in the spring and recently painted and ready for immediate occupancy. This is a signature property unlike any other property in the Oaks and must be seen to be fully appreciated. Oaks Club membership is required with a purchase.

Listed by CROWN PROPERTIES GROUP INC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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Cordes Street Osprey FL 34229

Osprey, FLCordes Street

Price$229,990

Est. Mortgage: $/month

MLS Number A4514399

  • Land
  • Area Osprey
  • Mls Status Active
  • Acreage 0.25
  • Subdivision Cordes Cove

NO HOA! Excellent location, close to everything, including our famous Siesta beach and Nokomis beach! Build your Dream Home on the water with 102 ft of canal frontage! You can canoe from your backyard to the Bay. Imagine living in paradise where you can enjoy beautiful beaches, Sarasota downtown, Venice historical district, Legacy trail for bicyclists and not only, Ringling Museum, St Armand Circle and beautiful Lido Key, Mote aquarium and the list goes on and on... Check out the neighboring North Creek Estates, Palmer Ranch, and The Oaks gated communities with million dollar homes! The adjacent lot is available for sale as well. Building plans and existing survey are available per request.

Listed by VETERANS REALTY INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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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tbd Cordes Street Osprey FL 34229

Osprey, FLtbd Cordes Street

Price$229,990

Est. Mortgage: $/month

MLS Number A4514558

  • Land
  • Area Osprey
  • Mls Status Active
  • Acreage 0.32
  • Subdivision Cordes Cove

NO HOA! Excellent location, close to everything, including our famous Siesta beach and Nokomis beach! Build your Dream Home on the water with 120+ ft of canal frontage! You can canoe from your backyard to the Bay. Imagine living in paradise where you can enjoy beautiful beaches, Sarasota downtown, Venice historical district, Legacy trail for bicyclists and not only, Ringling Museum, St Armand Circle and beautiful Lido Key, Mote aquarium and the list goes on and on... Check out the neighboring North Creek Estates, Palmer Ranch, and The Oaks gated communities with million dollar homes! The adjacent lot is available for sale as well. Building plans and existing survey are available per request.

Listed by VETERANS REALTY INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to MFRMLS as of October 19, 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.