176 Homes For Sale in Osprey, FL

Sort by:
Est. Payment$8,200,000
3 Beds | 4 Baths | 3,311 Sqft

230 N Casey Key Rd, Osprey, FL 34229

House For Sale

Private Beachfront Peninsula Paradise, almost 9 acres, in Southwest Florida, perfect for a developer. This is the largest single-family Gulf-front property currently for sale in Sarasota County. Magnificent splendor! Once in a lifetime opportunity to own 8.83 Acres (6.25 upland, private lagoon, and submerged land) of Gulf (400 ft frontage) to Bay on Casey Key, one of the most prestigious old Florida addresses you can aspire to achieve. This island is the destination for people who love the Florida lifestyle but want a high level of privacy and seclusion. Bring your boat to your own private blue lagoon with dock. Mature landscaping with inspiring banyan and palm trees. Venice airport to fly in your private plane is just minutes away. Property should be able to accommodate a helipad too. Amazing three-generation family winter estate owned since 1951. The property includes a single-family Estate Cottage with a gorgeous granite kitchen, pecky cypress walls and ceilings, a guesthouse with a two-car garage, and a detached two-car garage. While livable, the value is in the land. You can build your dream home and enjoy the breezes and fresh Gulf air. Words do not do this property justice. Take a look at the photos and video, and see yourself enjoying the warm picture-perfect sunsets while you stroll your very own private beach. As per Sarasota County, there are three buildable lots.

Est. Payment$543,000
4 Beds | 3 Baths | 2,346 Sqft

661 Crane Prairie Way, Osprey, FL 34229

House For Sale

Serene and private western sunset views visible from this enchanting Lee Wetherington-built home in the maintenance-free community of Willowbend. Two lanais capture breezes and breathtaking views of the pool and sparkling lake. There is a peaceful waterfall for entertaining and zen-like relaxing. The brilliantly designed gourmet kitchen has been upgraded with exquisite cabinetry, granite and top-of-the-line Frigidaire Professional Series Appliances, including natural gas range. Wrap yourself in luxury in a sophisticated and spacious Ashley II split floor plan boasting tray ceilings, dramatic arches, abundant crown molding, wood valances & blinds, and a very spacious Master Suite with dual sinks and walk-in closets. On a practical note: new AC 2017, interior paint, new Hot Water heater 2019, newer tile floor in dining, newer carpet in bedrooms, toilets replaced to comfort level. High-speed internet, cable television, yard maintenance, as well as a community pool, spa, fitness center, pickleball court, and playground included in the low HOA fees. All this, and minutes to white sand beaches, Pine View School, as well as downtown Sarasota, Venice, and the new Osprey Publix. Toss aside notions of new construction, this one is better than new.

Let's get you that Dream Home!

Ron Gerdes

(941) 549-8942
Est. Payment$649,000
3 Beds | -- Baths | 4,364 Sqft

76 Osprey Point Drive, Osprey, FL 34229

House For Sale

This custom, Harry MacEwen built residence is located behind the exclusive gates of The Oaks Country Club, situated on more than a quarter-acre of property and surrounded by lush, manicured vegetation. Flourishing in lovely features, the light and airy interior includes crown molding, tray ceilings, plantation shutters, custom built-ins, formal dining a few steps from the generous living room, plus den with gas fireplace. Glass French doors in multiple rooms open to the pool deck and enhance this home's inviting atmosphere. The eat-in cook's kitchen has been updated and features hardwood flooring, granite countertops and backsplash, stainless-steel appliances (includes a six-burner Viking gas range with grill and Viking hood), planning desk, Butler's pantry, breakfast bar and dining nook. The split bedroom layout is ideal when you want to enjoy private nights. The master suite is tucked away in a quiet eastern spot. One guest suite occupies the west, while another spacious suite encompasses the second level. The Oaks is a secluded community overlooking Sarasota's beautiful bay and Spanish Point, located just a short distance from downtown Sarasota. Social club membership is required and offers more than 1,000 acres on the front of Little Sarasota Bay surrounded by luxurious residential communities. Enjoy first-rate amenities including two 18-hole championship golf courses, tennis courts, heated swimming pool, croquet, library, game room and three dining facilities.

Est. Payment$599,000
3 Beds | 2 Baths | 1,810 Sqft

121 Dory Lane, Osprey, FL 34229

House For Sale

Come Live on Vacation! Southbay Yacht & Racquet Club, one of the most desirable communities in the area, with a Deep-Water Marina, premiere location and low HOA fees! This Super Clean Move-In Ready 3 bedroom 2 bath has many upgrades and features gorgeous hardwood floors, new high-end kitchen cabinetry, granite counter-tops, plus matching bathroom vanities and granite. The pool has just been resurfaced and the Newer Tile Roof is less than five years old. Another plus is the numerous "pocket sliding doors" opening onto the large covered pool-side lanai, the walls of glass actually disappear which makes the lanai and pool area just another room of the house! Bedrooms all have new carpet, nice inside laundry room, large eat-in kitchen, over-size garage are a few more perks. The Southbay community offers residents the ability to walk, bike or golf cart to shopping and dining, plus walking trails, large clubhouse, community pool, fitness center, pickle ball and tennis courts in addition to the marina. Perhaps the best thing about Southbay is the location, nestled in between Sarasota and Venice and remarkably not one red light all the way to the Tampa airport! The beaches are just minutes away! Yes, you have found paradise!

Est. Payment$550,000
3 Beds | -- Baths | 2,240 Sqft

346 South Creek Drive, Osprey, FL 34229

House For Sale

*MOVE-IN-READY* NOW is the time! OWNERS HIGHLY MOTIVATED* Stunningly remodeled Arthur Rutenberg home in South Creek, in a gated, "West of the Trail", bay front community of just 69 exquisite residences. This 3/2 pool home has the classic split plan. Kitchen and living room each have a Tubular Sky-lite and the family room has 2 sky lights and a wood burning fireplace. The Guest Wing includes the Pool Bath and the Laundry Room. The paver pool deck has a Summer Kitchen and lush greenery! You want NEW, here is a partial list: Complete KITCHEN (all granite, hard wood cabinetry and stainless steel appliances), continuous flooring throughout, completely Re-Plumbed, New Roof, New Garage Door, New Master Bath, Master Bath Hurricane Window, Master Bath Jet Tub, Guest Bath, Laundry Room with Granite Counter tops and top of the line Bosch Washer & Dryer, an Invisible Fence, a newly replaced Back Flow Meter, New Hot Water Heater, New Leaded Glass Front Door, New Duct work and an epoxy floored garage as well as PGT windows throughout,a workroom in the garage and a well for lawn irrigation. Residents enjoy the community tennis courts, pickle ball court, playground, basketball court and a day dock. The neighborhood has class A schools including the famed Pine View School and is close to both Siesta Key and Casey Key (Nokomis) Beaches as well as Oscar Scherer State Park. Be sure to see this extensively remodeled home as it is truly a JEM .

Est. Payment$800,000
3 Beds | -- Baths | 2,778 Sqft

385 North Point Unit 604, Osprey, FL 34229

House For Sale

One or more photo(s) has been virtually staged. Lovely condo in Meridian at The Oaks Preserve. Ready for you to come and make it your own!

Est. Payment$1,200,000
3 Beds | -- Baths | 3,706 Sqft

42 Osprey Point Drive, Osprey, FL 34229

House For Sale

Have you been imagining what your home in Florida should look like? Well, think big! This 3 bedroom, plus office and bonus room, 3 bath custom built-home with whole house impact glass in The Oaks Bayside will not only meet, but exceed, every expectation you could have. Walk up the wide pavered driveway and you will immediately be beckoned to enter and explore all this special home has to offer. Step through the beautiful iron doors with eyebrow transom, and you are welcomed to the warm, and artfully designed space, that make this house the perfect choice for the country club lifestyle. Every detail is amazing, from the light-filled great room, open kitchen with high end stainless steel appliances, to the spacious master suite with an aquarium window, a door to the lanai, and a gorgeous bath with soaking tub, stand-alone shower and an enormous amount of storage. Stroll out onto the lanai and you know you will have found your sanctuary. Beautiful pavers surround the pool and spa, and extends to all the covered areas. This is the place to sit in solitude and take in the beauty of the tropics as the sun sets, or entertain and dine with a group of your friends, utilizing the outdoor kitchen. The original high-quality build of this house with garages for three cars, has been enhanced by recent updates that include LED lighting in the house and garage, a whole house water softener, salt system for the pool, new irrigation system, new gutters, and a 20 KW whole house generator. Tour this house and you will never want to leave; you will want to make it your own. And when you do, you can take advantage of all that the mandatory membership in The Oaks Club has to offer: the bayside community dock, two championship golf courses, 12 HAR-TRU tennis courts (4 lighted), a junior Olympic community pool, manicured croquet court, three on-site restaurants, and a wide variety of recreational and social options.

Est. Payment$1,600,000
5 Beds | -- Baths | 5,698 Sqft

468 Walls Way, Osprey, FL 34229

House For Sale

This 4 bedroom home with 4 baths, and 2 half bath enjoys one of the best locations in the Oaks Clubside. Idyllically situated at the end of a cul-de-sac, on a beautifully landscaped half acre lot, this home offers privacy, tranquility and beautiful lake views. From the moment you pull in to the pavered circular driveway you will be intrigued by this majestic home, and want to explore all it has to offer. Enter through the artfully designed door with leaded glass transom and side lights and you will immediately see how elegant this home is. The spacious lower level floor plan offers you everything you need for comfortable every day living to gracious entertaining with a formal dining room, gourmet kitchen with Butler's pantry and wet bar, breakfast room, office, family room and a large first-floor master suite with its own sitting room, access to the lanai, his-and-hers walk-in closets and a luxurious marble bathroom. Go up the stunning sweeping staircase and you have reached a second living space, perfect for guests or extended family. With two additional suites, a bonus room, and a second laundry space there is room and privacy for all in the amazing home. Exit the home from one of the many French doors, and you will find that the outside is just as incredible as the inside with a large covered area, an open-air pool and spa, huge deck and gorgeous views. There is so much to love about this home including intricate crown moldings, custom built-ins, fiber-optic lighting, cherry wood flooring, four stone and wood encased fireplaces and elevator, that you truly must see it to fully appreciate all it has to offer. Membership in The Oaks, Sarasaota's finest golf and country club, is available and required.

Est. Payment$600,000
3 Beds | -- Baths | 2,778 Sqft

401 N Point Road Unit 504, Osprey, FL 34229

House For Sale

Welcome home to this 5th floor residence in Meridian at The Oaks Preserve, with PRIVATE 2 CAR GARAGE and GOOD WATER VIEWS. As you step into the rotunda foyer you will immediately be struck with how spacious this 2,778 sq ft unit is. With three bedrooms, a den/study and formal dining room there is plenty of space for residents and guest alike. Plan your meals at the kitchen desk, and then decide where to serve them; there are plenty of options. Perhaps you'd like to have a pre-dinner cocktail on the screened balcony. Nestled above the tree tops this vantage point offers a good water view, and is the place to witness spectacular sunsets. No matter what you decide to do, you will find it delightful in this luxury condo. Outside you can enjoy the Meridian residents-only pool, spa and workout room, or take advantage of the offerings of The Oaks Clubside. With two distinct 18-hole championship golf courses, a top-tier tennis program with 12 HAR TRU tennis courts (4 lighted), WellFit Center, three onsite restaurants, and a wide variety of social and recreational options, The Oaks is truly the finest in country club living. Membership is available and required.

Est. Payment$650,000
3 Beds | -- Baths | 3,048 Sqft

58 Fairway Oaks Lane, Osprey, FL 34229

House For Sale

This beautiful three bedroom home with large office has only had one owner. Lovingly maintained, it offers easy-living; there are no steps throughout the house. Behind the gates of The Oaks Clubside, this home is beautifully situated on a private cul-del-sac. With a Southern exposure in the back, the screened lanai is the perfect place to enjoy the abundant sunshine as you spend a pleasant afternoon in the pool or spa. Or sit under the covered area in the shade, taking in the gorgeous panoramic lake and golf course views. Inside, neutral colors, tall ceilings and disappearing sliding doors make the open floor plan light and bright. From the leaded glass front doors to the beautiful lot with mature trees, everything about this house is perfect for living the country club lifestyle in comfort and quiet elegance. The Oaks, a private gated community close to world-famous gulf beaches, features two championship golf courses, 12 HAR-TRU tennis courts (4 lighted), a state-of-the art fitness center and wide variety of dining, social and recreational options. Membership is available and required.

Est. Payment$950,000
3 Beds | -- Baths | 2,778 Sqft

385 N Point Road Unit 803, Osprey, FL 34229

House For Sale

PRIVATE TWO CAR GARAGE, GORGEOUS WATER VIEWS! This penthouse-level 3 bedroom (plus study) 3 bath residence is the second largest unit available in Meridian at The Oaks Preserve. Step off your private elevator, open the doors and you are welcomed to a place you will be proud to call home. Greeted by gleaming diagonally laid wood floors, sunshine, and spectacular views, you will know that your dream of living the luxury condo lifestyle has come true. The spacious and open floor plan leaves plenty of room for day-to-day living, as well as entertaining. The kitchen is open and boast stainless steel appliances and has a breakfast bar for casual meals. There is a small dinette for intimate dining, and a separate dining room for larger, more formal gatherings. The master bedroom is a sanctuary with gorgeous views and a luxurious bath. The good-size bedrooms, and two additional bathrooms with walk-in showers, make it easy for guest to stay in privacy and comfort. The large screened balcony provides the ideal venue for relaxation. Imagine starting the day with a cup of coffee and the sound of the birds as they awake, an afternoon spent here with a good book and a cool drink, or toasting the end of another perfect day in paradise while taking in a breathtaking sunset. On the north side of the building this unit is a short walk to the Meridian residents-only pool, spa and workout room. And with the mandatory club membership, you may also take advantage of all the offerings of The Oaks Clubside: two incredible 18-hole golf courses, 12 HAR TRU tennis courts (four lighted), the state-of-the art 7,500 square foot WellFit Center, a junior Olympic community pool, three onsite restaurants, and a wide variety of social and recreational activities.

Est. Payment$349,000
3 Beds | -- Baths | 1,589 Sqft

496 Meadow Sweet Circle, Osprey, FL 34229

House For Sale

This charming move-in ready home is located in the Cottages of Rivendell, a tree-lined neighborhood of 84 maintenance free homes with its own community center, activities, and heated pool. This Ardendale model features 3 bedrooms, 2 baths, a large eat-in kitchen with 2 pantry closets, combination Great Room and dining area in a spacious open floor plan. French doors lead to a screened lanai surrounded by lush landscaping. Wood floors, tile in wet areas and carpet in 2 guest bedrooms. The 2-car attached garage has ample space for storage. Enjoy the walking path, community park and spectacular views of nature at its finest! This sought after community is conveniently located between Venice and Sarasota and is a short drive to beaches, boating, shopping and much more! Low maintenance fee covers all ground maintenance, water for irrigation, community pool and clubhouse.

Est. Payment$599,000
2 Beds | -- Baths | 2,104 Sqft

3968 Waypoint Avenue, Osprey, FL 34229

House For Sale

Relish the ease of newer luxury living at this Taylor Morrison built home, completed in 2017. You will immediately fall in love with this home's modern, move-in ready condition, just a few steps from the bay, with delightful community waterfront amenities and boating options. Flourishing in captivating builder upgrades, the sunlit ambiance of this contemporary residence is perfected by its lovely finishes throughout. The chic, 2,100-square-foot layout features a pleasing neutral decor, wood-grain Porcelain tile flooring, high tray ceilings, crown molding, impact front door and front windows, storm shutters, as well as Synergy Smart system. The open concept offers formal dining steps from the gourmet kitchen (featuring granite countertops and backsplash, natural gas stainless steel appliances, tongue and groove custom cabinetry, plus breakfast nook) that overlooks the great room and pavered pool deck beyond. Situated in a private spot, the master retreat features lush stain-resistant carpet, bay windows with lush views of the grounds, en-suite bathroom with separate commode room and walk-in closet. The den could effortlessly be converted to a third bedroom if that suits your needs. Outdoor entertaining is the perfect finishing touch, with its covered lounge and dining area (plumbing and electric installed for an optional summer kitchen), as well as the gas heated swimming pool. Bayside is a wonderful newer neighborhood located behind secure gates and overlooking the peaceful waters of Little Sarasota Bay. Residents appreciate the deep-water day dockage with a charming landing area, kayak storage and fishing pier. Enjoy sunny leisure walks and bike rides on Bay Street's Legacy Trail that is only minutes away.

Est. Payment$375,000
3 Beds | 2 Baths | 2,255 Sqft

1884 Amethyst Lane, Osprey, FL 34229

House For Sale

Nestled amid lush greenery in The Oaks Preserve community of Emerald Woods, this three-bedroom home on a cul-de-sac enjoys magnificent natural beauty and intimacy. One of only 36 homes, the residence is distinguished and comfortable with an open floorplan of coffered ceilings, crown molding, and nooks for taking in the surrounding serenity. A kitchen with breakfast nook and built-in desk area overlooks the pool and preserve. The master suite is large and filled with character, offering a sitting area for a quiet escape or reading alcove and two walk-in closets. Two additional bedrooms accommodate friends and loved ones, with one featuring custom built-ins for a future den or office. Towering trees and beautiful landscaping are best enjoyed by the quartz pool with waterfall. The Oaks Preserve is a maintenance-free community optimally located 15 minutes from Siesta Beach and 20 minutes from downtown Sarasota and Venice. Exclusive and vibrant with an active social calendar, the required Oaks Club membership affords residents 36 holes of championship golf, 12 lighted Har-Tru tennis courts, state-of-the-art fitness center, resort-style pool, bocce ball and croquet courts, and dining experiences.

Est. Payment$400,000
3 Beds | -- Baths | 1,999 Sqft

102 Turquoise Lane, Osprey, FL 34229

House For Sale

Cozy up in comfort in this 3 bedroom, 2 bath home in Emerald Woods. Completely remodeled and recently landscaped, this home offers so many fine details. The kitchen is a cook's delight with quartz countertops, high-end appliances and soft close cabinet doors and drawers. The master bedroom suite has a spacious bathroom with soaking tub and stand-alone shower. The other two bedrooms are good-sized, carpeted and light and bright. The main living areas feature wood-look ceramic tile. Step out of the large sliding doors and you will be delighted by the outdoor living space. The screened lanai is a tropical retreat. Dine under the covered area, watch tv, or relax in the new Hybrid system heated saltwater pool and spa. Surrounded by native plantings, there is no better place to enjoy a tranquil afternoon, or the serenity of the setting sun. Privacy abounds in this enclave of only 33 homes behind the gates of The Oaks Preserve. Membership in The Oaks Club, Sarasota's finest golf and country club, is available and required.

Est. Payment$474,900
3 Beds | 2 Baths | 2,238 Sqft

1345 Thornapple Dr, Osprey, FL 34229

House For Sale

One of the most sought-after models in Lee Wetherington built Maintenance-Free Willowbend. This Opal was built with many high-end finishes, and upgrades were added to make this a stunning residence. The open Great Room, with a rare opening to the kitchen, features 12-foot ceilings, triple sliders, double tray ceiling, oversized crown molding, Plantation Shutters, 8-ft doorways & chair rails. Privacy and tranquility from an ideally positioned parcel on a wide greenbelt with preserve views gives the feeling of spaciousness. Master suite with tray ceiling, sitting area, walk-in closets, and luxurious bathroom. Incredible gourmet kitchen with high-quality cabinetry, granite, stainless, and natural gas cooking. The covered lanai has a heated sparkling pool with an infinity-edge spa for seamless indoor/outdoor living. For peace of mind, easy install Armor Screen hurricane protection added in 2017. On a practical note, many recent notable upgrades: AC replaced with 5-ton Trane in 2017, re-screened lanai 2019, paver driveway and walkway, Pool/spa resurfaced in 2017 with new heater in 2019. Close to the community heated pool/spa, fitness room, and pickleball/basketball court. 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 short distance to the Osprey Publix.

Est. Payment$280,000
2 Beds | -- Baths | 1,449 Sqft

164 Explorer Drive Unit 103, Osprey, FL 34229

House For Sale

Absolutely stunning condo in the perfect location. Located between downtown Sarasota and Venice, you have access to the Legacy Trail, Bay Street Park, Osprey Fishing Pier, Historic Spanish Point, I-75 and more! This unit is in a GATED COMMUNITY with a WATER VIEW unlike any other. This GROUND LEVEL floor plan backs up to a lake and offers a split bedroom, PLUS A DEN, an OPEN CONCEPT FLOOR-PLAN, high ceilings, PROFESSIONAL DECOR, granite counters, large kitchen island, pantry closet, stainless steel appliances, and luxury chandelier and lighting throughout. Crown molding, tray ceilings and spacious bedrooms and bathrooms make this a very comfortable and luxurious condo. Live the lifestyle without the maintenance and expense. Enjoy the community POOL, CLUBHOUSE AND FITNESS ROOM. LOW TAXES, NO CDD. Unique Condo with EXTENDED GARAGE. Won't last long, call for a private showing today.

list-24px Created with Sketch. width="24" height="24" viewBox="0 0 24 24" version="1.2" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" overflow="visible" preserveAspectRatio="none" > version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >