Location: Osprey
Do Not Show Listings
14041 BELLAGIO WAY #316, OSPREY, FL 34229
$8,000581 Days on yellowkey MLS ID: A4622973
INCREASED by $250 (3.2%) on 04/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2058 Built: 2006Community: Villas At Bellagio Harbor VillageCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: AVAILABLE FOR SEASON 2027 - 3 MONTH MIN REQUIRED. MINUTES TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd floor end unit. Upon entering, you are met with a spacious foyer which leads to the nicely appointed rooms. The kitchen has wood cabinets and granite counters, stainless steel appliances and comes fully equipped. Off of the kitchen is the living/dining area with sliding glass doors opening onto the large, spacious balcony overlooking the bay/harbor. The master suite has a king-sized bed, large walk-in closet, en-suite bathroom with separate shower and soaking tub, and private water closet. Enjoy more water views from the master bedroom with sliders opening onto the balcony. The 2nd bedroom is nicely furnished with a queen-sized bed, bedroom 3 has 2 twin beds, and guest bathroom has a walk-in shower and single vanity. There is a large separate laundry room with washer, dryer, a sink and plenty of storage cupboards. Wake up to the amazing waterfront views and enjoy your morning coffee on the furnished balcony. Osprey Harbor Village has it all! The Community has a resort-style bay-front heated pool and spa, sauna room, state-of-the-art fitness facility and a clubhouse with flat-screen TV's, kitchen, BBQ grills, fishing pier, boat docks, kayak launch, boat storage, on-site full-service marina and waterfront restaurant. covered under building garage parking for two cars, with elevators leading to your condo. Only minutes to the incredible Nokomis Beach, Siesta Key, and Venice Beach, shopping, dining, including the renowned Casey Key Fish House and Deep Lagoon, and walking distance to Blackburn Point Park! Easy access to I75 to University Town Center and Mall where there is an abundance of shops and restaurants.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Chrissie Cummings (772-532-8229)
51 MACEWEN DR #12, OSPREY, FL 34229
$2,25032 Days on yellowkey MLS ID: A4686127
REDUCED by $150 (6.3%) on 04/01/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 623 Built: 1990Community: OaksCondo
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A combined bedroom/living room, new kitchenette with quartz countertop, dining nook, office/dressing room, well designed bathroom with walk-in shower, office/dressing room, and stacked washer/dryer. Lobby elevator provides access to the second floor. Windsor Lodge Residents have their own private swimming pool and club house. Centrally located and 15 minutes to Siesta Key Beach. Note: Residents of Windsor Lodge do not have access to The Oak Club amenities. Available now for an seven plus month lease at $2250 month.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Patrice Ivan (941-993-0823)
260 HIDDEN BAY DR #504, OSPREY, FL 34229
$5,000220 Days on yellowkey MLS ID: A4664275
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1950 Built: 2019Community: Edgewater/Hidden Bay Ph Ii BldCondo
Remarks: Annual Turnkey Furnished or short term seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French doors, and powder room in an open floor plan. The kitchen is large with solid wooden soft close, shaker style cabinetry topped with slab granite counters with a breakfast bar on peninsula with seating for 4. This room has a tray ceiling and is complimented with stainless steel appliances. The dining area will seat six comfortably and has your amazing water views. The condo also features a large laundry room with sink, granite counters for folding, hanging rack and upper and lower extra storage, as well as assigned parking garage for one with adjacent huge storage closet. This is a secure community with gated access to the community, and controlled lobby access, and for your weather concerns there are catagory 5 hurricane grade windows recently installed. The building itself is built like a tank-poured concrete floors and walls between units reinforced with rebar. The amenity package in this community is impressive, with a large clubhouse with full catering kitchen, lounge, library, fitness center, resort style pool and spa with tables and umbrella's and a covered shaded area, BBQ grills and outdoor dining area in a Tiki Hut, and a board walk leading to an island with fountains spraying! Tennis or pickleball-YES! There is also a trail at the rear of the community leading near the water on a board walk. This slice of heaven can also be rented during HIGH SEASON ( December thru April) at $6000/month + 13% tax. You will also find yourself convenient to shopping, dining, Siesta Key Beach, and downtown Sarasota with theater, opera, museums and more fun! Call today for your incredible home!
Listing is courtesy of: RENT SARASOTA (941-328-8999)
Listing Agent: Cody Smith (404-991-0209)
280 HIDDEN BAY DR #202, OSPREY, FL 34229
$3,59575 Days on yellowkey MLS ID: A4680472
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1937 Built: 2024Community: Edgewater/Hidden Bay Ph 3Condo
Remarks: Be the first to call this brand-new condo in Edgewater at Hidden Bay home. The kitchen showcases a sleek, modern design, complemented by solid wood cabinetry and quartz countertops, creating an ideal space for both everyday living and effortless entertaining. Appliances include a stainless-steel refrigerator, microwave, range, and dishwasher. Large windows bring in an abundance of natural light and ha partial views of Little Sarasota Bay. Located down the hall is a All three bedrooms are thoughtfully designed for everyday comfort, with the primary suite featuring dual closets and an immaculate en suite bathroom for added convenience! A full-size washer and dryer are included for hassle-free laundry days. Underbuilding covered and secured parking provides each unit with one assigned space, and locked storage units across the main building additional storage. Basic cable and internet are included. Sorry, no pets for renters. Welcome to Edgewater at Hidden Bay! Located in Osprey, Florida on the shores of Little Sarasota Bay, you'll find a vibrant, gated, waterfront condominium community that's rich with amenities such as a newly renovated clubhouse with catering kitchen and fitness room, a resort-style pool and spa, tennis and pickleball courts, a Tiki hut for grilling and entertaining, a kayak launch and meandering boardwalks that access a pond with water features and a fishing pier that allows you to watch nightly sunsets. Submit all applications to Ryntal Property Management ONLY! Qualifications: We run a complete background check that includes credit, income verification, prior landlord, and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550.
Listing is courtesy of: PMI SOUTHWEST FLORIDA (941-237-0011)
Listing Agent: Nancy Guerrero (941-400-8134)
280 HIDDEN BAY DR #201, OSPREY, FL 34229
$3,79578 Days on yellowkey MLS ID: A4679931
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2168 Built: 2024Community: Edgewater/Hidden Bay Ph 3Condo
Remarks: WOW WOW WOW. This is a must see. Impressive upscale living!! Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space for both everyday living and entertaining. Expansive windows fill the interior with natural light while offering partial views of Little Sarasota Bay, enhancing the home's bright and inviting atmosphere. The spacious bedrooms and designer bathrooms provide comfort and style, while the flexible office space adds valuable functionality for work or relaxation. For added convenience, the condo includes a full-size washer and dryer. Under the building is a covered and secured parking lot, providing each unit with (1) assigned parking spot for added security. Locked storage units across the main building also feature additional storage! Basic cable and internet are included. Sorry, no pets for renters. Hidden Bay offers a serene, resort-style environment surrounded by scenic waterways and lush green spaces. Residents enjoy access to a community pool, tennis and pickleball courts, a clubhouse, and a fully equipped fitness center, making it the perfect setting for those seeking comfort, convenience, and a touch of luxury. Qualifications: We run a complete background check that includes credit, income verification, prior landlord, and eviction history.
152 NAVIGATION CIR #107, OSPREY, FL 34229
$4,5001615 Days on yellowkey MLS ID: A4517611
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1528 Built: 2016Community: Bay Street VillageCondo
Remarks: BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with solid wooden cabinetry, topped with slab granite counters and breakfast bar and complemented with stainless steel appliances. The master suite is spacious with a king bed, walk in closet and en suite bathroom with walk in shower and double vanity. There are two additional bedrooms-one with a queen size bed and one set up as a den with a pull out couch. The amenity package features a resort style heated pool, club room, fitness center and BBQ grills. Bay Street Park is right across the street and you'll find yourself close to the beach, downtown Sarasota or Venice, the Legacy Trail, shopping, dining and museums. Available NOW AND DURING HIGH SEASON (DECEMBER THRU APRIL). This community is governed by a homeowners association. Approval may include an application, background screening, fees, and an approval process. Contact the agent for details. Call now for your next vacation in the Florida sunshine!
5100 JESSIE HARBOR DR #504, OSPREY, FL 34229
$6,950344 Days on yellowkey MLS ID: A4651384
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2143 Built: 2004Community: Blackburn Harbor ResidencesCondo
Remarks: CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $6,950/MONTH. Beautiful direct waterfront 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and 2 bathrooms. As you step inside the foyer, you are met with a bright and open floor plan with a separate dining area, large living room leading onto the covered and furnished balcony with its magnificent water views! The spacious and beautifully updated kitchen has granite countertops and stainless-steel appliances and is fully equipped. The primary suite has a king-sized bed, en-suite bathroom with a large walk-in shower, a separate soaking tub, and dual sinks. There are two additional guest rooms, one with a queen-sized bed and the other has 2 twin beds, plus a separate guest bathroom with walk-in shower, large granite vanity area with a single sink, and a separate laundry room with full-size side-by-side washer and dryer. The condo has an assigned parking space in the underground garage. Blackburn Harbor is a gated community and offers many amenities, which include a heated pool, fitness center, clubhouse, pickleball and tennis courts, shuffleboard, kayak launch, boat dock and fishing pier. In addition, there is a gazebo, outdoor grills and walking trails. The waterway leads out to the Intracoastal Waterway, with access to the Gulf of Mexico. You are in walking distance to Oscar Scherer Park, a short drive to the beautiful gulf beaches of Nokomis Beach, Casey Key, South and North Jetty, Venice Beach, Caspersen Beach, and the famous Siesta Key Beach! Plus, there is an abundance of shopping and dining, from the beautiful Historic Venice to Downtown Sarasota which is full of entertainment of all kinds! Np pets allowed.
280 HIDDEN BAY DR #203, OSPREY, FL 34229
$3,795 MLS ID: A4680486
Remarks: This second-story unit in Edgewater at Hidden Bay is ready for move-in and is furnished or unfurnished. The apartment includes 3 bedrooms, 2 bathrooms, modern finishes, and steady natural light throughout. The kitchen provides ample cabinet storage, a breakfast bar, quartz countertops, and all major appliances, including a stainless-steel refrigerator, microwave, dishwasher, and range. The open living area connects to a screened balcony for additional usable space! The primary bedroom also includes access to the screened balcony, with additional details including dual walk-in closets and an en suite bathroom for added privacy. Two additional bedrooms are included in this unit, complete with spacious closet space for all your wardrobe needs. A guest bathroom down the hall and a laundry room with additional storage complete the rest of this apartment! Underbuilding covered and secured parking provides each unit with one assigned space, and locked storage units across the main building additional storage. Basic cable and internet are included. Sorry, no pets for renters. Welcome to Edgewater at Hidden Bay! Located in Osprey, Florida on the shores of Little Sarasota Bay, you'll find a vibrant, gated, waterfront condominium community that's rich with amenities such as a newly renovated clubhouse with catering kitchen and fitness room, a resort-style pool and spa, tennis and pickleball courts, a Tiki hut for grilling and entertaining, a kayak launch and meandering boardwalks that access a pond with water features and a fishing pier that allows you to watch nightly sunsets. Submit all applications to Ryntal Property Management ONLY! Qualifications: We run a complete background check that includes credit, income verification, prior landlord, and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550.
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