Location: Osprey , 34229
Do Not Show Listings
110 WOODLAND PL #110, OSPREY, FL 34229
$225,00012 Days on yellowkey MLS ID: A4696738
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1979 Tax: $2,840 (2025)Community: Pine Run IiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,840
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: FURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beauty and modern living. This two-bedroom, two-bath condo is nestled within the serene 20+ acres of lush native Florida landscape. As you step inside, you'll be greeted by a spacious and inviting living area, thoughtfully designed to maximize comfort and functionality. The condo offers two well-appointed bedrooms, each offering ample space. Pine Run is a vibrant community that offers a variety of amenities for your enjoyment. Take a dip in one of the two community pools, perfect for cooling off on a sunny Florida day. Stay active and engage in friendly competition on the tennis courts or try your hand at pickleball. For those who enjoy the beach, you'll be delighted to discover that the condo is less than half a mile away from the Gulf of Mexico. Spend your days basking in the warm sun, strolling along the sandy shores, or indulging in water activities. Pine Run is not just a place to live, it's a lifestyle. With its picturesque surroundings, abundant amenities, and proximity to the Gulf of Mexico, this condo offers the perfect blend of tranquility and convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)
Listing Agent: Echo Belser Pa (941-720-4961)
97 SUGAR MILL DR, OSPREY, FL 34229
$1,950,00054 Days on yellowkey MLS ID: A4691789
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4885 Built: 1990Monthly Fee: $483 Tax: $16,651 (2025)Community: OaksSingle Family
Taxes:$16,651
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.
Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)
Listing Agent: Maria Domenech (978-204-3219)
242 HIDDEN BAY DR #602, OSPREY, FL 34229
$700,000152 Days on yellowkey MLS ID: A4678883
REDUCED by $19,000 (2.6%) on 04/23/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1932 Built: 1999 Tax: $7,518 (2025)Community: Baypointe Vista 1Condo
Taxes:$7,518
Remarks: Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features high ceilings, tall interior doors, and crown molding, creating a bright and welcoming coastal interior. The great room accommodates both living and dining areas and opens to an enclosed waterfront sunroom, an ideal space for morning coffee, sunset views, or quiet time overlooking the bay. The kitchen includes a counter-height breakfast bar, pantry storage, and an adjacent dining nook, offering both function and ease for everyday living or entertaining. A den provides flexible space for a home office or guest use. The primary suite features multiple closets and an en suite bath with dual vanities, a soaking tub, walk-in shower, water closet, and a dedicated makeup vanity area. A second bedroom includes an adjoining bath and walk-in closet. Luxury vinyl flooring has been added in the bedrooms and den. Laundry is located inside the residence. The condominium includes a private, fully enclosed two-car garage. Furnishings are included and may remain or be removed at the buyer’s preference. Hidden Bay is a gated waterfront community set along Little Sarasota Bay, offering a clubhouse with fitness center, heated pool and spa, tennis and pickleball courts, kayak storage and launch, and a boardwalk through mangroves leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay is conveniently positioned between Sarasota and Venice, with nearby access to shopping, dining, the Legacy Trail, and area beaches.
Listing is courtesy of: FIRST LIGHT REAL ESTATE (941-650-2256)
Listing Agent: Cathy Rustin (941-650-2256)
730 FORDINGBRIDGE WAY, OSPREY, FL 34229
$710,0005 Days on yellowkey MLS ID: A4697358
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2182 Built: 2002Monthly Fee: $120 Tax: $6,488 (2025)Community: Rivendell WoodlandsSpa: YesSingle Family
Taxes:$6,488
Middle School: Sarasota Middle
Remarks: There’s a quiet kind of beauty in a home that just feels right the moment you walk in, where the light pours through the windows, the spaces flow effortlessly, and every detail invites you to slow down and stay awhile. Welcome to this thoughtfully designed 3-bedroom + den, 2-bath retreat tucked inside the beloved Woodlands at Rivendell. The kind of neighborhood where tree-lined streets and timeless charm set the tone for everyday living. Step inside and you’re greeted by an airy, open layout that feels both spacious and warm. The main living spaces are grounded by rich, hand-scraped engineered hardwood floors, while large sliding doors disappear into the walls, blurring the line between indoors and out in the most beautiful way. Out back, the home truly comes to life. The gas-heated, saltwater pool and spa, with its soft, cascading glass waterfall, creates a peaceful backdrop for everything from slow mornings to lively evenings with friends. The lanai has been freshly painted, giving the entire outdoor space a clean, refreshed feel that’s ready to be enjoyed year-round. The kitchen sits at the heart of the home, open, inviting, and designed for gathering. With an induction cooktop, stainless steel appliances, generous cabinetry, and a walk-in pantry, it’s as functional as it is welcoming. Tucked just off the main living area, the den offers a quiet place to work, read, or simply unwind, made even better by its natural light and calming views of the pool and pond. The split floor plan creates a sense of privacy, with two guest bedrooms positioned toward the front of the home and the primary suite set apart as its own retreat. Here, you’ll find two walk-in closets, soft natural light, and sliding doors that lead directly to the pool. The ensuite bath feels like a spa escape, complete with a soaking tub, walk-in shower, dual vanities, and a private water closet. And it’s not just beautiful, it’s been thoughtfully updated. In 2024, the home was refreshed with new interior paint, lanai floor paint, a portable generator, and new washer, dryer, and refrigerator. In 2025, a new HVAC air handler was installed, and in 2026, brand-new carpet was added to the bedrooms. Plantation shutters throughout add a timeless finishing touch, while every update has been made with care to ensure comfort and ease for years to come. Beyond the home, the location brings together the very best of Florida living, just minutes from Nokomis Beach, Siesta Key, downtown Sarasota, and Venice. With easy access to I-75 and US-41, and nestled alongside Oscar Scherer State Park and Pine View School, Rivendell offers both convenience and a sense of peaceful retreat. This is the kind of home that doesn’t just check the boxes, it tells a story. One of light, warmth, and living well every single day. Home is being offered partially furnished.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christina Gaskill (941-539-0445)
89 NAVIGATION CIR, OSPREY, FL 34229
$345,00033 Days on yellowkey MLS ID: A4694435
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1449 Built: 2014 Tax: $3,931 (2025)Community: Bay Street VillageCondo
Taxes:$3,931
Remarks: Virtually Staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of relaxation, comfort, and everyday convenience. From the moment you walk through the door, the tranquil pond views immediately draw your attention, creating a sense of calm that carries throughout the home. Imagine starting your mornings on the screened lanai with coffee in hand, overlooking the sparkling water feature while enjoying the warm Florida breeze and peaceful surroundings. With over 1,400 square feet of thoughtfully designed living space, this beautifully maintained 2-bedroom, 2-bathroom condo also features a versatile den, separate laundry room, and attached one-car garage. Rare first-floor units with water views and this level of convenience are highly desirable for full-time residents, seasonal owners, and investors alike. The open-concept floor plan was designed to maximize both comfort and entertaining. The kitchen showcases granite countertops, solid wood cabinetry, stainless steel appliances, stylish backsplash details, a spacious island, and breakfast bar seating that flows seamlessly into the bright and inviting living area. Crown molding, modern lighting, fresh neutral paint, and updated flooring throughout elevate the home with a clean and timeless feel. The spacious primary suite serves as a private retreat featuring peaceful water views, a large walk-in closet, linen closet, and an updated en-suite bathroom complete with dual sinks and a custom walk-in tile shower. A generously sized guest bedroom, beautiful guest bath, and flexible bonus room provide endless possibilities for guests, a home office, hobby space, or additional lounge area. Bay Street Village offers true maintenance-free living with resort-style amenities including a sparkling pool, fitness center, clubhouse, and beautifully maintained grounds. Centrally located between Sarasota and Venice, residents enjoy quick access to world-renowned Gulf beaches including, Nokomis Beach, and Venice Beach, along with downtown Sarasota, marinas, waterfront dining, shopping, golf, entertainment, Sarasota Bay, the Legacy Trail, and countless local restaurants and attractions. Located near the nationally recognized Pine View School and tucked away from the heavy tourist traffic while still remaining close to everything, this condo offers the perfect combination of convenience, comfort, and the relaxed coastal lifestyle that everyone dream about when moving to Florida. Whether you are searching for a primary residence, seasonal escape, or investment opportunity, this exceptional waterfront condo delivers location, lifestyle, and value all in one. Schedule your private showing today and experience firsthand why this hidden gem in Bay Street Village is the perfect place to call home.
Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)
Listing Agent: Jozefina Wells (941-993-3051)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$270,00075 Days on yellowkey MLS ID: A4689541
REDUCED by $10,000 (3.6%) on 06/04/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2017 Tax: $3,507 (2025)Community: Bay Street VillageCondo
Taxes:$3,507
Remarks: Virtually Staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **SELLER FINANCING AVAILABLE** **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
4226 FRONTIER LN #103, OSPREY, FL 34229
$299,00078 Days on yellowkey MLS ID: A4687965
REDUCED by $20,000 (6.3%) on 05/16/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2018Monthly Fee: $475 Tax: $3,542 (2025)Community: Bay Street VillageCondo
Taxes:$3,542
Remarks: Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage provides added convenience and storage. Upstairs, the bright, open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. The well-appointed kitchen features 42" cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in pantry, seamlessly flowing into the dining and living areas. Step out onto your large, screened-in lanai to enjoy peaceful mornings or evening cocktails. The generously sized primary suite offers a walk-in closet and an ensuite bath with dual vanities and a tiled walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Ideally located in Osprey, between Sarasota and Venice, you’ll enjoy a quiet, tucked-away setting with shopping, dining, and daily conveniences just minutes away. Bay Street Village residents enjoy resort-style amenities including a heated pool, fitness center, and clubhouse. With reasonable HOA fees covering exterior maintenance, roof, water, sewer, and gated access (and no flood insurance required) this is truly low-maintenance ownership at its best. Perfect as a full-time residence, seasonal escape, or investment opportunity this is Florida living, simplified.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kate Kwiecinski (412-477-9720)
619 OAK RIVER CT, OSPREY, FL 34229
$609,90041 Days on yellowkey MLS ID: A4692331
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2047 Built: 1997Monthly Fee: $25 Tax: $5,484 (2025)Community: Bay Oaks EstatesSpa: NoSingle Family
Taxes:$5,484
Remarks: Virtually Staged. Back on the market due to buyer financing. Move-in ready Bay Oaks pool home featuring a beautifully renovated kitchen, stunning spa-inspired primary bath, updated flooring, and a huge private fenced backyard. Situated on an oversized 0.38-acre corner lot, this home offers the perfect combination of modern updates, privacy, and outdoor living. Welcome to this thoughtfully renovated pool home in sought-after Bay Oaks Estates, perfectly positioned on an oversized 0.38-acre corner lot in the heart of Osprey. Featuring 3 bedrooms plus a dedicated office, 10-foot ceilings, a huge fenced backyard, and extensive modern updates throughout, this move-in-ready residence offers a rare blend of style, comfort, and effortless indoor-outdoor living. One of the home’s standout features is the oversized fenced backyard, offering a rare combination of space, privacy, and flexibility. The screened lanai, private pool, and expansive outdoor area create the perfect setting for entertaining and year-round enjoyment. Framed by mature landscaping and a newer concrete tile roof (2021), the home creates a welcoming first impression from the moment you arrive. A large driveway and covered parking area provide abundant convenience. New flooring throughout (2025), brand new electrical panel, updated lighting, fresh interior paint, and carefully selected finishes create a clean, cohesive modern aesthetic rarely found in the neighborhood. Inside — 10-foot ceilings, abundant natural light, and a thoughtfully designed layout create an elevated sense of space and openness. Smart-home features include an ecobee thermostat, keypad entry, and a Samsung all-in-one smart washer and dryer. At the center of the home, the fully remodeled kitchen combines style and function with granite countertops, white shaker cabinetry, stainless steel appliances, modern finishes, and an expansive breakfast bar that opens seamlessly to the main living areas. The spacious primary suite serves as a true retreat with two walk-in closets and a beautifully remodeled bath featuring quartz countertops, dual vanities, a freestanding soaking tub, and a frameless glass walk-in shower. Perfectly positioned between The Oaks Club and Stoneybrook Golf & Country Club, Bay Oaks offers the feel of luxury golf-course living without the fees. Families will especially appreciate being just 3 miles from Pine View School, consistently ranked among the top public schools in the nation. Just 6 miles from Siesta Key and 4 miles from Casey Key, this prime Osprey location places you near marinas, golf courses, the Legacy Trail, shopping, dining, and Sarasota’s coastal lifestyle.
Listing is courtesy of: FISHMAN GROUP REALTY LLC (763-443-1761)
Listing Agent: Ross Fishman (763-443-1761)
7204 JESSIE HARBOR DR #7204, OSPREY, FL 34229
$395,0005 Days on yellowkey MLS ID: A4697473
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1255 Built: 1985 Tax: $3,281 (2025)Community: Heron HouseSpa: NoCondo
Taxes:$3,281
Remarks: **BEAUTIFULLY UPDATED CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO** Featuring 2 Beds and 2 Full Baths, this FULLY RENOVATED, 2ND FLOOR unit features an Impressive Kitchen with quartz counters, stainless steel appliances, new solid wood cabinets while the Spacious Owner’s Suite boasts custom built-in cabinets/closets and an equally Elegant Bath. CoreTec Vinyl Flooring throughout (except guest bedroom). Enjoy the serene and natural surroundings from your elevated, sprawling and screened balcony which is accessible from multiple rooms via sliding doors. This Secure and Gated Community offers the ultimate Florida Lifestyle! Amenities include Community Pool, Tennis and Pickleball Courts, Clubhouse with Fitness Center, Boat Dock (subject to availability), Kayak launch and storage, Gazebo with BBQ, etc. Private covered parking and storage are located on the ground level within the building. Blackburn Harbor is ideally situated in Osprey between Sarasota and Venice and is just minutes minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer! **RECENTLY COMPLETED PROJECTS INCLUDE: ASPHALT PAVING, IRRIGATION, WALKWAYS, WALKWAY LIGHTING, LIGHTING at TENNIS AND PICKLEBALL COURTS, etc.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
557 CRANE PRAIRIE WAY, OSPREY, FL 34229
$599,00012 Days on yellowkey MLS ID: A4696823
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2172 Built: 2005Monthly Fee: $397 Tax: $3,953 (2025)Community: Willowbend Ph 4Single Family
Taxes:$3,953
Remarks: Under contract-accepting backup offers. Welcome to this impeccably maintained, MAINTENANCE FREE home in the highly desirable Willowbend community, with tranquil LAKEVIEWS, exceptional amenities and an unbeatable LOCATION. Built by renowned Lee Wetherington and lovingly maintained by its original owner, this quality-constructed residence features a spacious open split-bedroom floor plan with 3 bedrooms plus den, 2 baths, and abundant storage throughout. The kitchen boasts natural wood cabinets with granite counters, a breakfast bar and newer stainless appliances with natural gas for cooking and a pantry for additional storage. The heart of the home opens to a stunning extended screened lanai surrounded by lush vegetation overlooking a private water view, where you can enjoy breathtaking sunrises and watch Florida's natural wildlife in a peaceful setting. Additional upgrades to this immaculate home include an EV charging station, whole-house carbon water filtration system, and natural gas service for the stove, dryer, and water heater. HOA fees provide outstanding value and include lawn maintenance, irrigation, high-speed internet, cable, and access to resort-style amenities including a community heated pool, fitness center, playground and pickleball courts. Ideally situated within a mile of Pine View School and just moments from Oscar Scherer State Park and the Legacy Trail, this home also offers quick access to Nokomis Beach, only two miles away. Trader Joe's, Whole Foods, shopping, dining, and everyday conveniences are all nearby, making this location truly second to none. Enjoy the perfect combination of comfort, convenience, low-maintenance living, and the Florida lifestyle in one of the area's most sought-after neighborhoods. Whether you're enjoying your morning coffee while watching the sunrise over the water, biking the nearby Legacy Trail, or spending the afternoon at Nokomis Beach, this exceptional home offers the very best of Florida living.
Listing Agent: Lori Lockhart, Pa (941-724-0595)
401 N POINT RD #504, OSPREY, FL 34229
$880,00012 Days on yellowkey MLS ID: A4696459
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2778 Built: 2003Monthly Fee: $400 Tax: $8,767 (2025)Community: Meridian At The Oaks PreserveSpa: NoCondo
Taxes:$8,767
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thoughtfully designed, this exceptional 5th floor residence in The Meridian at The Oaks Preserve offers tranquil water and preserve views, a fantastic floor plan, and the rare convenience of a private 2-car garage just steps to the elevator lobby. The expansive split-bedroom floor plan includes 3 bedrooms, 3 full baths, and a private den/study/office that can easily function as a 4th bedroom, providing exceptional flexibility for both everyday living and visiting guests. Filled with natural light, the spacious great room and dining areas flow seamlessly to the generous terrace with upgraded ceramic tile, where peaceful water and preserve views create a serene backdrop for relaxing or entertaining. The custom kitchen, redesigned in 2023, is both elegant and functional, featuring soapstone countertops, Bosch appliances, roll-out cabinetry, Everpure water filtration, a tray ceiling, and detailed crown molding. The primary suite is a private retreat, offering picturesque water views, a custom-designed walk-in closet, and a beautifully appointed bath with Italian tile, dual vanities, and stunning stone countertops. Custom built-ins, upgraded closet systems, and a thoughtfully designed laundry room further enhance the home's comfort and functionality. Residents of The Meridian enjoy lushly landscaped grounds, winding pathways, a community pool and spa, fitness center, and outdoor grilling area. Membership in The Oaks Club is required, providing access to one of Sarasota's most distinguished private club lifestyles, including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art wellness center, resort-style pool, multiple dining venues, a vibrant social calendar, and an elegant clubhouse. Ideally located near Historic Spanish Point, Pine View School, Siesta Key Beach, and downtown Sarasota, this exceptional residence offers a rare combination of luxury, privacy, natural beauty, and resort-inspired living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
754 PINE RUN DR #754, OSPREY, FL 34229
$259,00044 Days on yellowkey MLS ID: A4693150
REDUCED by $10,000 (3.7%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1379 Built: 1973 Tax: $3,176 (2025)Community: Pine Run ISpa: NoCondo
Taxes:$3,176
Remarks: Virtually Staged. Rarely available and truly one-of-a-kind, this beautifully updated ground-floor 2-bedroom, 2-bath residence offers an exceptional combination of privacy, architectural character, and an unbeatable location. Designed around a stunning private open-air atrium, the home features 8-foot glass doors on three sides, flooding the interior with natural light and creating a seamless indoor-outdoor connection rarely found in condominium living. The thoughtfully designed floorplan delivers a tranquil, nature-inspired experience—particularly from the south bedroom wing, where walls of glass frame peaceful wooded views, offering a remarkable sense of serenity and privacy. Beautifully modernized for today’s lifestyle, the kitchen and living spaces have been opened into a sophisticated great-room design, ideal for entertaining and everyday comfort. Timeless Saltillo Mexican tile flooring runs throughout, adding warmth, texture, and character. Additional conveniences include covered carport parking, a large private storage closet, and tasteful updates that make this residence completely move-in ready. Residents enjoy an impressive collection of resort-style amenities, including two heated pools—one dramatically overlooking a wildlife-filled lagoon—along with two cedar saunas, a fitness center, a Florida-style clubhouse, scenic walking trails, BBQ gas grills, an outdoor gas fireplace, kayak storage, and tennis and pickleball courts. Perfectly positioned for an active coastal lifestyle, this premier location places you just minutes from Nokomis Beach, Oscar Scherer State Park, multiple kayak launches, a public boat ramp, and the Legacy Trail, offering miles of biking and recreation connecting Venice and Sarasota. Nearby favorites include Casey Key Fish House, Historic Spanish Point, waterfront dining, medical facilities, and endless local conveniences. Everyday living couldn’t be easier—walk to Publix, CVS, Ace Hardware, shops, restaurants, fitness centers, Walmart, and the Post Office, or enjoy quick access to everything the area has to offer without needing a car. Families will appreciate proximity to the highly acclaimed Pine View School for the Gifted—the only standalone public gifted school in Florida and consistently ranked among the state’s best. Combining exceptional privacy, thoughtful design, resort-style amenities, and unmatched convenience, this is a rare opportunity to own a distinctive, beautifully updated home in one of the area’s most desirable locations—perfect for those seeking the ideal balance of nature, accessibility, and modern coastal living.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Sasha Volosevych (971-703-0307)
401 N POINT RD #301, OSPREY, FL 34229
$475,000830 Days on yellowkey MLS ID: A4603773
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2594 Built: 2003Monthly Fee: $367 Tax: $6,783 (2023)Community: Meridian At The Oaks PreserveCondo
Taxes:$6,783
Tax Year: 2023
Remarks: Virtually Staged. Short Sale. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and make it uniquely your own. Check out the virtually staged photos to help you imagine what you could do with this great floor plan. This condo offers space for year-round living, or to use as a welcoming winter retreat, with room for family and friends to visit. Wouldn’t it be lovely to sit on the private terrace and listen to the birds sing as the sun sets on another perfect day? The unit has a one car under building parking space. It is a short walk to the Meridian residents-only fitness room, spa and heated pool. The Oaks Club has two championship golf courses, 12 HAR TRU tennis courts (4 lighted), croquet and pickleball courts, a state-of-the art fitness center, junior Olympic community pool, and offers a wide variety of dining and recreational options, and social activities. When you open the door to your new home here, you have opened the door to the best in Gulf Coast country club living. Membership in The Oaks Club is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership.
Listing Agent: Steve Abbe (941-400-3969)
1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229
$599,00078 Days on yellowkey MLS ID: C7524397
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2006 Built: 2004Monthly Fee: $980 Tax: $6,502 (2025)Community: Blackburn Harbor Waterfront ViCondo
Taxes:$6,502
Remarks: Welcome home! This GULF ACCESS, WATERFRONT condo w/ AVAILABLE BOAT SLIPS BEHIND THE UNIT, in the highly sought-after Blackburn Harbor community is ready for its new owners. Offering over 2,000 SQFT, this beautifully updated 3 BED, 2.5 BATH residence with an ATTACHED 2 CAR GARAGE is ideally positioned as a SECOND-FLOOR, END UNIT at the END OF A CANAL—delivering unmatched PRIVACY, VAULTED ceilings, and MILLION DOLLAR WATER & SUNSET VIEWS that feel like a daily postcard. As an added bonus a NEW HVAC & HOT WATER HEATER were just installed! Lush tropical landscaping welcomes you to a private side entrance, while the building’s exclusive setting—just four units total—places you in one of the most desirable locations within the community. Perfectly situated at the edge of the MARINA, you are just STEPS from your BOAT, making it effortless to enjoy GULF ACCESS and endless days exploring nearby WATERWAYS, waterfront DINING, and hidden gems like Snake Island. Inside, this residence blends comfort and coastal elegance with a thoughtfully designed SPLIT FLOOR PLAN for ultimate privacy. The home features warm COASTAL decor, NEUTRAL PAINT, NEW KITCHEN APPLIANCES, GRANITE COUNTERTOPS, SOLID WOOD CABINETRY, custom light fixtures, and window treatments throughout. The open-concept living space flows seamlessly to a LARGE SCREENED LANAI overlooking the water, community park, and glowing SUNSET skies. FURNISHINGS ARE OPTIONAL. Set within a GATED, FINANCIALLY SOUND community spanning approximately 11 acres, residents enjoy an amenity-rich, resort-style lifestyle including a HEATED POOL, CLUBHOUSE, FITNESS ROOM, TENNIS & PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, BBQ GAZEBO, and scenic walking paths surrounded by lush Florida foliage. The vibrant social calendar offers something for everyone—water aerobics, monthly happy hours, bingo/game nights, pickleball club, book club, and more. Ideally located near US-41, this home offers convenient access to Nokomis Beach, Oscar Scherer State Park, the Legacy Trail, Downtown Venice, Downtown Sarasota, I-75, and Sarasota Memorial Hospital Venice Campus—placing the very best of Florida living right at your fingertips. Whether you're boating to the Gulf, enjoying sunset views from your lanai, or embracing the active waterfront lifestyle, this is truly the Florida Dream come to life. Schedule your private showing today! PLEASE CLICK ON THE VIDEO OF THE UNIT.
Listing is courtesy of: DOWNING FRYE REALTY, INC. (239-261-2244)
Listing Agent: Mackenzie Davis-Mahan (941-993-3272)
14401 MASTHEAD DR, OSPREY, FL 34229
$2,995,000111 Days on yellowkey MLS ID: A4684834
REDUCED by $155,000 (4.9%) on 06/12/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2665 Built: 2017Monthly Fee: $643 Tax: $874 (2025)Community: BaysideSpa: YesSingle Family
Taxes:$874
Remarks: 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 where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.
Listing Agent: Mackenzie Longueuil (941-961-4023)
4428 CONCHFISH LN, OSPREY, FL 34229
$548,000371 Days on yellowkey MLS ID: A4656074
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1861 Built: 2018Monthly Fee: $147 Tax: $5,936 (2024)Community: Palms/Casey KeySpa: NoSingle Family
Taxes:$5,936
High School: Pine View School
Tax Year: 2024
Remarks: Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. The residence has hurricane shutters, Low-E windows, and a generator hook-up. A large 26x10 covered lanai provides space for relaxing and entertaining. The Palms at Casey Key is a lovely neighborhood with low HOA fees that offers a sense of privacy. Imagine the ease of having your boat just minutes away at the nearby Casey Key Boat Launch, ready whenever you are. They say location is everything, and this home truly delivers on that promise. Ideally situated, it offers immediate access to everyday conveniences: restaurants, grocery stores, and a quick connection to I-75. Dog lovers will appreciate the brand-new dog park nearby, perfect for playtime and socializing. Just under a mile from your front door, the Casey Key Boat Launch and the lively Tiki Bar invite you to unwind and enjoy days by the water. Families will love the close proximity to the prestigious Pine View School, renowned for academic excellence and ranked as the number one high school in Florida, the second-highest elementary school in the US, and the third-highest middle school in the US. Beyond the neighborhood, you'll find easy access to Siesta Key Beach, top-tier golf courses, vibrant cultural attractions, and exciting entertainment options. With low HOA fees and no CDD fees, this home offers the freedom to live your dream Florida lifestyle, without the rising costs of new construction. Move-in ready and like-new, this residence is a perfect blend of character and delightful charm. Store your boat, enjoy the community, and embrace life with ease and comfort. Don’t miss your chance to claim your own piece of paradise!
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Mariana Georgieva (941-809-0416)
408 PARK TRACE BLVD, OSPREY, FL 34229
$595,000111 Days on yellowkey MLS ID: A4685004
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $20,000 (3.3%) on 06/01/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 2003Monthly Fee: $54 Tax: $4,652 (2025)Community: Park Trace EstatesSingle Family
Taxes:$4,652
Remarks: Under contract-accepting backup offers. 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 heated saltwater pool with a FastLane system, 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 signature royal blue Hestan refrigerator, into an inviting living room ideal for entertaining. From there, step out to a screened patio overlooking the water to relax in total comfort. The spacious master suite features dual California Closets, a luxurious remodeled bathroom, and an adjoining room that serves as a private office or reading nook. Throughout the home, plantation shutters provide elegant light control and privacy. The property is finished with a side-entry two-car garage featuring custom California Closets storage and a Tesla charger. Positioned just steps from the pristine Legacy Trail for biking and recreation, this home provides the perfect combination of style and lifestyle. Home is available fully furnished. The home is exceptionally well-maintained, featuring a high-efficiency HVAC system (New AC 2017/Air Handler 2020) with a programmable thermostat, a central vacuum system, and an artistic hidden TV in the living room. Recent kitchen and laundry upgrades include a 2018 washer and dryer alongside newer appliances (2020–2022). The private courtyard is equally impressive, boasting a new pool screen (2022), new pool equipment (2024), and an Endless Pool Fastlane feature for a premium fitness experience. Property is located in Flood Zone X (flood insurance generally not required).
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jennie Lascelle (941-504-0102)
1361 NEW FOREST LN, OSPREY, FL 34229
$545,00061 Days on yellowkey MLS ID: A4691036
REDUCED by $5,000 (0.9%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2074 Built: 2002Monthly Fee: $292 Tax: $5,783 (2025)Community: Rivendell WoodlandsSingle Family
Taxes:$5,783
Remarks: One or more photo(s) has been virtually staged. Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile roof, tranquil lake views, and a spacious lanai overlooking the water, perfect for relaxing or entertaining. Enjoy stunning lake views from the dining room, creating a bright and inviting everyday setting. HOA maintained lawn care adds convenience and low maintenance living. The backyard is a tropical retreat with fruit trees including sugar apple, guava, and plum. Prime location near Oscar Scherer State Park, Casey Key beaches, shopping, dining, and the Legacy Trail. Rare combination of location, lifestyle, views, and school district appeal.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
156 BISHOPS COURT RD, OSPREY, FL 34229
$1,289,00047 Days on yellowkey MLS ID: A4691664
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3112 Built: 1990Monthly Fee: $858 Tax: $8,394 (2025)Community: OaksSpa: YesSingle Family
Taxes:$8,394
Remarks: One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces, create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor, new lanai screening and aluminum framing, exterior paint completed in 2025, new air conditioning for the main floor, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
360 N POINT RD, OSPREY, FL 34229
$1,495,00016 Days on yellowkey MLS ID: A4695959
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2913 Built: 2022Monthly Fee: $400 Tax: $9,588 (2025)Community: OaksSpa: NoSingle Family
Taxes:$9,588
Remarks: Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership
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