Osprey Real Estate, Homes and Condos for sale

All Osprey homes currently listed for sale in Osprey as of 09/21/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Osprey homes for sale or other Osprey real estate, please contact us and one of our knowledgeable Osprey REALTORS® would be pleased to assist you.


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$7,900,000
814 N CASEY KEY RD, Osprey FL 34229
4
BEDS
6
BATHS
6,552
SQFT
$1,206
$/SQFT
1.19
ACRES
2011
BUILT
"Throughout his illustrious career, gold medal winner from the American Institute of Architects, Guy Peterson, believes in essentialism a concept that demands design by analysis and reduction, rather than stylistic imitation and embellishment. Peterson, in collaboration with international architect and designer Robert Couturier, general contractor, Michael K. Walker & Associates and the current owners, spared no efforts in design, resourcing of materials or monetary expenditures in creating this magnificent Gulf to Bay contemporary masterpiece; that s won multiple design awards. Located on the coveted north end of the barrier island of Casey Key, this 3-level residence stands as a beacon of achievement in architectural design, yet inside, it lives with comfort, spaciousness and minimalistic style. Throughout the home, the shell concrete floors and mahogany surfaces bring elements of the outdoors in, creating an environment that is enriching and peaceful. And the abundance of hurricane strength windows and sliding doors, that stretch nearly everywhere from floor to ceiling and from wall to wall, bring in views of the ocean and saltwater pool in the front and Sarasota Bay and the old-growth Gnarly Oak trees in the back. This 1.2 acre home, which boasts 4 en-suite bedrooms, 2 half baths, a spacious office, elevator, 4-car garage, a dozen outdoor terraces and sun decks, reflection pools, a dock with lift & an ultra-premium kitchen with opaque glass surfaces, offers a rare ownership opportunity."
$6,499,000
411 N CASEY KEY RD, Osprey FL 34229
9
BEDS
11
BATHS
9,127
SQFT
$712
$/SQFT
1.10
ACRES
1977
BUILT
"PRICE REDUCED-1.5M-Live like a midcentury Hollywood starlet transported to the modern era in a stunning seaside one-of-a-kind estate. This coveted North Casey Key, 300-foot Gulf of Mexico frontage property consists of two remarkable homes of 4,000 and 5,000 square feet in a completely private walled-in compound consisting of three lots. The main residence has dramatic dark marble floors, oversized crown molding, brass touches and other midcentury decorative accents that turn this residence into a statement piece. Between the two residences, relax by the resort-style pool or cool off after a friendly tennis match. Host a weekend retreat in the equally stunning guest residence. Matching the Art Deco-style of the main house, the guest enclave includes a chef kitchen, dining room and fireplace. Each of the five bedrooms includes an en-suite bathroom. The lushly landscaped residence has sweeping views from multiple balconies and decks and guaranteed stellar sunset views from every angle. Sun, sand, sea and luxury combine to complete this fashionable resort compound. Proximity to downtown Sarasota or Venice with privacy that s hard to match, and now at a price that s hard to beat."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $7,995,000 TO $6,499,000 
$5,495,000
1044 N CASEY KEY RD, Osprey FL 34229
6
BEDS
8
BATHS
6,829
SQFT
$805
$/SQFT
1.20
ACRES
1937
BUILT
"LAFFIN PLACE A Gated Bayfront Estate on 1.2 acres on the private North end of Casey Key with deeded access to a private beach to enjoy spectacular sunsets. The property with main house, guest house & bunk room, both with separate baths offers nearly 7000 square feet of living space. The lush landscaping with mature stately oaks & many inviting outdoor terraces and patios, overlook the ICW and views of the Gulf of Mexico. An enclosed boat house with observation deck can store a 24 foot boat and the dock accommodates a 45 foot boat. The main house offers 5 bedrooms, 5 full baths & powder room. Many of the rooms on the main floor, including the master suite, open to screened porches with spectacular views of the bay. The property has 3600 sqft of outdoor living space, including an outdoor kitchen & dining area. A chef s kitchen with a breakfast area and fireplace, offers 2 dishwashers, stainless appliances, ice maker & 6 burner gas oven. The living room has a fireplace separate dining & family rooms. Upstairs you will find a bedroom, den, bonus room opening to a terrace, porch, and widow's walk to view magnificent sunsets. The detached guest cottage has an updated bathroom and separate bunk room with private bath. Water features within the property include a spacious walled pool and screened courtyard with one of 4 fountains found on the grounds. Built in 1937, the home is reminiscent of Casey Key when vacation cottages were built for entertaining in harmony with the naturalness of the Island environment."
$5,250,000
916 N CASEY KEY RD, Osprey FL 34229
6
BEDS
6
BATHS
5,318
SQFT
$987
$/SQFT
1.50
ACRES
1973
BUILT
"Location, Location, Location! NEW PRICE ADJUSTMENT! North Casey Key beachfront tropical oasis. 200ft of private beach on the Gulf, 2 homes on the beach, main residence on the bay w/dock & lift. Once on the property you are amazed by the mature tropical lush botanical garden landscaping surrounding the home. Through the front doors of the 3 BR main house you have luxurious neutral marble throughout your great room, kitchen & living room. The living room overlooks the Bay, access to the pool, volume ceilings, fireplace & wet bar w/exotic finishes that are sure to WOW. In the kitchen you can enjoy top of the line appliances by Thermador while enjoying friends/family in the living room, or while gathering around the breakfast bar. The master bedroom is the perfect place to relax w/French door access to the pool & Bay. The master bathroom is adorned w/exquisite finishes. The main house has a pool & lanai w/pool cabana, outdoor shower, & Bay views. There is a large patio that extends to the private dock w/lift. Continue to the other side of the estate there's 2 guest houses both w/unobstructed views of the Gulf of Mexico for miles. The 1st guest house boasts cathedral columns on the outside, walls of glass, terrace, wet bar & elevator access to all levels, private 200 ft. beachfront & tower balcony to enjoy year-round sunsets. The 2nd guest house is perfect for overflow guests or live in help. Both the main & guest houses have oversized 2 car garages. An estate w/old world elegance. Seller encourages Offers!!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $5,950,000 TO $5,250,000 
$4,450,000
112 OSPREY POINT DR, Osprey FL 34229
6
BEDS
7
BATHS
8,973
SQFT
$496
$/SQFT
0.60
ACRES
1989
BUILT
"Most desirable location in The Oaks Bayside Country Club; truly a boater's Dream! Featuring your own Private Dock with 3 Power Lifts..12,000/16,000. Driving thru this Private Gated Community you are surrounded by a Canopy of Mature Oak trees. The Grand circular driveway leads into a Double Grand Stairway to the Double doors. The Ambiance of the custom 22+ft. ceilings with 3 Custom Stone Fireplaces with new Hardwood and Stone floors through out. Its Magical View of the Bay with the Amazing sunsets are perfect for Entertaining to Comfort Living. 1 Million in custom renovations (see Attachments). Extra large Master Suite with incredible Bay views. 5+ Garage for the custom car collector. Large non conforming In-Law Suite. The Oaks is a Five Star Platinum Club."
* LISTED OVER 120 DAYS 
$3,825,000
1208 N CASEY KEY RD, Osprey FL 34229
4
BEDS
5
BATHS
3,202
SQFT
$1,195
$/SQFT
1.19
ACRES
1950
BUILT
"Experience all the warmth and charm that this 1950 Old Florida beach house has to offer on exclusive North Casey Key. Rarely do you find privacy and exquisite walking beach in tandem. Set on beautiful oak studded grounds spanning 100 feet of pristine beachfront and bay frontage complete with boat dockage, this home is the epitome of casual island living. Upon entering the home, the open living room has exposed pecky cypress beams and a fireplace with cypress and Crab Orchard stone catch your eye. Yellow pine floors, new kitchen elements including marble countertops, new floors, stove, microwave, buffet with display shelving, a built-in planning desk and tongue & groove cypress paneling are featured. The family room has great views through the French doors to the Bay and is situated adjacent to an office replete with bookshelves and a sitting area. On the first level are 2 en-suite bedrooms with updated baths. An additional full bath is located near the family room and kitchen. The pecky cypress staircase ushers you to the spacious master suite with a fireplace and a tongue & groove cypress mantle. Along with his and her baths there is a spacious walk-in closet and French doors onto the bayside terrace. A bunkroom that sleeps 6 is also located on the 2nd floor. Impact rated windows were added in 2011. Enjoy the slow pace of this incredible island where there are no traffic lights or commercial development only the sound of lapping waves and the relaxed pace of the privileged few who call Casey Key home."
* LISTED OVER 120 DAYS 
$3,800,000
121 N CASEY KEY RD, Osprey FL 34229
4
BEDS
6
BATHS
4,096
SQFT
$928
$/SQFT
0.49
ACRES
1969
BUILT
"Privacy abounds behind the gated entry to this unique Spanish Mediterranean beachfront home hidden away in tropical splendor on the sparkling blue waters of the Gulf of Mexico. Attention to detail is not lacking in this gorgeous 4 bedroom 5 1/2 bath pool home that was rebuilt in 1991. Unique, charm and character are three words that best describe the ambiance of this island oasis. From the custom wrought iron banister leading up to the master bedroom to the pecky cypress doors to the fun tile colors of the car wash shower you will be impressed with the quality of appointments throughout the house. The quarry tile & wood floors give a feeling of warmth. The large picture windows and sliding glass doors let the light in & offer spectacular vistas of palms, beach and water. Open them and let the tropical breezes flow in! The master bedroom is the piece de resistance of the home with 2 full bathrooms, open air and screened balconies,and a remarkable sitting area with a wet bar. To top it off take the circular staircase to the roof top deck which gives you panoramic views of the bay and Gulf. The swimming pool invites you to it's courtyard setting with an extensive patio area. Just open the house and the entertainment possibilities are endless. The guest quarters over the garage offers a full bathroom and could be used as an art studio, office or exercise room. The appeal of Casey Key begins at the swing bridge on Blackburn Point and extends to the 7 miles of winding road and tropical beauty to behold!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,999,000 TO $3,800,000 
$3,540,000
854 N CASEY KEY RD, Osprey FL 34229
4
BEDS
4
BATHS
3,462
SQFT
$1,023
$/SQFT
1.50
ACRES
1975
BUILT
"REDUCED! 1.5 acre Gulf-to-Bay Priced to sell on Exclusive North End Casey Key. The private beach with no public access is a luxury of privacy that few places offer & is part of the magic of Casey Key. Majestic sprawling old oaks & cedar trees giving it an unspoiled Old Florida feeling. The large 2 bedroom 2 bath contemporary style main house was built in the early 1970's. Gulf and Bay views from almost every room, high ceilings, a wrap-around courtyard & lots of natural light. The 2 bedroom 2 bath guest house was built in 2002 with stunning Gulf views from the great room & master bedroom, bamboo flooring & Plantation shutters throughout. Downstairs is an over-sized two car garage, a bonus room & a full bathroom. The guest house offers a great opportunity to be on site during a remodel or construction of the main house. This property is over 500 ft deep, 180 ft of Gulf front and approximately 120 ft on the bay. Option to install dock with boat lift on the bay, hydrographic survey is completed. The location is very convenient with Pine View School, ranked in the top ten public schools in the nation, just off the island. Venice airport with 5000 feet of runway accommodates most private jets. Also the Key allows for very easy access to I75, shopping, dining, Sarasota or Venice. From the moment you cross over the historic swing bridge it is apparent you have arrived in a unique place. On the Exclusive North End of the Key, where the road narrows & life slows down, it is extra special! See 3D Video!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,690,000 TO $3,540,000 
$3,275,000
1042 N CASEY KEY RD, Osprey FL 34229
4
BEDS
5
BATHS
4,781
SQFT
$685
$/SQFT
0.68
ACRES
1980
BUILT
"Open your blinds each morning and say to yourself, GOOD MORNING BEAUTIFUL! This majestic residence on the Sarasota Bay offers expansive bay views, lush tropical landscape and exclusive deeded beach access on the treasured north end of Casey Key. This IMMACULATELY MAINTAINED home is ready for you to move in and enjoy! Many thoughtful design elements to cherish such as Chicago brick and oak wood floors, vaulted ceilings, two wood burning fire places, custom Frank Lloyd Wright entry doors, spacious living and great light throughout the entire house! Custom touches such as wood covered ceilings on the back porch, brick walkways in the garden, and private porches create charm in every nook. This home offers THE PERFECT LAYOUT for formal gatherings or casually entertaining loved ones poolside overlooking the bay. The kitchen is fully loaded with high-end appliances, storage and elegance. Enjoy breakfast with breathtaking sunrise views from your over-sized dinette. The family room is spacious yet cozy with a wood burning fire place and french doors leading to the back lanai. Hide away in your elegant master bedroom featuring en suite and custom window treatments. The additional bedrooms are on a split plan each with designated en suites awarding your family/guests privacy. Enjoy the outdoors: kayak, paddle board or boat, nature walks/bird watching at nearby Oscar Scherer and Blackburn Point Park or bike the Legacy Trail. EXTRAS: STEAM ROOM, SEPARATE OFFICE, BONUS ROOM, KAYAK LAUNCH, BOATHOUSE FOR 25FT+ BOAT."
* LISTED OVER 120 DAYS 
$2,790,000
136 OSPREY POINT DR, Osprey FL 34229
5
BEDS
8
BATHS
6,461
SQFT
$432
$/SQFT
0.67
ACRES
2005
BUILT
"Opportunity of a Life Time! This magnificent three-level mansion is located in the exclusive private gated community Oaks Bayside. This home is priced to sell and is below market and replacement value. Exquisite Brazillan cherry wood flooring through out. The Amazement just begins as you open the double mahogany door a Grand Foyer which features 22 ft. ceilings with custom molding thru out. Spacious open floor plan opens up to kitchen and family room offering a full bar area with 150+ bottle wine cooler. Large poolside lanai area featuring an infinity edge heated swimming pool,spa, fully equipped summer kitchen with sunset overlooking Little Sarasota Bay Oaks Country Club rated 2019-2020 Platinum Clubs of America."
* LISTED OVER 120 DAYS 
$1,695,000
285 SUGAR MILL DR, Osprey FL 34229
4
BEDS
6
BATHS
5,578
SQFT
$304
$/SQFT
1.25
ACRES
1989
BUILT
"Escape to Paradise. Located in the waterfront community of Oaks Bayside, this one-of-a-kind walled and gated estate is a private oasis perfect for entertaining guests or for multi-generational living. The expansive open pool and patio area is positioned between the main house and the guesthouse to provide not only a luxurious resort like feel but allow for the utmost privacy. The main house has been designed to feature a luxurious master suite and his and her offices that could be easily transformed into additional bedrooms. The living and dining rooms open to the lakefront lanai and a second pool creating a wonderful entertaining space. The kitchen and adjacent family room boast cherry wood cabinetry, granite countertops, large island, professional appliances and walk-in pantry. The 1,200 SF guesthouse includes 2 bedrooms and bathrooms as well as a great room and kitchenette. There is also a separate air-conditioned garage, studio, pool cabana or gym depending on your interests. This home features impact resistant garage doors and hurricane zone approved screen protectors for all openings. The gated community of Oaks Bayside is part of The Oaks Club, one of the area s most exclusive private clubs featuring award winning golf, tennis, pool, fitness center and multiple dining options. Located minutes from nationally ranked Pine View School, the Legacy Bike Trail, Siesta Key and Casey Key beaches and all that Gulf Coast living has to offer. Lot 111 which is part of the property could be sold separately."
$1,695,000
643 FERNWALK LN, Osprey FL 34229
4
BEDS
5
BATHS
5,246
SQFT
$323
$/SQFT
0.51
ACRES
2001
BUILT
"Elegantly defined, european and traditional, custom build home in the cul-de sac private street of the gated community of The Oaks. The moment you pull into the circular paver driveway and porte cochere, set on the lush tropical landscaping, you will see the meticulous attention to details. Inside you will experience the grand wall of glass showcases, dramatic high ceilings offering views of the magnificent pool/spa and outdoor kitchen from the main living area. And if you love to entertain, this gourmet kitchen is ideal with granite countertops, wood cabinetry, stainless steel appliances open to the specious family room with a wet bar. Master suite with office, his and hers walk in closets and master bath are located on one wing of the house, while other guests bedrooms are on the opposite wing. Upstairs you will find a private suite with a balcony overlooking the pool. The Oaks club feature two championship golf course, tennis courts, dinning rooms, state of the art fitness and many more. Club membership is available and required. Only one look and it will take your breath away."
$1,695,000
91 OSPREY POINT DR, Osprey FL 34229
4
BEDS
6
BATHS
5,100
SQFT
$332
$/SQFT
0.40
ACRES
1983
BUILT
"Iconic architecture in Sarasota s premiere golf and country club. This magnificent 4-bedroom estate was designed and built by Bo MacEwen and brims with the essence of warm, Southern hospitality. Bo was the original architect for The Oaks and he created this lakefront testament to form, symmetry, and serenity as his own residence. Renovated in 2017, every detail expresses an effortless sense of style & charm. Step inside the regal entry gallery with 12 ceilings and black & white marble floors. Host unforgettable evenings in the lavish living room with paneled gas fireplace, built-in bookshelves, and French doors leading to screened porch with long lake views. Let the spirit of culinary adventure take over in the new kitchen with custom cabinetry, Sub Zero refrigerator, Wolf range, quartz countertops & porcelain tile flooring. Master suite is designed as an inner sanctuary where lake views are in concert with elaborate details including moldings, bamboo floors, fireplace, and dressing room. Luxuriate in the master bathroom with large shower, marble tile & elegant vanity. Three additional en suite bedrooms are spaced throughout the home to maximize privacy for your guests. Exterior living spaces are perfectly in tune with gardens, lush landscaping & the private natural surroundings. New saltwater pool with travertine terracing overlooks the lake. The Club boasts two 18-hole championship golf courses, first class amenities, while Sarasota s cultural treasures and white-sand beaches are moments away."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,795,000 TO $1,695,000 
$1,599,000
361 CEZANNE DR, Osprey FL 34229
3
BEDS
3
BATHS
3,277
SQFT
$488
$/SQFT
0.52
ACRES
2014
BUILT
"Discover alluring views from within this rarely available, exquisite three-bedroom custom residence in Sorrento Shores with 420ft of waterfront. Surrounded by water on two sides overlooking lush, natural splendor, the scenic waterway provides not only a tranquil backdrop to view the sunrise but an ideal place for your boat to dock when you are not taking it out to the Intracoastal Waterway. Built in 2014 and designed with unrivaled comfort and style in mind, the home is perfectly suited for family living and entertaining. 16 coffered ceilings blend with wood-like tile floors, while a fireplace in the family room creates an elemental experience. The gourmet kitchen includes two ovens, granite surfaces, induction cooktop, plenty of counter space, and breakfast bar. Serene views and a thoughtful layout provide environments where one can linger happily for hours. Three bedrooms all overlook the water while an office creates a designated space for checking off your to-do list. The enclosed lanai with brick pavers extends the home s living area and the infinity-edge, salt-water pool with swim jet allows for a waterfront nighttime swim while you gaze at the stars. Set on a quiet cul-de-sac, beautiful landscaping and lush trees are complemented by the paver driveway. The home is centrally located in Osprey, within minutes of the soft sands of Casey Key. The Intracoastal Waterway beckons any boating enthusiast with waterfront dining, natural scenery, birds, manatees and dolphins at play."
* LISTED OVER 120 DAYS 
$1,500,000
425 MACEWEN DR, Osprey FL 34229
5
BEDS
6
BATHS
5,153
SQFT
$291
$/SQFT
0.62
ACRES
1999
BUILT
"This spacious 5 bedroom, 5.5 bath home offers over 5,100 square feet of living space and overlooks the par 3 fourth hole of The Oaks Heron Course. The huge gourmet kitchen features top of the line stainless steel appliances including a gas range. You will love custom-designed backsplash and gorgeous granite. The master bedroom is light and bright with a gas fireplace and coffee bar. This is the perfect place to get ready for a busy day on the course or at the beach, or to end it, relaxing in the lap of luxury. The master bath is ready for the cover of a designer magazine, with lovely marble floors, glass shower, granite countertops, and a great soaker tub. The other 4 large bedrooms each have their own bathroom. Five sliding doors, two that pocket into the walls, allows the outside to come in. Use this incredible lanai with an outdoor bar and kitchen, dining area, pool and spa to entertain day or night, while taking in beautiful views. You will love this home so much you may never want to leave it, but when you do, you can take advantage of all the amenities of The Oaks, a 2019-2020 Platinum Club of America, with two championship golf courses, an award-winning tennis program, a state-of-the-art fitness center and a wide variety of dining, recreational and social offerings. Club membership is available and required."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $1,475,000 TO $1,500,000 
$1,498,246
350 SUGAR MILL DR, Osprey FL 34229
4
BEDS
4
BATHS
4,100
SQFT
$365
$/SQFT
0.67
ACRES
2020
BUILT
"Pre-Construction. To be built. The Oaks Bayside. One of the few remaining homesites available to build your Dream Home with Henson Contractors. There is no time requirement for building and there is freedom to select another builder of your choice. The majestic Oaks and framed by the grounds of historic Spanish Pointe captures the natural beauty of Old Florida. Designed as an Open Great Room Floor plan with Step Tray Ceilings, Crown Molding, Wood or Tile Floors throughout, Cooks Kitchen with Wolf and Sub-Zero Appliances and an enormous Master en-Suite with His & Hers Walk-in Closets. The attached Floor Plan and Feature Sheet from Henson describes the spectacular interior upgrades, distinguishing exteriors and the benefits of building with the best of today's codes. The land consists of 1.5 lots, appx 29,000 sqft and has been surveyed. Your options are unlimited. The Oaks Club membership is required and offers access to an exclusive array of amenities - including two Championship 18-hole Golf Courses, 12 Har-Tru Hydro Grid Tennis Courts, a heated Junior Olympic Pool, playground and professional Croquet Court. A magnificent, 42,000 sqft Clubhouse includes dining venues for every occasion and a variety of social activities. Discover the ultimate backdrop for your Country Club lifestyle today!"
$1,450,000
860 MACEWEN DR, Osprey FL 34229
4
BEDS
7
BATHS
5,084
SQFT
$285
$/SQFT
0.55
ACRES
1998
BUILT
"THE EXCLUSIVE OAKS GOLF & TENNIS COUNTRY CLUB! Only Platinum and Elite club in the Sarasota Area (Top 10 Nationwide). This well designed home with gourmet kitchen has top of the line appliances with adjoining breakfast area, and is open conveniently to the family gathering area for comfortable entertaining. All bedrooms are en-suite. Open split floor plan, formal living and dining room. Many upgrades in this lovely home. Grande entry way, custom try and vaulted ceilings , triple crown molding throughout, fireplace in the family room, gym, game room, privet putting green and much more. The spacious lanai, offers pool with a spa, and a great outdoor kitchen that is perfect for entertaining friends an family while overlooking the 16th hole. Paver circular driveway with expansive parking areas, attractive landscape and over size garage, This superb setting provides a secluded and tranquil living environment, yet is minutes from beaches, shopping, the arts, and the airport. The Oaks Country Club offers two 18 hole championship golf courses, 12 Har-Tru tennis courts, a croquet lawn, bocce, three dining rooms from casual to formal, new fitness facility with spa, and an active social calendar to keep you busy year round."
$1,450,000
168 COASTAL HAMMOCK CT, Osprey FL 34229
3
BEDS
4
BATHS
4,924
SQFT
$294
$/SQFT
0.48
ACRES
1993
BUILT
"Reduced.Bayfront in the Oaks. Custom designed walled Mizner-style estate in private cul-de-sac location with a 5 stop elevator. Views from several areas showcasing the gulf and bay. Very livable floor plan with expansive master suite offering a separate sitting room and octagonal bath all separate on its own level. Upstairs guest area has its own media room and small bar. Solid wood doors, extensive woodwork and built-ins, impact doors and windows, top floor sun deck, hand carved stone fireplace and entry columns lend a distinctive elegance to the house. Shellstone entry of 14' vaulted ceiling, banked by French doors and windows overlooks a suspended pool deck above the back lawn and preservation area. Kitchen features Sub-zero, Asko dishwasher and new island cooktop surrounded by granite. Small wet bar with wine refrigerator is adjacent to the living room and family area. This home is filled with light and the privacy and quiet is unmatched. Canoeing and kayak water to the back, no dock allowed. A spectacular location in the top country club in Sarasota which features 36 holes of golf, tennis, bocce ball, croquet and a new fitness center plus gourmet dining in an active social community. Membership in the Oak's Club is required."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,500,000 TO $1,450,000 
$1,350,000
854 MACEWEN DR, Osprey FL 34229
4
BEDS
6
BATHS
9,081
SQFT
$149
$/SQFT
0.78
ACRES
2003
BUILT
"Offering over 9,000 square feet of exquisite living space, this richly-detailed custom home is nestled on a guarded, private cul-de-sac. Entertain guests or simply relax as a family in the multitude of well-designed rooms from the living room with inviting fireplace, to the wood paneled study, theater room with stage and open kitchen, family room and breakfast nook. Rich granite, cherry cabinetry, a generous island and a breakfast bar are the signature elements of the kitchen, while the formal dining room with beautifully illuminated tray ceiling is the ideal environment for special occasions. The master suite is a reflection of comfortable luxury, with its two over-sized walk-in closets, attached nursery/fitness area and an elegant bath featuring two individual sinks, a large walk-in shower and a serene garden tub. The second level features two tremendously sized bedrooms, a loft and screened terrace. Step out to the spectacular screened lanai to soak in the atmosphere of your pool with fire features, a summer kitchen and gorgeous Floridian landscape views. The Oaks offers every luxury amenity you can image: 2 championship golf courses, 12 HAR-TRU tennis courts, fitness center, croquet, pool, playground, social, dining and a spectacular clubhouse."
$1,340,000
497 WEBBS CV, Osprey FL 34229
6
BEDS
7
BATHS
6,863
SQFT
$195
$/SQFT
0.45
ACRES
1992
BUILT
"Seller will pay $25k toward club membership with approved contract. Located in the exclusive gated community of The Oaks Bayside. Totally remodeled home with too many improvements to list, everything is new including; new roof, air conditioners, new flooring, new kitchens and baths, new pool, lanai screens, new travertine around pool, quartz in kitchen, marble in baths and the list goes on. As you enter the house you are met with a spectacular wooden staircase and high ceilings. Master suite has large walk-in closet with custom built-ins. Huge master bathroom. One laundry room located on upstairs level as well as one off the kitchen on the downstairs level. Almost 400 sq. ft. bonus room above garage with 7th bathroom, not part of listed square footage. Adjoining guest wing completely separate from main house living area. This area has two full bedrooms with 2 bathrooms, living area and full kitchen and would be ideal to be for live-in help, mother-in-law or guest suite. Seller will assist with required Country Club Membership. The Oaks, where members enjoy an exclusive array of amenities including two championship 18-hole golf courses, 12 Har-Tru Hydro-Grid tennis courts, a heated Junior Olympic pool, playground and professional croquet court. Pristine Gulf beaches, the arts, shopping and restaurants are within easy reach."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,390,000 TO $1,340,000 
$1,295,000
158 PUESTA DEL SOL, Osprey FL 34229
4
BEDS
4
BATHS
4,404
SQFT
$294
$/SQFT
0.45
ACRES
2006
BUILT
"Welcome to Villa Del Sol, an Italian inspired Oasis across the street from the Bay with a deeded dock and boat lift just steps from your front door. Located within a quaint gated community of just 8 homes, situated halfway between Sarasota and Venice, this home has so much to offer. A builders own home with no expense spared in the amenities and finishes that this as-new home offers. From the moment you approach, you can appreciate the custom design with it's large pavered circular driveway, side entry 3 car garage and beautiful mature landscaping and cypress wood eaves adorning the home. Then the real treat begins when you walk through the front door, with the wood and travertine floors and exquisite built-in features. The kitchen is a chef's dream, with gas 5 burner stove, dual dishwasher, built in Sub-zero and solid Alder wood Cabinetry. Formal living and dining areas, as well as additional family room on main level all with access to the tranquil and expansive pavered lanai, pool and summer kitchen which offers plenty of area for entertaining. Master bedroom has dual walk in closets with built ins and a master bath to die for...separate vanities, large shower as well as a jetted tub with chandelier above it. The rest of the first floor has a large den, laundry as well as an additional bedroom and another full and a half bath. Upstairs are 2 additional bedrooms, another living area (game room) with pool table and bar as well as a fully wired media room! This home truly is paradise found."
$1,295,000
340 OSPREY POINT DR, Osprey FL 34229
5
BEDS
7
BATHS
6,002
SQFT
$216
$/SQFT
0.78
ACRES
1998
BUILT
"If you want to live an enviable lifestyle with the comfort of being surrounded by nature, combined with the elegance of country club living, this 5 bedroom French Country styled home, with 5 full and 2 half baths is perfect for you! Play an early round of golf or tennis, enjoy a gourmet lunch at the club, kayak on the North Creek all the way to Siesta or Casey Key, where you can watch a picture-perfect sunset over the Gulf, and end by relaxing in your incredible lanai featuring a custom pool with waterfalls and hot tub. Amazingly spacious, with two stories of living area, the floor plan offers room and privacy for everyone. A grand foyer & formal dining room with cove lighting welcome you into this gorgeous home. The updated kitchen overlooks the living room and breakfast area. The master bedroom has wood floors, his-and-hers closets, a beautiful large master bath and a nice sitting area overlooking the pool and spa. Upstairs you will find large bedrooms. A private stairway off the kitchen leads you to a huge mother-in-law suite with full bath. The interior is complimented by an expansive lanai. The deck is covered with beautiful marble tile and has a large covered area. The Oaks, a Distinguished Emerald Club and private gated community close to world-famous gulf beaches features two championship golf courses, 12 HAR-TRU tennis courts, a state-of-the art fitness center & wide variety of social & recreational options. Membership is available & required."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,350,000 TO $1,295,000 
$1,272,000
402 WALLS WAY, Osprey FL 34229
4
BEDS
4
BATHS
3,464
SQFT
$367
$/SQFT
0.64
ACRES
2014
BUILT
"Built in 2014 by Todd Johnston Homes, this spectacular waterfront property exhibits unsurpassed excellence in design and detail. Situated on a premier one acre lot, the outdoor lighting showcases the professional landscaping. Host day and night-time parties with equal grace and elegance when you welcome guests through the grande entry doors and breathtaking foyer, to reveal a large pool and hot tub. Open kitchen/family room floor plan. All windows/doors hurricane impact rated. Extremely powerful, hospital grade air filters keep this house clean and fresh. A jewel on Florida s peaceful Sun Coast close to downtown Sarasota, Siesta and Venice Beaches, The Oaks Club is the embodiment of beauty and vitality. This private, member-owned country club offers the finest of amenities including golf, spa, tennis, fitness and croquet. The most attractive feature of The Oaks Club, however, is its celebrated social calendar and community life. A VERY UNIQUE, UPDATED PROPERTY AT THE OAKS!!!"
$1,200,000
419 WALLS WAY, Osprey FL 34229
4
BEDS
5
BATHS
5,523
SQFT
$217
$/SQFT
0.59
ACRES
1988
BUILT
"A recent price reduction makes this spectacular 4 bedroom, 4.5 bath colonial an opportunity too good to pass by! If you are a discriminating buyer, seeking the utmost in fine, country club living, you need to look no further. There is a reason this cul-de-sac is known as The Street of Dreams . Drive down it and as you pull into the large circular driveway, you will be greeted with huge 2 story columns & widow s walks reminiscent of the old south. Oversized double mahogany doors open to a curved double stairway & a two story foyer. The interior of this home features 2 master bedrooms, and 2 guest bedrooms, all with private bathrooms; a large kitchen that opens to the breakfast area and family room with furniture grade cabinets and high-end granite; 4 wood burning fireplaces with stone mantles, crown molding, a butler s pantry, & wood floors. The exterior will make you say, This is the best lot in The Oaks! It features a large paver pool deck with hot tub and offers breath-taking 270 degree lake & golf course views. The perfect place to enjoy your coffee on a beautiful morning, or to toast another gorgeous sunset at the end of the day. All of this, and the privilege of joining one of the area's most exclusive golf and country clubs; The Oaks is a recent recipient of the Distinguished Emerald Club of the World award from Board Room magazine, representing the top 4% of all private clubs. Membership is available and required."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,400,000 TO $1,200,000 
 
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