Location: Osprey, 34229
Do Not Show Listings
385 N POINT RD #304, OSPREY, FL 34229
$1,100,000179 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,845
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
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 is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
780 SARABAY RD #16, OSPREY, FL 34229
$425,000Listed 07/14/2026 10:10AM 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
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2024
Middle School: Laurel Nokomis Middle
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)
401 WALLS WAY, OSPREY, FL 34229
$1,775,000165 Days on yellowkey MLS ID: A4680312
1 Days Off yellowkey (back on 6/18/2026)
REDUCED by $25,000 (1.4%) on 05/31/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4387 Built: 1990Monthly Fee: $133 Tax: $16,158 (2025)Community: Oaks 2 Ph 1Single Family
Taxes:$16,158
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Accepting Backup Offers. Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, & finishes throughout. The heart of the home is a curated chef’s kitchen featuring a bespoke butcher block island, professional-grade Viking double ovens, and sleek quartz countertops. High-end functionality includes dual KitchenAid dishwashers and custom cabinetry. The primary living spaces flow seamlessly to a wet bar and wood-burning fireplace, ideal for post-round entertaining. An extraordinary floating staircase of hand-built Hungarian wood leads to a versatile upper level with a private balcony overlooking the course. The primary suite serves as a sanctuary, entered through exquisite hand-carved doors imported from Turkey. This retreat features French doors leading to a private courtyard, custom walk-in closets, and a whirlpool jacuzzi tub. Outdoor living is centered around the pool and an expansive lanai with a fully equipped summer kitchen. Notable infrastructure includes a 3-car garage, three AC units, and clear hurricane shutters. This residence offers an elevated Sarasota lifestyle with immediate proximity to world-class golf and the exclusive amenities of the Oaks community. Please note membership of The Oaks is required.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Andrea Stultz (941-929-6529)
730 FORDINGBRIDGE WAY, OSPREY, FL 34229
$685,00025 Days on yellowkey MLS ID: A4697358
2 Days Off yellowkey (back on 7/14/2026)
REDUCED by $25,000 (3.5%) on 07/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2182 Built: 2002Monthly Fee: $120 Tax: $6,488 (2025)Community: Rivendell WoodlandsSpa: YesSingle Family
Taxes:$6,488
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. There’s a quiet kind of beauty in a home that just feels right the moment you walk in, where the light pours through the windows, the spaces flow effortlessly, and every detail invites you to slow down and stay awhile. Welcome to this thoughtfully designed 3-bedroom + den, 2-bath retreat tucked inside the beloved Woodlands at Rivendell. The kind of neighborhood where tree-lined streets and timeless charm set the tone for everyday living. Step inside and you’re greeted by an airy, open layout that feels both spacious and warm. The main living spaces are grounded by rich, hand-scraped engineered hardwood floors, while large sliding doors disappear into the walls, blurring the line between indoors and out in the most beautiful way. Out back, the home truly comes to life. The gas-heated, saltwater pool and spa, with its soft, cascading glass waterfall, creates a peaceful backdrop for everything from slow mornings to lively evenings with friends. The lanai has been freshly painted, giving the entire outdoor space a clean, refreshed feel that’s ready to be enjoyed year-round. The kitchen sits at the heart of the home, open, inviting, and designed for gathering. With an induction cooktop, stainless steel appliances, generous cabinetry, and a walk-in pantry, it’s as functional as it is welcoming. Tucked just off the main living area, the den offers a quiet place to work, read, or simply unwind, made even better by its natural light and calming views of the pool and pond. The split floor plan creates a sense of privacy, with two guest bedrooms positioned toward the front of the home and the primary suite set apart as its own retreat. Here, you’ll find two walk-in closets, soft natural light, and sliding doors that lead directly to the pool. The ensuite bath feels like a spa escape, complete with a soaking tub, walk-in shower, dual vanities, and a private water closet. And it’s not just beautiful, it’s been thoughtfully updated. In 2024, the home was refreshed with new interior paint, lanai floor paint, a portable generator, and new washer, dryer, and refrigerator. In 2025, a new HVAC air handler was installed, and in 2026, brand-new carpet was added to the bedrooms. Plantation shutters throughout add a timeless finishing touch, while every update has been made with care to ensure comfort and ease for years to come. Beyond the home, the location brings together the very best of Florida living, just minutes from Nokomis Beach, Siesta Key, downtown Sarasota, and Venice. With easy access to I-75 and US-41, and nestled alongside Oscar Scherer State Park and Pine View School, Rivendell offers both convenience and a sense of peaceful retreat. This is the kind of home that doesn’t just check the boxes, it tells a story. One of light, warmth, and living well every single day. Home is being offered partially furnished.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christina Gaskill (941-539-0445)
204 WINDWARD DR, OSPREY, FL 34229
$850,00064 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)
51 MACEWEN DR #11, OSPREY, FL 34229
$235,000172 Days on yellowkey MLS ID: A4679180
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 623 Built: 1990Monthly Fee: $142 Tax: $2,367 (2025)Community: The Oaks ClubSpa: NoCondo
Taxes:$2,367
Remarks: Withing the prestigious The Oaks Golf and Country Club, at the Windsor Lodge, this second-floor, maintenance-free, lakeside efficiency features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted. As an investment, as a weekend get-away or for visiting family and friends: Enjoy the country club lifestyle at The Oaks Club, a private, member-owned club in Osprey, Florida. Mandatory membership required with purchase as first time buyers at The Oaks. Amenities include two championship 18-hole golf courses, twelve tennis courts, four pickleball courts, a state-of-the-art Fitness/WellFit Center, croquet courts, clubhouse with three restaurants, banquet facilities, and an active social calendar.
Listing is courtesy of: 342 REAL ESTATE (941-685-0509)
Listing Agent: Sabine Spycher (941-685-0509)
173 NAVIGATION CIR #107, OSPREY, FL 34229
$319,50029 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.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
408 PARK TRACE BLVD, OSPREY, FL 34229
$595,000131 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)
206 FOUR KNOT LN, OSPREY, FL 34229
$1,850,00020 Days on yellowkey MLS ID: A4695429
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2411 Built: 1991Monthly Fee: $219 Tax: $9,449 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$9,449
Remarks: Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club - Marina Community. The thoughtfully designed split floor plan is ideal for indoor-outdoor living. Multiple rooms overlook and open directly onto the covered lanais and the private heated pool, which is framed on three sides by the home creating a stunning courtyard oasis. Dramatic floor-to-ceiling impact-rated windows and sliders (2020) frame beautiful pool views, while soaring ceilings and an abundance of natural light enhance the bright, open feel. The luxurious primary suite includes an adjoining office/den and an ensuite bath with soaking tub and custom cabinetry. Two guest bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed adds flexibility for guests or workspace. Step inside to discover stunning 12” x 72” Ceramica Sant’Agostino Italian porcelain plank tile flooring (Barkwood Ash) throughout, soaring ceilings, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint (2025). The chef-inspired kitchen features all-new custom cabinetry, quartz countertops, a large center island with seating for 8-10, high-end 2025 GE Monogram appliances (including 48” refrigerator, induction cooktop, and wall oven/microwave), a built-in wine refrigerator, and excellent storage. The open dining area includes a beautifully integrated bar with custom cabinetry and a fireplace (ready for insert). Additional highlights include dual-zone A/C systems (new 2025), new Electrolux stackable washer and dryer (2025), spacious laundry room with utility sink and coffee/tea bar, new concrete tile roof (2020), re-plumbed (2007), oversized 2-car garage with epoxy floor and custom storage, mature tropical landscaping with irrigation, private outdoor shower, and room to add a 4th-bedroom with ensuite bath or additional garage storage. Located in the desirable Southbay Yacht & Racquet Club - Marina Community, this premier boating community features a private 172-slip deep-water marina that can handle vessels up to 58 feet for very reasonable fees. Residents enjoy low HOA fees and a wonderful social atmosphere with a clubhouse, fitness center, heated community pool, spa, tennis courts, pickleball, basketball, bocce, playground, kayak launch/storage, jet ski pads, and more. This golf cart-family friendly community offers easy access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, and tiki bars. All interior and exterior furnishings, artwork, TVs, potted plants, and outdoor gas grill with pizza oven are available for purchase separately via bill of sale. This is a must-see, comprehensively updated home in Southbay.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Leighton Allenby (239-537-4563)
480 ORISKANY CT, OSPREY, FL 34229
$1,500,000134 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
$799,90020 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!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
116 WOODLAND PL #116, OSPREY, FL 34229
$254,90033 Days on yellowkey MLS ID: A4696616
REDUCED by $15,000 (5.6%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1979Monthly Fee: $820 Tax: $1,893 (2025)Community: Pine Run IiCondo
Taxes:$1,893
Remarks: Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such as cabinetry and showers. Enjoy the spacious rooms with the master bedroom having a walk in closet plus another closet. Each bedroom features its own small balcony - perfect for your morning coffee. The lanai off the livingroom will become a focal point for easy living offering a private wooded back yard area. Kitchen features white cabinets with quartz countertops, tile backsplash and stainless steel appliances. A carport plus two exterior storage closets are also nice benefits. The Pine Run neighborhood is an active community offering many activities including pickleball and tennis. There are two pools - the main pool by the club house and fitness center offers gas grills and a scenic view. The second pool is just a short walk from this condo. Kayak storage is available in the neighborhood with a boat and kayak launch just up the street at the Blackburn Point park. This location offers the best of everything. Located between Sarasota and Venice, you are within easy reach of both. Nokomis Beach is 5 miles away, Siesta Key Beach is 9 miles away! The intracoastal waterway is just up the road leading to the ever popular Casey Key Fish House and Tiki Bar. Many other restaurants, shopping and major roads are close at hand. Come see for yourself what makes this condo and Pine Run so special!
5100 JESSIE HARBOR DR #304, OSPREY, FL 34229
$725,00083 Days on yellowkey MLS ID: A4690942
REDUCED by $10,000 (1.4%) on 06/16/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2004 Tax: $6,004 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$6,004
Remarks: Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.
Listing Agent: Suki Scollo (941-587-2289)
1801 HIGHLAND RD, OSPREY, FL 34229
$289,900301 Days on yellowkey MLS ID: N6140508
REDUCED by $10,000 (3.3%) on 06/03/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1165 Built: 1999Monthly Fee: $150 Tax: $2,578 (2025)Community: Towns-End ShoresSpa: NoTownhouse
Taxes:$2,578
Remarks: One or more photo(s) has been virtually staged. Welcome to this light-filled, beautifully maintained 2-bedroom, 2-bath townhome in the highly desirable Town-End Shores community of Osprey. With LOW HOA FEES $150.00 PER MONTH and GROUND MAINTENANCE INCLUDED IN FEE this townhouse is designed for comfortable living and easy entertaining, the open-concept main level features a spacious living room, dining area, and a bright Florida room with sliding glass doors that fill the home with natural light. The stunning kitchen showcases granite countertops, contemporary cabinets, Stainless Steel Appliances and space for gathering with family and friends. Architectural details including tray ceilings, crown molding, and 9-foot ceilings add elegance, while wood-look tile and luxury vinyl plank flooring provide beauty and durability throughout. Upstairs, you'll find two bedrooms, including a spacious primary suite with a walk-in closet. A rare bonus for a townhome, the attached two-car garage offers ample room for vehicles, storage, and hobbies. Residents enjoy access to the community pool, perfect for cooling off on warm Florida days or relaxing poolside. Ideally located just minutes from world-renowned Gulf beaches, shopping, restaurants, Oscar Scherer State Park, and the Legacy Trail, this home offers the best of Florida's outdoor lifestyle. Whether you're searching for a full-time residence, a winter getaway, or an investment opportunity, this move-in-ready townhome is one you won't want to miss. Schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-486-8686)
Listing Agent: Kimberly Werla, Pa (941-979-2757)
4428 CONCHFISH LN, OSPREY, FL 34229
$548,000391 Days on yellowkey MLS ID: A4656074
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1861 Built: 2018Monthly Fee: $147 Tax: $5,936 (2024)Community: Palms/Casey KeySpa: NoSingle Family
Taxes:$5,936
High School: Pine View School
Remarks: Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. The residence has hurricane shutters, Low-E windows, and a generator hook-up. A large 26x10 covered lanai provides space for relaxing and entertaining. The Palms at Casey Key is a lovely neighborhood with low HOA fees that offers a sense of privacy. Imagine the ease of having your boat just minutes away at the nearby Casey Key Boat Launch, ready whenever you are. They say location is everything, and this home truly delivers on that promise. Ideally situated, it offers immediate access to everyday conveniences: restaurants, grocery stores, and a quick connection to I-75. Dog lovers will appreciate the brand-new dog park nearby, perfect for playtime and socializing. Just under a mile from your front door, the Casey Key Boat Launch and the lively Tiki Bar invite you to unwind and enjoy days by the water. Families will love the close proximity to the prestigious Pine View School, renowned for academic excellence and ranked as the number one high school in Florida, the second-highest elementary school in the US, and the third-highest middle school in the US. Beyond the neighborhood, you'll find easy access to Siesta Key Beach, top-tier golf courses, vibrant cultural attractions, and exciting entertainment options. With low HOA fees and no CDD fees, this home offers the freedom to live your dream Florida lifestyle, without the rising costs of new construction. Move-in ready and like-new, this residence is a perfect blend of character and delightful charm. Store your boat, enjoy the community, and embrace life with ease and comfort. Don’t miss your chance to claim your own piece of paradise!
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Mariana Georgieva (941-809-0416)
120 WOODLAND PL #120, OSPREY, FL 34229
$299,0003 Days on yellowkey MLS ID: D6148025
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: 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)
2251 JESSIE HARBOR DR #2101, OSPREY, FL 34229
$359,00011 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: 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)
2309 JESSIE HARBOR DR #2402, OSPREY, FL 34229
$497,00012 Days on yellowkey MLS ID: A4698434
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2006 Built: 2006 Tax: $5,978 (2025)Community: Blackburn Harbor Waterfront VillasSpa: NoCondo
Taxes:$5,978
Remarks: West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass doors opening to a screened lanai over the water, and side windows that keep natural light moving through the unit all day. Canal views extend from the main living and dining areas into the primary suite, giving the heart of the home a constant connection to the water. The primary suite features a private slider to the lanai, dual closets, and an ensuite bath with dual sinks, a jetted garden tub, and a walk-in shower. The second bedroom is a spacious ensuite with a walk-in closet. The third bedroom, with its French doors, works equally well as a guest room, home office, or flex space. The kitchen and ensuite baths feature solid wood cabinetry and granite countertops. Updated stainless steel appliances complete the kitchen. Major systems: A/C (2016), water heater (2021). Blackburn Harbor is a gated, 11-acre waterfront community with a heated pool, tennis and pickleball courts, BBQ gazebo, kayak storage and launch, and a boat dock rental program (subject to availability), with easy access to the Intracoastal Waterway and the Gulf of Mexico just beyond. No trailering, no storage hassles — just head out on the water and return to the convenience of your own dock. HOA: $980/month. Pets welcome up to 40 lbs. Minutes from Nokomis Beach, The Legacy Trail, Downtown Venice, Oscar Scherer State Park, Sarasota Memorial Hospital Venice Campus, nationally acclaimed Pine View School, and the dining and shopping along US-41 — centrally located between Sarasota and Venice. Minutes away from I-75 and the 681 connector. A rare opportunity to live, entertain, and boat from the same address. Schedule your private showing today.
Listing Agent: Christine Pope (941-685-5565)
108 WOODLAND PL #108, OSPREY, FL 34229
$285,0004 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!
89 NAVIGATION CIR, OSPREY, FL 34229
$320,00053 Days on yellowkey MLS ID: A4694435
REDUCED by $25,000 (7.2%) on 06/27/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1449 Built: 2014 Tax: $3,931 (2025)Community: Bay Street VillageCondo
Taxes:$3,931
Remarks: Virtually Staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of relaxation, comfort, and everyday convenience. From the moment you walk through the door, the tranquil pond views immediately draw your attention, creating a sense of calm that carries throughout the home. Imagine starting your mornings on the screened lanai with coffee in hand, overlooking the sparkling water feature while enjoying the warm Florida breeze and peaceful surroundings. With over 1,400 square feet of thoughtfully designed living space, this beautifully maintained 2-bedroom, 2-bathroom condo also features a versatile den, separate laundry room, and attached one-car garage. Rare first-floor units with water views and this level of convenience are highly desirable for full-time residents, seasonal owners, and investors alike. The open-concept floor plan was designed to maximize both comfort and entertaining. The kitchen showcases granite countertops, solid wood cabinetry, stainless steel appliances, stylish backsplash details, a spacious island, and breakfast bar seating that flows seamlessly into the bright and inviting living area. Crown molding, modern lighting, fresh neutral paint, and updated flooring throughout elevate the home with a clean and timeless feel. The spacious primary suite serves as a private retreat featuring peaceful water views, a large walk-in closet, linen closet, and an updated en-suite bathroom complete with dual sinks and a custom walk-in tile shower. A generously sized guest bedroom, beautiful guest bath, and flexible bonus room provide endless possibilities for guests, a home office, hobby space, or additional lounge area. Bay Street Village offers true maintenance-free living with resort-style amenities including a sparkling pool, fitness center, clubhouse, and beautifully maintained grounds. Centrally located between Sarasota and Venice, residents enjoy quick access to world-renowned Gulf beaches including, Nokomis Beach, and Venice Beach, along with downtown Sarasota, marinas, waterfront dining, shopping, golf, entertainment, Sarasota Bay, the Legacy Trail, and countless local restaurants and attractions. Located near the nationally recognized Pine View School and tucked away from the heavy tourist traffic while still remaining close to everything, this condo offers the perfect combination of convenience, comfort, and the relaxed coastal lifestyle that everyone dream about when moving to Florida. Whether you are searching for a primary residence, seasonal escape, or investment opportunity, this exceptional waterfront condo delivers location, lifestyle, and value all in one. Schedule your private showing today and experience firsthand why this hidden gem in Bay Street Village is the perfect place to call home.
Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)
Listing Agent: Jozefina Wells (941-993-3051)
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