Search Results: Single Family Homes in Osprey for Sale

1216 N CASEY KEY ROAD
OSPREY FL 34229

Residential / Single Family Residence

5 Bed  ·  6 Bath  ·  2 Half Baths  ·  8,050 SqFt  ·  $1,335/SqFt

Days on Market: 311

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....»

121 N CASEY KEY ROAD
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,096 SqFt  ·  $1,660/SqFt

Days on Market: 116

County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1969
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

Newly Remodeled Gulf-Front Mediterranean Villa on Casey Key Framed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline. Just minutes from the cultural and dining destinations of Venice and Sarasota, the residence offers unrivaled privacy, architectural beauty, and Gulf Coast living beyond compare. Behind a gated entry, the main residence features three bedrooms and three-and-a-half baths, thoughtfully remodeled with no detail spared. Distinctive design elements include wood beams and moldings, Mexican tile and wood floors, brick accents, hand-painted ... Read more....»

144 N CASEY KEY ROAD
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  1 Half Bath  ·  5,397 SqFt  ·  $1,018/SqFt

Days on Market: 188

County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 2003
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes

Located on the exclusive stretch of North Casey Key, this private waterfront estate offers a rare blend of resort-style living, protected boating water, and direct Gulf beach access in one of Sarasota County’s most coveted coastal enclaves. Set on over half an acre along Little Sarasota Bay, this durably constructed residence, engineered for strength and storm protection, delivers a private, resort-style waterfront lifestyle defined by mature tropical landscaping, sweeping views of the Intracoastal Waterway and the Gulf of America, and exceptional privacy. With a private beach easement providing direct Gulf access and a 100-foot dock featuring dual 12,000-lb lifts, water, ... Read more....»

730 SARABAY ROAD
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  1 Half Bath  ·  6,308 SqFt  ·  $871/SqFt

Days on Market: 93

County: Sarasota
Subdiv/Community Name: Sarabay Acres
Legal Subdivision Name: SARABAY ACRES
Year built: 2011
Garage: Yes 7 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 2.00

Premier Intracoastal Estate in Osprey 4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront Acres A rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is a convergence of residential luxury and unparalleled waterfront living. The two-story home sits at the end of a long drive behind a gated entrance and tranquil pond. With approximately 100 feet of bay frontage, the property provides an uncommon level of seclusion. A private dock and boat lift rated for 15,000 pounds offer instant access to Little Sarasota Bay. With no fixed bridges in the way, vessels of any height can sail straight ... Read more....»

101 OSPREY POINT DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  1 Half Bath  ·  5,087 SqFt  ·  $983/SqFt

Days on Market: 1

County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: THE OAKS
Year built: 1985
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes

A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a ... Read more....»

854 N CASEY KEY ROAD
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  3,462 SqFt  ·  $1,372/SqFt

Days on Market: 1

County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: ACREAGE & UNREC
Year built: 1975
Garage: Yes 2 vehicles
Waterfront: Yes
Lot Size (in acres): 1.49

On the quiet and coveted stretch of North Casey Key, where century-old oaks meet the shoreline, and the land unfolds uninterrupted from Gulf to bay, this extraordinary 1.5-acre estate offers a rare opportunity to steward one of the island’s most incredible homesites. With 180 feet of private Gulf frontage and exceptional depth across to the intercoastal, the property is defined by its scale, privacy, and quiet permanence—offering a setting that feels both expansive and deeply secluded beneath a canopy of mature coastal forest. Here, the rhythm of the water and the natural beauty of the land create an environment that ... Read more....»

324 BAYSHORE DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  1 Half Bath  ·  4,389 SqFt  ·  $968/SqFt

Days on Market: 2

County: Sarasota
Subdiv/Community Name: Bay Acres Sub
Legal Subdivision Name: BAY ACRES - RESUB
Year built: 2000
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to the Intracoastal Waterway. Even more spectacular is the beautiful water and natural beauty of Midnight Pass which is just to the north of this property and sandbar relaxation just a short boat ride away. This home features all the right spaces and updates- it features a smartly renovated main house comprised of three bedrooms, three and a half bathrooms and spacious office, as well ... Read more....»

854 MACEWEN DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  2 Half Baths  ·  9,081 SqFt  ·  $428/SqFt

Days on Market: 100
Cumulative Days on Market: 390

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. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the lanai, where golf course views frame the heated pool, spa, and outdoor kitchen. The first-floor primary suite is a true retreat, featuring high ceilings, multiple closets, and a flexible sitting area that can serve as a nursery, gym, or private ... 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: 70

County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: PALMER
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

One or more photo(s) has been virtually staged. If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out. Each bedroom opens to the outdoors with bay breezes and water views, while majestic oaks and lush tropical landscaping create a timeless Old Florida setting. Launch your kayak from the backyard, walk your private beach access every ... Read more....»

135 TINA ISLAND DRIVE
OSPREY FL 34229

Residential / Single Family Residence

3 Bed  ·  4 Bath  ·  1 Half Bath  ·  2,572 SqFt  ·  $1,283/SqFt

Days on Market: 126

County: Sarasota
Subdiv/Community Name: Sorrento Shores
Legal Subdivision Name: SORRENTO SHORES
Year built: 1965
Garage: Yes 4 vehicles
Waterfront: Yes

Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and encompassing 6,254 square feet under roof, this home was built for strength, safety, and peace of mind. The main living area is elevated to 18 feet, well above flood levels. Inside, you’ll find an open-concept design with soaring ... Read more....»

662 FERNWALK LANE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  4,359 SqFt  ·  $654/SqFt

Days on Market: 1

County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1989
Garage: Yes 3 vehicles
Private Pool: Yes

**EXCEPTIONAL, FULLY RENOVATED, COUNTRY CLUB ESTATE HOME OFFERING TRANQUIL LAKE AND GARDEN VIEWS** ideally positioned on a serene interior cul-de-sac lot in Flood Zone X (no flood insurance required). Located behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. This expansive residence features 4 Bedrooms and 4 Full Bathrooms within a thoughtfully designed floor plan. A comprehensive list of upgrades and amenities is available upon request and includes soaring 16-foot and vaulted ceilings, white oak and marble flooring, custom crown molding, plantation shutters, and extensive built-ins. The stunning ... Read more....»

236 SAINT JAMES PARK
OSPREY FL 34229

Residential / Single Family Residence

6 Bed  ·  6 Bath  ·  1 Half Bath  ·  6,246 SqFt  ·  $432/SqFt

Days on Market: 257

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 sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace anchors the dramatic sunken living room, while French doors and expansive windows flood the sunroom with natural light and frame sweeping golf course views. Step outside to three inviting patios—ideal for sunset cocktails, lively gatherings, or peaceful mornings overlooking the greens. A ... Read more....»

479 SOUTH CREEK DRIVE
OSPREY FL 34229

Residential / Single Family Residence

5 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,261 SqFt  ·  $609/SqFt

Days on Market: 90

County: Sarasota
Subdiv/Community Name: South Creek
Legal Subdivision Name: SOUTH CREEK
Year built: 1995
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes

Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant travertine pavers, with a covered dining area providing a perfect setting for shaded entertaining. An expansive waterfront deck extends beyond the screened lanai for lounging and alfresco dinners overlooking the water. Steps lead to a private dock with a 10,000-pound boat ... Read more....»

49 OSPREY POINT DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  3,953 SqFt  ·  $632/SqFt

Days on Market: 105

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  ·  $552/SqFt

Days on Market: 174

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....»

530 N MAC EWEN DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,346 SqFt  ·  $552/SqFt

Days on Market: 8

County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 4-C PT 3
Year built: 2002
Garage: Yes 3 vehicles
Private Pool: Yes

Located in the prestigious gated community of The Oaks Golf & Country Club in Osprey (Sarasota area), this elegant single-story residence at 530 N Mac Ewen Drive offers resort-style living with championship golf just steps away. Spanning 4,346 square feet under air and 5,837 square feet under roof on an oversized lot, the home features 4 bedrooms, 5 full bathrooms, 1 half bathroom, and a 3-car garage with built-in cabinets and the bonus of a car lift allowing for 4 cars in total. Presented fully furnished and turnkey, this meticulously maintained home is move-in ready and showcases exceptional craftsmanship throughout. ... 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: 61

County: Sarasota
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: CASEY KEY
Year built: 1973
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal for quiet retreats, reading or working from home. Enjoy serene views of the bay and Intracoastal Waterway from the primary suite, a coastal sanctuary. Set on over half an acre, the expansive backyard features a large screened-in pool and lush landscaping, ... Read more....»

180 LOOKOUT POINT DRIVE
OSPREY FL 34229

Residential / Single Family Residence

5 Bed  ·  3 Bath  ·  1 Half Bath  ·  3,236 SqFt  ·  $703/SqFt

Days on Market: 104

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 with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is 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 never-lived-in five-bedroom, 3.5 ... Read more....»

433 E MACEWEN DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  4,012 SqFt  ·  $561/SqFt

Days on Market: 18

County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 1998
Garage: Yes 3 vehicles
Private Pool: Yes

An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior craftsmanship designed to accommodate the seamless indoor-outdoor transfer so critical to Florida living. Most prominently the home features 12 foot high ceilings in most rooms, designed to maximize the home's grander, air ... Read more....»

362 MACEWEN DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  4,117 SqFt  ·  $546/SqFt

Days on Market: 15

County: Sarasota
Complex/CommunityName: THE OAKS
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1998
Garage: Yes 3 vehicles
Private Pool: Yes

Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with ... Read more....»

600 EAGLE WATCH LANE
OSPREY FL 34229

Residential / Single Family Residence

3 Bed  ·  3 Bath  ·  3,681 SqFt  ·  $596/SqFt

Days on Market: 115
Cumulative Days on Market: 302

County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 2
Year built: 1992
Garage: Yes 3 vehicles
Private Pool: Yes

One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3 BEDROOMS + STUDY/DEN, 3 FULL BATHS, High Ceilings, Crown Moldings, Gas Fireplace, Engineered Hardwood Flooring, Spacious Kitchen with New QUARTZ Counters and Stainless Steel appliances including premium brands such as SUBZERO and KITCHENAID, 3-Car Garage, Etc. An Expansive Primary Bedroom Suite ... Read more....»

85 SUGAR MILL DRIVE
OSPREY FL 34229

Residential / Single Family Residence

3 Bed  ·  3 Bath  ·  4,191 SqFt  ·  $513/SqFt

Days on Market: 105

County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1991
Garage: Yes 2 vehicles
Private Pool: Yes

**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainscoting, plantation shutters, LED lighting accents and MORE! NEW ROOF (2020). The CHEF’s KITCHEN boasts Quartzite counters, hardwood cabinetry, NEW Appliances include SUBZERO Refrigerator, WOLF Range and built-in coffee station, etc. The Spacious primary bedroom suite entails a bonus sitting area and multiple walk-in closets while the primary bath offers dual vanities, elegant soaking tub and custom-tiled shower. Enjoy the ... Read more....»

538 DOVE POINTE DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,346 SqFt  ·  $483/SqFt

Days on Market: 70

County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 4-C PT 3
Year built: 2002
Garage: Yes 3 vehicles
Private Pool: Yes

**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home showcases timeless architecture with a thoughtful layout and extensive 2023–2025 updates throughout. From its striking curb appeal to its serene outdoor living spaces, every detail has been meticulously curated. Inside, the home offers 4 EN SUITE ... Read more....»

140 N CASEY KEY ROAD
OSPREY FL 34229

Residential / Single Family Residence

3 Bed  ·  3 Bath  ·  1 Half Bath  ·  2,473 SqFt  ·  $849/SqFt

Days on Market: 135

County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1985
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

LIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibrant 3-bed, 3.5-bath waterfront retreat, perfectly positioned along the Intracoastal Waterway with dazzling, front-row views. Designed for unforgettable days on the water, this home features a stunning Aqua-Tech infinity edge heated pool with therapy jet ledge, where you can unwind while watching boats, jet skis, kayaks, and the occasional dolphin glide by. Set on a generous .49-acre lot with lush tropical landscaping, fresh exterior lighting, brand-new shell driveway, and beautifully re-stained cedar siding (2025), the home blends island charm with modern updates. A shared, deeded boat slip ... Read more....»

312 YACHT HARBOR DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  2,572 SqFt  ·  $776/SqFt

Days on Market: 142

County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1978
Garage: Yes 3 vehicles
Private Pool: Yes

One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a six-foot depth at mean low tide, the marina can accommodate 175 boats owned by its residents. In Southbay, the HOA fees are only $612 per quarter and it’s also affordable to keep your boat in a slip that includes water and electric. With the Southbay neighborhood in your backyard ... Read more....»

401 WALLS WAY
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  4,387 SqFt  ·  $410/SqFt

Days on Market: 15

County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1990
Garage: Yes 3 vehicles
Private Pool: Yes

Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, and finishes throughout. The heart of the home is a curated chef’s kitchen featuring a bespoke butcher block island, professional-grade Viking double ovens, and sleek quartz countertops. High-end functionality includes dual KitchenAid dishwashers and custom cabinetry. The primary living spaces flow seamlessly to a wet bar ... Read more....»

75 OSPREY POINT DRIVE
OSPREY FL 34229

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  4,001 SqFt  ·  $444/SqFt

Days on Market: 64

County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1983
Garage: Yes 2 vehicles
Private Pool: Yes

**STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters… situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks’ Clubhouse, boasts an impressive 253FT frontage along the highly sought-after Osprey Point Drive in the Bayside neighborhood often regarded as ... Read more....»

25 SUGAR MILL DRIVE
OSPREY FL 34229

Residential / Single Family Residence

3 Bed  ·  3 Bath  ·  1 Half Bath  ·  3,066 SqFt  ·  $553/SqFt

Days on Market: 1

County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1998
Garage: Yes 2 vehicles
Private Pool: Yes

METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite Bedrooms, 3 Full and 1 Half Baths. The Updated Kitchen features Quartz countertops, custom hardwood cabinetry, and premium appliances, including Sub-Zero and Wolf. A cozy family room with a wood-burning fireplace provides an inviting gathering space, while impressive Brazilian ... Read more....»

480 ORISKANY COURT
OSPREY FL 34229

Residential / Single Family Residence

3 Bed  ·  3 Bath  ·  1 Half Bath  ·  3,208 SqFt  ·  $528/SqFt

County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: OAKS
Year built: 1999
Garage: Yes 3 vehicles
Private Pool: Yes

Tucked away on a quiet street within the prestigious Oaks Club, this elegant residence overlooks the fairway of the Heron 14. This is a rare opportunity to find a home on a premium golf course lot and have the additional privacy of a preserve view across the street. Designed by Toll Brothers, this meticulous 3 bedroom; plus den home offers gracious, entertaining and comfortable everyday living. A well -appointed kitchen opens seamlessly to a family gathering areas, creating an effortless flow for hosting family and friends. Step outdoors to your private oasis and serene dream backyard. A new roof ... 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: 467

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....»