Location: Osprey, 34229
Do Not Show Listings
204 WINDWARD DR, OSPREY, FL 34229
$1,050,00019 Days on yellowkey MLS ID: A4693139
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2486 Built: 1986Monthly Fee: $86 Tax: $4,761 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,761
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Spacious 3-bedroom, 3-bath home featuring high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. This home combines comfort and style with light-filled living spaces. Enjoy Florida living at its best with a private pool and amazing lanai area with plenty of covered patio. The oversized two car garage provides plenty of space for a golf cart. Located in a highly sought-after Marina community offering a clubhouse and resort-style amenities. There are recreational activities for all ages, tennis, pickleball, bocce ball, playground, kayak launch and storage, jet ski pads, fishing & boating. Southbay Yacht & Racquet Club is a community like no other in that it has a private 172 boat slip Marina with deep water able to accommodate boats up to 58 feet. Walk, bike or take your golf cart to beaches, shopping, restaurants & tiki bars.
Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)
Listing Agent: Sharon Lewis (941-966-5400)
4284 EXPEDITION WAY #NA, OSPREY, FL 34229
$325,000106 Days on yellowkey MLS ID: A4681835
REDUCED by $14,900 (4.4%) on 05/12/2026
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
Elementary School: None
High School: None
Middle School: None
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)
730 SARABAY RD, OSPREY, FL 34229
$4,995,000192 Days on yellowkey MLS ID: A4672618
1 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 5.5 Gar: 7 Liv Area Sq Ft: 6308 Built: 2011 Tax: $47,200 (2024)Community: Sarabay AcresSpa: YesSingle Family
Taxes:$47,200
Tax Year: 2024
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf through nearby Midnight Pass. Positioned along 100 feet of Little Sarasota Bay frontage, it includes a private dock and 15,000-lb boat lift. Inside, the residence provides over 6,300 square feet of living space, soaring ceilings, walls of windows, and sweeping bay views. Wide-plank oak and floor-to-ceiling hurricane-impact windows frame generous living spaces designed for entertaining and an open-plan gourmet kitchen. The primary suite includes a spa-inspired bath and spacious walk-in closets. Upstairs, three en suite bedrooms feature views over the bay; an additional room offers flexibility as a sitting room or fifth bedroom. Outside, a large travertine terrace, resort-style pool and hot tub, propane fire pit, and broad bayside lawn showcase Sarasota’s brilliant sunsets. A four-car attached garage and air-conditioned, detached three-car garage offer space for car collectors, or for an artist’s studio or home gym. Ideally located between Sarasota and Venice, the home has easy access to Siesta Key and Nokomis beaches as well as to the many cultural attractions of Sarasota’s downtown. Additionally, the home has a documented history of no flooding, water intrusion, or hurricane damage, providing significant peace of mind. This bayfront estate is a unique combination of lush acreage, secure elevation, boating access, and luxury coastal living—a complete waterfront lifestyle.
Listing is courtesy of: ROBERT SLACK LLC (352-229-1187)
Listing Agent: Debbie Baraona (941-350-8723)
186 WINDWARD DR, OSPREY, FL 34229
$599,900142 Days on yellowkey MLS ID: N6142087
0 Days Off yellowkey (back on 5/13/2026)
REDUCED by $49,600 (7.6%) on 05/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2505 Built: 1983Monthly Fee: $204 Tax: $7,566 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$7,566
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. Price was dropped $50,000 on 5/7! Survey and pool quote are available! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**As of Jan 2026, there is marina space available immediately (no wait list) and fees range between $169-$705 per quarter depending on what size you require.This is subject to change.**This listing went pending in March. When the buyers couldn't secure their financing, it went back on market. No inspections have been done.**
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Brittany Coleman, Pllc (941-539-5023)
227 SAINT JAMES PARK, OSPREY, FL 34229
$885,000122 Days on yellowkey MLS ID: A4679867
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2071 Built: 1986Monthly Fee: $142 Tax: $4,611 (2025)Community: Oaks 2 Ph 1Single Family
Taxes:$4,611
Remarks: Experience the charm and wonderful location of this golf course home on Saint James Park, the leafy and quiet cul-de-sac where you can walk to tennis, golf, pickleball, croquet, heated pool and state of the art fitness center all within The Oaks Country Club, where the luxury lifestyle awaits! This 2 bedroom, 2 bath traditional home overlooks the first hole of the Eagle Golf course, and is being offered completely furnished, easy to maintain, and is move in ready. The roof is new in 2024, and all windows and sliding doors are newer and hurricane impact. Custom designed by Bo MacEwen, the architect who designed the clubhouse, features include crown molding, wainscoting, built-ins throughout, a wood burning fireplace, split bedrooms, both ensuite with wood floors, and open views from most rooms. The kitchen has a light and bright breakfast area. The expansive screened lanai is 20 feet by 48 feet, and the oversized two car garage has a charging station for your electric car. Saint James Park is the residential area closest to the athletic facilities so residents can easily walk or bike to all facets of the club, including dining as well as a social atmosphere that encourages all to stay engaged in all The Oaks Club has to offer. For those electing golf, the ability to play the two courses is immediate, no waiting period. Also, The Oaks has been designated a Platinum Club of America, and an Emerald Club, signifying it’s standing among the finest in Florida, not to mention 20 minutes to the best beaches in Sarasota County! Membership is required, either Social or Golf. Be sure to see this special home and begin enjoying a well rounded lifestyle!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Rosalie Phillips (941-544-4430)
320 TROPIC DR, OSPREY, FL 34229
$195,00019 Days on yellowkey MLS ID: A4692490
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1199 Built: 1980Monthly Fee: $430 Tax: $1,438 (2024)Community: ArborsManufactured Home
Taxes:$1,438
Remarks: One or more photo(s) has been virtually staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and lighting. The possibilities are endless as this space can be kept for leisure or used to build an additional home. The seller invested $28,000 in fundamental upgrades, includin g: New subflooring and moisture barrier, Laminate flooring throughout main living areas and bathrooms, and Fresh carpeting in bedrooms and the Florida Room. The interior features an open floor plan with two bedrooms. The primary suite includes dual walk-in closets and a ensuite bath. This home is light and bright with a comfortable Florida Room—perfect for morning coffee or evening relaxation. A large outdoor shed offers abundant storage and includes a washer and dryer. This desirable lot is located in the pet-friendly section of the park. Monthly dues include an impressive list of amenities: access to the clubhouse, heated community pool, lawn service, water, garbage pickup, sewer, cable TV, and internet. The Seller recently spent $28,000 on a new sub floor, new moisture barrier, New laminate flooring in kitchen, dining, great room, bathrooms, and hallway. New carpet in both bedrooms and Florida room. There’s even an on-site storage area for your boats, RVs, or kayaks for a small fee! The location is unbeatable—close to Casey Key, the Legacy Trail, Walmart, shopping, restaurants and the Nokomis and Siesta Key Beaches. You’re also just a short drive from historic downtown Venice and the lively attractions of downtown Sarasota. The community also offers an active clubhouse, heated pool, dog run, shuffleboard, exercise area, and regular social events.
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Susan Retzke (941-544-5558)
447 N SHORE DR, OSPREY, FL 34229
$499,00086 Days on yellowkey MLS ID: A4684009
REDUCED by $16,350 (3.2%) on 05/12/2026
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 is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Lauren Sisco (904-652-9387)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$280,00050 Days on yellowkey MLS ID: A4689541
REDUCED by $10,000 (3.4%) on 05/12/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2017 Tax: $3,507 (2025)Community: Bay Street VillageCondo
Taxes:$3,507
Remarks: 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. **SELLER FINANCING AVAILABLE** **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
1811 HIGHLAND RD, OSPREY, FL 34229
$417,000211 Days on yellowkey MLS ID: TB8443161
REDUCED by $5,000 (1.2%) on 05/12/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 1997Monthly Fee: $150 Tax: $4,299 (2024)Community: Towns-End ShoresSpa: NoTownhouse
Taxes:$4,299
Remarks: PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches. Walking distance to Casey Key Mainland (Chef Rolfs), private community Shoreland Park & Oscar Scherer State Park. Minutes away from COSTCO, Publix, Target, Richard's, YMCA Potter Park, waterfront dining (Casey Key Fish House & Tiki bar - waterfront , Spanish Point restaurant & Tiki Bar. The townhouse is close to Laurel Rd and Sarasota Memorial Hospital. Property is managed by owner. Timely response to accommodate your needs. Summary of amenities: PARKING: 2-CAR TANDEM GARAGE HOA PRIVATE COMMUNITY 1 BLOCK FROM INTERCOASTAL SCREENED BALCONY CEILING FANS VAULTED CEILING CENTRAL AIR UPGRADED TALL CABINETS GRANITE COUNTERTOP STAINLESS STEEL APPLIANCES CONVECTION RANGE/OVEN/AIRFRYER MICROWAVE DISHWASHER IN-SINK DISPOSAL SMART REFRIGERATOR DINING ROOM & FAMILY ROOM MASTER BEDROOM WITH WALK-IN CLOSET MASTER BATH GUEST BEDROOM ADDITIONAL STORAGE IN LOWER FLOOR OR GARAGE AIR CONDITIONING WASHER/DRYER SPRINKLER SYSTEM COMMUNITY SWIMMING POOL WITH LOUNGE CHAIRS + USE OF CASEY KEY MAINLAND POOL WALK/BIKE TO TOP RATED PINEVIEW SCHOOL, WALLMART, POST OFFICE, LEGACY BIKE TRAIL CLOSE TO SIESTA KEY, NOKOMIS BEACH, VENICE BEACH, OSCAR SCHERER STATE PARK HUGE FURNISHED BONUS ROOM ON FIRST FLOOR OUTDOOR GRILL Turn-key ready!
Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)
Listing Agent: Stephen Hachey (813-863-3948)
393 N POINT RD #604, OSPREY, FL 34229
$795,000482 Days on yellowkey MLS ID: A4638035
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2778 Built: 2001Monthly Fee: $367 Tax: $9,625 (2024)Community: Meridian At The Oaks PreserveSpa: YesCondo
Taxes:$9,625
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room. Experience the epitome of seamless indoor-outdoor living in this expansive condo that spans nearly 2,800 square feet. Designed to emulate the ambiance of a single-family home, the open floor plan features a great room, a separate dining area, and a versatile den. The great room impresses with soaring 10-foot ceilings, floor-to-ceiling windows, and sliding doors that effortlessly blend the indoors with the outdoors, leading to a large, screened balcony with breathtaking water views. This harmonious flow floods the living space with natural light and offers a tranquil backdrop of sparkling vistas. The spacious kitchen is a culinary delight, boasting an eat-in area and granite high bar countertops, perfect for casual meals and entertaining guests. The popular split floor plan provides privacy and convenience, featuring 3 bedrooms and 3 baths. The den adds a layer of versatility to the home. The large kitchen includes an eat-in space and granite high bar countertops. The luxurious primary suite is separate from the guest rooms for privacy and includes stunning water views, large walk-in closets, and a luxurious bathroom. Additional features include an elegant entry, and an exclusive private foyer and elevator. The lanai is equipped with electric hurricane shutters ensuring safety and peace of mind. This secure building offers a wonderful lifestyle with private entry and elevator access. This unit is available for purchase fully furnished and is well-maintained. The Oaks community offers a distinguished, 24-hour guarded country club experience with numerous accolades, including Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World. Amenities include three restaurants, a ballroom, two 18-hole championship golf courses, an award-winning racquets program with 12 Har-Tru Hydro-Grid tennis courts, 4 pickleball courts, a wonderful croquet facility, a state-of-the-art fitness center, a junior Olympic heated community swimming pool, bocce, a basketball court, a playground, a 7000 square foot fitness center, a brand new $9,000,000 dining room and bar with outdoor dining overlooking the golf course. Residents of the Meridian enjoy private amenities, including a heated pool and spa, a fitness center, and an outdoor grill. The Oaks provides well-lit sidewalks, ideal for strolls around the 100-acre preserve. It also boasts scenic trails, perfect for biking and walking while taking in the views of nature. The Oaks is just minutes from the nationally ranked Pine View School the Legacy Bike Trail, shopping, and area beaches. It is conveniently situated near both Venice and Sarasota, offering easy access to the amenities and attractions of both cities, while providing a beautiful, luxurious, and well-rounded country club lifestyle. Membership is required, and there is no waitlist for golf or social membership. Be sure to make an appointment to see this stunning condominium **ENJOY THE 3D VIRTUAL TOUR**
14021 BELLAGIO WAY #309, OSPREY, FL 34229
$899,995113 Days on yellowkey MLS ID: A4681589
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2199 Built: 2006Monthly Fee: $1,585 Tax: $9,062 (2024)Community: Villas/Harbor VillageSpa: YesCondo
Taxes:$9,062
Remarks: Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy access to pristine beaches, fine dining, and boutique shopping. Walkable to local restaurants and boat docks, the community is both conveniently located and peacefully serene. Offering 2,199 square feet of thoughtfully designed living space, this residence has been enhanced for comfort and style. Updates include new lighting throughout, featuring four coastal ceiling fans and elegant Caprice chandeliers. The spacious primary suite and two additional bedrooms feature new cordless blinds and window treatments, creating private and tranquil retreats. Bathrooms have been refreshed with new toilets, fresh paint, and an updated vanity in the powder room. The well-appointed kitchen showcases shaker-style cabinetry and enjoys stunning Intracoastal and sunset views. Step onto the private lanai and enjoy seamless indoor-outdoor living with direct access to the pool area. Newly installed retractable screens provide shade and privacy when desired while preserving expansive water views. Outdoor enthusiasts will appreciate the on-site kayak storage and launch area, perfect for exploring the surrounding waterways. Located in southwest Osprey, this exceptional residence offers both a beautiful home and a vibrant waterfront community. Residents enjoy access to a resort-style pool, hot tub, sauna, and open-concept gathering spaces—creating a lifestyle where every day feels like a vacation.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Tristin Hopler (941-735-3520)
51 MACEWEN DR #5, OSPREY, FL 34229
$235,00040 Days on yellowkey MLS ID: A4689838
REDUCED by $65,000 (21.7%) on 05/11/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 595 Built: 1990Monthly Fee: $142 Tax: $3,079 (2025)Community: Windsor Lodge At The OaksCondo
Taxes:$3,079
High School: Pine View School
Remarks: Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.
Listing is courtesy of: 342 REAL ESTATE (941-685-0509)
Listing Agent: Sabine Spycher (941-685-0509)
222 GLENWOOD AVE, OSPREY, FL 34229
$275,00024 Days on yellowkey MLS ID: TB8504427
0 Days Off yellowkey (back on 5/9/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 952 Built: 1990 Tax: $3,409 (2025)Community: Tb Ogburns AddSingle Family
Taxes:$3,409
Remarks: Take advantage of a RARE OPPORTUNITY in real estate with the current owners ASSUMABLE MORTGAGE at 2.75%! Step out your french doors and wake up to the songs of birds, as you sip coffee in your lanai. The day ahead is whatever you want! What"s your pleasure? Beach? Siesta Key (#1 in US multiple times) is minutes away. Nature Hiking? Oscar Scherer State Park is even closer to your front door. The same goes for Restaurants, Shopping, Golfing and even Tiki Bars. Or maybe a day in Sarasota, at the Ringling Museum, Mote Marine Laboratory, or Jungle Gardens. And that night you can catch a show at the Van Wezel, Asolo Reperatory, or Florida Studio Theater. Afterwards return home to the charm of your bungalow in the sun. Beautiful rosewood floors sparkle to welcome you as you head to a stainless steel decked kitchen for a snack to bring into the open living/dining room and once again visit the french doors. NEWER A/C 2018. NEW LONG LASTING METAL ROOF AND NEW BEAUTIFUL GARAGE DOOR (2025). This home is surrounded by everything you could ever want at an AMAZING Price!
Listing is courtesy of: JAY ALAN REAL ESTATE (855-529-2526)
Listing Agent: Zalysia Kaczmarczyk (813-853-3536)
1361 NEW FOREST LN, OSPREY, FL 34229
$550,00036 Days on yellowkey MLS ID: A4691036
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: 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)
18 N CASEY KEY RD, OSPREY, FL 34229
$1,750,000222 Days on yellowkey MLS ID: A4669083
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
Remarks: 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)
1116 BEACHCOMBER CT #3, OSPREY, FL 34229
$545,00057 Days on yellowkey MLS ID: A4688310
1 Days Off yellowkey (back on 5/5/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 2005Monthly Fee: $1,133 Tax: $5,376 (2025)Community: Blackburn Point Marina VillageCondo
Taxes:$5,376
Remarks: Under contract-accepting backup offers. LOCATION, LOCATION, LOCATION! Nestled within the highly desirable gated enclave of Blackburn Point Marina Village, this beautifully maintained 3-bed, 2.5 bath residence is ready to welcome its new owners. This bright and airy two-story unit features soaring ceilings and a spacious open floor plan, creating an inviting and comfortable living environment. The main living areas are enhanced with tile flooring and flow seamlessly into a well-appointed kitchen, complete with Corian countertops, a breakfast bar, center island, closet pantry, and stainless-steel appliances, perfect for both everyday living and entertaining. The dining area features pocketing sliders that extend the living space to the enclosed lanai, already plumbed for a full outdoor kitchen, offering the ideal indoor-outdoor Florida lifestyle. The primary suite is conveniently located on the ground floor and offers a private retreat with an ensuite bathroom featuring dual vanities, a garden tub, and a walk-in shower. Upstairs, two additional bedrooms and a full bath provide privacy and comfort for guests or family. Step outside to the patio, an ideal setting to relax and enjoy a quiet afternoon or evening cocktail in the Florida sunshine. Additional features include an oversized one-car garage with under-stair storage, a new A/C system (2025), and a new roof (2025), providing peace of mind for years to come. Residents of Blackburn Marina Village enjoy access to a heated community pool, a fully equipped outdoor kitchen, and a vibrant social calendar for those who wish to participate. Ideally located with easy access to Gulf beaches, Blackburn Point Marina, dining, and shopping, this exceptional property truly offers the best of Florida living!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christine Green (941-914-2463)
678 FAITH AVE, OSPREY, FL 34229
$749,000170 Days on yellowkey MLS ID: A4674865
REDUCED by $26,000 (3.4%) on 05/08/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 2583 Built: 1995 Tax: $5,871 (2025)Community: Trinity AcresSingle Family
Taxes:$5,871
Elementary School: Pine View School
Middle School: Pine View School
Remarks: Private Key West–style retreat on 2.53 wooded acres in Osprey. Rarely does a property of this size become available in such a convenient location—just minutes from Pine View School, shopping, restaurants, and the Intracoastal Waterway—yet offering the privacy and space of a true country setting. This combination of acreage and accessibility makes the home exceptionally unique for the area. A generous 37x60 paver-brick patio surrounds the screened lap-style pool, now protected by a freshly updated pool cage. Multiple French doors open to wide second-floor decks overlooking the peaceful wooded backdrop. A recently added metal roof enhances durability, longevity, and value. Inside, the home features oak hardwood floors, vaulted tongue-and-groove cypress ceilings, and a striking wood-burning fireplace that add warmth and character throughout. The kitchen and baths retain their classic charm and present an excellent opportunity for updating to suit modern preferences. The flexible layout includes two potential primary suites and a first-floor bonus room with full bath that works well for guests or creative uses. The lower level remains plumbed for a second kitchen and laundry, offering an easy path for future installation or multigenerational living. With no deed restrictions and an expansive amount of usable land, this country estate in town offers endless potential—whether for hobbies, animals, enhancements, or simply enjoying the quiet beauty of its natural surroundings.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Troy Sacco (941-445-3939)
21 BAYHEAD LN, OSPREY, FL 34229
$850,000257 Days on yellowkey MLS ID: A4664085
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2246 Built: 2002Monthly Fee: $458 Tax: $4,221 (2024)Community: Bishopscourt At The Oaks PreserveSpa: YesSingle Family
Taxes:$4,221
Remarks: Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preserve offers the perfect blend of comfort, style, and privacy. And you can BUY WITH CONFIDENCE — THE PROACTIVE SELLERS HAVE COMPLETED INSPECTIONS IN ADVANCE TO SHARE WITH BUYERS, GIVING YOU CLARITY FROM THE START. No guessing…what you see, and what you don’t see, is what you get! From the moment you arrive at the pavered driveway, the pride of ownership is unmistakable. Double leaded-glass front doors open to a light-filled interior designed for effortless Florida living. Just off the entry, a dedicated home office features plantation shutters and a ceiling fan. The formal dining room showcases a decorative ceiling and a beautiful built-in buffet with glass-front cabinetry. The open kitchen features new granite countertops, stainless appliances, a breakfast bar, chef’s desk, and built-in wine and beverage cooler. The adjoining breakfast nook with an aquarium window, overlooks the sparkling pool and spa. The master suite is exceptionally spacious, offering a sitting area with built-in window seat and large walk-in closets with glass-front storage. The updated en suite bathroom has granite countertops, dual sinks, a soaking tub, separate shower, and marble accents. Two well-sized guest bedrooms provide generous closet space, and the updated guest bath includes granite and marble finishes. The air conditioned 2-car garage with epoxy flooring offers abundant storage. This home backs to a lush, tropical preserve, ensuring privacy for the pool and spa. The lanai features two distinct areas: a large, covered space with outdoor kitchen and ceiling fan for shaded dining, and a sun-splashed pool and spa area under a screened enclosure. You can also enjoy the nearby Bishopscourt community pool. With mandatory membership, this home offers access to all of
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
570 BLACKBURN POINT RD #LNG42, OSPREY, FL 34229
$35,900142 Days on yellowkey MLS ID: A4677438
REDUCED by $3,100 (7.9%) on 05/06/2026
Bed: Bath: 0.0 Tax: $278 (2025)Community: Dry Slips At Bellagio VillageDock-Rackominium
Taxes:$278
Remarks: Welcome to OSPREY HARBOR VILLAGE. This boat rackominium was built as a category 3 hurricane-rated building. Store your boat out of the sun and protected from the harsh Florida weather. This 3rd-level rack measures 28'L x 12'W x 8.5'H and can accommodate a boat with dimensions of 28'L x 11'W x ~6.5'H (measure height from the keel to the highest fixed point on the boat). This rackominium features concierge service with onsite fuel, work racks, wash down service, engine flushing, bait shop (deli, drinks, fishing tackle, bait, store, etc.) There is also a pump-out station, fish cleaning tables, restrooms, and professional full-time and friendly staff! Here's how it works...Call ahead and have your boat "splashed" and fueled, arrive and enjoy your day on the water, return to the dock and the staff pulls your boat, flushes the engine(s), washes the outside, and places it back in your OWN rack for next time! Osprey Harbor Village is very close to Midnight Pass, the Venice Inlet out to the gulf, and near to many boatable restaurants and picnic islands! Take the stress out of boating. Stop trailering your boat to the ramp, and buy a boat rack out of the elements with always the prospects of future appreciation on your investment! Buy today.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joe Cleary (941-650-8485)
764 SARABAY RD #8, OSPREY, FL 34229
$450,00093 Days on yellowkey MLS ID: A4683747
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981Monthly Fee: $1,650 Tax: $2,936 (2025)Community: Heron Bay Club Sec IVilla
Taxes:$2,936
Remarks: One or more photo(s) has been 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 is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)
Listing Agent: Michael Christo (508-735-6797)
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