Location: Osprey , 34229
Do Not Show Listings
61 BAYHEAD LN, OSPREY, FL 34229
$1,185,000Listed 04/15/2026 5:23PM 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,573
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
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
Elementary School: None
High School: None
Middle School: None
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!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Karen Geiger (941-928-8889)
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
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
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.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
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 is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
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
Middle School: Sarasota Middle
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)
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)
402 MACEWEN DR, OSPREY, FL 34229
$1,750,0001 Day on yellowkey MLS ID: A4690018
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3565 Built: 1999Monthly Fee: $142 Tax: $13,800 (2025)Community: OaksSingle Family
Taxes:$13,800
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)
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)
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: Best value in Pine Run now priced at $200,000 after a $25,000 price improvement. This updated 2-bedroom, 2-bath condo offers 1,325 square feet of bright, open living with vaulted ceilings, a spacious layout, and a screened lanai overlooking lush, private greenery. The kitchen features stainless steel appliances, glass backsplash, and a functional breakfast nook with natural light. The primary suite includes direct lanai access, creating an ideal indoor-outdoor flow. Located in the highly desirable Pine Run community, residents enjoy resort-style amenities including two heated pools, tennis and pickleball courts, fitness center, clubhouse, and over 20 acres of scenic walking trails. Just minutes to Nokomis Beach, Casey Key, dining, and shopping. Low-maintenance living with exceptional value ideal for full-time, seasonal, or investment use.
Listing Agent: Derek Edwards (941-929-3183)
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)
14041 BELLAGIO WAY #214, OSPREY, FL 34229
$700,0002 Days on yellowkey MLS ID: A4689731
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1799 Built: 2006Monthly Fee: $1,248 Tax: $6,254 (2025)Community: Villas At Bellagio Harbor VillageSpa: NoCondo
Taxes:$6,254
Remarks: Waterfront Sanctuary/Boater's Paradise at the Osprey Harbor Village - 3 Bedrooms | 2 Bathrooms | Direct Intracoastal Frontage - Rare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and Intracoastal Waterway. The open concept design features 9’5” tray ceilings, impact windows and doors, and solid wood cabinetry, granite countertops, kitchen island, and kitchen island bar—ideal for entertaining, anchored by a neutral, airy palette with timeless finishes. The split bedroom layout provides privacy, with a spacious primary suite featuring a spa style bath, separate tub and shower, and direct access to an oversized 270 sq. ft. waterfront balcony from the bedroom. Each window is a curated lens, framing the hues of the Bay and the sculptural silhouettes of architectural lines of Mediterranean inspired Villas. Days here are defined by the rhythmic play of light reflecting across the water and the silent flight of ospreys, eagles, and pelicans—a true haven for the bird watcher seeking a quiet refuge. Whether you are hosting a sunset gathering on your private balcony or entertaining your guests at the community terrace, the club room or embarking on a day of boat excursion to the newly opened Midnight Pass, the lifestyle here is one of effortless coastal elegance. Community amenities include a deep water harbor marina with wet and dry slips, resort pool, clubhouse, fitness center, hot tubs, kayak storage, and launch. Centrally located between Sarasota and Venice, and minutes from Venice, Nokomis, Siesta Key, and Casey Key, Oscar Scherer State Park, Spanish Point, Legacy Trail, and cultural and retail amenities of Sarasota. This property stands as a resilient sanctuary of enduring value. For the resident who values privacy, prestige, and the restorative power of nature, this is the definitive Osprey address. Schedule your private tour today.
Listing Agent: Veronica Lee (609-651-0305)
238 PALM AIR DR, OSPREY, FL 34229
$179,9002 Days on yellowkey 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: 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 12'x15' that includes front-loading washer/dryer and a sink 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, dog park, 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)
172 SEA ANCHOR DR, OSPREY, FL 34229
$895,000155 Days on yellowkey MLS ID: A4671745
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2283 Built: 1977Monthly Fee: $204 Tax: $8,870 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$8,870
Remarks: Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring, saltwater pool and newer cage, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball, tennis, bocci ball, kayak storage, jet ski pads and boat slips. Spend evenings sitting by the community pool looking out over the marina watching amazing sunsets. Walk, bike our take a golf cart to nearby shopping, restaurants and tiki bars. A definite value in an amazing community!
Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)
Listing Agent: Sharon Lewis (941-966-5400)
32 SIESTA CIR W, OSPREY, FL 34229
$69,0001 Day on yellowkey MLS ID: A4690063
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 480 Built: 1968Monthly Fee: $215 Tax: $555 (2025)Community: ArborsMobile Home
Taxes:$555
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.
252 SUN AIR CIR, OSPREY, FL 34229
$215,00055 Days on yellowkey MLS ID: A4683143
REDUCED by $10,000 (4.4%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1979Monthly Fee: $215 Tax: $1,087 (2025)Community: ArborsManufactured Home
Taxes:$1,087
Remarks: Welcome to easy Florida living in The Arbors of Osprey! This beautifully updated 2-bedroom, 2-bath manufactured home offers modern finishes, thoughtful upgrades, and a spacious open layout designed for comfort and entertaining. Step inside to discover newer tile and laminate flooring flowing throughout the home. The remodeled kitchen is a true showstopper, featuring raised-panel cabinetry, quartz countertops, a striking stone backsplash, center island, pantry, and plenty of prep and storage space. The open floor plan seamlessly connects the kitchen to the dining area and spacious family room, perfect for gatherings or relaxed everyday living. The spacious primary suite offers a walk-in closet and an updated ensuite bath complete with dual sinks in a new vanity, newer lighting and mirror, and a walk-in shower. The guest bedroom is versatile and inviting with a convenient Murphy bed, while the second bath has been tastefully updated with a tub/shower combination, new vanity lighting, and mirror. Enjoy Florida’s sunshine year-round in the bright Florida room filled with loads of windows, or unwind on the screened, enclosed lanai. Plantation shutters throughout the home. Additional highlights include a utility shed with washer and dryer, non-skid surface in lanai and driveway. Major system updates for peace of mind include a 6-year-old roof with transferable warranty, newer A/C, tankless hot water heater, 98% plywood subflooring, and cement board subfloor in the kitchen and dining room. 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. This fully furnished, move-in ready home blends quality upgrades with relaxed Florida charm. Schedule your private showing today and start enjoying the lifestyle you deserve!
102 WINDWARD DR, OSPREY, FL 34229
$690,000148 Days on yellowkey MLS ID: A4671793
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2134 Built: 1986Monthly Fee: $219 Tax: $3,540 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$3,540
Remarks: NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space. A long driveway adds convenient additional parking. Southbay Yacht & Racquet Club is a golf-cart-friendly community featuring a recently remodeled 10,000 sq. ft. clubhouse with a fitness center, pool, and large patio. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. Additional amenities include pickleball and tennis courts, bocce, shuffleboard, walking and biking paths, and a playground. The community is ideally situated between Sarasota and Venice, close to dining, shopping, entertainment, beaches, the Legacy Trail, and Pine View School.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: David Cyr (941-400-4691)
260 HIDDEN BAY DR #304, OSPREY, FL 34229
$694,00058 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 VENICE DOWNTOWN (941-388-9800)
Listing Agent: Janice Martin (941-225-9843)
403 LONGBOW TRL, OSPREY, FL 34229
$1,095,000150 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
Taxes:$9,020
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)
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