Location: Osprey
Keyword(s): Laurel Nokomis Middle
Keyword(s) Middle School: Laurel Nokomis Middle
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354 PINE RUN DR, OSPREY, FL 34229
$1,69533 Days on yellowkey MLS ID: A4691525
0 Days Off yellowkey (back on 5/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1973Community: Pine Run ISpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year:
Middle School: Laurel Nokomis Middle
Remarks: 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 (941-377-8400)
Listing Agent: Todd Roughton (941-377-8400)
293 HIDDEN BAY DR #203, OSPREY, FL 34229
$5,0002848 Days on yellowkey MLS ID: A4410764
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1568 Built: 2000 Tax: $3,620 (2021)Community: Hidden BayCondo
Taxes:$3,620
Tax Year: 2021
Remarks: AVAILABLE 2027 SEASON. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer & dryer inside unit. Nicely renovated with closet barn doors. Stainless appliances. Detached one car garage immediately in front of condo and plenty of parking. PET OKAY with owner approval and nonrefundable pet fee. Resort style community pool, heated spa, fitness room, tennis courts, reading room, BBQ area with covered bar for guests, community clubhouse with kitchen. Short distance to shores of Little Sarasota Bay, Casey Key, Siesta Key. Fishing pier. Easy commute to shopping, restaurants and more. NO CATS. OWNER HAS ALLERGIES. CALL AGENT FOR MORE INFORMATION. Rentals under 6 months are subject to Sales and Tourist tax(13%). Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received.
Listing is courtesy of: WAGNER REALTY (941-756-7800)
Listing Agent: Alba Lange (941-704-3026)
852 MACEWEN DR, OSPREY, FL 34229
$7,000314 Days on yellowkey MLS ID: A4659277
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4519 Built: 1992Community: Oaks 2 Ph 2Spa: YesSingle Family
Remarks: **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. NEW HURRICANE IMPACT SLIDING DOORS and WINDOWS; ROOF (2015). THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World. 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. **ENJOY VIEWING THE 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
4219 FRONTIER WAY #105, OSPREY, FL 34229
$2,40020 Days on yellowkey MLS ID: N6144275
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1244 Built: 2017Community: Bay Street VillageSpa: NoCondo
Remarks: 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! $2400 per month 12 month minimum. Tenant Occupied until June 22, 2026.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
293 TURQUOISE LN, OSPREY, FL 34229
$5,750871 Days on yellowkey MLS ID: A4594860
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2271 Built: 2001Community: OaksSpa: NoSingle Family
Remarks: **RARE RENTAL OPPORTUNITY (UNFURNISHED)** This STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the SECURE GATES of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. 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.
3929 WAYPOINT AVE, OSPREY, FL 34229
$4,50073 Days on yellowkey MLS ID: A4686669
0 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2115 Built: 2017Community: BaysideSpa: YesSingle Family
Elementary School: Venice Elementary
Remarks: ANNUAL RENTAL - Pristine Single family home in the highly sought after community of Bayside in Osprey. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins. Kitchen is complete with Gas Range, Oversized Island, Quartz Countertops and walk in pantry. Guest bedrooms each have en suite bathrooms too along with one powder bath! Outdoor space is remarkable from the heated pool and spa with southern exposure plus a bonus outdoor kitchen with built in Gas fireplace. Tandem 3 car garage will allow for ample storage for bikes and kayaks. Bayside is a fabulous place to be with opportunity to kayak and paddle board everyday. Bayside also has sunset lovers in mind with a private dock and waterfront sitting area perfect for evening romance. Minutes away from shopping, Venice Beach, Siesta Key Beach, Nokomis Beach and Casey Key Beach. Lots of time to go biking with the new Legacy trail and Oscar Scherer Park. Unfurnished*No smoking* 1st, last & Security for move in!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
51 MACEWEN DR #12, OSPREY, FL 34229
$2,25078 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
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
$5,000266 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)
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