Location: Osprey , 34229
Do Not Show Listings
448 E MACEWEN DR, OSPREY, FL 34229
$2,100,000126 Days on yellowkey MLS ID: A4687195
0 Days Off yellowkey (back on 7/11/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3768 Built: 1998Monthly Fee: $142 Tax: $9,639 (2025)Community: OaksSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,639
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. **IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid appliances. The expansive primary suite is a true retreat, complete with multiple walk-in closets, dual vanities, a soaking tub, and a custom-tiled shower. Enjoy Florida living at its finest on the screened lanai, featuring a heated pool and spa, travertine marble pool deck, and a large covered entertaining area—all overlooking tranquil golf course and garden views for ultimate privacy. Additional highlights include a 3-car garage and thoughtfully designed indoor-outdoor living spaces perfect for entertaining or relaxing. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
120 WOODLAND PL #120, OSPREY, FL 34229
$299,00021 Days on yellowkey MLS ID: D6148025
0 Days Off yellowkey (back on 7/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1979 Tax: $2,712 (2025)Community: Pine Run IiSpa: NoCondo
Taxes:$2,712
Remarks: Under contract-accepting backup offers. Over $80,000 in upgrades and designer renovations by renowned Murray Homes, a symbol of luxury in Sarasota. The team included an architect, designer, and contractors to transform this Pine Run end-unit, second-floor condo into a stunning modern coastal retreat. Featuring a completely reimagined light and bright open floor plan and custom kitchen with quartz countertops, custom cabinetry, floating shelves, designer tile backsplash, stainless appliances, and workstation sink, this move-in-ready home also offers luxury wide-plank flooring throughout, beautifully updated bathrooms, newer HVAC, fresh interior paint, contemporary lighting, new trim, doors, hardware, and window treatments, new ceiling fans, new stackable washer and dryer. Primary bedroom is ensuite with a walk-in closet and both bedrooms enjoy a private balcony. The spacious screened lanai is private and overlooks lush tropical landscaping, creating the perfect setting to relax and enjoy Florida living. There is an abundance of storage closets and attic space. Covered end-unit parking with storage and guest parking. Walk to shopping and waterfront bars and restaurants. Ideally located just minutes by bike to Nokomis Beach, Casey Key, Oscar Sherer State Park, and the Legacy Trail, Pine Run offers resort-style amenities including two pools, tennis and pickleball courts, kayak storage and launch, a clubhouse, and gym. Luxury, location, and lifestyle—all in one exceptional, and updated-to-like-new condo ready for you to call home.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Kim Kruysman (941-441-6628)
347 BAYSHORE DR, OSPREY, FL 34229
$699,00081 Days on yellowkey MLS ID: A4693374
REDUCED by $40,000 (5.4%) on 07/07/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2216 Built: 2013 Tax: $879 (2025)Community: Bay Acres - ResubSingle Family
Taxes:$879
Elementary School: None
High School: None
Middle School: None
Remarks: This custom built 2 Bedroom plus Den home is located in the Osprey subdivision Bay Acres, west of the trail, in an established neighborhood along Little Sarasota Bay between Sarasota and Venice. This location allows easy access to I-75, top rated schools to include the magnet school Pine View , and Nokomis and Siesta Key Beaches, and all amenities of both cities. This home includes over 4000 sq ft of total space that includes a 2 plus car garage with over 1400 Sq. Ft. of space- part of the garage having a large open area previously used as a hobby room that can be converted to an area to meet your needs-possible extra car storage, boat storage, jet ski storage. The interior of the home has many nice features including a very nice large kitchen , dining room with tray ceilings, floors are gorgeous-real hardwood and wide planked. This well-built home has impact windows, a metal roof, a large covered porch and fenced yard. This small waterfront community will allow you to keep your Boat/Trailer or RV on your property. Property is in Flood Zone X. The Community Park of Bay Acres also has some boat slips upon availability and Kayak storage and launch for a small fee. You can be out in Gulf waters through midnight pass in minutes. Around the corner is Blackburn Point Boat Ramp, and many waterfront restaurants. Looking for the perfect place to put down roots? Come see why this friendly neighborhood and home can make your dreams a reality. Easy to show
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Sharon Sprow (813-817-9931)
14041 BELLAGIO WAY #214, OSPREY, FL 34229
$700,000109 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. With new metal roof, exterior and interior paint completed in 2025, 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 is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Veronica Lee (609-651-0305)
599 PINE RANCH EAST RD, OSPREY, FL 34229
$825,000358 Days on yellowkey MLS ID: A4660895
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2188 Built: 1995Monthly Fee: $23 Tax: $3,484 (2024)Community: Bay Oaks EstatesSpa: NoSingle Family
Taxes:$3,484
Tax Year: 2024
Middle School: Laurel Nokomis Middle
Remarks: **EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers an expansive, private retreat complete with walk-in closets, dual vanities, Jacuzzi tub, custom-tiled shower, Italian smart toilet-bidet, etc. A complete List of Recent Upgrades is attached and available upon request and includes but is not limited to NEW Kitchen & Baths, Interior and Exterior Paint, whole home LED lighting and smart fans, built-in Sound System, Flooring (tile, luxury vinyl, carpet), Washer & Dryer, water filtration, exterior LED lighting, pavered driveway, Irrigation system, privacy fence, storage shed and So Much MORE! Relish in the utmost Florida lifestyle with a Saltwater Pool in a large, screened lanai with covered seating area while overlooking the serene and private landscape. Enjoy peace of mind with NEW HURRICANE IMPACT WINDOWS and DOORS, MASONRY Wall Construction, and a structure situated in Flood Zone “X”. LOW HOA. Ideally Located close to Area Beaches including #1-Rated SIESTA BEACH, the Popular LEGACY BIKE TRAIL, #1-Rated PINE VIEW SCHOOL, Shopping, Downtown Sarasota and Venice cultural venues, and all that Florida’s Gulf Coast Living has to offer. **PLEASE ENJOY VIEWING THE 3D VIRTUAL TOUR**
919 TRANQUILITY CIR, OSPREY, FL 34229
$774,90038 Days on yellowkey MLS ID: N6144801
0 Days Off yellowkey (back on 7/1/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2854 Built: 2001Monthly Fee: $158 Tax: $6,634 (2025)Community: North Creek EstatesSpa: NoSingle Family
Taxes:$6,634
Remarks: BEACH LOVERS & ADVENTUROUS NATURE LOVERS — YOUR FLORIDA DREAM HOME AWAITS! This STUNNING 4-BR/3.5 BATH POOL HOME offers an OPEN CONCEPT, SPLIT FLOOR PLAN designed for comfortable living and effortless entertaining. The luxurious Primary Suite is your private retreat, featuring Dual Walk-In Closets, 2 separate vanities, 2 private toilet closets, and a relaxing garden tub. The heart of the home is the OVERSIZED KITCHEN with a Breakfast Bar, Island, Under Cabinet Lighting, Dinette, Walk-In Pantry, SS Appliances, and a GAS STOVE—all overlooking the spacious Great Room. Enjoy additional living space with a Formal Dining Room AND Separate Living Room, both offering SGD that open to your Outdoor your Private Tropical Oasis with Pool Bath Access, complete with a resurfaced SALTWATER POOL, Expansive Paver Lanai, and plenty of room for Entertaining. Best of all, the backyard offers direct access to Little Sarasota Bay via North Creek, making it perfect for Kayaking, Paddle Boarding and Fishing. Recent updates include: * NEW Roof (2026) * Two A/C Systems (2020 & 2023) * Pool Resurfaced (2023) * Lanai Rescreened (2018) * Paver Patio (2019) * Water Heater (2021) * Tile flooring throughout—NO carpet! Ideally located just 15 minutes from world-famous Siesta Key Beach, and close to the Legacy Trail, A-rated Sarasota County Schools, Shopping, Dining, and Entertainment. NO CDD, LOW HOA This home truly offers the best of Florida living—whether you’re relaxing poolside, launching your kayak from your backyard, or spending the day at the beach, THE ONLY THING MISSING IS NEW HOMEOWNERS! Call today to schedule your private showing.The beach is calling… Have you?
Listing is courtesy of: AYERS AND ASSOCIATES REAL ESTATE (941-837-2778)
Listing Agent: Ro Palladino (917-903-1776)
486 YACHT HARBOR DR, OSPREY, FL 34229
$1,400,00015 Days on yellowkey MLS ID: A4700109
0 Days Off yellowkey (back on 7/20/2026)
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2939 Built: 1981Monthly Fee: $219 Tax: $7,320 (2025)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$7,320
Remarks: Welcome to this exceptional Southbay home featuring the rare and highly desirable 3 car garage! From the moment you step inside, you’ll appreciate the elegant finishes, soaring tray and vaulted ceilings with crown molding, and beautiful travertine flooring throughout. The entry opens to the spacious dining area and leads into the oversized Greatroom which flows seamlessly into the chef-inspired kitchen, offering an abundance of cabinetry, generous counter space, a center island, Thermador induction cooktop, two sinks, pull-out drawers, pantry, and a bright dinette highlighted by a stunning aquarium window. Just beyond the kitchen is an impressive butler’s pantry featuring extensive u-shaped cabinetry a second refrigerator, laundry room and a convenient third full bath. The adjacent den is warm and inviting with a fireplace and corner sliding glass hurricane rated doors leading to the lanai and outdoor kitchen. A unique office or craft room with wood-paneled sliding doors can be closed off for privacy or opened to expand the living space. The spacious primary suite offers two walk in closets and lanai access through sliding glass doors, while two additional bedrooms share a well appointed guest bath and privacy pocket door. Just inside from the garage, you’ll find a convenient drop zone and half bath. Major updates include: NEW TRANE A/C INSTALLED 4/25, HURRICANE RATED WINDOWS, AQUARIUM WINDOW WITH ACCORDION STYLE WRAP AROUND HURRICANE SHADE, COVERED LANAI AREA WITH REMOTE CONTROLLED ELECTRONIC HURRICANE METAL SHADE, H/W TANK 2 YEARS OLD, NEW LED POOL LIGHT, NEWER SALTWATER VARIABLE SPEED POOL PUMP (5 YEARS OLD), NEWER LANAI FANS, ROOF 2015/2017, OVERSIZED PAVER DRIVEWAY 2015, RE-PLUMBED 2015, NEW IRRIGATION 2015, ECO WATER SOFTENER & R/O SYSTEM, LEASED WATER FILTRATION SYSTEM. Located in the highly sought-after Southbay Yacht & Racquet Club, residents enjoy an active lifestyle with a private marina offering low dock fees exclusively for Southbay homeowners. Situated on the intracoastal Waterway, the marina accommodates boats of nearly every size. This golf cart-friendly community also features an updated clubhouse with ballroom, gathering room, two kitchens, fitness center, card room, and library. Outdoor amenities include a community pool, tennis and pickleball courts, kayak launch and storage, bocce court, basketball courts and playground. All this is perfectly located in desirable Osprey, just minutes from shopping, restaurants, Pineview School, major roadways, downtown Venice and Sarasota, and the beautiful beaches of Nokomis and Siesta Key. Don’t miss this incredible opportunity to own one of Southbay’s most feature-rich homes! Schedules your private showing today.
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
2251 JESSIE HARBOR DR #2101, OSPREY, FL 34229
$359,00029 Days on yellowkey MLS ID: A4698891
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1400 Built: 2006 Tax: $4,920 (2025)Community: Blackburn Harbor Waterfront ViCondo
Taxes:$4,920
Remarks: Under contract-accepting backup offers. INCREDIBLE VIEWS!....INCREDIBLE LOCATION!...You Will be Wowed by the LONG WATER & SUNSET VIEWS in this Bright and Spacious (2) Bedroom (2) Bath Corner Unit with PRIVATE GARAGE located in Blackburn Harbor Waterfront Villas, a PET FRIENDLY Gated 11 acre Waterfront Resort-Style Community with: HeatedPool; Fitness Center; Kayak Storage & Launch; BBQ Gazebo; Dog Park; Walking Trails; Pickleball/Tennis and****BOAT SLIPS****for easy "no bridges" access to Intracoastal & Gulf......Abundance of Storage; Ideal Split Bedroom Floor Plan; TILE THROUGHOUT & Expansive Screened Lanai---providing the Ultimate Indoor/Outdoor Living and PERFECT for Morning Coffees, Enjoying Your Favorite Podcast and of course, SUNSET COCKTAILS!....Blackburn Harbor 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)
4424 CONCHFISH LN, OSPREY, FL 34229
$550,00073 Days on yellowkey MLS ID: A4691622
1 Days Off yellowkey (back on 7/20/2026)
REDUCED by $35,000 (6.0%) on 07/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2370 Built: 2017Monthly Fee: $125 Tax: $4,467 (2026)Community: Palms/Casey KeySpa: YesSingle Family
Taxes:$4,467
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Situated in the highly sought-after community of Palms at Casey Key, this beautifully maintained 2017-built home offers the perfect blend of comfort, style, and location. With low HOA fees and no CDD fees, this property delivers exceptional value in one of Osprey’s most desirable areas. From the moment you arrive, the paver driveway and lush tropical landscaping create a warm and welcoming first impression. Inside, the home opens to a bright and airy great room where tray ceilings and expansive triple-panel sliding glass doors allow natural light to pour in, creating an effortless connection between indoor and outdoor living. Designed with both everyday living and entertaining in mind, the kitchen serves as the heart of the home with a large center island offering ample seating, white cabinetry, stainless steel appliances, and a spacious corner pantry for additional storage. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, while the owner’s suite feels like a relaxing retreat with tray ceilings, a large walk-in closet, dual vanities, and a walk-in glass shower. Step outside to your private patio overlooking the in-ground spa — the perfect place to unwind after a beach day, enjoy a quiet evening under the stars, or cool off during warm Florida afternoons. Location is everything, and this home truly delivers. Ideally situated just minutes from nationally ranked Pine View School, less than a mile from the Casey Key boat launch and waterfront tiki bar, and only about 15 minutes to both Nokomis Beach and Siesta Key Beach, you’ll enjoy easy access to some of the area’s best boating, dining, shopping, golf, parks, and coastal lifestyle amenities. Whether you're looking for a full-time residence or the perfect Florida retreat, this home offers the lifestyle so many buyers are searching for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ashley Wallace (941-302-2586)
401 N POINT RD #301, OSPREY, FL 34229
$459,900868 Days on yellowkey MLS ID: A4603773
REDUCED by $15,100 (3.2%) on 07/20/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2594 Built: 2003Monthly Fee: $367 Tax: $6,783 (2023)Community: Meridian At The Oaks PreserveCondo
Taxes:$6,783
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2023
Middle School: Brookside Middle
Remarks: Virtually Staged. Short Sale. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and make it uniquely your own. Check out the virtually staged photos to help you imagine what you could do with this great floor plan. This condo offers space for year-round living, or to use as a welcoming winter retreat, with room for family and friends to visit. Wouldn’t it be lovely to sit on the private terrace and listen to the birds sing as the sun sets on another perfect day? The unit has a one car under building parking space. It is a short walk to the Meridian residents-only fitness room, spa and heated pool. The Oaks Club has two championship golf courses, 12 HAR TRU tennis courts (4 lighted), croquet and pickleball courts, a state-of-the art fitness center, junior Olympic community pool, and offers a wide variety of dining and recreational options, and social activities. When you open the door to your new home here, you have opened the door to the best in Gulf Coast country club living. Membership in The Oaks Club is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
1474 LANDVIEW LN, OSPREY, FL 34229
$1,400,00049 Days on yellowkey MLS ID: A4696853
0 Days Off yellowkey (back on 7/18/2026)
REDUCED by $75,000 (5.1%) on 07/07/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3246 Built: 1977Monthly Fee: $219 Tax: $9,834 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$9,834
Remarks: Under contract-accepting backup offers. Elevated luxury throughout this Southbay beauty! Step inside this one of a kind two story home and you will feel like you are at a top resort! You will enter the foyer overlooking the living room and dining room area, just perfect for entertaining highlighting a built-in buffet with wine cooler. Open the sliding glass doors ahead and enter the exquisite out door living area, heated salt water pool, spa, outdoor kitchen and dining area, all adding up to the feeling of relaxed elegance. The kitchen is a dream! Top of the line Thermador appliances including a smooth induction top stove, built in oven and microwave and for the ultimate in extravagance - a built in Thermador coffee maker. Quartzite counter tops, over sized island, custom pantry, sliding glass doors to exterior help complete this gathering spot. Located on the first floor is the spacious master suite with triple sliding doors looking onto the lanai area. Master bath with tub and an oversized window looking onto a private zen garden. The spacious second bedroom currently used as an office features corner windows and has a full luxury guest bath right out side its door. The oversized family room with vaulted ceiling and wood beam accents will be a great family retreat with a built in new state of the art fireplace and TV. Unique pebbled wallpaper adorns one wall to help maintain the resort feel. First floor laundry with built in cabinets is also on the first level. Upstairs you will find two nice sized bedrooms plus a full bath with double bowl sinks. The upstairs bonus room is a fun hideaway for a play room, office, or workout room, featuring glass French doors. Plenty of storage in this home with several attic accesses. Other important features include plantation shutters through-out, one new A/C unit in 2025, attic TAP insulation installed 2025, stackable washer and dryer 2024, new GAF coating on TPO flat roof (lanai), interior painted 2024, extensive landscaping 2025 including addition of a side private patio, and lanai wood ceiling 2025 and new hurricane rated glass in double front door. All the beautiful furnishings and decor items in the home are negotiable as well. So many more details you will just have to come and see for yourself. The Southbay Yacht and Racquet Club is a vibrant community with many amenities, activities and offers it’s own marina to residents. The marina dock fees are low and has space for most boat sizes. Also in the marina is a kayak launch and storage on site. The renovated clubhouse offers a fitness center, 99 person ballroom, livingroom, two kitchens, pool, bocce balls, tennis and pickleball. Centrally located between Sarasota and Venice, area beaches, restaurants and shopping. The local favorite restaurant, Casey Key Fish House & Tiki Bar is right down the road! Southbay is a fabulous place to live and play - and as they say, come and buy your boat a home!
811 SARABAY RD, OSPREY, FL 34229
$449,00039 Days on yellowkey MLS ID: A4697921
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1211 Built: 1950 Tax: $1,130 (2025)Community: Harms SubSpa: NoSingle Family
Taxes:$1,130
Remarks: Under contract-accepting backup offers. Nestled on a generous 0.74-acre lot, this 2-bedroom, 1-bath residence offers 1,211 square feet of living space in a peaceful, private setting just moments from Sarasota Bay. Set back on a semi-private driveway and surrounded by mature landscaping and fruit trees, this property provides a rare opportunity to enjoy the charm and character of Old Florida living while remaining close to all of Sarasota’s modern conveniences. The expansive lot offers ample space for outdoor living, gardening, recreation, or future improvements. Whether you’re seeking a private retreat, a renovation project, an investment opportunity, or the ideal site to build your dream home, this property presents endless possibilities. The existing home is livable and full of potential, offering a solid foundation for updates and customization to suit your vision. Enjoy the serenity of a large homesite with the added benefit of being just minutes from Sarasota Bay, local parks, shopping, dining, entertainment, and the area’s renowned Gulf Coast beaches. Properties with this combination of lot size, privacy, location, and potential are becoming increasingly difficult to find. Whether you’re an investor, builder, or buyer looking to create something special, this unique property is ready for its next chapter.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Ariel Howell (941-539-8794)
816 SHADOW BAY WAY, OSPREY, FL 34229
$655,00081 Days on yellowkey MLS ID: A4690226
0 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2251 Built: 1998Monthly Fee: $120 Tax: $4,453 (2025)Community: RivendellSpa: NoSingle Family
Taxes:$4,453
Remarks: Under contract-accepting backup offers. Set within Rivendell's 400 acres of lakes, preserves, and open spaces, this Osprey pool home checks the boxes buyers rarely find together: a quiet, established neighborhood, a long list of owner-completed upgrades, and no CDD fees. If you're looking for a move-in-ready foundation you can personalize over time, this one deserves a look. Major upgrades include: • NEW ROOF and GARAGE DOOR (2023) • NEW A/C (2021) • New dishwasher and garbage disposal (2020) • New pool pump (2017) • Irrigation well deepened (2016) • New pool cage (2015) • Replumbed (2012) Additional features include a portable generator that conveys with the sale. Inside, high ceilings and abundant natural light create an airy atmosphere throughout. Granite countertops in the kitchen and all bathrooms. The split floor plan separates the primary suite from guest bedrooms, while the main living areas open through sliding glass doors to the covered lanai and private pool, an ideal setup for entertaining or everyday Florida living. The generous 3-car garage adds flexibility for storage, hobbies, or workspace. Rivendell is known for its scenic preserve setting, walking trails, heated community pool, and peaceful park-like atmosphere. Residents enjoy convenient access to the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, Siesta Key Beach, shopping, dining, and everyday conveniences along US-41. Approximately 1 mile from Pine View School, consistently ranked among the top public schools in the nation. Low HOA fees, no CDD fees, and a location close to beaches, nature, and everyday conveniences make this a rare find in one of Osprey's most established communities.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Katrin Pfitzenreiter (917-543-8560)
780 SARABAY RD #16, OSPREY, FL 34229
$425,00018 Days on yellowkey MLS ID: TB8528486
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1574 Built: 1981Monthly Fee: $1,617 Tax: $5,281 (2024)Community: Heron Bay Club Sec ISpa: YesVilla
Taxes:$5,281
Remarks: Waterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! NEW DOCK & PIER Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. Enjoy carefree coastal living with maintenance-free grounds and an all-inclusive HOA that covers insurance, roof, exterior maintenance, landscaping, roads, pool and tennis facilities, docks/boat slips, cable TV, high-speed internet, water, trash and sewer. This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry and new countertop, The vaulted-ceiling living room offers tranquil lake views overlooking the bay, with many evenings capped by stunning sunsets over the Bay. STORAGE! in addition to the garage there is an interior attic! Outside, a 587 sqft courtyard with a hot tub invites outdoor relaxation and entertaining and expands the indoor-outdoor living space to 2,161 sqft Community amenities include a heated bayside swimming pool, tennis court, a fishing pier, kayak launch, and dockage for 10 boats—complete with electric and water—available to residents at NO COST. This is a very private location. Located directly on Little Sarasota Bay with no fixed bridges near MIDNIGHT PASS, residents enjoy the highly sought-after Osprey location close to Siesta Key and Sarasota’s rich cultural attractions. Nokomis beach is only a few miles away. Enjoy waterfront dinning at Casey Key Fish House, The Point and Deep Lagoon Oyster House. Highly-rated medical facilities, major airports, and shopping destinations are within close driving distance. You have arrived at your final destination.
Listing is courtesy of: RMS ELITE PROPERTIES (727-821-1999)
Listing Agent: Mark Segreto (941-444-2270)
408 PARK TRACE BLVD, OSPREY, FL 34229
$595,000149 Days on yellowkey MLS ID: A4685004
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $20,000 (3.3%) on 06/01/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 2003Monthly Fee: $54 Tax: $4,652 (2025)Community: Park Trace EstatesSingle Family
Taxes:$4,652
Remarks: Under contract-accepting backup offers. Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart of the home is a beautiful central courtyard with a heated saltwater pool with a FastLane system, around which the main living spaces are thoughtfully arranged. An en-suite guest bedroom with private courtyard access provides a secluded retreat perfect for visitors. The open-concept interior flows seamlessly from the kitchen, complete with a signature royal blue Hestan refrigerator, into an inviting living room ideal for entertaining. From there, step out to a screened patio overlooking the water to relax in total comfort. The spacious master suite features dual California Closets, a luxurious remodeled bathroom, and an adjoining room that serves as a private office or reading nook. Throughout the home, plantation shutters provide elegant light control and privacy. The property is finished with a side-entry two-car garage featuring custom California Closets storage and a Tesla charger. Positioned just steps from the pristine Legacy Trail for biking and recreation, this home provides the perfect combination of style and lifestyle. Home is available fully furnished. The home is exceptionally well-maintained, featuring a high-efficiency HVAC system (New AC 2017/Air Handler 2020) with a programmable thermostat, a central vacuum system, and an artistic hidden TV in the living room. Recent kitchen and laundry upgrades include a 2018 washer and dryer alongside newer appliances (2020–2022). The private courtyard is equally impressive, boasting a new pool screen (2022), new pool equipment (2024), and an Endless Pool Fastlane feature for a premium fitness experience. Property is located in Flood Zone X (flood insurance generally not required).
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jennie Lascelle (941-504-0102)
4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229
$318,000148 Days on yellowkey MLS ID: N6143250
0 Days Off yellowkey (back on 7/15/2026)
REDUCED by $10,000 (3.0%) on 06/22/2026
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: Under contract-accepting backup offers. Virtually Staged. 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)
401 N POINT RD #304, OSPREY, FL 34229
$695,000368 Days on yellowkey MLS ID: A4659785
REDUCED by $5,000 (0.7%) on 06/30/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2778 Built: 2003Monthly Fee: $367 Tax: $8,473 (2024)Community: Meridian At The Oaks PreserveSpa: YesCondo
Taxes:$8,473
Remarks: Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step inside and discover a home where space abounds and possibilities flourish. With three generously sized bedrooms, plus a dedicated dining room (currently being used as a den) and a versatile office/den or 4th bedroom, this home provides all the room you need to work, relax, and entertain, with the flexibility to use the rooms as you see fit. The great room is bathed in natural light, its gleaming wood floors enhancing the clean, contemporary lines of the interior. The updated kitchen will delight any home chef, offering optimal space for cooking and storage, whether you are preparing a casual breakfast or hosting a formal dinner. Enjoy your meals in the dining room, at the breakfast bar, in the cozy nook, or take them outside to the large, screened balcony, where a ceiling fan and the serene backdrop of a lush tropical preserve provide the ideal setting for alfresco dining. The small dry bar with wine cooler and cabinets to store your drink supplies and display your glassware is the perfect addition for when you are entertaining guests. Retreat to a sumptuous master suite. The large, carpeted bedroom is filled with natural light, and outfitted with a ceiling fan, plantation shutters, and custom closets. The master bathroom has been beautifully redone. With a soaking tub, separate shower and water closet, this space is absolutely gorgeous. Every inch of this unit has been curated to deliver both style and functionality, ensuring you feel pampered at every turn. Additional features include a large laundry room, Kevlar roll down hurricane shutters, two premium parking spaces and high-quality upgrades throughout. Club membership is required with homeownership. Residents of Meridian enjoy exclusive access to a private pool, relaxing spa, and a fully equipped workout room. Beyond these, The Oaks offers an impressive array of amenities including 36 holes of championship golf across two courses, twelve HAR-TRU tennis courts (four lighted), a state-of-the-art Wellfit Center, three on-site restaurants with year-round dining, croquet, bocce and pickleball courts and an active social calendar. There is currently no waiting list for either Golf or Sports/Social membership.
678 FAITH AVE, OSPREY, FL 34229
$749,000233 Days on yellowkey MLS ID: A4674865
1 Days Off yellowkey (back on 7/4/2026)
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: Under contract-accepting backup offers. 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 Agent: Troy Sacco (941-445-3939)
385 N POINT RD #304, OSPREY, FL 34229
$1,100,000197 Days on yellowkey MLS ID: A4678422
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2778 Built: 2000Monthly Fee: $400 Tax: $5,845 (2025)Community: Meridian At The Oaks PreserveCondo
Taxes:$5,845
Remarks: **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled interior designed to impress. Premium upgrades include engineered hardwood and tile flooring, a spectacular chef’s kitchen with quartz countertops and high-end appliances, crown molding, and beautifully updated bathrooms throughout. The owner’s suite showcases serene views, private balcony access, a spacious walk-in closet, and a stunningly redesigned spa-inspired primary bath. Enjoy breathtaking western sunset views from the oversized balcony—perfect for relaxing or entertaining. Additional highlights include a climate-controlled storage unit and one covered parking space. Meridian I offers exceptional value with a new roof (2024) and new elevators (2025/2026 – in progress). Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, plus full access to The Oaks Club’s renowned amenities. A must-see residence combining luxury, space, and lifestyle. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts (4 lighted), 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.
173 NAVIGATION CIR #107, OSPREY, FL 34229
$319,50047 Days on yellowkey MLS ID: N6144704
REDUCED by $8,500 (2.6%) on 07/13/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 2015 Tax: $2,892 (2025)Community: Bay Street VillageCondo
Taxes:$2,892
Remarks: Immaculate and lightly lived-in 3BR/2BA condo in the gated community of Bay Street Village, offering beautiful water views with a fountain from the main living areas, the primary suite, and the screened lanai. The popular Ibis floor plan features an open-concept kitchen, dining, and great room with 42" upper cabinets, granite countertops, a custom tile backsplash, and stainless-steel appliances. The designer-level, fully customized laundry room includes soft-close custom cabinets, a laundry sink, a custom backsplash, and a stacking washer and dryer, providing exceptional storage and functionality. The primary suite offers a water view, a barn-door entry to the bath, a custom frameless glass shower enclosure with stone flooring, a linen closet, custom closet organizers, and a designer ceiling fan with light. Bedroom two also features custom closet organizers, while bedrooms two and three include custom ceiling fans. Ceiling fans are additionally installed in the great room and the lanai for enhanced comfort. Plantation shutters are installed in the entry foyer, primary bedroom, bedrooms 2 and 3, and the family room, adding style, privacy, and a cohesive look throughout the home. Additional upgrades include upgraded carpet on the stairs and in the primary bedroom, keyless front-door entry, keyless man-door entry, and an exterior garage door keypad. Quality construction provides peace of mind with hurricane-impact windows and doors, concrete block construction, a tile roof, and a paver driveway. The monthly condo fee covers water, sewer, exterior maintenance, landscaping, gated entry, a heated resort-style pool, cabana, fitness center, and clubhouse. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key, the Legacy Trail, Oscar Scherer Park, Sarasota and Venice shopping and dining, and A-rated Pine View School. Maintenance-free Florida living at its best.
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