Location: Osprey
Do Not Show Listings
402 MACEWEN DR, OSPREY, FL 34229
$1,750,0002 Days on yellowkey MLS ID: A4690018
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3565 Built: 1999Monthly Fee: $142 Tax: $13,762 (2025)Community: OaksSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,762
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that stretch endlessly from the expansive screened lanai. Spanning over 3,500 square feet, this beautifully appointed single level home features three generously sized bedrooms, a dedicated office, and three-and-a-half baths, all thoughtfully designed to balance sophistication with everyday comfort. From the moment you enter, a sense of understated elegance unfolds—gracious formal living spaces anchored by a statement fireplace, soaring tray ceilings, intricate crown molding, and an abundance of natural light that enhances every architectural detail. The primary suite serves as a true retreat, offering impressive proportions, a substantial walk-in closet, and a spa-inspired bath designed for relaxation. Additional living spaces flow effortlessly, including a well-equipped laundry room with custom built-in workspace, ideal for modern living. Every inch of the home reflects careful attention to detail, from the finishes to the functional layout. Outdoors, the residence truly shines. The screened lanai becomes a private sanctuary, complete with a sparkling pool and spa, perfectly positioned to capture sweeping views of the 4th hole. Whether entertaining guests or enjoying quiet evenings, this space delivers an elevated indoor-outdoor lifestyle synonymous with luxury coastal living. Enhancing both comfort and peace of mind, the home is equipped with a whole-house generator, and Security Camera's outside and the oversized three-car side entrance garage and circular paver driveway provide both convenience and impressive curb appeal. Quick notes to take away: Roof - 2023 / A/C (both units) - 2024 Ownership within The Oaks grants access to an unparalleled private club experience. Residents enjoy two championship 18-hole golf courses, impeccably maintained HAR-TRU tennis courts, newly introduced pickleball facilities, and a state-of-the-art Wellness and Fitness Center exceeding 7,500 square feet. Complemented by an exceptional culinary program and a vibrant calendar of curated social events, The Oaks offers a lifestyle defined by elegance, activity, and connection. Club membership is required, within this distinguished Sarasota community.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Steven Kepecz, Pa (941-376-6411)
4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229
$329,90041 Days on yellowkey MLS ID: N6143250
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 2018 Tax: $3,781 (2025)Community: Bay Street VillageCondo
Taxes:$3,781
Remarks: Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen closet, lighted 10× makeup mirror, and a bidet-ready outlet. The second and third bedrooms also include custom ceiling fans and 2" blinds. The dining area is accented by a custom light fixture and accordion blinds on the balcony sliding doors. The balcony is enhanced with a tropical palm-leaf ceiling fan and outdoor curtains for added shade and comfort. The great room is fitted with plantation shutters for added elegance. A spacious laundry room includes a washer and dryer. Added features-Ring Doorbell, Keyless Entry on Front Door as well as an Exterior Garage door keypad. The monthly condo fee includes water, sewer, exterior and grounds maintenance, gated entry, heated resort-style pool, cabana, fitness center, and club room. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key Beach, the Legacy Trail, Sarasota and Venice dining and shopping, Oscar Scherer Park, and A-rated Pine View School. Maintenance-free Florida living at its best.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
32 SIESTA CIR W, OSPREY, FL 34229
$69,0002 Days on yellowkey MLS ID: A4690063
0 Days Off yellowkey (back on 4/16/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 480 Built: 1968Monthly Fee: $215 Tax: $555 (2025)Community: ArborsMobile Home
Taxes:$555
Elementary School: None
High School: None
Middle School: None
Remarks: Charming and affordable 1-bedroom, 1-bath mobile home in desirable Osprey, FL! Situated on a spacious corner lot, this cozy residence offers great potential with a price that reflects the opportunity to update and make it your own. The open living room flows seamlessly into the kitchen, with space for a small dining table—perfect for casual living. The primary bedroom features a convenient built-in desk or makeup area, adding both function and charm. Durable metal siding and roofing provide peace of mind, while the extra-wide carport offers ample covered parking, complemented by additional public parking along the side lot. Enjoy Florida living outdoors with tropical palm trees welcoming you home, a large screened lanai for relaxing or entertaining, and a handy storage shed. Washer and dryer are included for added convenience. A great opportunity to own in a prime location with plenty of potential—don’t miss it! Located in the desirable Arbors community in Osprey, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area and a full calendar of social activities. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Karen Geiger (941-928-8889)
522 LUMINARY BLVD, OSPREY, FL 34229
$647,00069 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
Middle School: Laurel Nokomis Middle
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 is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$290,0006 Days on yellowkey MLS ID: A4689541
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: One or more photo(s) has been 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. **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)
353 S SHORE DR, OSPREY, FL 34229
$1,200,00015 Days on yellowkey MLS ID: A4688006
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1968Monthly Fee: $10 Tax: $3,904 (2025)Community: Sorrento Shores Rep Of 2Spa: NoSingle Family
Taxes:$3,904
Remarks: Welcome to Sorrento Shores—where location, lifestyle, and waterfront living come together beautifully. Perfectly positioned on a generous .36-acre canal-front lot, this 3-bedroom, 2-bath pool home offers direct access to the Intracoastal Waterway just a few homes down the canal. A true boater’s dream, your private dock provides quick and easy access to some of the area’s most beloved waterfront destinations. Cruise north to Casey Key Fish House, or the newly reopened Midnight Pass. You could also head south toward Venice to enjoy Pop's Sunset Grill and Pelican Alley. Spend your days at Snake Island, or venture through the jetties to the open waters of the Gulf of Mexico —where the possibilities for exploration are endless. Inside, the home features a spacious and flexible floorplan with a kitchen, dining room, living room, and den, along with an indoor laundry room. Two of the three bedrooms are private ensuites, offering ideal comfort for guests or multi-generational living. The home is being offered turnkey (with select personal exclusions), making it move-in ready for immediate enjoyment or seasonal use. Step outside to your impressive 27x40 enclosed lanai with pool, creating an expansive outdoor living space perfect for entertaining or unwinding in your own private tropical setting. In addition to the 2-car garage, a large storage shed provides added convenience, and there is dedicated space to park your boat trailer right on the property—no off-site storage needed. Major updates provide peace of mind: New roof -July2025, 3rd nail installed in rafters-July 2025, Pool Heater (Electric)-December 2025, New Pool Cage (Picture frame)- January 2025, Primary bath remodeled- August 2025, Guest Bath (partial remodel)-August 2025, Interior painted-September 2025, Popcorn ceiling removed and ceiling painted-August 2025. New Septic System-2024 Sewer pipes lined-2023/2024 New water heater-2024 A/C (2018) Sorrento Shores is a hidden gem offering a voluntary HOA of just $125/year and no CDD fees, delivering a relaxed coastal lifestyle without the burden of high community costs. Whether you’re searching for a winter retreat, full-time residence, or investment opportunity, this property stands out with its rare combination of quick Intracoastal access, expansive lot size, private dock, and prime location.
Listing Agent: Phyllis Coviello (941-408-3265)
4284 EXPEDITION WAY #NA, OSPREY, FL 34229
$339,90062 Days on yellowkey MLS ID: A4681835
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1430 Built: 2017 Tax: $2,934 (2025)Community: Bay Street VillageCondo
Taxes:$2,934
Remarks: Welcome to Bay Street Village, a gated, maintenance-free community in Osprey between Sarasota and Venice. The tile roofs and paver driveway provide Florida charm. This move-in-ready 3-bed, 2-bath condo features an open layout, IMPACT glass, and a private screened balcony with a pond view. The kitchen offers a large granite counter with seating and a newer refrigerator. The primary suite includes a walk-in closet and an en-suite bath with dual sinks and a step-in shower. A split floorplan adds privacy, and the attached one-car garage provides extra storage. Community amenities include a heated pool, fitness center, and clubhouse. Bay Street Park is directly across the street and is walkable—includes a dog park for your furry friend. Water is included in the monthly fee. Conveniently located near Nokomis Beach, Oscar Scherer State Park, The Legacy Trail, Publix, restaurants, shopping, and both US-41 and I-75, this condo offers easy, low-maintenance Florida living in a central coastal location in a very nice community.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Grace Bonaccorso (941-580-1362)
244 WOODLAND DR #244, OSPREY, FL 34229
$200,000182 Days on yellowkey MLS ID: A4667419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1980 Tax: $2,685 (2025)Community: Pine Run IiiCondo
Taxes:$2,685
Remarks: Turnkey-Furnished & Best Value in Pine Run Now Offered at $200,000 (Recently Reduced $25,000). Move right in and start enjoying the Florida lifestyle with this beautifully updated 2-bedroom, 2-bath condo offering 1,325 square feet of bright, open living. Featuring vaulted ceilings and an airy layout, this residence feels spacious and inviting from the moment you walk in. The kitchen showcases stainless steel appliances, a sleek glass backsplash, and a sunlit breakfast nook perfect for everyday living or entertaining. The primary suite offers direct access to the screened lanai, creating a seamless indoor-outdoor flow with peaceful views of lush, private greenery. Being sold turnkey-furnished, this is a true move-in-ready opportunity just bring your suitcase. Located in the highly sought-after Pine Run community, residents enjoy resort-style amenities including two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and over 20 acres of scenic walking trails. All just minutes from Nokomis Beach, Casey Key, dining, and shopping. Low-maintenance, turnkey living at an unbeatable price, ideal for full-time, seasonal, or investment use.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
250 HIDDEN BAY DR #301, OSPREY, FL 34229
$725,00084 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)
759 FORDINGBRIDGE WAY, OSPREY, FL 34229
$727,000Listed 04/16/2026 12:39PM MLS ID: O6399774
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
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)
447 N SHORE DR, OSPREY, FL 34229
$515,35042 Days on yellowkey MLS ID: A4684009
REDUCED by $19,550 (3.7%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1874 Built: 1964 Tax: $4,243 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,243
Remarks: Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!
Listing Agent: Lauren Sisco (904-652-9387)
61 BAYHEAD LN, OSPREY, FL 34229
$1,185,0001 Day on yellowkey MLS ID: A4685559
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3180 Built: 1993Monthly Fee: $458 Tax: $4,573 (2025)Community: OaksSpa: YesSingle Family
Taxes:$4,573
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New Carpeting plus a 5-Piece Master Bath w/Soaking Tub; Formal Living and Dining Room are Open w/Tall Ceilings, Slider to Pool plus a Den/Library Room off the Living Room and Solid Wood Plank Flooring throughout; Open Kitchen w/Granite Counters and Breakfast Room w/Slider to Pool joined by a Family Room w/Fire Place and Solid Wood Plank Flooring; Pool Bath w/French Door, Main Floor Laundry Room w/Sink, Fabulous Upstairs Suite perfect for Guests or Extended Family w/Bonus Room, 2 Guest Bed Rooms w/Jack and Jill Bath; Extensive Crown Molding, Plantation Shutters thoughout, (2026) New Interior Paint, Central Vac, Large Side Load 2 Car Garage w/Storage, Newly Resurfaced Pool and Spa in the Screened-in Court Yard Entertaining Area, Court Yard Entry Gate, (2025) Brand New Designer Flat Tile Roof, (2026) Painted Pool Deck, (2026) Brand New Paver Driveway. WITH A FEW SIMPLE TOUCHES YOU CAN MAKE THIS HOME ABSOLUTELY FABULOUS! Have VISITORS Coming? NO PROBLEM. THIS HOME MAKES THE PERFECT ENTERTAINING OR SEASONAL FLOOR PLAN OFFERING A PRIVATE UPSTAIRS GUEST SUITE! Neighborhood Community Features: Local Community Pool, 24-Hour Secured Guard Gate, Lush Florida Landscaping and Irrigation are all included in the Maintenance Free Living. The OAKS GOLF & COUNTRY CLUB IS ONE OF SARASOTA'S PREMIER EQUITY "Creme de la Creme" GOLF COMMUNITIES! This amazing COUNTRY CLUB Features: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World Golfing (One of America’s Healthiest Clubs), Three Restaurants, Ballroom, Two 18-Hole Championship GOLF Courses, Award-Winning RACQUET Program w/12 HAR-TRU Hydro-Grid TENNIS COURTS, 4 PICKLE-BALL Courts, CROQUET, State of the Art FITNESS Center, Junior Olympic Heated Pool, Bocce Ball and Basketball Court, Playground Area plus so much more! Located just Minutes to the Top Rated Pine View School, Legacy Bike Trail, Florida's Best Coastal Beaches, Restaurants, Shopping and Costco. THE OAKS CLUB EQUITY MEMBERSHIP IS REQUIRED w/NO WAIT-LIST for SOCIAL or GOLF Memberships. Buyer Bonus: Seller is offering $40,000 towards Buyer's Equity Club Membership!!! ***Most Furnishings are Available Under a Separate Contract.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Anne Thomas, Pa (941-993-7700)
166 EDGEWOOD DR, OSPREY, FL 34229
$167,00015 Days on yellowkey MLS ID: A4687852
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 959 Built: 1977Monthly Fee: $215 Tax: $919 (2025)Community: ArborsManufactured Home
Taxes:$919
Remarks: Welcome to easy Florida living in The Arbors of Osprey! This charming 2-bedroom, 2-bath manufactured home offers comfort, updates, and plenty of space to relax and entertain. Step inside to a spacious living room filled with natural light, perfect for gathering with family and friends. The updated kitchen features warm wood cabinetry and a brand-new refrigerator (2025), making meal prep both stylish and functional. A separate dining area with a built-in buffet adds character and convenient storage. The primary suite provides a peaceful retreat with an ensuite bath, while the guest bedroom includes a desirable walk-in closet for added storage. Enjoy year-round sunshine in the light and bright Florida room, or unwind on the large screened lanai—ideal for enjoying Florida’s beautiful weather. Additional highlights include a storage shed with laundry, plywood underlayment replaced in 2014, and durable luxury vinyl flooring throughout. Major updates offer peace of mind with a new roof (2025), AC system (2023) and carport (2025). Located in the pet section of the community, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, and a full calendar of social activities. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. Come see why so many love calling The Arbors home!
665 CRANE PRAIRIE WAY, OSPREY, FL 34229
$719,000198 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.
664 CRANE PRAIRIE WAY, OSPREY, FL 34229
$887,00055 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.
479 SOUTH CREEK DR, OSPREY, FL 34229
$2,495,000136 Days on yellowkey MLS ID: N6141722
0 Days Off yellowkey (back on 4/15/2026)
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4261 Built: 1995Monthly Fee: $150 Tax: $11,095 (2024)Community: South CreekSpa: YesSingle Family
Taxes:$11,095
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant travertine pavers, with a covered dining area providing a perfect setting for shaded entertaining. An expansive waterfront deck extends beyond the screened lanai for lounging and alfresco dinners overlooking the water. Steps lead to a private dock with a 7,000-pound boat lift and a DEDICATED KAYAK LAUNCH, creating seamless access to the Intracoastal lifestyle. Inside, five generously sized bedrooms each feature ensuite baths and large walk-in closets, with two bedrooms conveniently located on the first floor along with a dedicated office, den, or bonus room. The renovated kitchen is designed for both beauty and function with a Thermador cooktop, Jenn- Airconvection and built-in ovens, a large island, and a passthrough window for effortless outdoor entertaining. The dining area overlooks the pool and includes hurricane-impact sliding doors, a coffee or dry bar with mini-fridge, and additional custom cabinetry for storage. The living room is highlighted by soaring ceilings, transom windows, additional hurricane impact sliding glass doors, and charming shiplap ceiling details, creating a light-filled coastal ambiance. Upstairs, three additional bedrooms and a loft gathering area overlook the living space below, with the true primary suite on the second level along with two waterfront-view bedrooms, all featuring ensuite baths and generous closets, plus a second-floor laundry hookup for added convenience. A spacious three-car garage and elegant U-shaped driveway complete the home. This home has been replumbed and features new lift motors (2025). Located within a gated community offering a basketball court, day dock, playground, and low HOA fees, this property is just 5 miles to Nokomis Beach on Casey Key, 15 miles to downtown Sarasota, 6 miles to the Island of Venice, and 6 miles to Sarasota Memorial Hospital, with Oscar Scherer State Park right nearby for nature lovers and outdoor enthusiasts.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
4173 FRONTIER LN #4173, OSPREY, FL 34229
$289,0006 Days on yellowkey MLS ID: A4689582
2 Days Off yellowkey (back on 4/15/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2019 Tax: $2,478 (2025)Community: Bay Street VillageCondo
Taxes:$2,478
Remarks: Under contract-accepting backup offers. INCREDIBLE CHARM!....INCREDIBLE LOCATION!.....You will be ENAMORED by this Highly Sought After (2) Bedroom (2) Bath Heron Floor Plan with PRIVATE GARAGE in the PET FRIENDLY Gated Community, Bay Street Village. This Meticulously Maintained One Owner corner unit residence features BRIGHT SPACIOUS INTERIORS; Hurricane Impact Windows and a Generous Screened Lanai---perfect for enjoying Morning Coffee while listening to your Favorite Podcast or just relaxing with Evening Cocktails.....Meal Prep is Easy with OVER-SIZED KITCHEN ISLAND; Stainless Steel Appliances and Pantry for Extra Storage....Bay Street is Conveniently Located to EVERYTHING: Shopping; Dining; Recreation; the New Sarasota Memorial Hospital; Legacy Bike Trail and just minutes to MULTIPLE BEACHES, including TOP RATED SIESTA KEY!.....Ideal as Year-Round, Vacation or Investment Property.
Listing Agent: Mike Martino (773-619-8593)
1801 HIGHLAND RD, OSPREY, FL 34229
$299,900212 Days on yellowkey MLS ID: N6140508
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1165 Built: 1999Monthly Fee: $150 Tax: $2,578 (2025)Community: Towns-End ShoresSpa: NoTownhouse
Taxes:$2,578
Remarks: One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and entertaining. Elegant tray ceilings, crown molding, and 9-foot ceilings enhance the first floor living space. The flooring is a beautiful wood look tile and LVP throughout the home. Upstairs, you’ll find both bedrooms, including the primary suite with a walk-in closet. As an extra bonus, there is a two-car garage. There is a community pool where you can enjoy a refreshing swim or relax poolside. Venture out to nearby Gulf beaches, shopping, dining, Oscar Sherer State Park and the Legacy Trail. Whether you’re looking for a year-round residence or a seasonal retreat, this home is the perfect fit. Don’t miss this opportunity—schedule your showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-486-8686)
Listing Agent: Kimberly Werla, Pa (941-979-2757)
14041 BELLAGIO WAY #218, OSPREY, FL 34229
$999,000147 Days on yellowkey MLS ID: A4672639
REDUCED by $100,000 (9.1%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2374 Built: 2006Monthly Fee: $1,649 Tax: $6,459 (2024)Community: Villas At Bellagio Harbor VillageCondo
Taxes:$6,459
Remarks: MOTIVATED SELLER. Bring an offer! Elevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY FURNISHED home offers 2,374 sq ft of well-appointed living space, and water views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo includes a DEEDED 40' wet slip—($125,000 value) providing immediate access to boating, fishing, and the Intracoastal Waterway. This home features high ceilings, brand new flooring throughout, an open layout, and a spacious kitchen with premium cabinetry and high-end appliances. The large living and dining areas flow seamlessly onto a covered balcony that overlooks the marina and bay—perfect for sunset views and outdoor dining. The primary suite is a true retreat with water views, balcony access, and a brand-new designer bathroom with a spa soaking tub, rain shower with bench seating, under-floor lighting, and modern double vanities. Residents enjoy a private, resort-style atmosphere with a heated bayside pool and spa, clubhouse, fitness center, sauna, billiards, BBQ grills, and a full-service marina. Ideally situated between Sarasota and Venice and minutes to Midnight Pass beach, this location offers easy access to waterfront dining at Casey Key Fish House and Deep Lagoon, nearby parks, and all the coastal conveniences of Osprey. This is a rare opportunity to own a spacious waterfront condo with refined interiors, exceptional views, two assigned parking spot, and a dedicated 40’ slip—all within a beautifully maintained, luxury marina community. New Metal Roof on all buildings Oct 2025, AC replaced in 2020, new kitchen and bathrooms in 2024, brand new luxury vinyl flooring replaced January 2026.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kelli Eggen (941-376-9844)
1348 THORNAPPLE DR, OSPREY, FL 34229
$535,0007 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, irrigation and internet 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 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)
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