1216 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 6 Bath · 2 Half Baths · 8,050 SqFt · $1,460/SqFt
Days on Market: 24
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1999
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.10
This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water ... Read more....»
144 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 5,397 SqFt · $1,258/SqFt
Days on Market: 4
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 2003
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12,000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request. The front elevation is framed by a raised lawn with a stone wall, a paver driveway and manicured landscaping. As you approach the home, the travertine steps lead you to the new custom front door, where dramatic water views of the bay immediately greet you ... Read more....»
622 BAYSHORE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
6 Bed · 5 Bath · 4,893 SqFt · $1,165/SqFt
Days on Market: 41
County: Sarasota
Subdiv/Community Name: Bay Acres Sub
Legal Subdivision Name: BAY ACRES - RESUB
Year built: 2022
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! Welcome to 622 Bayshore Drive - where coastal luxury meets modern sophistication on one of the most sought-after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78-acre gated estate, this custom-built, contemporary masterpiece offers 90 feet of pristine waterfront, unmatched privacy, and a lifestyle defined by serenity, style and seamless connection to the water. Designed for those who crave the extraordinary, this six-bedroom, five-bath residence is a showpiece of elevated design and quality craftsmanship, built just three years ago with the finest materials and storm-resilient features. ... Read more....»
1049 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 2,582 SqFt · $1,840/SqFt
Days on Market: 2
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1990
Garage: Yes 5 vehicles
Waterfront: Yes
Lot Size (in acres): 1.06
Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies the timeless beauty of Old Florida living, offering a tranquil retreat with direct gulf-to-bay access. The three-bedroom, three-bath home exudes Mediterranean coastal charm and invites you to embrace the serenity of coastal life. With an expansive living room, formal dining room, country ... Read more....»
854 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 2 Half Baths · 9,081 SqFt · $462/SqFt
Days on Market: 224
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 2003
Garage: Yes 4 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. **NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE** Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game Room w/ Wet Bar, Loft, Balcony, etc. and even includes highly coveted, oversized and split 4-CAR GARAGE(s). This MOVE-IN READY home has been tastefully updated and is ideal for indoor and outdoor entertaining! The elegant first level primary bedroom suite features high ceilings, multiple ... Read more....»
1042 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,781 SqFt · $784/SqFt
Days on Market: 85
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: PALMER
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
EXCEPTIONAL WATERFRONT RESIDENCE on the exclusive island of North Casey Key is a rare opportunity to own a piece of coastal Florida. Nestled in the sought-after Palmer neighborhood, this home has been lovingly maintained by the same discerning owners since 1999—a testament to the pride, care, and attention poured into every detail over the years. Set on an expansive 0.68-acre lot with 131 feet of Sarasota Bay frontage with two deeded private beach access points, the property is enveloped in lush tropical landscaping and exudes timeless Old Florida charm. The interior showcases a traditional layout with formal living and dining ... Read more....»
112 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 8,635 SqFt · $405/SqFt
Days on Market: 92
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to impress—and now invites a new owner to make it their own. The ground floor has been thoughtfully prepared for renovation, providing a blank canvas to bring your vision to life. Whether you imagine a guest or in-law suite, a luxury garage with a gaming lounge, a ... Read more....»
550 DOVE POINTE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 7,842 SqFt · $421/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 2006
Garage: Yes 4 vehicles
Private Pool: Yes
Sited at the end of a quiet cul-de-sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota County’s most exclusive communities. Perfectly positioned on over three-quarters of an acre, the residence boasts serene preserve and fairway views, capturing the essence of Florida luxury living. Inside, discover graciously sized rooms, soaring ceilings, and abundant natural light that fills every space. The formal living room with gas fireplace and the formal dining room provide elegant spaces for entertaining. The open-concept kitchen and family room are the heart of ... Read more....»
662 FERNWALK LANE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 4,359 SqFt · $687/SqFt
Days on Market: 179
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 3 vehicles
Private Pool: Yes
**FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay. An Expansive Floorplan entails 4-BEDs plus 4-FULL BATHS while a full list of EXCEPTIONAL FEATURES is available upon request and includes Soaring 16ft and Vaulted Ceilings, Impressive White Oak and Marble Floors, Custom Crown trim, Plantation Shutters, many Built-Ins…to name a few. The Gorgeous, Chef’s Kitchen showcases marble counters, custom hardwood cabinetry ... Read more....»
236 SAINT JAMES PARK
OSPREY FL 34229
Residential / Single Family Residence
6 Bed · 6 Bath · 1 Half Bath · 6,246 SqFt · $464/SqFt
Days on Market: 84
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1986
Garage: Yes 2 vehicles
Private Pool: Yes
Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilings, marble floors, and crystal chandeliers. A Louis XVI fireplace anchors the sunken living room, while French doors and expansive windows invite sunlight into the sunroom with breathtaking golf course views leading to three patios perfect for entertaining or relaxation. A brick path winds through lush gardens to the adjacent guest house. This nearly 2,000 sq ft guest house features ... Read more....»
49 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,953 SqFt · $682/SqFt
Days on Market: 141
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, ... Read more....»
852 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 4,519 SqFt · $564/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 1992
Garage: Yes 3 vehicles
Private Pool: Yes
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, ... Read more....»
340 OSPREY POINT DR
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 6,001 SqFt · $417/SqFt
Days on Market: 50
County: Sarasota
Subdiv/Community Name: Oaks The
Legal Subdivision Name: OAKS
Year built: 1998
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a spacious 3-car side-load garage. Stately columns welcome you to the grand double-door entry, where you’ll step inside to find gleaming marble floors, soaring ceilings, and plantation shutters that set the stage for timeless sophistication. The thoughtfully designed floor plan includes a private ... Read more....»
18 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,977 SqFt · $1,189/SqFt
Days on Market: 59
County: Sarasota
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: CASEY KEY
Year built: 1973
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Beautifully remodeled in 2012, this bayfront residence combines elegance, functionality and an enviable location. The living room, kitchen and family room are great places to gather, and the split floor plan provides room for all, privacy to retreat with a good book or work from home options. The classic coastal style provides a view of the bay and intracoastal waterway from the primary bedroom. Set on more than half an acre, the expansive backyard and large screened pool provides a bayfront tropical paradise. The deeded easement directly across the street takes you to a private sandy beach where you’ll want ... Read more....»
180 LOOKOUT POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 3,236 SqFt · $711/SqFt
Days on Market: 52
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1986
Garage: Yes 2 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club—an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this five-bedroom, 3.5-bath, 3,236-square-foot home blends solid block construction with high-end design and cutting-edge technology. No detail was overlooked including a standing seam metal roof, all new high-velocity impact windows, hurricane-rated garage doors and fully integrated Alexa features throughout. Wide-plank wood floors lead through a thoughtfully designed layout featuring ... Read more....»
67 SUGAR MILL DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2 Half Baths · 4,020 SqFt · $497/SqFt
Days on Market: 159
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 2 vehicles
Private Pool: Yes
This is your rare chance to claim a spectacular estate in Sarasota’s premier golf and country club community THE OAKS. This elegant home seamlessly blends timeless architecture with resort-style living. Beyond the private gates, step into over 4,000 square feet of refined interiors featuring dramatic ceilings, architectural columns, and panoramic views. The expansive layout includes 4 bedrooms, 5 bathrooms, formal and casual living spaces, and an executive Office/Den/Bourbon Tasting Room. The gourmet kitchen is perfectly equipped for culinary entertainment, with custom cabinetry, premium appliances, and a spacious island that flows into the family room. A luxurious owner’s suite provides a private ... Read more....»
600 EAGLE WATCH LANE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 3,681 SqFt · $541/SqFt
Days on Market: 105
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 1992
Garage: Yes 3 vehicles
Private Pool: Yes
Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generous 0.71-acre lot with wide views of the third hole of the Heron Golf Course. Nearly every aspect of the property has been updated—new roof, impact-rated windows and doors, flooring, trim, countertops, appliances, resurfaced pool and spa, new pool cage, and a resurfaced driveway—making it truly move-in ready. Inside, the layout is open and light-filled, with 14-foot ceilings in the formal living and dining rooms, a reimagined kitchen that opens to a casual dining area, and a spacious family room ... Read more....»
140 SUGAR MILL DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 3,286 SqFt · $600/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 2 vehicles
Private Pool: Yes
**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The Impressive Kitchen features Silestone Counters, Premium Appliances including SUBZERO and WOLF, Large Island with sitting area, separate dry bar, etc. The Expansive Primary Bedroom Suite entails a Large Walk-In Closet with custom built-ins and spacious bath with dual vanities, quartz counters, seamless ... Read more....»
909 MACEWEN DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 4,241 SqFt · $400/SqFt
Days on Market: 321
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PHASE 2
Year built: 1991
Garage: Yes 2 vehicles
Private Pool: Yes
**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private ... Read more....»
360 N POINT ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 2,913 SqFt · $539/SqFt
Days on Market: 363
Cumulative Days on Market: 564
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 3 PH 1
Year built: 2023
Garage: Yes 2 vehicles
**DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen features a large island sitting area, Bosch appliances including 5-burner Gas range, wine storage, etc. while the adjacent great room and dining room are ideal for entertaining and showcase Vaulted and High Ceilings, a cozy fireplace and engineered hardwood ... Read more....»
402 WALLS WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,464 SqFt · $433/SqFt
Days on Market: 106
Cumulative Days on Market: 382
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 2014
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Welcome to timeless elegance and modern comfort in The Oaks Clubside. This stunning 4-bedroom plus den/office, 3.5-bath home, built in 2014 by Todd Johnson Homes, blends country modern style with refined sophistication. Situated on an oversized .64-acre corner lot, this courtyard-style residence is designed for effortless Florida living. Step through grand double wood doors into an inviting space where soaring ceilings, an open floor plan, and abundant natural light create an airy, welcoming ambiance. The home features tile and hardwood floors, hurricane impact windows and doors, a spacious 3-car garage, and thoughtful architectural details throughout.The gourmet kitchen is a chef’s ... Read more....»
296 PINE RANCH TRAIL
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 3,481 SqFt · $417/SqFt
Days on Market: 78
County: Sarasota
Subdiv/Community Name: Pine Ranch East
Legal Subdivision Name: PINE RANCH EAST
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
Lot Size (in acres): 1.14
**THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a nearby golf course, offering tranquil views and peaceful surroundings. With no rear neighbors, you'll enjoy the privacy and serenity that your 1 acre+ lot affords. Have a boat or RV? This community is deed restricted but there ... Read more....»
1527 BUOY LANE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,830 SqFt · $452/SqFt
Days on Market: 26
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1989
Garage: Yes 2 vehicles
Private Pool: Yes
Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround ... Read more....»
1484 SEAFARER DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,479 SqFt · $359/SqFt
Days on Market: 46
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1987
Garage: Yes 3 vehicles
Private Pool: Yes
Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coast’s most coveted communities—where every day feels like a vacation! Southbay boasts a world-class private marina with 172 deep-water slips, accommodating yachts up to 55 feet, along with personal watercraft and kayaks. Slip rentals are available and offered at a highly competitive rate, making this an exceptional value for boating enthusiasts. This remarkable residence is one of the largest in the community and offers a rare 3-car, side-load garage with a dedicated workshop—perfect for collectors, creatives, or anyone in need of additional space. Step outside to your private oasis: ... Read more....»
820 PLACID LAKE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 4 Bath · 3,938 SqFt · $305/SqFt
Days on Market: 149
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL WOODLANDS
Year built: 2002
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
***carpet was professionally cleaned 3/26/25*** Discover this beautiful, expansive 5-bedroom, 4-bathroom home offering 3,938 sq. ft. of living space on a 10,548 sq. ft. lot. Designed for both comfort and elegance, this residence features an open-concept floor plan with crown molding throughout, custom solid wood-designed cabinets, induction oven, a glass tile backsplash, stainless steel appliances, and granite countertops. The spacious kitchen also includes a large island and a matching breakfast table—both with granite countertops—providing generous in-kitchen seating. A wine bar adds a touch of sophistication, while the separate formal dining room is perfect for larger dinner parties. The kitchen is ... Read more....»
201 EAGLENOOK WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 3,379 SqFt · $355/SqFt
Days on Market: 110
County: Sarasota
Subdiv/Community Name: Pine Ranch
Legal Subdivision Name: PINE RANCH
Year built: 1992
Garage: Yes 3 vehicles
Private Pool: Yes
Lot Size (in acres): 2.00
Nestled in the exclusive Pine Ranch community of Osprey, Florida, this 4-bedroom, 3-bath estate offers a rare opportunity for those seeking privacy, tranquility, and a healthier way of living. Situated on just over two acres of lush, tree-canopied land, this meticulously maintained home is designed for comfort, sustainability, and connection to nature. From the moment you enter the long private driveway, the serenity of this property welcomes you home. Every room is bathed in natural light, offering breathtaking views of the expansive pool, spa, and surrounding greenery, creating a peaceful retreat for relaxation and rejuvenation. The spacious kitchen is ... Read more....»
120 LOOKOUT POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,925 SqFt · $410/SqFt
Days on Market: 177
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1985
Garage: Yes 3 vehicles
Private Pool: Yes
Spacious Custom built home featuring an oversized corner yard, High Ceilings, Updated Kitchen and Bathrooms, Family Room with Wood Burning Fireplace, 3 Bedrooms, 3 Full Baths and a Bonus Room/ 4th Bedroom upstairs. Entertain in the Large Lanai with Outdoor Kitchen overlooking the Pool and wide Greenbelt view. The Stylish and Durable new Metal Roof will protect you for years to come, full Hurricane protection. Attached 2 car garage with workbench and a 3rd garage for your Golf Cart, Boat, Kayak, Bikes etc. All in the Amazing Southbay & Racquet Club where the true Florida Lifestyle thrives! Private Marina, ... Read more....»
227 SAINT JAMES PARK
OSPREY FL 34229
Residential / Single Family Residence
2 Bed · 2 Bath · 2,071 SqFt · $505/SqFt
Days on Market: 179
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1986
Garage: Yes 2 vehicles
**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking the Eagle Golf Course and Ideally Located near the Clubhouse and Campus of World Class Amenities, this Distinctive LIGHT AND BRIGHT floorplan offers 2-BEDS, 2 FULL BATHS, 2-Car Oversized Garage with EV Charging and features unique architectural details throughout including beautiful crown moldings, wainscoting, cozy fireplace, engineered hardwood and tile floors, built-in sound ... Read more....»
766 SHADOW BAY WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 3,438 SqFt · $290/SqFt
Days on Market: 67
County: Sarasota
Subdiv/Community Name: Rivendell The Woodlands
Legal Subdivision Name: RIVENDELL
Year built: 1998
Garage: Yes 2 vehicles
Private Pool: Yes
Community Pool: Yes
Waterfront: Yes
Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized pool with a generously sized spa and ambient lighting, perfect for evening relaxation. Inside, the wide, open floor plan boasts soaring ceilings and abundant natural light, creating an airy and uplifting atmosphere. Multiple living areas flow seamlessly into a spacious kitchen and family room, all opening to a covered lanai ideal for everyday ... Read more....»
599 PINE RANCH EAST ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,188 SqFt · $455/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Bay Oaks Estates
Legal Subdivision Name: BAY OAKS ESTATES
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
**EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers an expansive, private retreat complete with walk-in closets, dual vanities, Jacuzzi tub, custom-tiled shower, Italian smart toilet-bidet, etc. A complete List of Recent Upgrades is attached and available upon request and includes but is not limited to ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.
