Osprey Real Estate, Homes and Condos for sale

All Osprey homes currently listed for sale in Osprey as of 10/19/2017 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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$14,500,000
1160 N CASEY KEY RD, Osprey FL 34229
5
BEDS
8
BATHS
10,125
SQFT
$1,432
$/SQFT
2.00
ACRES
2009
BUILT
"Welcome to EVENTIDE. This gated, impeccably designed estate, privately positioned on the treasured N. end of Casey Key, sweeps from a sandy walking beach on the Gulf of Mexico to a protected yachting lagoon on Blackburn Bay. Composed of over 10,000 sq. ft. & designed to celebrate family & guests, this astonishing estate inspires a spirit of togetherness that integrates with the art of waterfront living. Crafted with a range of the world's most coveted woods, luxury finishes, & modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water views. Formal & casual spaces unite elegantly, including the living room with cypress wood beams, Bayfront billiard room & deluxe kitchen. The expansive bedroom floor features a guest wing of three suites, while the private master wing hosts two individual baths & a spacious office that could create a fifth bedroom, media suite or nursery. Additional spaces for recreation & relaxation have been accomplished to make use of every inch of the estate. Arched windows & French doors line the living room & open to the dazzling outdoor spaces; including a two-story lounge with fireplace & summer kitchen, & an open stone terrace with infinity pool. Elevator access & garages for nine vehicles add ultimate convenience. Enjoy boating from the deep water dock, with a 2nd dock for additional watercraft. Casey Key is a haven of serenity, minutes from shopping & a world-class private golfing, tennis & dining club."
* LISTED OVER 120 DAYS 
$8,900,000
411 N CASEY KEY RD, Osprey FL 34229
9
BEDS
11
BATHS
9,127
SQFT
$975
$/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 black 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 
$4,499,000
144 N CASEY KEY RD, Osprey FL 34229
4
BEDS
5
BATHS
5,397
SQFT
$834
$/SQFT
0.60
ACRES
2003
BUILT
"Villa dei Sogni (House of Dreams) presents an architectural masterpiece framed by finely crafted limestone columns and details throughout the exterior/interior created by artisans around the world. As you approach the residence from the walkway through the front lawn past the fountain, up the steps & through the impressive mahogany front door, your eye is drawn through the generous marble foyer, into the great room with its walls of glass taking you outside through the wrap-around balcony to the inviting pool, manicured gardens, and out to Little Sarasota Bay. The well planned layout provides multiple areas to enjoy outdoor living whether sipping morning tea/coffee from the master balcony, dining al fresco, or sunset viewing and star-gazing from the rooftop balcony with its forever views of the Gulf of Mexico and Bay. Interior space includes 2 generous master suites, separate living, dining, chef s kitchen, office and 2 additional ensuites. Auto collectors will appreciate the oversized conditioned garage.This bay front property on over half an acre of land, plus submerged land, offers the best in waterfront living with boating from your private basin & deeded beach easement. Casey Key's 8-mile island has fewer than 400 single family homes situated between Sarasota & the historic town of Venice with a municipal airport & 5,000 ft of runway. The absence of high rise condominiums adds to Casey Key's charm; it's a place that continues to captivate the world's most discerning with its endless beauty & privacy."
$3,999,000
532 N CASEY KEY RD, Osprey FL 34229
5
BEDS
6
BATHS
6,024
SQFT
$664
$/SQFT
0.73
ACRES
2002
BUILT
"Villa Crescendo is the epitome of harmony blending the views and sounds of the beach and bay waters from every room. Casey means a proclamation of peace that truly defines exclusive Casey Key. If you are looking for tranquility, privacy and a quality home for a family retreat you have found it! Whether it s a sunset walk on the beach, an afternoon swim in the pool or an early morning fishing excursion from your dock you can have it all. A Phipps Designed residence built in 2002 features quality construction pilings, stucco over concrete block, 2008 impact windows and glass, 4 car garage with 1rst floor storage and air conditioned play area. The first living level has the wow factor of 2 story dramatic living room with a double sided fireplace that faces the more casual family, kitchen and eating areas. Oversized light squares of marble floors create cool elegance. The 5th bedroom on the first level is positioned away from the 3 other upstairs guest rooms, all with en suite baths, an entertainment area, separate entrance, screened terrace, and an elevator that goes to all floors. The Master suite with a double door entry has his and her baths, closets and another private screened terrace. Located on the North end of the key you have easy access to the mainland for shopping and cultural activities. Nearby is a private airport and the exclusive Oaks Country Club, well known for its championship golf, tennis and dining. A treasure rarely found!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $4,450,000 TO $3,999,000 
$3,700,000
1224 N CASEY KEY RD, Osprey FL 34229
4
BEDS
4
BATHS
3,427
SQFT
$1,080
$/SQFT
1.05
ACRES
1956
BUILT
"Privacy: Check, Beach: Check, Old Florida Charm: check, Tranquility: Check. Your beach bungalow dream now realized on the pristine Island of Casey Key. Live in while you design your dream home on the very private north end, or this little jewel maybe worth saving if you like old Florida charm with a casual beach vibe. The overall living space is 3,427 square feet with 4 bedrooms and 4 baths. Gulf to bay property amongst multi million dollar luxury homes with miles of walking beach. 100 feet on the bay for boating and 100 feet on the white sandy shoreline. Call for a confidential showing when your privacy is a must. Sold AS IS."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,900,000 TO $3,700,000 
$3,680,000
50 W BAY ST, Osprey FL 34229
7
BEDS
7
BATHS
6,659
SQFT
$553
$/SQFT
3.68
ACRES
1917
BUILT
"Discover a once-in-a-lifetime opportunity to RESTORE, BUILD, or DEVELOP on 3.68 acres directly on Sarasota Bay in scenic, historic Osprey just south of The Oaks. Dating back to the late 1800's and known as one of the first properties to be settled, this sweeping site captures a true sense of Old Florida, while offering exciting new possibilities. The options include the creation of a dream principal estate compound to restore the existing homes or to build new. Alternatively, a buyer can opt to develop an enclave of homes, with approval in place to build on 13 individual lots with boat docks already permitted for each site, as well as 10 acres of submerged land on this astounding waterfront location. Osprey, positioned between the world-class destinations of Sarasota and Venice, is the best of both worlds with a small town feeling with tree-lined streets that end with glimpses of Sarasota Bay, and is minutes from vibrant shops, restaurants, arts and culture of downtown Sarasota. This remarkable waterfront property invites you to become the next chapter of its history."
$3,499,000
730 SARABAY RD, Osprey FL 34229
4
BEDS
6
BATHS
6,308
SQFT
$555
$/SQFT
2.00
ACRES
2011
BUILT
"OSPREY WATERFRONT ESTATE. **See the special 3D virtual tour.**Centrally located to all your favorite spots like Downtown Sarasota, ST Armands Circle, Historic downtown Venice and all the area beaches including world famous Siesta Key. This home is all about the lifestyle. Imagine setting off in your boat for lunch at Marina Jacks or exploring the many great fishing spots along the Intracoastal. There are no fixed bridges if you want to venture out into the Gulf. Wake up in your tranquil bedroom to a magnificent view and plan your day relaxing in your Florida home or set off on a mini adventure to see some of the many local sights. This home was built with attention to detail on one of the last two acre lots in the area. Stunning views surround you in this custom home. Soaring coffered ceilings and wide plank light oak floors give an elegant ambiance while the gourmet kitchen, complete with wine bar, is there for when you want that home cooked meal. The first floor Master Suite will please you with it's spa like bathroom and fully customized closets. Take the stairs or elevator to the second floor to find three additional ensuite bedrooms plus a bonus room for your guests. If you like entertaining, this home is built with you in mind. Spill out to the spacious outdoor area and take a swim in the resort style salt water pool or just hang out with friends and family and enjoy a gorgeous sunset or two. The grounds are low maintenance and very private. This home must be seen to be believed."
$3,499,000
420 N CASEY KEY RD, Osprey FL 34229
5
BEDS
9
BATHS
6,846
SQFT
$511
$/SQFT
0.57
ACRES
1968
BUILT
"Rebuilt in 2006, this classic coastal home is sited on 100 feet of bay front with deeded beach access. The main home is protected with impact glass Andersen windows & doors, automated hurricane shutters, a safe room, elevator and a whole house generator. It was expertly designed with desirable amenities including a steam shower, exercise room and wine cellar. Although less than 12 years old, this home has been impeccably maintained including a Pebble Tec pool surface, a new spa completed in 2015 and Carrier Coastal HVAC in 2017. The master bedroom overlooks the pool, gardens and bay front with his and her baths, connected with abundant closet space. The other generously sized bedrooms each have a full bath. One private suite has a separate entrance for in-home staff, nanny quarters or extended family living. The kitchen was designed for every culinary pursuit and features Wolf/Sub Zero appliances, cherry cabinetry and is open to the main gathering room, which is truly the heart of this home. With partial views of the Gulf of Mexico off the front lanai, retractable screens provide year round entertaining. Overlooking the pool, there is a full outdoor kitchen and dining area and a detached guest house offers a bedroom, full bath and morning kitchen. The Trex resurfaced dock overlooks the Intracoastal Waterway and the existing pilings make boat dockage a breeze. This home is located on North Casey Key, arguably the most desirable section, known for privacy and exclusivity."
* NEW LISTING 
$3,495,000
0 PALMETTO AVE, Osprey FL 34229
4
BEDS
5
BATHS
4,827
SQFT
$724
$/SQFT
1.20
ACRES
2017
BUILT
"Looking for a little peace and quiet and big Bay views? Consider this dream home designed by esteemed architect, Clifford A. Scholz, a little further south of downtown Sarasota and capitalize on the savings. When you consider the all-in price for this proposed Perrone constructed new home on an idyllic stretch of bay frontage vs. Bird Key or Harbor Acres, the short drive equals substantial savings. Located just south of The Oaks and Spanish Point on a Canopy Road with approximately 1.2 acres and spanning 120 of Bay frontage this British West Indies style home is comprised of approximately 4800 sq. feet, 2 master suites, 2 guest bedrooms, all 5 star luxurious finishes, concrete block construction, convertible indoor/outdoor living room with wood burning fireplace and is situated amongst impressive luxury homes and noteworthy owners. Boaters will appreciate the long dock to depths accommodating 30+ foot craft and the old covered boat slip just itching to be remodeled. Located in A11 with 12 minimum elevation. A new home on a piece of Old Florida land just doesn t get any better."
* 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 
$3,250,000
1027 N CASEY KEY RD, Osprey FL 34229
4
BEDS
3
BATHS
2,990
SQFT
$1,087
$/SQFT
0.40
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, 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 - $3,490,000 TO $3,250,000 
$3,100,000
931 BLUE HERON OVERLOOK, Osprey FL 34229
5
BEDS
7
BATHS
6,977
SQFT
$444
$/SQFT
0.59
ACRES
2007
BUILT
"Experience life in one of Florida s finest Country Clubs, The Oaks, from this exquisitely crafted estate home. Strategically positioned to overlook the signature Heron Golf Course, this extraordinary residence presents over 6,900 sq. ft. of space in which to live comfortably & entertain gloriously. A spectacular all-new travertine motor court leads the way to towering double Ash doors, which open to reveal the compelling woods, stone & architecture one might expect to find in a luxury mountaintop lodge. Whether preparing a family breakfast or perfecting your signature dish for a special celebration, the marble kitchen is designed for creating the finest culinary experiences. Also on the 1st level is the divine master retreat, which pampers owners with custom walk-in closets & a heavenly, spa-inspired bathroom. Accessible by a wrought-iron staircase or elevator, upstairs presents three en-suite bedrooms, game room, exercise room, sitting area with library balcony, & magical art deco home theater room with custom stadium style seating & 3D projection onto a 144 film screen. Indulge in the pinnacle of alfresco living from an outdoor space inspired by world s finest boutique resorts- where a screened saltwater pool, spa, gazebo, full summer kitchen, waterfalls & astonishing fairway views. An oversized 4 car garage is a finishing stroke of this masterpiece. The Oaks Club presents world-class lifestyle amenities including golf, tennis, croquet, fitness center, elegant restaurants and fabulous social clubs."
$3,000,000
162 OSPREY POINT DR, Osprey FL 34229
4
BEDS
5
BATHS
6,807
SQFT
$441
$/SQFT
0.63
ACRES
2007
BUILT
"Secluded sanctuary for nature lovers. Luxury home can often be an oxymoron. The luxury may exist, but what makes a house a home ? This property answers that question, as it embodies the true meaning of the phrase. The classic elegance of this residence never overshadows the comfortable living it allows you & your guests to enjoy, while surrounded by the finest in materials, details and amenities. You know from the minute that you approach, that this 4 bedroom, 4.5 bath is going to exceed all expectations as soon as you arrive on the private, secluded grounds within The Oaks Bayside. One look at the brass front doors, handmade in Ecuador, & you know you must see all the interior has to offer. From 16th century Tuscan, an amazing transition from Renaissance to Art Deco takes place as you step over the threshold. Looking up from the gleaming Calcutta gold marble floors you take in the sweeping stairway & Art Deco columns. Exploring the rest is the real treat! Every room reveals another treasure.The 56 lanai & pool deck are accented by a salt water infinity pool, six-person hot tub & Balinese style waterfall & lily pond. The master suite is a luxurious retreat with an extra-large glass, tile & marble steam shower; his-and-hers walk-in closets & a cedar closet. Enjoy all the other custom features this home offers; a 37KW generator, well-fed sprinklers, hurricane glass rails on all three terraces, fire pit on the widow s walk, wine storage & so much more. You truly must see this home to appreciate it!"
* LISTED OVER 120 DAYS 
$2,999,000
136 OSPREY POINT DR, Osprey FL 34229
5
BEDS
8
BATHS
6,461
SQFT
$464
$/SQFT
0.67
ACRES
2005
BUILT
"One of the most beautiful homes in Sarasota, this immaculate residence in the Oaks Bayside is a flourish of custom finishes and designer upgrades inside and out. Located on an oversized parcel (more than half an acre) overlooking the preserve and tranquil waters of Little Sarasota Bay. The expanse of the stunning five bedroom plus office and family room layout encompasses more than 6,400 SF. Immediately fall in love with the Brazilian cherrywood flooring throughout, 18crown moldings, cathedral ceilings, Pella windows, three-stop elevator, LifeTouch LED lighting system, central vacuum, whole-house generator and more that this residence offers. The formal dining room, with a convenient Butler s Pantry a few steps away, easily seats twelve. Equipped with professional-grade appliances, Verde Butterfly granite countertops and maple wood cabinetry, the gourmet kitchen is a chef s dream. This space opens to the family room, offering a full bar area with 150+ bottle wine cooler, as well as a charming breakfast nook. The extensive master retreat, with separate his and her bathrooms and walk-in closets, rests in a secluded northeast corner on the second level. Spacious guest suites (including one master-sized), media and bonus rooms are located on the south side, for optimal privacy. Walls of glass and French doors enhance the light, open atmosphere and lead out to the poolside lanai, featuring an infinity-edge heated swimming pool, spa, fully-equipped summer kitchen and peaceful water views to relax the day away."
$2,580,000
521 S SHORE DR, Osprey FL 34229
4
BEDS
5
BATHS
4,472
SQFT
$577
$/SQFT
0.90
ACRES
2017
BUILT
"PRE-CONSTRUCTION TO BE BUILT, sited on the Intracoastal Waterway. The Mindera Model of John Cannon Homes with nearly 4500 square feet of living area (6658 sf total under roof) has 4 bedrooms, 4.5 baths, a den and a Bonus room, photos courtesy of John Cannon Homes. A 3-car garage and a spacious pool area with an outdoor kitchen all are overlooking the Intracoastal Waterway across from Casey Key. A new boat dock is already in place. Buyers have the ability to customize or purchase Lot separately and may design their own plans. Please see vacant lot listing under MLS #A4161427. Enjoy Gulf sunsets that paint the sky vibrant & inspiring palette of colors. This parcel is one of the last developable properties available of this size and quality along the Intracoastal Waterway in Sarasota County. This serene lot in Sorrento Shores is tucked away from the hustle and bustle, yet located close to Venice and Sarasota. Some of the best of dining, entertainment, and shopping just minutes away from your private Floridian oasis."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,590,000 TO $2,580,000 
$2,475,000
418 N CASEY KEY RD, Osprey FL 34229
4
BEDS
3
BATHS
2,334
SQFT
$1,060
$/SQFT
0.34
ACRES
1957
BUILT
"A true Florida beach house, in excellent condition, is a rare and special find. This home has been pristinely maintained and features an updated kitchen with room for gathering and entertaining, Sub-Zero refrigeration with freezer drawers, Kitchen Aid cook top, convection-microwave double wall ovens and separate wine cooler. The dining room and great room overlook the Gulf of Mexico. You ll be drawn to the windows and view that spans the back of this home. Vintage baths have new fixtures and all were re-piped. Other recent investments make it easy to move right in: Newer HVAC, washer, dryer, hurricane shutters, gutters, roofing, acryl-a-coat exterior paint and beautiful landscaping, including palm trees, new irrigation and drainage, all designed and maintained by award winning Grant s Gardens. The new paver patio and beach access stairs lead to a sandy private beach. Sunsets are plentiful and if you can tear yourself away from this retreat, restaurants, shopping, Venice Island and downtown Sarasota afford the best for those seeking true beachfront living and a Florida lifestyle."
* NEW LISTING 
$2,250,000
95 OSPREY POINT DR, Osprey FL 34229
5
BEDS
6
BATHS
7,500
SQFT
$300
$/SQFT
0.74
ACRES
1990
BUILT
"French Chateaux with guest house and 4+ (tandem) car garage in The Oaks Bayside. This incredible Bo MacEwen designed masterpiece was finished in 1997 and major renovations were done in 2001. As you enter the main house you are met with a spectacular wooden double staircase, 25+ foot ceilings, and an enormous crystal chandelier. Old world charm abounds with elegant custom details throughout. Features like custom mill work from floors to ceilings, hand carved wood doors, elegant brass hardware, and pecky cypress beams, all lovingly restored since 2012 including most mechanicals downstairs flooring in 2016. Master bedroom and second suite are on the main floor with 2 additional on-suite bedrooms upstairs. A beautiful chef s kitchen, 2 fire places, large closets with lots of storage, and light fixtures that are works of art, complete the interior of this one of kind home. The home is situated on two elegantly landscaped lots covering of an acre and overlooking a large lake complete with a lighted fountain. The vast covered patio with a slate floor is designed for entertaining with a full Viking kitchen and a huge balcony overlooking the large salt water pool. Situated on the second lot, the 1,000 sqft. Guest house, built in 2001, is a completely self-contained 1 bedroom 1 bath with large kitchen, gorgeous d cor and two balconies. The Oaks is located minutes from the top ranked Pine View School and #1 Ranked US Beach, Siesta Key. Membership in The Oaks Club, Sarasota s Premier Country Club, is required."
$2,195,000
412 BAYSHORE DR, Osprey FL 34229
3
BEDS
4
BATHS
3,533
SQFT
$621
$/SQFT
0.83
ACRES
2004
BUILT
"Paradise Found! This private waterfront estate built by John Cannon in 2004 is situated on almost an acre with 162ft of waterfront footage offering panoramic views of Little Sarasota Bay and extraordinary sunsets over Casey Key. A private setting, a long paver brick drive winds past mature Florida friendly landscaping and a variety of fruit trees leading up to a porte-cochere and striking double glass entry doors. The residence, 3,533 AC sf, rests on one level, custom built for wheel chair access. This desirable Great Room plan includes a Master Suite with luxurious bath and Private Sitting Room; 2 Guest Bedrooms with Baths, Formal Dining, Office, Laundry / Mud Room, Walk-in Pantry, Powder Bath, Inside AC Storage and a Two Car and One Car Garage. The screened Lanai opens with a remote onto an expansive pool deck. An infinity edge pool, heated spa, outdoor kitchen and gas fireplace compose the perfect spot for outdoor entertaining. A long dock with 8K boat lift offers another quiet spot to watch the sunsets. A gas Fireplace is a focal point that separates the Dining room and provides cozy ambiance on cool winter nights. Adjacent to the great room, the spacious, eat-in kitchen features beautiful wood cabinetry, granite countertops and backsplash, stainless steel appliances, breakfast bar / island and an office nook. Thoughtful upgrades include 13ft stepped and decorative ceilings, 10ft ceiling in bedrooms, hurricane shutters throughout with some operated remotely, 2 zoned HVAC & a 17.5 KW standby generator."
* LISTED OVER 120 DAYS 
$1,971,000
285 SUGAR MILL DR, Osprey FL 34229
5
BEDS
6
BATHS
5,578
SQFT
$353
$/SQFT
0.68
ACRES
1989
BUILT
"An award-winning golf club, #1 beach, nationally ranked school and peace of mind. What more could you ask for? Updated to the hurricane standards, this home features impact resistant garage doors and high velocity hurricane zone approved screen protectors for all openings in all three buildings. This walled and gated lakefront estate features a beautifully designed 2 or 3 bedroom main house with attached garage, a 1,200-square-foot 2 bedroom guesthouse, 2 dramatic lakefront pools and a separate air-conditioned, 2-car garage that could also be used as a pool cabana or private gym. Unique architectural elements and high-end finishes include solid wood doors, perimeter crown molding, tray ceilings, marble and wood flooring and French doors. The living and dining rooms open completely to the lakefront pool and capture the gentle cool breeze flowing across Little Sarasota Bay. The kitchen is open to the family room and includes rich cherry wood cabinetry, granite countertops, large island, professional appliances and walk-in pantry. The family room opens to both pool areas and provides access to the guesthouse across the shared courtyard. Oaks Bayside is a gated Bayfront community and part of The Oaks Club, one of the areas most exclusive private clubs and recent recipient of the Distinguished Emerald Club of the World award from BoardRoom magazine. Located just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area beaches and all that Gulf Coast living has to offer."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,150,000 TO $1,971,000 
$1,895,000
324 OSPREY POINT DR, Osprey FL 34229
5
BEDS
5
BATHS
5,758
SQFT
$329
$/SQFT
0.97
ACRES
1998
BUILT
"Perfectly positioned along North Creek in the Oaks Bayside, this architecturally significant and beautifully designed residence is uniquely representative of what modern buyers are looking for in a home. Understated elegance, clean lines, dramatic windows, high ceilings and a functional floor plan combine to create a modern living space. The design is brought to life by fine finishes and quality craftsmanship including Philippine shell stone, Jerusalem marble and maple wood flooring, granite and travertine countertops, Birdeye maple cabinets, premium appliances, and many additional refinements. The combined living and dining room is perfect for entertaining and opens to the outdoor pool and spa area. For more casual entertaining, the large kitchen and breakfast nook flow seamlessly into the family room as well as to the outdoor living space. The four bedrooms in the main house each provide privacy and flexibility for use as an office, studio, etc. The separate guesthouse boasts walls of glass overlooking the lush grounds and multiple room options perfect for providing visitors with their own space. Oaks Bayside is a gated Bayfront community and part of The Oaks Club, one of the areas most exclusive private clubs and recent recipient of the Distinguished Emerald Club of the World award from BoardRoom magazine, representing the top 4% of all private clubs. The Oaks is just minutes from Downtown Sarasota and of all restaurants, nightlife and cultural activities living on the gulf coast has to offer."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,995,000 TO $1,895,000 
$1,650,000
145 SHORELAND DR, Osprey FL 34229
4
BEDS
5
BATHS
4,112
SQFT
$401
$/SQFT
0.51
ACRES
2004
BUILT
"Look no further! Exceptional property, exceptional value. 151 feet of waterfront offers stunning views of the Intracoastal Waterway & South Creek Bayou. Custom designed & built in 2004, this lovely residence presents both tasteful & timeless architecture. Come experience outstanding Florida outdoor living featuring wraparound terraces upstairs, oversized covered lanai, pool & spa and wonderful gardens to stroll. Preferred south by southwest exposure in back. Over 4,100 square feet of immaculate interior perfection. Two master suites offer choice of ground floor convenience or stunning upstairs panoramic views of the acre grounds, peaceful waterways & native mangroves. Loaded with fine millwork & custom details, enjoy the openness & drama of 22-foot coffered ceiling in the grand living room. Practical floor plan features 4 bedrooms plus den/library, 3 full baths & 2 half baths. Soft & comfortable interior, yet light & bright. New dock built in 2014 offers water, electric & lift. Whole house generator & security system for peace of mind. Gas-heated pool, fireplace & appliances. Lovingly maintained by original owners. Quiet serenity awaits at this convenient preferred Osprey location, offering easy to both Sarasota and Venice. Close to magnificent public parks, beautiful beaches, nationally ranked Pine View School, fine dining & endless recreational activities. This is Florida living at its finest!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,750,000 TO $1,650,000 
$1,649,999
854 MACEWEN DR, Osprey FL 34229
4
BEDS
6
BATHS
9,081
SQFT
$182
$/SQFT
0.78
ACRES
2003
BUILT
"Immerse yourself in luxury! One of the most exquisite estate offerings is nestled within the Oaks most distinguished Clubside enclaves. This incomparable dream unfolds over 9,000 square feet of quality craftsmanship including automated smart home technology. The expansive gourmet kitchen hosts cherry cabinetry, double thick granite counter tops with commercial grade stainless steel appliances. The kitchen is open to a family room which flows into a billiard or game room area which hosts an extensive wet bar area. This state-of-the-art and comfortable home is ideal for a large family while being an entertainer s dream. This 4 bedroom estate holds a first level master suite which is a haven of elegance and tranquility. There is an ideal space for a nursery or exercise room directly off the master suite. You can also work comfortably from home in the private, wood paneled fireplace office. The home has a private bedroom with separate entrance which is ideal for maid quarters or in-law suite. The second level hosts a large theater room, separate sitting space and outdoor screened patio area. This home of boundless warmth and timeless style extends to the outdoor living space with large pool, cascading stone spa and elegant gas flames. This sprawling gem embraces laid back Florida luxury! Club Members enjoy championship golf courses, spectacular dining & social activities."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,749,000 TO $1,649,999 
$1,600,000
393 NORTH POINT RD #1002, Osprey FL 34229
3
BEDS
3
BATHS
3,738
SQFT
$428
$/SQFT
2001
BUILT
"This 3 bedroom, 2.5 bath PENTHOUSE with PRIVATE 2 CAR GARAGE in Meridian at The Oaks Preserve is the definition of luxury. Discriminating buyers know that true luxury in a home comes from a combination of quality appliances and finishes, quiet elegance and an amazing location that offers the finest of views, activities and lifestyles. From sunrise to dramatic color-drenched sunsets over the Gulf, your days will be filled with the joy of elegant country club living. Walk through the courtyard to the secure entrance, and take your private elevator to this amazing 3,700 square foot residence. As you enter you will be struck by the classic appointments, and the quality and care that is in every detail. Beautiful Travertine floors span the unit and create the backdrop for graceful living. The kitchen is a gourmet s delight with maple cabinets, Miele double ovens, a Thermador induction range and two Fisher Paykel dishwashers. The luxurious master bathroom features a steam shower, Onex counters, a large jetted tub and his-and-hers closets. With a soundproof media room, Lutron lightening system, customer mill work and Sub Zero wine storage system, you d think you couldn t ask for more! But, this unit has a TWO CAR PRIVATE GARAGE, motorized screens on the balcony and for Meridian residents only, your own community pool, spa and fitness center. Offering all this plus everything that being a member of The Oaks, Sarasota s finest golf and country club, has to offer. Membership is available and required."
$1,500,000
497 WEBBS CV, Osprey FL 34229
6
BEDS
7
BATHS
6,341
SQFT
$237
$/SQFT
0.45
ACRES
1992
BUILT
"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 a 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 - $1,549,000 TO $1,500,000 
 
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