Location: Bay Street Village, Osprey
Do Not Show Listings
89 NAVIGATION CIR, OSPREY, FL 34229
$345,0008 Days on yellowkey MLS ID: A4694435
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1449 Built: 2014 Tax: $3,931 (2025)Community: Bay Street VillageCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,931
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: One or more photo(s) has been 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)
4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229
$328,00085 Days on yellowkey MLS ID: N6143250
REDUCED by $1,000 (0.3%) on 05/20/2026
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
Middle School: Sarasota Middle
Remarks: One or more photo(s) has been 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)
4226 FRONTIER LN #103, OSPREY, FL 34229
$299,00053 Days on yellowkey MLS ID: A4687965
REDUCED by $20,000 (6.3%) on 05/16/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2018Monthly Fee: $475 Tax: $3,542 (2025)Community: Bay Street VillageCondo
Taxes:$3,542
Remarks: Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage provides added convenience and storage. Upstairs, the bright, open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. The well-appointed kitchen features 42" cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in pantry, seamlessly flowing into the dining and living areas. Step out onto your large, screened-in lanai to enjoy peaceful mornings or evening cocktails. The generously sized primary suite offers a walk-in closet and an ensuite bath with dual vanities and a tiled walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Ideally located in Osprey, between Sarasota and Venice, you’ll enjoy a quiet, tucked-away setting with shopping, dining, and daily conveniences just minutes away. Bay Street Village residents enjoy resort-style amenities including a heated pool, fitness center, and clubhouse. With reasonable HOA fees covering exterior maintenance, roof, water, sewer, and gated access (and no flood insurance required) this is truly low-maintenance ownership at its best. Perfect as a full-time residence, seasonal escape, or investment opportunity this is Florida living, simplified.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kate Kwiecinski (412-477-9720)
4284 EXPEDITION WAY #NA, OSPREY, FL 34229
$325,000106 Days on yellowkey MLS ID: A4681835
REDUCED by $14,900 (4.4%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1430 Built: 2017 Tax: $2,934 (2025)Community: Bay Street VillageCondo
Taxes:$2,934
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to Bay Street Village, a gated, maintenance-free community in Osprey between Sarasota and Venice. The tile roofs and paver driveway provide Florida charm. This move-in-ready 3-bed, 2-bath condo features an open layout, IMPACT glass, and a private screened balcony with a pond view. The kitchen offers a large granite counter with seating and a newer refrigerator. The primary suite includes a walk-in closet and an en-suite bath with dual sinks and a step-in shower. A split floorplan adds privacy, and the attached one-car garage provides extra storage. Community amenities include a heated pool, fitness center, and clubhouse. Bay Street Park is directly across the street and is walkable—includes a dog park for your furry friend. Water is included in the monthly fee. Conveniently located near Nokomis Beach, Oscar Scherer State Park, The Legacy Trail, Publix, restaurants, shopping, and both US-41 and I-75, this condo offers easy, low-maintenance Florida living in a central coastal location in a very nice community.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Grace Bonaccorso (941-580-1362)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$280,00050 Days on yellowkey MLS ID: A4689541
REDUCED by $10,000 (3.4%) on 05/12/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2017 Tax: $3,507 (2025)Community: Bay Street VillageCondo
Taxes:$3,507
Remarks: One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **SELLER FINANCING AVAILABLE** **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
184 EXPLORER DR, OSPREY, FL 34229
$294,90027 Days on yellowkey MLS ID: A4692249
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1244 Built: 2016Monthly Fee: $475 Tax: $3,474 (2025)Community: Bay Street VillageSpa: NoTownhouse
Taxes:$3,474
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: Luxury Corner Residence in Osprey | Top-Rated Pine View School District. Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities. This FULLY FURNISHED 2-bedroom, 2-bathroom home with a private garage showcases light-filled, open-concept interiors, enhanced by hurricane-impact windows and elegant finishes throughout. The spacious layout is designed for both comfort and entertaining, featuring an oversized kitchen island, stainless steel appliances, and generous storage. Step outside to your private screened lanai, perfect for relaxing mornings or unwinding in the evening in a peaceful, tropical setting. Highlights include: Highly sought-after corner unit for added privacy and natural light Private garage + additional parking Resort-style community with pool Pet-friendly neighborhood Meticulously maintained, move-in ready condition Ideally located just minutes from Siesta Key Beach, Nokomis Beach, dining, shopping, and the Legacy Trail, this property also offers proximity to the nationally recognized Pine View School, consistently ranked among the top public schools in Florida. Whether you are looking for a primary residence, seasonal retreat, or investment property, this home delivers both lifestyle and long-term value. Luxury, location, and top-tier education—this is Osprey living at its finest.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Claudia Dybala (773-318-5796)
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