Location: Osprey
Do Not Show Listings
486 YACHT HARBOR DR, OSPREY, FL 34229
$1,400,0008 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,320
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
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
$359,00022 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
Middle School: Sarasota Middle
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
$550,00066 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)
108 WOODLAND PL #108, OSPREY, FL 34229
$285,00015 Days on yellowkey MLS ID: A4699279
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1979 Tax: $3,100 (2025)Community: Pine Run IiCondo
Taxes:$3,100
Remarks: Bring your furniture and move right in to this popular Pine Run neighborhood. No need to worry about remodeling this condo! New coastal look ceramic tile throughout the entire home! New kitchen and appliances, new guest bathroom, new doors throughout, new light fixtures, and newly painted. Wow! First floor condo offers more outdoor living space. The patio off the main entry offers privacy and has access from the dinette area. A spacious center atrium feels like a peaceful retreat. The main covered lanai off the living room and dining room is screened in with a door to the back yard. Each bedroom has it’s own small patio with privacy fence. Kitchen is nicely equipped with washer and dryer in the dinette closet area. The hallway has large almost floor to ceiling windows looking onto the center atrium for a very open feel. Pine Run is an active community nestled between mature landscaping and trees, with many activities including pickleball, tennis, kayak storage and two swimming pools! Launch your kayaks in the Blackburn Point Park and boat launch just down the road. Pine Run is conveniently located near shopping, restaurants, major roads and Casey Key Fish House and Tiki Bar. Sarasota is about 13 miles away, Venice about 7 miles. Area beaches are close at hand with Nokomis Beach just 5 miles and Siesta Key Beach is 9 miles. You are in the heart of paradise! Come see for yourself!
401 N POINT RD #301, OSPREY, FL 34229
$459,900861 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
$1,400,00042 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!
619 OAK RIVER CT, OSPREY, FL 34229
$609,90072 Days on yellowkey MLS ID: A4692331
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2047 Built: 1997Monthly Fee: $25 Tax: $5,484 (2025)Community: Bay Oaks EstatesSpa: NoSingle Family
Taxes:$5,484
Remarks: Under contract-accepting backup offers. Virtually Staged. Back on the market due to buyer financing. Move-in ready Bay Oaks pool home featuring a beautifully renovated kitchen, stunning spa-inspired primary bath, updated flooring, and a huge private fenced backyard. Situated on an oversized 0.38-acre corner lot, this home offers the perfect combination of modern updates, privacy, and outdoor living. Welcome to this thoughtfully renovated pool home in sought-after Bay Oaks Estates, perfectly positioned on an oversized 0.38-acre corner lot in the heart of Osprey. Featuring 3 bedrooms plus a dedicated office, 10-foot ceilings, a huge fenced backyard, and extensive modern updates throughout, this move-in-ready residence offers a rare blend of style, comfort, and effortless indoor-outdoor living. One of the home’s standout features is the oversized fenced backyard, offering a rare combination of space, privacy, and flexibility. The screened lanai, private pool, and expansive outdoor area create the perfect setting for entertaining and year-round enjoyment. Framed by mature landscaping and a newer concrete tile roof (2021), the home creates a welcoming first impression from the moment you arrive. A large driveway and covered parking area provide abundant convenience. New flooring throughout (2025), brand new electrical panel, updated lighting, fresh interior paint, and carefully selected finishes create a clean, cohesive modern aesthetic rarely found in the neighborhood. Inside — 10-foot ceilings, abundant natural light, and a thoughtfully designed layout create an elevated sense of space and openness. Smart-home features include an ecobee thermostat, keypad entry, and a Samsung all-in-one smart washer and dryer. At the center of the home, the fully remodeled kitchen combines style and function with granite countertops, white shaker cabinetry, stainless steel appliances, modern finishes, and an expansive breakfast bar that opens seamlessly to the main living areas. The spacious primary suite serves as a true retreat with two walk-in closets and a beautifully remodeled bath featuring quartz countertops, dual vanities, a freestanding soaking tub, and a frameless glass walk-in shower. Perfectly positioned between The Oaks Club and Stoneybrook Golf & Country Club, Bay Oaks offers the feel of luxury golf-course living without the fees. Families will especially appreciate being just 3 miles from Pine View School, consistently ranked among the top public schools in the nation. Just 6 miles from Siesta Key and 4 miles from Casey Key, this prime Osprey location places you near marinas, golf courses, the Legacy Trail, shopping, dining, and Sarasota’s coastal lifestyle.
Listing is courtesy of: FISHMAN GROUP REALTY LLC (763-443-1761)
Listing Agent: Ross Fishman (763-443-1761)
329 BAY VISTA AVE, OSPREY, FL 34229
$429,00016 Days on yellowkey MLS ID: A4699464
REDUCED by $16,000 (3.6%) on 07/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1346 Built: 1963 Tax: $4,306 (2025)Community: Bay Acres - ResubSingle Family
Taxes:$4,306
Remarks: Welcome to 329 Bay Vista Ave., Osprey, FL 34229—a rare opportunity to own a beautifully renovated 2-bedroom, 2-bathroom home on an expansive lot (0.47 acre!!!) with no HOA, no deed restrictions, and endless possibilities. Inside, you'll find a thoughtfully updated interior that's move-in ready, offering the perfect blend of comfort and style. Whether you're looking for a full-time residence, seasonal retreat, or investment property, this charming home provides easy, low-maintenance living in one of Osprey's most desirable locations. Situated on a generously sized homesite, this property offers the flexibility that's becoming increasingly difficult to find. Whether you've been dreaming of adding a pool, building a detached garage or workshop, parking your RV or boat, creating a garden oasis, or expanding the existing home, the space is here to bring your vision to life. Without the limitations of an association, you have the freedom to truly make this property your own. For those who love the Florida waterfront lifestyle, this location is hard to beat. Enjoy being just minutes from the Intracoastal Waterway, public boat ramps, Casey Key, Nokomis Beach, and waterfront dining, while having the added peace of mind of being outside of a flood zone. It's the best of both worlds—close to the water without the added concerns that often come with waterfront living. Conveniently located near the Legacy Trail, Oscar Scherer State Park, shopping, dining, top-rated schools, and with easy access to both Sarasota and Venice, this home combines location, flexibility, and lifestyle. Whether you're looking for your first home, a winter escape, or a property with room to grow, 329 Bay Vista Ave. delivers a unique combination of updated living, land, and freedom that's becoming increasingly rare to find. Bring your boat, your RV, your ideas, and your vision—because with this oversized lot, no HOA, and endless potential, the possibilities are truly limitless.
Listing is courtesy of: THE SHORELINE FL REALTY LLC (941-544-1133)
Listing Agent: Rodrigo Posada (941-544-1133)
811 SARABAY RD, OSPREY, FL 34229
$449,00032 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
$655,00074 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
$425,00011 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
Tax Year: 2024
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
$595,000142 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
Elementary School: None
High School: None
Middle School: None
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
$318,000141 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
$695,000361 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
$749,000226 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 is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Troy Sacco (941-445-3939)
385 N POINT RD #304, OSPREY, FL 34229
$1,100,000190 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.
Listing Agent: Mark Lyda (941-586-2670)
204 WINDWARD DR, OSPREY, FL 34229
$850,00075 Days on yellowkey MLS ID: A4693139
REDUCED by $75,000 (8.1%) on 07/13/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2486 Built: 1986Monthly Fee: $219 Tax: $4,761 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$4,761
Remarks: Don't miss this opportunity to own a home in a desirable private marina community. This spacious 3-bedroom, 3-bath home features high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. An amazing Value! A combination of 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. Southbay Yacht & Racquet Club is a highly sought-after Marina community offering a clubhouse, resort-style amenities and 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)
173 NAVIGATION CIR #107, OSPREY, FL 34229
$319,50040 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.
480 ORISKANY CT, OSPREY, FL 34229
$1,500,000145 Days on yellowkey MLS ID: A4684136
REDUCED by $35,000 (2.3%) on 07/09/2026
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3208 Built: 1999Monthly Fee: $142 Tax: $6,365 (2024)Community: The Oaks ClubSpa: NoSingle Family
Taxes:$6,365
Remarks: Tucked away on a quiet street within the prestigious Oaks Club in Osprey, Fl; This elegant residence overlooks the fairway of the Heron 14. This home sits on a Premium golf course lot with additional privacy view across the street . Designed by Toll Brothers, this one story, 3200 sq. Ft. home with 3 bedroom ( plus office ) offers gracious entertaining and comfortable everyday living. A well-appointed kitchen with newer appliances opens seamlessly to a family room for hosting family and friends. Step outside to your private oasis and serene backyard, a perfect place to read or host your Book Club. A new roof and pool cage(2023) have been added. This home has a 3-car garage with an electric car charger. Living in the Oaks Club means enjoying two Championship golf courses, 12 har-tu tennis courts, 4 pickleball courts, gorgeous croquet lawns and a State of the art fitness center with an outdoor heated pool. Membership is required for home ownership. In this premier Golf and Country Club. Enjoy the vibrancy of downtown Sarasota for culture, arts, dining, and shopping. Just a short distance to the world-renowned Siesta Beach and the Gulf coast of Florida. Stop by to learn about the active social calendar - a place to make wonderful memories.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Susan Pelton (941-321-1007)
1495 LANDVIEW LN, OSPREY, FL 34229
$799,90031 Days on yellowkey MLS ID: A4697993
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2474 Built: 1988Monthly Fee: $219 Tax: $5,328 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$5,328
Remarks: Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room used as a game room with your own pool table. Dining room offers a built in bar area. Nicely equipped cherry kitchen opens to family room with fireplace and sliding glass doors onto the courtyard. Travertine floors are also in the diningroom, kitchen and family room. The primary suite is located on one side of the home while the other two bedrooms are on the other side. The primary suite also looks onto the pool area. The large courtyard offers plenty of covered space for lounging plus solar heated pool, and an above ground hot tub! All furniture can be left with the home and is negotiable if you are looking to move right in and start enjoying the fabulous Florida lifestyle. OTHER BENEFITS OF THE HOME INCLUDE RECENTLY REPLACED A/C, A GENERATOR, ROOF APROX. 13 YEARS OLD, POOL RESURFACED IN 2009. Speaking of lifestyle…there is none finer than living in Southbay! The marina which is exclusive to Southbay residents offers low dock lease fees. Renovated club house has much to offer including a ballroom, casual “livingroom” areas, two kitchens, fitness center, card room, library, community pool, pickleball courts, tennis courts and activities galore! Picturesque views, walking trails, kayak launch, kayak storage, playground, bocce ball court and more. Come explore Southbay, you won’t be disappointed!
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