Osprey Real Estate, Homes and Condos for sale

All Osprey homes currently listed for sale in Osprey as of 03/24/2019 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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$7,995,000
411 N CASEY KEY RD, Osprey FL 34229
9
BEDS
11
BATHS
9,127
SQFT
$876
$/SQFT
1.10
ACRES
1977
BUILT
"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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $8,299,000 TO $7,995,000 
$6,250,000
916 N CASEY KEY RD, Osprey FL 34229
6
BEDS
6
BATHS
5,318
SQFT
$1,175
$/SQFT
1.50
ACRES
1973
BUILT
"Location, Location, Location! NEW PRICE Over the bridge to the north end of the beachfront escape of Casey Key you arrive at the tropical oasis of this 3 residence estate w/Gulf of Mexico & Bay views. Once on the property you are amazed by the tropical lush landscaping surrounding the circular drive making it feel like a botanical garden. 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 are 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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $7,975,000 TO $6,250,000 
$4,500,000
121 N CASEY KEY RD, Osprey FL 34229
4
BEDS
6
BATHS
4,096
SQFT
$1,099
$/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!"
$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."
$3,950,000
854 N CASEY KEY RD, Osprey FL 34229
4
BEDS
4
BATHS
3,462
SQFT
$1,141
$/SQFT
1.50
ACRES
1975
BUILT
"Check out the 3D Imaging Video! 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!"
* LISTED OVER 120 DAYS 
$3,450,000
608 N CASEY KEY RD, Osprey FL 34229
5
BEDS
3
BATHS
3,086
SQFT
$1,118
$/SQFT
1.50
ACRES
1916
BUILT
"This prime 1.5 acre property has 175 ft. of Gulf front and 175 ft. of Little Sarasota Bay front and is more than 450 ft. deep. Secluded by mature oaks, palms, pines, agave and an enormous banyan tree, the rustic residence has changed little since it was built in 1916. It's unlikely the Old Florida homestead, constructed of pecky cedar can be salvaged, but perhaps the 10 ft. ceilings, hardwood floors, 4 fireplaces, original blown glass sconces, French doors and lunette windows will provide an inspiration to the buyer. Submerged pilings that extend into Little Sarasota Bay is evidence of an old dock that once stood on the property. Construction of a new dock would complete what could be one of the finest estates on Casey Key. OF NOTE: This is one of the first homesteads on Casey Key and is said to have served as lodging for adventurers and their guides who arrived by boat to hunt the lushly vegetated 8 mile long barrier island at the turn of the century. Seller may consider some financing."
* LISTED OVER 120 DAYS 
$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."
$3,100,000
1224 N CASEY KEY RD, Osprey FL 34229
5
BEDS
5
BATHS
3,427
SQFT
$905
$/SQFT
1.07
ACRES
1956
BUILT
"Priced to Sell in Mega Mansion Neighborhood. Great Opportunity to get over an Acre of Gulf-to-Bay on the Private Road section of the Exclusive North End of Casey Key where the Individual properties own the beach. So you may have your dogs on the beach if you like! The original house built in the 1950 s is four bedrooms & 3 full bathrooms with classic Terrazzo floors & great views of the Gulf & the Bay. The high beamed ceilings, fireplace, open floor plan with walls of glass are reflective of today s contemporary style. A two car garage and large upstairs garage apartment built in the 1970 s in connected by a covered garden walkway. Picnic on your private beach under the pines on one of the widest beaches in Sarasota County or fish from your own private dock. Priced below land value for quick sale."
$2,995,000
410 N CASEY KEY RD, Osprey FL 34229
3
BEDS
3
BATHS
2,006
SQFT
$1,493
$/SQFT
1.45
ACRES
1971
BUILT
"Stunning residence nestled on an oversized 1.45-acre lot along the shores of Little Sarasota Bay, located in the exclusive residential barrier island of Casey Key. Deeded Beach access to the Gulf of Mexico and two docks for many vessel types allow exciting days on the water. A modernized home with 3 bedrooms of which two are master suites. The first level with en-suite bath has tranquil views of the bay and pool, an upper-level master was an addition to the home in 2004 with tray ceiling, ipe wood flooring and overlooks the expansive property from a private balcony. A stylish bathroom with double walk-in shower has a view to the Gulf of Mexico. Celebrate a casual coastal life from the great room and kitchen areas which wraparound the sparkling pool. Outdoor living and entertaining revolve around the adjacent decks, all while soaking in the tempting views. On a practical note: all very well maintained with newer AC s, roof, and impact windows. Minutes to culturally rich downtown Sarasota, shopping, restaurants, Legacy Bike Trail and Pine View School. The North end of Casey Key is where your pulse slows, and time stands quite still, but just for the few who claim this idyllic lifestyle."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,250,000 TO $2,995,000 
$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."
$2,750,000
1027 N CASEY KEY RD, Osprey FL 34229
4
BEDS
3
BATHS
2,990
SQFT
$920
$/SQFT
0.42
ACRES
1991
BUILT
"Cross over a historic swing bridge into the serenity of private North Casey Key. Here, in this tranquil community nestled along a winding island road, is a rare opportunity to own a slice of paradise not on the market for 40 years. The custom-built, Key West styled residence lays a short distance from the exclusive Casey Key beach. Come home to collect sand dollars and shark teeth, fish from your backyard and absorb pristine Gulf-front views. An intelligent, elevated coastal design centers a modern floor plan around a soaring vaulted great room. Four bedrooms plus a loft allows ample space for guests and family retreats. Walls of windows with transom details and doors open onto an expansive deck, where the wide-open views of the turquoise waters of the Gulf of Mexico steal your breath away. Recent upgrades include new paint inside and out, a new metal roof in 2016, 2 new AC units in 2018, updated LED lighting and on a practical note, the home has electric roll down shutters for peace of mind. The lower level garage accommodates five to six vehicles. Remember, you can own a home anywhere, but there is a limited number of opportunities to live on North Casey Key Road. Balance, privacy and proximity with nearby Sarasota, Venice, Pine View School, Legacy Trail, shopping, dining and I-75 from the tranquility of an island retreat."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,995,000 TO $2,750,000 
$1,995,000
91 OSPREY POINT DR, Osprey FL 34229
4
BEDS
6
BATHS
5,100
SQFT
$391
$/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 - $2,375,000 TO $1,995,000 
$1,695,000
320 BAYSHORE DR, Osprey FL 34229
3
BEDS
3
BATHS
3,195
SQFT
$531
$/SQFT
0.44
ACRES
1961
BUILT
"Bayfront, Osprey Rarely does a property become available that combines the charm, character, and direct Bayfront location that this architecturally designed 3+ bedroom/ 3 bath, Island Style home quietly boasts. Featuring lush courtyard entry, metal roof, terrazzo floors, high ceilings, windows galore, multiple patios, sunny pool, and tranquil sunsets over a wide Bay view; All add up to a truly serene sanctuary. Escape into Old Florida, with a contemporary twist, that is only moments away from shopping, restaurants, beaches, and a short drive to all that Sarasota has to offer. For the discerning who wish to enjoy the true Florida lifestyle at home, and when compelled to venture out, know 320 Bayshore will be a welcome retreat upon return. A unique opportunity, that is available for the first time in 19 years."
$1,500,000
168 COASTAL HAMMOCK CT, Osprey FL 34229
3
BEDS
4
BATHS
4,924
SQFT
$305
$/SQFT
0.48
ACRES
1993
BUILT
"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 - $1,599,000 TO $1,500,000 
$1,500,000
409 N POINT RD #1003, Osprey FL 34229
3
BEDS
3
BATHS
2,778
SQFT
$540
$/SQFT
2004
BUILT
"Don't be shy - Owner wants it sold - bring all offers! The best Penthouse views in all of Meridian! Experience the luxurious Florida lifestyle with gorgeous open views that encompass Casey Key, Siesta Key, Downtown Sarasota, Little Sarasota Bay & the Gulf. This private, rarely available corner residence is located in a fabulous gated community offering the best in luxurious living. An elevator leads you to a private foyer appointed with marble floors & a bright & elegant interior that has been professionally decorated with no expense spared. Well appointed with custom silk draperies, plantation shutters, gleaming hardwood floors, soaring 10 ft ceilings, crown molding, 2 new A/C units & more. The remodeled open concept kitchen features warm wood cabinetry, stainless steel appliances, tray ceiling, & breakfast bar that overlooks the spacious living area with captivating views. Open the 4 panel sliders & enjoy gorgeous sunsets from the expansive lanai with roll down shutters. This exceptional residence also includes a separate dining room, 2 car garage attached, & hurricane resistant doors & windows. Nestled behind the gates of The Oaks Preserve directly on Little Sarasota Bay. Owners enjoy a secure lobby, pool, fitness center & a convenient location close to Sarasota s award-winning beaches, dining, shopping, boating, & state parks. Located in the beautiful golf community of The Oaks which offers two 18 hole courses, 12 Har-Tru tennis courts, croquet, clubhouse & dining. Oaks Club membership required."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,650,000 TO $1,500,000 
$1,400,000
419 WALLS WAY, Osprey FL 34229
4
BEDS
5
BATHS
5,523
SQFT
$253
$/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 - $1,450,000 TO $1,400,000 
$1,399,000
854 MACEWEN DR, Osprey FL 34229
4
BEDS
6
BATHS
9,081
SQFT
$154
$/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 oversized 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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,450,000 TO $1,399,000 
$1,399,000
676 EAGLE WATCH LN, Osprey FL 34229
5
BEDS
7
BATHS
5,399
SQFT
$259
$/SQFT
0.74
ACRES
1992
BUILT
"Just Reduced $100,000. Classic elegance at The Oaks Club Side! This custom built 5400sf single story has been extensively renovated to include fresh interior paint throughout, new high-end hardwood floors and new bathrooms. Master suite has 2 large walk-in closets with built-ins. Master also has his and her full individual bathrooms. All other bedrooms include closet enclosures. Gourmet kitchen includes double oven range, 36 and 42 cu ft stainless GE Monogram refrigerators and dishwasher. Large office with custom wall built-ins. 20 x 40 deep-water pool and spa is excellent for use as a Lap Pool. The new poolside summer kitchen is great for entertaining. Home includes crown moldings throughout and 9' interior doors. Spacious oversize side entry 3 car garage will satisfy Use AS ISme-site is on a large private cul-de-sac setting backing to the 5th Heron Green and adjacent to a 2 acre nature preserve providing great privacy. New irrigation well eliminates municipal irrigation water bills. Detailed house building plan is available. Owner will consider selling the home Turn-Key. Most furnishings are high-end by AICO (Michael Amini). Short term Owner financing available with qualified buyer. Use AS IS contract."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,445,000 TO $1,399,000 
$1,390,000
497 WEBBS CV, Osprey FL 34229
6
BEDS
7
BATHS
6,863
SQFT
$203
$/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."
$1,375,000
586 N MACEWEN DR, Osprey FL 34229
4
BEDS
6
BATHS
4,163
SQFT
$330
$/SQFT
0.55
ACRES
2001
BUILT
"Exceptional and meticulously maintained best describes this fabulous 4100+ sf, 4 bedroom, 5 1/2 bath, 5-car garage residence with golf course views in the highly acclaimed gated golf community - The Oaks Club. A serene and private setting, with golf course views and fabulous curb appeal. The gorgeous mahogany double doors welcome you to volume ceilings, formal and casual living spaces including a separate coffee/wine bar, fine detailing and features throughout. The thoughtful design, built for entertaining and enjoying family. Offering 18 Jerusalem marble floors, custom crafted built-ins, ceiling details with crown, top line appliances, solid wood cabinetry and more. A luxurious master retreat with three walk-in closets, dual vanities, separate whirlpool tub and walk-in shower. A truly extraordinary 3000 sf outdoor area with summer kitchen and stunning Lucas Lagoons designed pool and spa with 14 wide natural rock wall and waterfall, retractable awnings, private hot water shower, and your own 4-hole putting green will surely give you an envious tropical resort lifestyle. Updated with impact glass and sliders, fresh paint in and out, generator, water filtration system and amazing garage space with storage. The Oaks Club offers an elite staff and service level with tennis, swimming, fitness center and dining venues. Social or equity memberships available. Full feature sheet available."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,425,000 TO $1,375,000 
$1,350,000
340 OSPREY POINT DR, Osprey FL 34229
5
BEDS
7
BATHS
6,002
SQFT
$225
$/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 - $1,400,000 TO $1,350,000 
$1,335,000
12 N CASEY KEY RD, Osprey FL 34229
3
BEDS
3
BATHS
2,657
SQFT
$502
$/SQFT
0.50
ACRES
1978
BUILT
"Views, privacy and exclusive deeded access to a rare section of private beach are found in this adorable North Casey Key beach house. A brand new Owens Corning roof system comes with a 50-year transferable warranty. The great room s vaulted beamed ceiling features a fireplace and captivating views out the sliding glass doors. An oversized deck across the back of this home is the perfect place to entertain and enjoy the bayfront where nature abounds. The kitchen features a center island, breakfast nook and living/dining space overlooking the waterways. Spiral stairs lead to the entire 2nd floor, which is currently a dedicated master suite. This floor includes a small 2nd bedroom for a nursery, den or reading room. On the main floor, the 3rd bedroom has equally impressive waterfront views and a private balcony. Situated on half an acre with more than 90 feet of bayfront, the dock has 3-4 feet of water for boat access. This home is on a beautiful parcel, tucked way back from the road, yet provides easy on and off the key access via Blackburn Point Rd. The deeded beach easement is 5 feet wide and also provides 20 feet of beach frontage for all the sunbathing, shell seeking, relaxation and sunsets that your heart desires. Conveniently located between Sarasota and Venice, this is truly a special place to call home."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,395,000 TO $1,335,000 
$1,195,000
388 BUNKER HL, Osprey FL 34229
4
BEDS
6
BATHS
4,937
SQFT
$242
$/SQFT
0.59
ACRES
1999
BUILT
"Lush, luxurious, and private. This beautiful residence located in the much sought-after Oaks Club community offers a large, warm home situated at the end of a cul-de-sac on lushly landscaped grounds. High ceilings, marble flooring, crown molding and designer touches are custom crafted throughout the home. The large kitchen features a tray ceiling with recessed lighting, stainless appliances, center island, glass-front cabinets, a built-in desk, breakfast bar and an aquarium-style breakfast nook overlooking the pool and covered patio. The family room, just off the kitchen, has pocketing sliders to the covered terrace and pool deck with Chicago brick pavers. The formal living and dining rooms are also situated off the pool and terrace. The spacious and luxurious master suite and two en-suite guest suites are located on the first floor of the home with an additional bonus suite on the second level (potential fifth bedroom suite) featuring a private terrace. A divine, private one-bedroom guest cottage with living room and kitchenette is privately located with views of the two lakes. A covered outdoor kitchen completes this lovely home built for private enjoyment and gracious entertaining. All within the gated community of The Oaks, which offers two championship golf courses, 12 HAR-TRU tennis courts, state-of-the-art fitness center, croquet court, and a vast array of dining, social, recreational possibilities close to Legacy Trail. Club membership is required."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,300,000 TO $1,195,000 
$1,175,000
738 N MACEWEN DR, Osprey FL 34229
5
BEDS
6
BATHS
4,614
SQFT
$255
$/SQFT
0.60
ACRES
2003
BUILT
"Imagine how you d like to live the ultimate Florida lifestyle. Your vision can become a reality in this 5 bedroom, 5.5 bath two story home in The Oaks Clubside. Set back on a cul-de-sac lot, with gorgeous lake and golf views, the floor plan offers flexibility for the space to be used by residents and guests in a number of ways. The first floor master suite offers plenty of room, including a poolside sitting area, and luxurious bath. One of the two guest suites in also on the first floor, with another on the second. All have walk-in closets. But before heading upstairs, take in the light, bright space on the ground level. The formal living room with fireplace is the perfect setting for cozy fall evenings. The island kitchen has granite countertops and stainless steel appliances. Meals prepared here can be enjoyed at the breakfast bar, breakfast nook or in the formal dining room. Step outside and enjoy the views, over the expanse of the paver deck, pool and spa. Think about the great outdoor entertaining you can do utilizing the outdoor kitchen with granite countertops. Now on to the second floor which along with an en-suite guest bedroom, offers two more bedrooms with a Jack-and-Jill bath, and a gathering area that can be used for anything from a media room to a game room; it is all up to you and your vision. All this and more, behind the gates of Sarasota s premier golf and country club, The Oaks. Membership is available and required."
* LISTED OVER 120 DAYS 
 
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