Location: Osprey
Keyword(s): Venice Senior High
Keyword(s) High School: Venice Senior High
Do Not Show Listings
403 LONGBOW TRL, OSPREY, FL 34229
$1,095,000148 Days on yellowkey MLS ID: A4672081
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2770 Built: 1978Monthly Fee: $42 Tax: $9,020 (2024)Community: Pine RanchSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,020
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort, style, and Florida living. Step inside to find a bright, open interior with plenty of natural light, spacious living area, and a seamless connection between indoor and outdoor living. A newly remodeled kitchen with ample cabinetry and a seamless flow for entertaining. The primary suite provides a peaceful retreat with generous closet space and an en-suite bath and balcony with stunning views. Additional bedrooms are well-sized, making this home ideal for guests or a growing household. Enjoy Florida living at its best with an inviting private backyard inground pool framed by mature landscaping perfect for relaxing, gardening, or creating your own outdoor oasis. The backyard showcases a picturesque large pond, with a deck, making it an ideal spot for relaxing evenings. Additionally, this property features an in-law suite with one bedroom and one bathroom, ideal for guests or extended family. Whether you're seeking a full-time residence or a seasonal getaway, this Osprey gem delivers comfort, location, and value. With its prime Osprey location, easy access to Sarasota and Venice, and the natural beauty of the Gulf Coast just minutes away, this home offers exceptional value and an unbeatable lifestyle. A wonderful opportunity to own in one of Sarasota County's most desirable communities don't miss your chance to make 403 Longbow Trail your next home.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Edward Bieker, Pa (941-525-6473)
1019 SCHERER WAY, OSPREY, FL 34229
$735,000101 Days on yellowkey MLS ID: N6142144
0 Days Off yellowkey (back on 1/13/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2498 Built: 2004Monthly Fee: $120 Tax: $6,107 (2025)Community: Rivendell The WoodlandsSpa: YesSingle Family
Taxes:$6,107
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community of Rivendell. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. Open Floor plan boasts a 'Chef's Delight' kitchen with plenty of custom cabinets, quartz countertop, updated stainless steel appliance, under cabinet lighting and oversized aquarium window overlooking the lanai. Large living room with tray ceilings. Vaulted ceilings in the family room with a built-in as the focal point. Formal dining room with a palladium window allowing the sunlight in. Wow! describes the spacious screened lanai featuring a salt water heated in ground pool w/spa. Plenty of space for dining, entertaining and games. Backing to the preserve with additional fenced in yard area. Home is situated less than a mile from the Legacy Bike Trail, and nearby Oscar Scherer State Park, Nokomis beach, the Gulf historic downtown Venice, shopping, restaurants & schools. Freshly painted. Bright & Airy. One of the lowest HOA fees around. 3 car garage with EV charging station. Owned Tesla solar panels that keep the electric bills very low. The home checks all the boxes and a must see!
Listing is courtesy of: CENTURY 21 SCHMIDT REAL ESTATE (941-485-0021)
Listing Agent: Christine Appice (908-692-5062)
238 PALM AIR DR, OSPREY, FL 34229
$179,900Listed 04/14/2026 8:56AM MLS ID: A4689837
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1986Monthly Fee: $215 Tax: $1,562 (2025)Community: ArborsManufactured Home
Taxes:$1,562
Remarks: Professional photos coming soon! Fall in love with this beautifully maintained and upgraded 2 Bedroom, 2 Bathroom home located in the highly desirable The Arbors Mobile Home Park, extremely LOW HOA FEES covers CABLE, INTERNET, WATER, SEWER, TRASH and GROUND MAINTENANCE! You will have peace of mind with IMPACT-RESISTANT WINDOWS AND SLIDING GLASS DOORS, plus updated electrical panel. The kitchen has been tastefully renovated with new cabinetry, countertops, farmhouse sink, pull down faucet, stunning glass subway tiled backsplash, and premium stainless steel appliances including a French door refrigerator with two drawers and a super quiet dishwasher. The living room has barn style doors that opens to a large sun-kissed enclosed tiled florida room that features a vaulted ceiling, lots of windows and an additional portable AC unit for your comfort for enjoying your morning coffee and evening cocktails. The Primary Suite features an ensuite bath with a newer high vanity, decorative lighting, new toilet, and two spacious walk-in closets. The second bedroom is a Flexible Guest Space that includes a stylish, space-saving Murphy bed and its own walk-in closet. There is plenty of extra storage in the oversized attached shed that includes front-loading washer/dryer plus there is also a separate 8’x10’ workshop with hurricane straps and tie downs. Entertaining friends is easy in this open style concept home with plenty of outdoor space that includes a large covered carport, a spacious screened in lanai, and a private back patio with custom pavers. Attention to detail can be seen everywhere including the outdoor low voltage lighting around the entire exterior of the home and up-lighting shining on the palms creating a wonderful ambiance. The Arbors is in a premier 55+ Co-op community, amenities include Heated pool, clubhouse, shuffleboard, billiards, fitness equipment, and a dedicated RV/Boat parking in the community. Prime Location with minutes from Nokomis Beach, Siesta Key, and Casey Key. Easy access to shopping, dining, hospitals, airports and nature parks like Oscar Scherer.
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Susan Retzke (941-544-5558)
75 OSPREY POINT DR, OSPREY, FL 34229
$1,695,000146 Days on yellowkey MLS ID: A4672439
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4001 Built: 1983Monthly Fee: $967 Tax: $14,229 (2024)Community: OaksSpa: NoSingle Family
Taxes:$14,229
Remarks: **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 the “Park Avenue” of The Oaks Golf & Country Club. A gorgeous new 4ft x 4ft “Celini Agento Italian” tile accentuates the fresh color scheme throughout this well-appointed home complete with impressive fireplace, 14-inch crown moldings, wainscoting, palladium windows and much more! The nearby, private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. The Oaks-Bayside is a truly distinguished, 24hr guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the AERIAL VIDEO**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
312 YACHT HARBOR DR, OSPREY, FL 34229
$1,995,000193 Days on yellowkey MLS ID: A4667293
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2572 Built: 1978Monthly Fee: $219 Tax: $14,066 (2024)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$14,066
Remarks: One or more photo(s) has been virtually staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle within Southbay Yacht and Racquet Club. Considered one of the finest private residential marinas in the region, Southbay’s seven-acre deep water boat basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet, with six feet of water at mean low tide and slips for 175 resident owned boats. Even more remarkable, Southbay’s HOA fees are only $218.87 per month and marina slips remain highly affordable, including both water and electric. With the marina quite literally in your front yard and the charming Southbay neighborhood stretching behind you, this fully renovated waterfront home sits on one of only two waterfront streets in the entire community and features three bedrooms, four full baths and a versatile flex space office/fourth bedroom, with many rooms capturing beautiful water views. Inside, the residence welcomes you with an elegant tray ceiling entry, porcelain plank tile flooring and expansive open living spaces filled with natural light from an abundance of impact-rated windows and sliding glass doors. The beautifully designed entertainment kitchen with breakfast area flows seamlessly into the spacious family and dining rooms, creating a refined yet relaxed setting for everyday living and hosting guests. The outdoor living space is equally impressive, showcasing a newly built custom pool and spa framed by a panoramic clear span pool cage, an expansive stone tiled sun deck and generous covered areas for outdoor dining and entertaining. The private primary suite enjoys double door access to the pool and spa and features a luxurious bath with a deep soaking tub, frameless glass shower, dual vanities, large format tile and two custom walk in closets with built in organization systems. Two guest suites each include private en suites, with one offering marina views and the other opening directly to the pool terrace, both with custom closets. This move in ready residence also includes a three car garage, brick paver driveway and mature tropical landscaping. Just steps away, the newly renovated Southbay Yacht and Racquet Club clubhouse overlooks the marina and features a 99 person ballroom with catering kitchen and dance floor, a community gathering room with piano and entertainment area, fitness center, card room, library and meeting room. Residents also enjoy a geothermal heated pool, youth pool, covered waterfront patios, three tennis courts, four pickleball courts, bocce ball, shuffleboard, basketball court, kayak storage, a waterfront park, 20 acres of common grounds and five miles of scenic sidewalks. Southbay is golf cart friendly and offers an active social calendar with weekly gatherings, seasonal events and a vibrant Power and Sail Club. This is a rare opportunity to enjoy marina views, waterfront living and one of the Gulf Coast’s most beloved boating communities. Be sure to request the 50 page digital property catalog and watch the property film for a complete look at this exceptional residence.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Thomas Netzel (941-539-0633)
522 LUMINARY BLVD, OSPREY, FL 34229
$647,00067 Days on yellowkey MLS ID: A4676528
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2320 Built: 2005Monthly Fee: $420 Tax: $4,456 (2025)Community: Willowbend Ph 3Spa: NoSingle Family
Taxes:$4,456
Remarks: 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 chef's dream, featuring solid wood cabinetry, Corian countertops and new stainless appliances in January 2026 with gas cooking. Even the laundry room is aesthetically pleasing. The split floor plan affords two guest bedrooms conveniently behind a pocket door, sharing a bath, providing privacy to family and guests alike. The den/study includes a built-in office with a sizeable desk overlooking the lake. The family room boasts a wall of sliding glass doors with an adjacent corner pocket slider that opens wide, seamlessly transitioning to the tranquil outdoor living space. The extended lanai features two covered areas, ideal for relaxation, while the custom pond with waterfall add to the ambience and enjoyment of the tropical surroundings. Water views from most rooms in the home! A well-appointed dinette offers picturesque views of the waterfall and lake through a large aquarium window as well. The luxurious owner’s suite includes dual walk-in closets, dual sinks, a walk-in shower and a tub for ultimate comfort. The home is equipped with high-speed internet and streaming television, with yard maintenance and access to community amenities such as a pool, spa, fitness center, pickleball court and playground all included in the low HOA fees. Convenient to beautiful gulf beaches, Oscar Scherer State Park, Legacy Trail, Pine View School and waterfront dining, this residence offers an unparalleled lifestyle.
Listing Agent: Todd Currey (941-402-6000)
1348 THORNAPPLE DR, OSPREY, FL 34229
$535,0005 Days on yellowkey MLS ID: A4687822
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2171 Built: 2003Monthly Fee: $397 Tax: $4,051 (2025)Community: Willowbend Ph 1Spa: NoSingle Family
Taxes:$4,051
Remarks: Beautiful lakefront pool home in Willowbend showcases one of the wider, more open water views in the community, framed by an expansive three panel sliding glass door that fills the home with natural light. This three bedroom plus den, two bath residence offers over 2,100 square feet with a functional split floor plan and spacious living areas designed for comfortable everyday living and effortless indoor - outdoor flow. The private screened lanai overlooks the expansive lake and includes a pool, creating a peaceful setting to relax and enjoy Florida’s outdoor lifestyle. Many homes in the community are positioned along narrower sections of the lake, making this view especially appealing. The primary suite offers two walk-in closets, along with a bath featuring both a soaking tub and separate shower. The interior is original and presents an opportunity for a new owner to update and customize to their personal style. Recent improvements include a five year old air conditioning system and one year old water heater. Willowbend is a maintenance-free community with lawn care, landscaping, and irrigation included, conveniently located near the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, and Pine View School. Residents enjoy living in a beautifully established setting surrounded by lakes, preserves, and mature landscaping. Willowbend offers a community pool and spa, tennis and basketball courts, fitness center and playground. This property offers strong value for its location, view, and private pool, and is ready for its next owner to make it their own.
Listing is courtesy of: COLDWELL BANKER REALTY (941-487-1492)
Listing Agent: Margot Leonard (941-387-5050)
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000192 Days on yellowkey MLS ID: A4667263
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4096 Built: 1969Monthly Fee: $33 Tax: $37,172 (2024)Community: Casey KeySpa: NoSingle Family
Taxes:$37,172
Remarks: Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting. Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice and Sarasota. Behind a gated entrance, the home features three bedrooms, a private office, and three-and-a-half baths, all thoughtfully updated to celebrate its extraordinary Gulf-front setting. Expansive windows and sliding glass doors frame breathtaking water views while filling the interiors with natural light and coastal breezes. Rich architectural details reflect its hacienda-inspired design, including wood beams and moldings, barrel-brick ceilings, Mexican tile and wood floors, brick accents, artisanal mosaic tile, and hand-painted stair risers. Hurricane-impact windows and doors, a new roof, a new pool, and updated air-conditioning and pool equipment provide both peace of mind and modern comfort. The gourmet kitchen is beautifully appointed with custom cabinetry and Wolf appliances, creating an ideal setting for entertaining after a day on the beach. The primary suite is a private retreat with a sitting room, wet bar, soaking tub, walk-in closet, and private balcony overlooking the Gulf. Two additional en-suite guest bedrooms provide comfort and privacy for family and visitors. A spiral staircase leads to the rooftop deck, where panoramic views stretch from the Gulf to the Intracoastal Waterway. Outside, the courtyard-style pool, fountain, tiled terraces, and lush tropical gardens create a tranquil setting for authentic alfresco living. This is an exceptional opportunity to experience the privacy, beauty, and effortless lifestyle of Gulf-front living on Casey Key.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Napolitano (941-993-0025)
228 SAINT JAMES PARK, OSPREY, FL 34229
$1,695,00025 Days on yellowkey MLS ID: A4686681
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2425 Built: 1997Monthly Fee: $142 Tax: $10,787 (2025)Community: Oaks 2 Ph 1Spa: YesSingle Family
Taxes:$10,787
Remarks: Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new driveway, updated fencing, and refreshed landscaping. The open kitchen has been updated and offers quartz countertops, Sub-Zero refrigeration, a wine fridge, beverage drawers, custom cabinetry, walk-in pantry and an island that serves as a breakfast bar. The great room opens to the lanai with pool, spa, and golf views. The split plan provides privacy with a remodeled master suite featuring a spa-like bath and custom walk-in closet. The south side includes an en suite guest room and a third bedroom/office with lanai access and golf views. Additional features include a 2-car garage with epoxy floor and storage, plantation shutters, a newer roof (2020), hurricane shades and new Pella bay windows. Saint James Park offers easy access to all of The Oaks Club’s offerings: tennis. Pickleball courts, croquet lawn, a state-of-the are WellFit Center, and golf facilities. Members enjoy a wide variety of dining options and a robust social calendar.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
76 OSPREY POINT DR, OSPREY, FL 34229
$1,590,000141 Days on yellowkey MLS ID: A4672843
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4364 Built: 1986Monthly Fee: $475 Tax: $13,509 (2024)Community: Oaks BaysideSingle Family
Taxes:$13,509
Remarks: OWNER SAYS SELL! No Reasonable offer refused on this home that is already the lowest price per Square foot on the market! COMPLETELY UPDATED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available upon request. Inside, the spacious layout includes a formal dining room, formal living room, and a cozy den with gas fireplace. Crown molding, tray ceilings, plantation shutters, and custom built-ins elevate the elegance throughout. Multiple sets of French doors open to the very private pool area, filling the home with natural light and enhancing indoor–outdoor living. The chef’s kitchen has been refreshed and features a six-burner Viking gas range with grill, Viking hood, Sub-Zero refrigerator/freezer, butler’s pantry, breakfast bar, and dining nook. The primary suite boasts two walk-in closets and a recent down-to-the-studs, resort-level bathroom remodel—one that would make even the Ritz envious. One guest suite occupies the west wing, while a spacious second-level suite adds comfort and flexibility. Significant structural upgrades include NEW low-E hurricane-impact windows and skylights, roll-down hurricane shutters (front and rear), and a whole-house generator for added peace of mind. Exterior enhancements include a NEW paver driveway and pool deck, extensive landscape lighting, and a very private pool area with new built-in grill and bar. Located in one of the Gulf Coast’s premier country club communities, The Oaks offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center. Club membership is required with homeownership.
120 CANDYCE DR, OSPREY, FL 34229
$650,000160 Days on yellowkey MLS ID: A4667108
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 2103 Built: 1962 Tax: $10,123 (2024)Community: Sorrento ShoresSingle Family
Taxes:$10,123
Remarks: Under contract-accepting backup offers. This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such an incredible opportunity. Bring your vision, contractor, and creativity to design a space that’s entirely your own. Unlike many homes nearby, this property did not experience any flooding, offering peace of mind and a solid foundation for your renovation. Whether you’re an investor looking for your next project or a buyer eager to build sweat equity in a prime waterfront community, 120 Candyce Drive delivers both value and potential in one of Sarasota County’s most sought-after coastal neighborhoods. Ideally located just minutes from Nokomis Beach, Casey Key, and popular waterfront dining, this home combines location and opportunity with no HOA restrictions. Turn this waterfront fixer-upper into your stunning Florida escape.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
135 WOODLAND PL, OSPREY, FL 34229
$269,00015 Days on yellowkey MLS ID: A4687664
1 Days Off yellowkey (back on 4/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1979 Tax: $2,660 (2025)Community: Pine Run IiCondo
Taxes:$2,660
Remarks: Ideally located in the heart of Osprey, this private corner, first floor condo offers effortless Florida living just minutes from pristine Gulf beaches and less than half a mile from the Intracoastal Waterway. The sought after community at the entrance to Casey Key was designed to live in harmony with nature by Frank Folsum Smith of the Sarasota School of Architecture. This unit features a garden view with four patios that includes a rear lanai enclosed with sliding vinyl windows. A unique inner atrium with aquarium style glass windows adds architectural interest and abundant natural light while maintaining privacy. The unit features easy to maintain custom tile floors on the diagonal throughout with wood floor inspired ceramic tiles in the bedrooms. Since 2023, unit updates include all new kitchen appliances, new faucets, new PEX water lines, a new water heater as well as new paint inside and out. The unit also includes a deeded carport parking space and two storage closets. Onsite resort style amenities include two heated pools (one overlooking a lagoon), two cedar saunas, a fitness room, Florida style clubhouse, walking trails, BBQ gas grill, outdoor gas fireplace, kayak storage, pickleball and tennis courts. Within a mile is the Pine View School (the only standalone public gifted school in the state), Oscar Scherer State Park, 2 kayak launches, a public boat ramp, Casey Key Fish House, Walmart and a Post Office. Easily walk to Publix, Ace Hardware, CVS, shops and restaurants or bike to the Legacy Trail and Nokomis Beach. Exceptional privacy, easy access, and a premier location make this residence an outstanding opportunity. Priced to sell!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kim Azar-Calka (239-216-6205)
232 WOODLAND DR #232, OSPREY, FL 34229
$264,900152 Days on yellowkey MLS ID: A4671600
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1980 Tax: $2,202 (2025)Community: Pine Run IiiCondo
Taxes:$2,202
Remarks: This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within the Pine Run community is also good with an abundance of trees and landscaping creating a private setting from your lanai off the livingroom. You will feel like you are living in a tree house! This condo has had extensive work done in the last 6 years including ELECTRIC ON-DEMAND TANKLESS HOT WATER HEATER, NEW CUSTOM KITCHEN WITH DOVE TAIL DRAWER CHERRY CABINETS, FLOORING, PAINT, LIGHT FIXTURES, NEW BATHROOMS AND PLUMBING. Unique frosted glass sliding doors in the dinette area open to washer dryer combo plus a pantry area! Crown molding in the living and dining area give an elegant feel to the rooms, The roof, maintained by the HOA was replaced about 3 years ago. Pine run is an active, vibrant community with small clubhouse with fitness room, pickle ball, tennis and other activities just waiting for you. Come take a look! If you are comparing other condo's, this one has much to like!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
854 MACEWEN DR, OSPREY, FL 34229
$3,790,000177 Days on yellowkey MLS ID: A4668918
Bed: 4 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 9081 Built: 2003Monthly Fee: $133 Tax: $26,109 (2024)Community: Oaks 2 Ph 2Spa: YesSingle Family
Taxes:$26,109
Remarks: 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 office. Upstairs, guests enjoy their own wing complete with a loft, theater, and screened terrace—ideal for relaxing or hosting in style. A split four-car garage, custom finishes, and generous room throughout reflect the craftsmanship expected in one of Sarasota’s most distinguished country club communities. The Oaks offers 24-hour security, two championship golf courses, an acclaimed racquets program, fitness and wellness facilities, and fine dining—all just minutes from the beaches and top-rated schools. Experience this home for yourself—take the 3D virtual tour and book your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Joe Murphy (941-780-3260)
665 CRANE PRAIRIE WAY, OSPREY, FL 34229
$719,000196 Days on yellowkey MLS ID: A4666718
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2306 Built: 2003Monthly Fee: $420 Tax: $4,513 (2025)Community: Willowbend Ph 2Spa: NoSingle Family
Taxes:$4,513
Remarks: Discover a blend of comfort and sophistication in this meticulously maintained home in the desirable Willowbend community. The striking architecture of the Ashley floor plan makes it a favorite. Go into a serene oasis featuring breathtaking wide lake views overlooking a sparkling pool, complemented by desired western exposure that invites an abundance of natural light and showcases vibrant sunsets. Gourmet kitchen with natural gas range, stainless dishwasher and refrigerator (new 2026). The interior boasts custom features, including crown molding and elegant tray ceilings. This spacious four-bedroom, three-bath home includes a chef's kitchen outfitted with natural gas cooking, as well as a cozy eat-in area with an aquarium window that beautifully frames the pool and lake views. The owner's suite serves as a sanctuary, offering two walk-in closets and a luxurious bath complete with dual sinks, a walk-in shower, a soaker tub and a separate toilet for added privacy. Thoughtfully designed with a split floor plan, the home ensures guests enjoy ample separation from the owner's suite for optimal comfort. A full-size laundry room adds to the home’s convenience. This exceptional residence is a blank canvas for an extraordinary lifestyle, conveniently near downtown Venice and Sarasota, beautiful beaches, Pine View School and the Legacy Trail. With no CDD fees and in a preferred X flood zone, the low community fees cover ground maintenance, irrigation and access to a community pool and spa, gym, pickleball courts, as well as high-speed internet and DirecTV streaming. Embrace the lifestyle you’ve always dreamed of in this stunning Willowbend home.
480 ORISKANY CT, OSPREY, FL 34229
$1,599,00043 Days on yellowkey MLS ID: A4684136
REDUCED by $96,000 (5.7%) on 04/12/2026
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3208 Built: 1999Monthly Fee: $142 Tax: $6,365 (2024)Community: The Oaks ClubSpa: NoSingle Family
Taxes:$6,365
Remarks: 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 and pool cage (2023) have been added. Living in the Oaks Club means enjoying two championship golf courses,12 har-tru tennis courts, pickleball courts, gorgeous croquet lawns fitness amenities which Junior Olympic size heated pool and an active social calendar- all just minutes away from the cultural vibrancy of downtown Sarasota and the Gulf Coast's world renowned Siesta Beach. Membership in the Oaks Club, Sarasota's premier golf and Country club is required for home ownership.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Susan Pelton (941-321-1007)
664 CRANE PRAIRIE WAY, OSPREY, FL 34229
$887,00053 Days on yellowkey MLS ID: A4681662
REDUCED by $10,000 (1.1%) on 04/08/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2870 Built: 2003Monthly Fee: $437 Tax: $5,460 (2025)Community: Willowbend Ph 2Spa: YesSingle Family
Taxes:$5,460
Remarks: 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 entertaining area. The exterior boasts a three-car garage and a double-door that welcomes you into an inviting, spacious interior. The home’s open floor plan includes living/dining with views to the natural beauty, tile on diagonal, crown molding and vaulted ceilings. Handsome office/den to the front of residence. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, including built-in gas range and custom hood. Large walk-in pantry with oversized adjacent laundry room that has an additional deep closet. Dinette area features an aquarium window to take in the natural beauty. Family room is spacious with a corner pocket door that opens wide to let in Florida’s finest weather. The primary suite offers bamboo wood floors, double-tray ceiling and sitting area with French doors. California-style walk-in closets and a luxurious bath with dual sinks, a tub, walk-in shower and separate toilet. Each guest bedroom is generous in size with full bath in between. Additionally, it is a bonus living space with wood floors overlooking the serene setting. Third bath serves as pool bath. On a practical note, new water heater in 2026 and pool pump in December 2025. An amazing lifestyle awaits, all overlooking serene waterfront views teeming with wildlife such as eagles, osprey, otters, turtles and deer. The home is ideally near downtown Venice, Sarasota, Siesta Key, Nokomis Beach and Legacy Trail, offering easy access to cultural attractions, shopping, dining and recreational activities. Short distance to nationally ranked Pine View School. The community’s low fees include internet, Direct TV streaming, yard maintenance, irrigation, pool and spa, gym and pickleball, making this a harmony of luxury, comfort and stunning beauty.
250 HIDDEN BAY DR #301, OSPREY, FL 34229
$725,00082 Days on yellowkey MLS ID: A4679278
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2168 Built: 2017 Tax: $7,792 (2025)Community: Edgewater At Hidden BaySpa: YesCondo
Taxes:$7,792
Remarks: Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in Jan 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy maintenance tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area offers a built-in dry bar with wine refrigerator and opens to a large, screened-in terrace with privacy-screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, makeup vanity and walk-in shower. Additional features include a private den/office, in-unit laundry room, two full baths and a powder room, AC from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with kitchen and quartz bar, heated pool and spa, fitness center, library, tiki hut with grilling stations, pickleball and tennis courts, kayak launch, fishing pier, dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey just south of Sarasota, near area beaches, shopping and dining, and only minutes from Venice.
Listing Agent: Per Nordstrom, Pa (941-228-1080)
5100 JESSIE HARBOR DR #403, OSPREY, FL 34229
$679,900104 Days on yellowkey MLS ID: A4676382
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2004Monthly Fee: $1,027 Tax: $5,647 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$5,647
Remarks: This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid appliances, custom cabinet pullouts and the kitchen’s showstopper is the exquisite stone counter surfaces, which wow and make everyday cooking, or your gourmet meal preparation, a joy. Plantation shutters and remote-controlled blinds grace many of the windows. The views from your primary retreat vie for your attention thanks to the shimmering intracoastal front and center. Generous in size, the main retreat delights with a walk-in shower, large soaking tub, double vanities, a separate makeup area, private water closet and dual walk-in closets. The second bath features a recently installed walk-in tub, designed for enhanced comfort, ease and safety. Enjoy expansive water views from your fourth-floor balcony, where nesting birds, jumping fish and dazzling sunsets create a stunning backdrop for your daily pleasure. The inside laundry room and your two assigned parking spaces are under the building and out of the elements, adding to the opportunity. The lifestyle amenities in this friendly community include recently resurfaced tennis and pickleball courts, a heated swimming pool, a clubhouse with fitness area, kayak storage and launch, and fishing. Boat slips are available on a first-come basis for an additional fee. Enjoy a waterfront picnic under the gazebo, complete with grills, a walking path and pretty greenspace areas. Ideally close to shopping, dining, the crystal sand beaches and famed Oscar Scherer State Park, which offers biking, birdwatching, geocaching and over 15 miles of scenic hiking trails, and a natural lake for swimming, and the best part is the proximity, just across the street. Come be enchanted, as this slice of Florida paradise is one you won’t want to miss.
Listing Agent: Cindy Migone (941-812-7438)
1486 LANDVIEW LN, OSPREY, FL 34229
$850,000154 Days on yellowkey MLS ID: D6144630
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1869 Built: 1977Monthly Fee: $204 Tax: $7,488 (2025)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$7,488
Remarks: Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout, fully redesigned spa-inspired bathrooms with custom vanities, updated ceilings, recessed lighting, and interior shaker doors. The home was also re-piped for water and sewer, offering both modern comfort and long-term peace of mind. The light-filled living room, accented with elegant shiplap detail, opens effortlessly to the lanai, creating a graceful indoor-outdoor connection. Outside, a private retreat awaits with a resurfaced pool, new screen enclosure, and marble pavers. Generous covered space accommodates lounging, dining, and entertaining, while sliding doors from the primary suite, living room, and family room invite the outdoors in and enhance the home’s open, airy ambiance. The primary suite is a serene escape, thoughtfully positioned for privacy and direct access to the lanai. Custom closet systems throughout the home provide elevated functionality, while the epoxy-finished garage with built-in cabinetry delivers a polished, organized finish. Mature tropical landscaping and six-foot pitch apple plantings create a secluded backyard sanctuary, complemented by stately palms that frame the home with unmistakable Florida elegance. Southbay offers a distinguished, resort-style lifestyle with a newly renovated waterfront clubhouse featuring a grand ballroom, catering kitchen, and state-of-the-art fitness center overlooking the marina. Residents enjoy a heated pool, youth pool, tennis and pickleball courts, shuffleboard, bocce, basketball courts, walking trails, and an Intracoastal waterfront park. For boating connoisseurs, the community-owned deep-water marina provides direct Intracoastal access with no fixed bridges to the Gulf. Exclusive, low-fee boat slips accommodate vessels up to 55 feet and are available only to Southbay owners. A vibrant social calendar and golf-cart-friendly streets make it effortless to enjoy community events, nearby boutiques, waterfront dining, and local beaches. Ideally located near Pine View School—Florida’s #1 charter school and one of the nation’s premier gifted programs—this residence presents a rare opportunity to enjoy luxury living within an active, waterfront enclave. A sophisticated coastal retreat where lifestyle, privacy, and boating converge—welcome to Southbay.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Barbara Teyssier (304-671-6691)
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