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WINDSOR LODGE AT THE OAKS - A4695928 - 51 MAC EWEN DR #8, OSPREY, FL 34229 14 Days on yellowkey
$2,250 | Condo | 1 beds | 1.0 baths
Available NOW! Come lounge around in one of the finest golf communities where everyday can feel like a vacation. This elegant loft has a lovely view of the lake with the rolling green right behind it. Enjoy endless summer days basking in the sun at the pool which is only steps away! This loft is equipped with granite countertops, a full size washer and dryer, stainless steel appliances, fixtures and fittings, a walk in shower, and a king size bed. It is fully furnished and available for viewing now! Seeking annual rental; rent includes water, sewer, internet, basic cable & pest control.. Don't miss out on this one of a kind place to call home!
Listing is courtesy of: ROSSI & COMPANY INC
MERIDIAN AT THE OAKS PRESERVE - A4695871 - 409 N POINT RD #802, OSPREY, FL 34229 15 Days on yellowkey
$3,900 | Condo | 3 beds | 3.0 baths | 2 gar
Move right into this gorgeous remodeled turnkey furnished condo in desirable gated community of The Oaks Preserve. This community is waterfront on the Intercostal Waterway with soothing stunning views and sunsets to adore. Take the elevator directly up to your front foyer to your unit. This unit is filled with beaming natural light and upscaled furnishings through out. The new oak wood flooring, white wood cabinets, impressive stone quartz counter tops and new appliances will WOW you and your guests. The open kitchen is just stunning viewing into dinning, living area and water views. This 3 bedroom and 3 full baths condo is very welcoming and spacious. The third bedroom is set up as a den with a sleeper sofa. The master ensuite views out onto Florida's most desired water views and wildlife. This community offers a 24 hour manned gate for security, nice walking areas with canopy oak trees and luscious Florida plantings, Clubhouse, heated pool, hot spa, nice pool deck with shaded areas to lounge and a fitness center. Come see what Florida is all about in this immaculate breath taking condo with private 2 car garage.
Listing is courtesy of: JENNETTE PROPERTIES, INC.
EDGEWATER/HIDDEN BAY BLDG B PH - A4693277 - 260 HIDDEN BAY DR #401, OSPREY, FL 34229 38 Days on yellowkey
$4,850 | Condo | 3 beds | 2.5 baths | 2 gar
6 Month Minimum Lease Available. Experience the beauty of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking Little Sarasota Bay. Thoughtfully designed for both comfort and flexibility, the home includes a private den or home office, convenient in-unit laundry, and generous living spaces perfect for relaxing or entertaining. Nestled within Hidden Bay, a private 14-acre waterfront community, residents enjoy a peaceful coastal setting directly on the bay—just across from the pristine beaches of Casey Key and the Gulf of Mexico. At the heart of the community is a beautifully renovated clubhouse featuring elegant gathering spaces, a catering kitchen, fitness center, reading library, and dining room. Outside, unwind by the heated pool and spa, gather with friends at the Tiki hut grilling area, or relax beside the tranquil pond with cascading water features. For recreation and adventure, Hidden Bay offers tennis and pickleball courts, a kayak launch, pet park, and car wash station. A scenic elevated boardwalk winds through lush mangrove preserves, leading to a long fishing pier where residents can enjoy peaceful water views, cast a line, or simply take in the area’s breathtaking sunsets. Hidden Bay offers more than a home—it offers a true waterfront lifestyle. Rental rate includes basic cable, internet (expanded services available), water, trash, and pest control. Call for a private tour today. 6-12 month lease period
Listing is courtesy of: GULF COAST REALTY & MANAGEMENT
BAY STREET VILLAGE - N6144275 - 4219 FRONTIER WAY #105, OSPREY, FL 34229 39 Days on yellowkey
$2,300 Reduced | Condo | 2 beds | 2.0 baths | 1 gar
2 bedrooms. 2 baths, 1 car garage. Condo Unfurnished. Available July 1, 2026. Tenant Occupied until June 22, 2026. 2nd floor. Close to Beaches! Located 10 minutes to Nokomis Beach/Casey Key Beach or 15 minutes to Siesta Key Beach. Minutes by bike to Legacy Trail and Casey Key. Water, Sewer & trash included in the rent. This maintenance free community includes gated entry, resort style community pool, cabana, fitness room, and club room. The construction is concrete block, impact resistant glass windows, tile roof, and paver driveway. The community is conveniently located to Sarasota, Venice, Casey Key, the beaches, dining, shopping, the Legacy Trail, Oscar Scherer Park, and A+ Pineview School! Beautiful unit! $2300 per month 12 month minimum. Tenant Occupied until June 22, 2026.
Listing is courtesy of: EXIT KING REALTY
PINE RUN I - A4691525 - 354 PINE RUN DR, OSPREY, FL 34229 52 Days on yellowkey
$1,695 | Condo | 2 beds | 2.0 baths
This is an unfurnished 2 bedroom, 2 bathroom condo located in the Pine Run community in Osprey! This upper-level unit features vaulted ceilings, a mix of hardwood and tile flooring, and a distinctive courtyard-style layout that brings the outdoors inside. The kitchen features granite countertops, maple shaker-style cabinets with glass-front uppers, stainless steel appliances, a tile backsplash, and a peninsula with additional counter space. An eat-in area sits adjacent to a sliding glass door that opens to the private courtyard. The living room has wood-grain flooring, vaulted ceilings, and sliding glass doors opening to a balcony with treetop views. The dining area is open to the living room and shares the same vaulted ceiling. A hallway lined with sliding glass doors overlooks the private courtyard, filling the interior with natural light. The master bedroom has vaulted ceilings, sliding glass doors to a balcony, and a walk-in closet with built-in shelving. The master bathroom has a single vanity with a granite countertop and a tub/shower combination. The spare bedroom also features vaulted ceilings, sliding glass doors to a balcony, and custom built-in cabinetry with dresser drawers and upper storage. The spare bathroom has a pedestal sink and a walk-in shower. A laundry closet contains a stacked washer and dryer. The condo also features a private enclosed courtyard with a wood deck, accessible from both the kitchen and the hallway via sliding glass doors. Pine Run is set on over 20 acres of native Florida landscape in Osprey. Community amenities include two heated swimming pools, four tennis courts, pickleball courts, a fitness center, a clubhouse, and shell-covered walking trails that wind through the grounds. A community grilling area and fire pit overlooking a lake provide additional gathering spaces. Pine Run is located on Blackburn Point Road just west of U.S. 41, situated between Sarasota and Venice. The Legacy Bike Trail and Oscar Scherer State Park are nearby, and Blackburn Point Park with a kayak launch is close by. Casey Key and Nokomis Beach are a short drive away, and restaurants such as the Casey Key Fish House are nearby. Downtown Sarasota and downtown Venice are both easily accessible for shopping, dining, and cultural attractions. Please allow up to 30 days after lease signing for community approval before move-in. We score every application. If an application doesn't score high enough, the resident may be required to place the equivalent of two months' rent in a security deposit. Please be aware that leasing this property includes a non-optional Home Assistant Services Package that will cost an additional $39 per month. These services and their cost are separate from Tenant's monthly rent payment and all other payments described in the Lease or any separate Lease addendums. The Home Assistant Services offered are described in the Resident Welcome Packet which can be viewed on Sarasota Management's website.
Listing is courtesy of: SARASOTA MANAGEMENT & LEASING