408 PARK TRACE BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1,840 SqFt · $342/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Park Trace Estates
Legal Subdivision Name: PARK TRACE ESTATES
Year built: 2003
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart of the home is a beautiful central courtyard with a saltwater pool, around which the main living spaces are thoughtfully arranged. An en-suite guest bedroom with private courtyard access provides a secluded retreat perfect for visitors. The open-concept interior flows seamlessly from the kitchen, complete with a ... Read more....»
447 N SHORE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,874 SqFt · $285/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Sorrento Shores
Legal Subdivision Name: SORRENTO SHORES
Year built: 1964
Garage: Yes 1 vehicles
Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr ... Read more....»
14401 MASTHEAD DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 2,665 SqFt · $1,220/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Bayside
Legal Subdivision Name: BAYSIDE
Year built: 2017
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai ... Read more....»
107 SORRENTO DRIVE
OSPREY FL 34229
Residential / Single Family Residence
2 Bed · 2 Bath · 1,284 SqFt · $350/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Sorrento Shores
Legal Subdivision Name: SORRENTO SHORES
Year built: 1963
Garage: Yes 2 vehicles
This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from the living room, dining room, kitchen and primary bedroom to a spacious screened porch that overlooks a scenic pond and expansive yard. Whether entertaining guests or enjoying a quiet morning coffee, the outdoor living space extends your home beautifully. The kitchen is stylish and functional, ... Read more....»
819 SHADOW BAY WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2,145 SqFt · $298/SqFt
Days on Market: 2
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL
Year built: 2002
Garage: Yes 2 vehicles
Private Pool: Yes
Community Pool: Yes
Welcome to this stunning 2,145 square foot pool home in the premier community of Rivendell where maintenance-free living meets tropical elegance. Positioned on a beautifully landscaped corner lot, this meticulously maintained residence offers timeless style and thoughtful updates throughout. Recent improvements include 2026 irrigation valves, 2025 roof replacement, 2024 pool pump and a 2017 air conditioning system, providing peace of mind for years to come. Go onto the inviting front porch, the ideal setting for morning coffee. Enter through the elegant glass front door into a bright, open foyer filled with natural light. The spacious split floor plan seamlessly connects ... Read more....»
1211 LOST CREEK COURT
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,876 SqFt · $288/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL WOODLANDS
Year built: 2002
Garage: Yes 3 vehicles
**BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s lifestyle. Situated on an ideal corner lot, the home enjoys peaceful water views from the rear and a lovely park view from the front. Major updates include a brand-new kitchen with granite countertops and stainless-steel appliances, fresh interior and exterior paint, and new flooring throughout, including luxury vinyl plank, etc. Plantation ... 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....»
1471 SHOAL WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,798 SqFt · $536/SqFt
Days on Market: 6
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1985
Garage: Yes 2 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. This exceptional residence truly checks every box. Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the end of a quiet cul-de-sac and overlooking an expansive green space, the property feels even more open and serene. No expense has been spared in the home’s extensive upgrades, evident the moment you step inside. Eight-inch wide white ... Read more....»
664 CRANE PRAIRIE WAY
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 2,870 SqFt · $313/SqFt
Days on Market: 15
County: Sarasota
Subdiv/Community Name: Willowbend
Legal Subdivision Name: WILLOWBEND PH 2
Year built: 2003
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features unobstructed shimmering views of a wide lake and the natural beauty of the park, creating an extraordinary backdrop for an exceptional lifestyle. The idyllic setting includes a sparkling heated pool and spa. Summer kitchen has sink and stainless beverage refrigerator with large bar ... 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: 12
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....»
659 RIVENDELL BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,292 SqFt · $283/SqFt
Days on Market: 20
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL, THE WOODLANDS AT RIVENDELL
Year built: 2001
Garage: Yes 3 vehicles
Private Pool: Yes
Located within The Woodlands at Rivendell, this meticulously maintained single-family residence offers a sophisticated balance of comfort, functionality, and tranquil natural surroundings. Backing to a serene lake and protected preserve, the home enjoys exceptional privacy and peaceful water views. Designed with an open, split-bedroom floor plan, the residence features three bedrooms, two full baths, a dedicated office, and an additional pool bath—well suited for both everyday living and gracious entertaining. The owner’s suite serves as a private retreat, highlighted by a tray ceiling, two walk-in closets, and a spa-inspired bath with dual vanities, a soaking tub, Roman shower, and private ... Read more....»
156 BISHOPSCOURT ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 3,112 SqFt · $417/SqFt
Days on Market: 28
Cumulative Days on Market: 114
County: Sarasota
Subdiv/Community Name: Bishops Court At The Oaks Preserve
Legal Subdivision Name: BISHOPSCOURT AT THE OAKS PRESERVE
Year built: 1990
Garage: Yes 2 vehicles
Private Pool: Yes
This stunning three-bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. This charming Cape Cod sets the stage for comfortable, gracious living, enjoying private preserve views. A Sonos sound system plays throughout this gorgeous home! Sit back and enjoy a peaceful afternoons and twilight dinners on the lovely newly screened Florida room. There is an additional private rooftop outdoor deck (732 sq.ft.) accessed directly from the second floor living and recreation rooms. Recent renovations in 2023 include two main floor bathrooms with exquisite high-end decorator wall tiles, as well as Italian ... Read more....»
522 LUMINARY BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 3 Bath · 2,320 SqFt · $279/SqFt
Days on Market: 29
County: Sarasota
Subdiv/Community Name: Willowbend
Legal Subdivision Name: WILLOWBEND PH 3
Year built: 2005
Garage: Yes 2 vehicles
Waterfront: Yes
This exquisite three-bedroom, three-bath-plus-den, Lee Wetherington built home exemplifies intelligent design and beauty in the community of Willowbend. This Ashley floor plan is thoughtfully oriented to the south, allowing for abundant natural light and stunning lakefront views. The residence features inviting curb appeal with a paver-accented driveway and walkway, leading to an impressive custom double-door entry. Inside, high-end upgrades and recent enhancements contribute to the home's timeless character. The sophisticated interior showcases clean lines, intricate tray ceilings and tile flooring throughout main living areas. Crown molding and impressive lighting fixtures add elegance to the space. The gourmet kitchen is a ... Read more....»
472 PARK TRACE BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2,217 SqFt · $279/SqFt
Days on Market: 35
County: Sarasota
Subdiv/Community Name: Park Trace Estates
Legal Subdivision Name: PARK TRACE ESTATES
Year built: 2002
Garage: Yes 2 vehicles
Private Pool: Yes
Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for both everyday living and entertaining, with seamless indoor-outdoor flow to the private SALT WATER POOL. Enjoy mature landscaping on the large corner lot providing added space and privacy, with plenty of room to enjoy the beautiful surroundings. ... 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....»
767 FORDINGBRIDGE WAY
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,162 SqFt · $277/SqFt
Days on Market: 27
County: Sarasota
Subdiv/Community Name: Rivendell The Woodlands
Legal Subdivision Name: RIVENDELL WOODLANDS
Year built: 2002
Garage: Yes 2 vehicles
Set on a quiet cul-de-sac in The Woodlands at Rivendell, this furnished and thoughtfully maintained residence offers a peaceful setting surrounded by mature landscaping and wooded views. The extended foyer welcomes you into an open great-room layout spanning nearly 2,200 square feet, where high tray ceilings, plantation shutters, and hardwood flooring create a cohesive flow throughout the main living areas. The great room features floating shelves, an electric fireplace, and walls of glass sliders that open to a serene, screen-enclosed pavered patio overlooking private natural surroundings—ideal for morning coffee or evening relaxation. The gourmet kitchen was completely updated in 2022 and ... 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....»
227 SAINT JAMES PARK
OSPREY FL 34229
Residential / Single Family Residence
2 Bed · 2 Bath · 2,071 SqFt · $473/SqFt
Days on Market: 1
Cumulative Days on Market: 367
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS 2 PH 1
Year built: 1986
Garage: Yes 2 vehicles
Experience the charm and wonderful location of this golf course home on Saint James Park, the leafy and quiet cul-de-sac where you can walk to tennis, golf, pickleball, croquet, heated pool and state of the art fitness center all within The Oaks Country Club, where the luxury lifestyle awaits! This 2 bedroom, 2 bath traditional home overlooks the first hole of the Eagle Golf course, and is being offered completely furnished, easy to maintain, and is move in ready. The roof is new in 2024, and all windows and sliding doors are newer and hurricane impact. Custom designed by Bo ... Read more....»
650 CRANE PRAIRIE WAY
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 2 Bath · 2 Half Baths · 3,183 SqFt · $251/SqFt
Days on Market: 22
County: Sarasota
Subdiv/Community Name: Willow Bend
Legal Subdivision Name: WILLOWBEND PH 3
Year built: 2005
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Opportunities like this are increasingly rare in Willowbend. Offering over 3,180 square feet, this Lee Wetherington-built residence delivers exceptional scale, thoughtful architecture, and a preserve setting backing directly to Oscar Scherer State Park. With no rear neighbors and expansive natural views, the home offers privacy and tranquility while remaining minutes from beaches, dining, and cultural destinations. The interior lives large and light-filled, centered around a dramatic great room with a 12-foot double-tray vaulted ceiling that establishes an immediate sense of volume and architectural presence. The open floor plan allows spaces to flow comfortably for everyday living and entertaining, with generous room ... 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....»
919 TRANQUILITY CIRCLE CIRCLE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 2,854 SqFt · $280/SqFt
Days on Market: 46
County: Sarasota
Subdiv/Community Name: North Creek Estates
Legal Subdivision Name: NORTH CREEK ESTS
Year built: 2001
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
WOW! TOTAL OF 50,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle . This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy your own "Selby Garden" like setting .So hard to find such a private lot with this level of privacy so close to everything. Enjoy an open, spacious split-plan layout with Four bedrooms, formal and casual living spaces, and an open kitchen with ... 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....»
17 BAYHEAD LANE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,850 SqFt · $456/SqFt
Days on Market: 43
Cumulative Days on Market: 140
County: Sarasota
Subdiv/Community Name: Oaks The
Legal Subdivision Name: BISHOPS COURT AT OAKS PRESERVE
Year built: 1992
Garage: Yes 2 vehicles
Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No detail was overlooked in the renovation, resulting in a truly beautiful and thoughtfully designed home. The interior showcases high-end finishes throughout, including wood-look tile flooring, quartzite countertops, a stylish coffee bar, and a custom hood vent. The former Florida room has been transformed into a spacious family room, perfect for entertaining, while one of the three bedrooms is currently utilized as a home office. Outdoor living shines with a newly added side deck featuring a canopy for shaded dining, ... Read more....»
20 BAYHEAD LANE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 3,486 SqFt · $452/SqFt
Days on Market: 57
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: BISHOPS COURT AT THE OAKS PRESERVE
Year built: 2017
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
A rare opportunity to own a significantly newer, custom-built residence inside the exclusive The Oaks Club Preserve, where most surrounding homes were built decades earlier. Completed in 2017 and set on a lakefront lot in a non-flood zone, this move-in-ready, hurricane-secure home offers a level of modern construction, privacy, and peace of mind seldom found in this exclusive community. In addition, the home boasts a rare oversized 3 car garage plus attic with ample plywood floor storage and central vacuum. Wake up to shimmering water views with your morning coffee, open the 16-foot panoramic sliders, and let pleasant breezes flow ... Read more....»
186 WINDWARD DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,505 SqFt · $259/SqFt
Days on Market: 57
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1983
Garage: Yes 2 vehicles
Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for ... 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....»
524 SARABAY ROAD
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,760 SqFt · $238/SqFt
Days on Market: 64
County: Sarasota
Subdiv/Community Name: Bay Acres Sub
Legal Subdivision Name: BAY ACRES - RESUB
Year built: 1956
Garage: No
Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the post office and two Tiki bars. You can launch your kayak from the private waterfront park on a protected bay with dockage for boats up to 22 feet. There is a waiting list for the dockage. Bay ... Read more....»
365 S SHORE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,824 SqFt · $757/SqFt
Days on Market: 65
County: Sarasota
Subdiv/Community Name: Sorrento Shores
Legal Subdivision Name: SORRENTO SHORES
Year built: 1968
Garage: Yes 1 vehicles
Waterfront: Yes
Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined home remains unaffected by flooding AND IN FLOOD ZONE X, unfolds safely toward the water where EXPANSIVE BAY WINDOWS frame uninterrupted scenery. Step out your back door and hop on your boat for effortless days on the ... Read more....»
1303 THORNAPPLE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,929 SqFt · $350/SqFt
Days on Market: 68
County: Sarasota
Subdiv/Community Name: Willowbend
Legal Subdivision Name: WILLOWBEND PH 1
Year built: 2003
Garage: Yes 2 vehicles
Private Pool: Yes
INCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appointed FURNISHED Lee Wetherington residence with NEW $54,000 Barrel Tile ROOF (Nov 2025) in Sought After Willowbend---- A MAINTENANCE-FREE (lawn/landscaping/irrigation) Boutique Community ideally located near the Fitness Center and Community Pool, Pickleball Courts & Playground.....Generous-Sized Living Spaces with Bright/Spacious Open Floor Plan affording ease of INDOOR/OUTDOOR LIVING where you will Enjoy Morning Coffees and Twilight Sunsets lounging in Expansive Screened Lanai.....Elegantly Updated Throughout, including: Cabinets, Countertops, Flooring, Crown Molding and Ceiling Fixtures---other recent improvements include Garage Door, Pool Heater & Retractable Solar Shade. Abundance of Storage, Built-ins ... 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.