Location: Osprey
Do Not Show Listings
448 E MACEWEN DR, OSPREY, FL 34229
$2,100,000117 Days on yellowkey MLS ID: A4687195
0 Days Off yellowkey (back on 7/11/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3768 Built: 1998Monthly Fee: $142 Tax: $9,639 (2025)Community: OaksSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,639
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. **IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid appliances. The expansive primary suite is a true retreat, complete with multiple walk-in closets, dual vanities, a soaking tub, and a custom-tiled shower. Enjoy Florida living at its finest on the screened lanai, featuring a heated pool and spa, travertine marble pool deck, and a large covered entertaining area—all overlooking tranquil golf course and garden views for ultimate privacy. Additional highlights include a 3-car garage and thoughtfully designed indoor-outdoor living spaces perfect for entertaining or relaxing. THE OAKS is a 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 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
18 N CASEY KEY RD, OSPREY, FL 34229
$1,750,000276 Days on yellowkey MLS ID: A4669083
0 Days Off yellowkey (back on 6/1/2026)
REDUCED by $250,000 (12.5%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1977 Built: 1973 Tax: $24,015 (2024)Community: Casey KeySingle Family
Taxes:$24,015
Tax Year: 2024
Middle School: Laurel Nokomis Middle
Remarks: Under contract-accepting backup offers. Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal for quiet retreats, reading or working from home. Enjoy serene views of the bay and Intracoastal Waterway from the primary suite, a coastal sanctuary. Set on over half an acre, the expansive backyard features a large screened-in pool and lush landscaping, creating your own private tropical paradise by the water. The deeded easement directly across the street leads to a secluded sandy beach, offering endless days of sun, sea, and tranquility. The property remained unaffected by recent storms, a testament to its solid construction and meticulous upkeep. Recent upgrades include mew metal roofs on the home and garage (2020), HVAC system replacement (2020), new water heater (2021), PGT impact-rated windows and doors (2012) and new garage door (2012). Ideally situated for easy access on and off the key, this residence is also close to top-tier shopping, dining, golf, tennis and recreational amenities. With Sarasota and Venice just a short drive away, you’ll enjoy a balance of island living and urban convenience.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Valerie Dall'Acqua (941-445-7295)
422 BLUE GARDEN LN, OSPREY, FL 34229
$1,445,000311 Days on yellowkey MLS ID: A4664436
REDUCED by $50,000 (3.3%) on 07/10/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3872 Built: 1984Monthly Fee: $475 Tax: $7,339 (2024)Community: OaksSpa: YesSingle Family
Taxes:$7,339
Remarks: Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on a quiet cul-de-sac in The Oaks Bayside. A grand traditional residence, with generous sized rooms, flexible living areas, and a private outdoor setting, the possibilities here are limitless. Step into the marble entry through the double front doors, and you will love what you find inside. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna completes the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. The Oaks Club features two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options. There is currently no waiting list for either Golf or Sports/Social membership
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
127 PARK TRACE BLVD, OSPREY, FL 34229
$795,00080 Days on yellowkey MLS ID: A4692408
1 Days Off yellowkey (back on 5/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2463 Built: 2003 Tax: $4,379 (2025)Community: Park Trace EstatesSpa: YesSingle Family
Taxes:$4,379
Remarks: Flawless from top to bottom, this beautifully maintained Florida home offers over 3,000 sq. feet of indoor and outdoor living space, perfect for casual or elegant entertaining. With more than $175,000 in recent upgrades, this stunning water view property blends luxury with peace of mind. Highlights include a new roof, a refinished pool and spa with new heater, and built in Char Broil grill for the ultimate backyard escape. Lush tropical landscaping surrounds the front and back, adding year-round beauty and privacy. Inside, you will find a renovated gourmet kitchen, wood cabinetry, sleek porcelain tile floors, double tray ceilings, and remote-controlled Hunter Douglas blinds. The primary suite is a private getaway with a luxury spa style bath and custom bespoke closet, while six rooms boast gorgeous water views and natural light. In addition you will find an oversized garage with additional overhead storage and built-in work bench Located in the coveted Park Trace Estates in Osprey, you're just 6.5 miles from Siesta Key Beach, a short walk to the Legacy Trail, and jump on a kayak near-by at Oscar Scherer State Park. Adding even more appeal, it is also a short walk to the nationally acclaimed Pine View School. This move-in ready luxury home blends lifestyle, location, and exceptional quality in a beautiful community with HOA's of only $58 a month!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kim Azar-Calka (239-216-6205)
759 FORDINGBRIDGE WAY, OSPREY, FL 34229
$715,00098 Days on yellowkey MLS ID: O6399774
REDUCED by $34,000 (4.5%) on 07/09/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2950 Built: 2002Monthly Fee: $55 Tax: $7,129 (2025)Community: Rivendell WoodlandsSingle Family
Taxes:$7,129
Elementary School: None
High School: None
Middle School: None
Remarks: Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
429 PATTERSON AVE, OSPREY, FL 34229
$449,00027 Days on yellowkey MLS ID: A4697505
1 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1173 Built: 1979 Tax: $4,251 (2025)Community: Osprey Park 2Spa: YesSingle Family
Taxes:$4,251
Remarks: Under contract-accepting backup offers. Incredible opportunity with a $10,000 credit to buyers at closing for costs or a rate buy-down! This low-maintenance gem is fully updated with a NEW AC, brand-new ductwork, stylish new counters/backsplash, new dishwasher, and a beautifully refreshed bathroom. The backyard is a private oasis boasting a brand-new 2025 heated saltwater pool and spa. Location is unbeatable: just .4 miles from the ocean, 10~ minutes to Venice and world-famous Siesta Key, and just a couple miles to Sarasota Square where the upcoming Sarasota Square Mall is located. Walking distance to local ice cream shop, restaurants, Walmart, and dog park! Bring the toys—no HOA and plenty of boat parking. Dog friendly buyers will appreciate the custom made dog wash station! NO FLOOD INSURANCE REQUIRED!
Listing is courtesy of: MARCUS & COMPANY REALTY (941-932-8550)
Listing Agent: Brent Martin, Llc (941-231-4662)
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000292 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)
260 HIDDEN BAY DR #304, OSPREY, FL 34229
$694,000156 Days on yellowkey MLS ID: N6142969
REDUCED by $5,000 (0.7%) on 04/14/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1950 Built: 2019 Tax: $6,342 (2025)Community: Edgewater/Hidden Bay Ph 2 BldgSpa: YesCondo
Taxes:$6,342
Remarks: The Boca Residence: Spacious Living & Resort Style Discover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal getaway, this home provides a comfortable and highly livable environment. The experience begins with a proper foyer entry that opens into expansive living and dining areas, ideal for hosting family and friends. A dedicated den offers great flexibility as a home office, hobby room, or guest space. This residence is designed for privacy with a split-bedroom configuration, while the additional powder room adds everyday convenience for guests. High ceilings, generous room sizes, and multiple walk-in closets are complemented by a large private terrace that extends your living space outdoors. Beyond the front door, the community offers a host of resort-style amenities. Enjoy a heated pool and spa, a social clubhouse, a fitness center, and courts for both tennis and pickleball. A scenic boardwalk leads to outdoor grilling stations and a tropical Tiki hut gathering area, perfect for weekend get-togethers. To truly experience the lifestyle this home offers, we invite you to schedule your private tour during the sunset hour to see the incredible views that make this residence so special.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Jamie Styers (941-356-4135)
OSPREY, FL 34229
$799,00017 Days on yellowkey MLS ID: A4699089
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2607 Built: 2001Monthly Fee: $58 Tax: $5,777 (2025)Community: Park Trace EstatesSpa: YesSingle Family
Taxes:$5,777
Elementary School: Pine View School
Remarks: MODERN COASTAL MASTERPIECE | OVER $200,000 IN LUXURY UPGRADES | NEW ROOF | HEATED SALTWATER POOL | PINE VIEW SCHOOL DISTRICT Welcome to one of Park Trace Estates’ finest fully renovated homes, where sophisticated design, exceptional craftsmanship, and the Florida lifestyle come together in perfect harmony. This spectacular 4-bedroom, 3-bath residence has been extensively remodeled with over $200,000 in premium upgrades, creating a truly move-in-ready luxury retreat. From the moment you arrive, you’ll be captivated by the home’s outstanding curb appeal, featuring professionally designed tropical landscaping, an elegant paver walkway, and a welcoming entrance that immediately sets the tone for what’s inside. Step through the front door into a breathtaking open-concept floor plan showcasing soaring ceilings with custom decorative beams, an impressive floor-to-ceiling designer stone fireplace, abundant natural light, and exquisite designer finishes throughout. Every detail has been carefully selected to create a warm, elegant, and timeless coastal living experience. The heart of the home is the stunning chef’s kitchen, completely redesigned with premium finishes, featuring Bosch stainless steel appliances, oversized quartz countertops, custom cabinetry, and an expansive island perfect for entertaining family and friends. The spacious split-bedroom floor plan offers privacy and comfort, while three beautifully remodeled designer bathrooms provide a spa-like experience with luxury finishes and exceptional attention to detail.Expansive sliding glass doors seamlessly blend indoor and outdoor living, opening to your own private resort-style courtyard featuring a heated saltwater pool and spa, creating the perfect setting for entertaining or simply enjoying Florida’s year-round sunshine. Extensive Premium Improvements Include: ? NEW $60,000 Tile Roof ? NEW High-Efficiency HVAC System (2024) ? Completely Remodeled Designer Kitchen ? Premium Bosch Stainless Steel Appliances ? Oversized Quartz Countertops & Custom Cabinetry ? NEW Luxury Vinyl Flooring Throughout ? Three Fully Remodeled Designer Bathrooms ? Custom Floor-to-Ceiling Stone Fireplace ? Decorative Custom Ceiling Beams ? Freshly Painted Interior Throughout ? Freshly Painted Exterior ? Professionally Designed Custom Accent Walls with Premium Designer Finishes ? NEWER Saltwater Pool System ? NEW Pool Heater ? Aqua Whole-House Water Filtration System ? Water Softener ? NEW Water Heater ? NEW Vinyl Privacy Fence v Custom-designed green wall at the patio and at the entrance. ? Professionally Designed Tropical Landscaping (Approx. $20,000) ? Over $200,000 Invested in Quality Renovations & Improvements Located in the highly desirable Park Trace Estates, this exceptional property is just minutes from world-famous Siesta Key Beach, Nokomis Beach, the award-winning Pine View School, Legacy Trail, shopping, healthcare, and the natural beauty of Oscar Scherer State Park, offering kayaking, hiking, biking, and endless outdoor recreation. Situated in Flood Zone X with low HOA fees of approximately $55/month, this meticulously upgraded residence offers peace of mind, luxury, and an unbeatable location. This is more than a home—it’s a lifestyle. Every room reflects quality, craftsmanship, and thoughtful design. With over $200,000 invested in premium upgrades, this exceptional property is truly one of the finest opportunities currently available in Park Trace Estates.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Claudia Dybala (773-318-5796)
14021 BELLAGIO WAY #404, OSPREY, FL 34229
$1,100,00087 Days on yellowkey MLS ID: N6144070
REDUCED by $75,000 (6.4%) on 07/07/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2187 Built: 2006Monthly Fee: $1,644 Tax: $5,636 (2025)Community: Villas At Bellagio Harbor VillageCondo
Taxes:$5,636
Remarks: This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)
Listing Agent: Megan E. George, Pa (941-726-1998)
480 BLACKBURN POINT RD #5, OSPREY, FL 34229
$249,00021 Days on yellowkey MLS ID: A4698854
1 Days Off yellowkey (back on 7/6/2026)
Bed: Bath: 0.0 Built: 2006 Tax: $1,092 (2025)Community: Wet Slips At Bellagio Harbor VillageDock-Rackominium
Taxes:$1,092
Remarks: A rare find in Sarasota, this covered 50ft wet slip at Osprey Harbor Village offers the perfect blend of protection, convenience, and value. Located at 480 Blackburn Point Road in Osprey, just off the Intracoastal Waterway, this sheltered slip keeps your yacht out of the Florida sun with quick access north to Sarasota Bay or south to Venice and the Gulf of Mexico beyond. Enjoy the benefits of ownership without the million-dollar price tag of waterfront real estate, complete with water, electric, cable, pump-out services, a fuel dock, on-site restaurant, and secure, well-lit docks. Low quarterly fees make this an exceptional opportunity for any serious boater or investor!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Daniel Treiman (917-657-7495)
6100 JESSIE HARBOR DR #202, OSPREY, FL 34229
$850,00081 Days on yellowkey MLS ID: A4690969
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3771 Built: 2005Monthly Fee: $1,101 Tax: $8,698 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$8,698
Remarks: Virtually Staged. Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Angelic Tassos (917-450-0316)
14041 BELLAGIO WAY #318, OSPREY, FL 34229
$949,00042 Days on yellowkey MLS ID: A4696101
REDUCED by $50,000 (5.0%) on 07/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2086 Built: 2006Monthly Fee: $1,512 Tax: $7,362 (2025)Community: Villas At Bellagio Harbor VillageSpa: YesCondo
Taxes:$7,362
Remarks: Virtually Staged. Newly priced at $949,000. Boaters, sunset lovers, and buyers seeking a true Gulf Coast lifestyle will appreciate this spacious waterfront condominium in The Villas at Bellagio Harbor Village, complete with a 37 foot wet slip included in the sale. This 3 bedroom plus den, 2 bath residence offers 2,086 square feet of living space, plus large lanai, private elevator entry, and beautiful west facing views over the water and marina. The open floor plan features a generous great room, covered lanai, large kitchen with newly painted cabinetry, interior laundry room, and two assigned under building parking spaces that are next to each other. Water views are spectacular from entry, great room, kitchen and primary bedroom. Doors leading to lanai in great room, kitchen and primary bedroom. Residents of The Villas at Bellagio Harbor Village enjoy resort style amenities including a heated waterfront pool and spa, fitness center, clubhouse, sauna, kayak launch, gated entry, elevator access, and a marina setting. The community is ideally located near Blackburn Point, Casey Key, Oscar Scherer State Park, waterfront dining, shopping, beaches, Sarasota, Venice, and all that Osprey has to offer. Whether you are looking for a full time residence, seasonal retreat, or waterfront getaway with boating access, this condo delivers a rare combination of space, views, amenities, and an included wet slip in a beautiful coastal setting.
Listing is courtesy of: COLDWELL BANKER REALTY (941-487-1492)
Listing Agent: Margot Leonard (941-387-5050)
1361 NEW FOREST LN, OSPREY, FL 34229
$535,00090 Days on yellowkey MLS ID: A4691036
REDUCED by $10,000 (1.8%) on 07/07/2026
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: PRICE TO SELL. 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)
409 NORTH POINT RD #401, OSPREY, FL 34229
$560,00093 Days on yellowkey MLS ID: A4690812
REDUCED by $65,000 (10.4%) on 07/07/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2594 Built: 2004Monthly Fee: $367 Tax: $6,285 (2025)Community: Meridian At The Oaks PreserveSpa: NoCondo
Taxes:$6,285
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown molding, ceiling fans and custom lighting. The expansive kitchen features granite countertops and stainless-steel appliances and has a cozy breakfast nook. Practical concerns are addressed by things like electric hurricane shutters in addition to impact windows and doors, and a large laundry room. Meridian residents have use of their own pool, spa and workout room. And can take advantage of all the Oaks Club has to offer, two championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. There is currently no waiting list for either Golf or Sports/Social membership.
764 SARABAY RD #8, OSPREY, FL 34229
$425,000147 Days on yellowkey MLS ID: A4683747
REDUCED by $25,000 (5.6%) on 06/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981Monthly Fee: $1,617 Tax: $2,936 (2025)Community: Heron Bay Club Sec IVilla
Taxes:$2,936
High School: Pine View School
Middle School: Pine View School
Remarks: Virtually Staged. Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10 beautifully manicured acres, this home offers the ultimate Florida lifestyle. Enjoy resort-style amenities including a heated waterfront pool, tennis courts, kayak launch, fishing pier, and community docks with water and electric. Best of all, there are 10 free boat slips with no fixed bridges to the Gulf, making this a boater’s paradise, so bring your boat and go! This spacious two-bedroom, two-bath villa features sweeping views of Little Sarasota Bay, the Intracoastal Waterway, the community pond and pool. The open concept floor plan is enhanced by 15-foot ceilings, abundant natural light, and seamless indoor-outdoor living. Relax on the screened lanai, cool off in your heated waterfront pool and enjoy nightly sunsets that never get old. A private gated courtyard entry sets the tone for this unique home, complete with a new paved walkway and pet-friendly artificial turf, completely maintenance-free. Inside, enjoy ES Prestige impact-rated windows and sliding glass doors, all-new kitchen appliances, and an eat-in kitchen overlooking the courtyard. The primary suite offers lanai access through sliding glass doors and features two custom walk-in closets. The second bedroom also opens to the private courtyard and includes its covered lanai, perfect for guests or a home office retreat. Conveniently with quick access to Interstate 75, shopping, dining and beaches, this exceptional waterfront villa delivers boating, fishing, views and effortless Florida living in one remarkable package. A rare opportunity, this is waterfront living at its finest. Schedule your private showing today.
Listing Agent: Michael Christo (508-735-6797)
1367 THORNAPPLE DR, OSPREY, FL 34229
$569,00050 Days on yellowkey MLS ID: A4695210
1 Days Off yellowkey (back on 7/3/2026)
REDUCED by $10,000 (1.7%) on 07/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2182 Built: 2003Monthly Fee: $397 Tax: $5,745 (2025)Community: Willowbend Ph 1Spa: NoSingle Family
Taxes:$5,745
Remarks: Discover unparalleled luxury in this exquisite Lee Wetherington-built residence, ideally in Willowbend within Osprey. A grand entry hall with high-end finishes, tray ceilings and rich crown molding welcomes you to a home meticulously perfected by discerning sellers. This ideally positioned home boasts a ¼+ acre homesite with an expansive front yard, a roomy side-entry paver newly sealed driveway and an oversized garage, recently painted. Enjoy private outdoor living on the lanai and in the backyard, enhanced by mature landscaping for ultimate privacy and shade. Go inside to a stunning retreat featuring 20-inch porcelain tile throughout the entire residence, marble inlays, wide crown molding, elegant arches and plantation shutters, all within the popular Willow floor plan. An inviting gathering and dining room lead to the heart of the home, including an amazing gourmet kitchen with new stainless appliances and natural gas cooking, granite counters and trending painted cabinets. A separate breakfast nook offers tranquil views, while the family room, with its tray ceiling and triple sliders, opens to an outdoor haven. The spacious owner’s suite is a sanctuary, complete with walk-in closets, dual granite sinks, a walk-in shower, a deep garden tub and lanai access. Two additional bedrooms share a bath, and a lovely den/office features bay windows. Hurricane protection on all doors and windows installed in 2021 for peace of mind. Low HOA fees cover yard maintenance, irrigation, high-speed internet, streaming cable, a heated community pool/spa, fitness center, basketball, pickleball and playground. Location is everything! Enjoy proximity to beautiful Gulf beaches, Oscar Scherer State Park, Legacy Bicycle Trail, Pine View School, waterfront restaurants, tiki bars, Publix and new Foxtail Coffee. Experience the art of living in this extraordinary home with exceptional curb appeal and lush landscaping.
Listing Agent: Todd Currey (941-402-6000)
523 OAK BAY DR, OSPREY, FL 34229
$540,00041 Days on yellowkey MLS ID: A4696725
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2399 Built: 1998Monthly Fee: $25 Tax: $3,448 (2025)Community: Bay Oaks EstatesSingle Family
Taxes:$3,448
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully maintained 3-bedroom + den, 2-bath pool home nestled on a desirable corner lot, in a cul-de-sac, in Osprey. This home has been impeccably maintained and is an unbeatable location, this is the effortless Florida lifestyle you've been searching for. Peace of mind comes standard here. The roof is less than 7 years old, the AC was replaced just 2½ years ago, and the hot water heater is under 3 years old... meaning the big-ticket items are already handled, so you can simply move in and enjoy. You will find vinyl plank flooring, tile and carpet throughout. The care and attention put into this home shows in every corner. This home offers space to rest, work, entertain and relax...The flexible den offers the perfect home office, creative studio, 4th bedroom or guest retreat, whatever your lifestyle calls for? along with two spacious bathrooms. Then, step outside to your private screened pool, where the corner lot provides extra breathing room, privacy, and that open, airy feel that's so rare to find. Positioned in the heart of Osprey, this home is only minutes from the beloved Legacy Trail? which is ideal for cycling, jogging, and morning walks through some of Florida's most scenic natural surroundings. Nature lovers will also enjoy the proximity to Oscar Scherer State Park, offering kayaking, wildlife watching, and over 15 miles of trails. And when the beach calls, it's answered quickly. Nokomis Beach is just a short drive away for a casual sunset stroll, while the world-famous Siesta Key Beach, home to some of the whitest, finest sand on the planet, is within easy reach for those perfect beach excursions. 523 Oak Bay Drive checks every box: updated systems, private pool, flexible living space, and access to the very best of Florida's Gulf Coast. People also love the access to top-rated schools, including the nationally acclaimed Pine View School and Laurel Nokomis Elementary, making this the complete package for anyone looking to plant roots in one of Sarasota County's most sought-after communities. Homes like this don't last long. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
113 BURNEY RD, OSPREY, FL 34229
$999,50091 Days on yellowkey MLS ID: A4690672
0 Days Off yellowkey (back on 6/20/2026)
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2502 Built: 2020 Tax: $10,455 (2025)Community: Bel-AirSpa: YesSingle Family
Taxes:$10,455
Remarks: Under contract-accepting backup offers. **DON’T WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOME (2020) IS MOVE-IN READY AND PACKED WITH UPGRADES** Situated on a generous 0.52-acre lot near the end of a quiet cul-de-sac, the property offers a private backyard and NO HOA fees/restrictions. Bring Your Toys! Oversized circular driveway provides ample parking for a BOAT, RV, and additional vehicles. This Impressive Residence with 2502sf of heating living space, features 3 Bedrooms plus Study/Den, 2 Full and 1 Half Baths, and a 3-car tandem garage. The Light and Bright, Open Floor Plan is enhanced by tile flooring throughout, tray ceilings, Hurricane Impact Windows and Sliding Doors, plantation shutters, etc. The expansive kitchen is designed for both everyday living and entertaining, featuring a large island, hardwood cabinetry, and premium stainless-steel appliances including Thermador, Bosch, etc. The owner’s suite offers a large, divided walk-in closet and a luxurious en-suite bath with dual vanities and a custom-tiled shower. A spacious, screened lanai provides a beautiful view of the expansive, landscaped and private backyard while showcasing a Heated/Cooled, Saltwater Pool/Spa, along with a large, covered seating area and an Outdoor Kitchen BBQ, Quartzite countertop/sink —perfect for enjoying Florida’s outdoor lifestyle. The Ideally located with easy access to US-41 (Tamiami Trail), this home is just a short drive to world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229
$599,000107 Days on yellowkey MLS ID: C7524397
4 Days Off yellowkey (back on 6/25/2026)
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: Under contract-accepting backup offers. 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)
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