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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

Osprey is a tranquil coastal community tucked between Sarasota and Venice, offering a perfect blend of natural beauty and upscale living. Known for its peaceful vibe, top-rated schools, and access to the Intracoastal Waterway, Osprey is ideal for nature lovers and boaters. Residents enjoy quick access to parks like Oscar Scherer State Park, waterfront dining, and nearby beaches. With elegant neighborhoods, quiet streets, and a strong sense of community, Osprey is a hidden gem on Florida’s Gulf Coast.

One of the most popular communities provided by Michael Graf

145

# of Listings

3

Avg # of Bedrooms

$531

Avg. $ / Sq.Ft.

$1,267,951

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

145 Properties Found. Page 8 of 10.

This condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets from the large balcony. A private two-car garage. Three bedrooms, three full baths and 2,000 square feet of living area. The building has a new roof, the elevator was just replaced, and yet the condo dues were just reduced by $500 a quarter! The spacious screened-in balcony overlooks greenery and the Intracoastal Waterway and offers room for dining and relaxing. The gated resort-style community Hidden Bay offers a heated pool and spa, a grass-thatched tiki hut with grilling stations, a lighted tennis court plus two lighted pickleball courts. For water lovers, there is a kayak launch and a 500-yard elevated boardwalk that winds through lush mangroves. The beautifully renovated clubhouse features a catering kitchen with countertop seating, a fully stocked reading library and a fitness room. The location combines a peaceful, gated waterfront community with convenient access to nearby shopping, dining, recreation and only eight miles to Siesta Key, consistently ranked as one of the best beaches in the U.S. For cycling enthusiasts, the nearby Legacy Trail offers 20-plus miles of scenic, paved biking trails.

OSPREY

232 HIDDEN BAY DRIVE 504

3 Beds

3 Baths

2,000 Sq.Ft.

$599,000

MLS#: A4668602

This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.

OSPREY

1337 COPPERWOOD DRIVE

3 Beds

2 Baths

2,172 Sq.Ft.

$595,000

MLS#: A4666722

Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet, and two full baths. The spacious great room includes living and dining areas, elegant crown moldings, tray ceilings, built-ins and plantation shutters for timeless style. The open kitchen offers a breakfast bar, Corian countertops, and a bright breakfast nook with bay windows ideal for casual dining. Go outside to enjoy a large, fenced-in backyard with exotic palm and fruit trees, and a screened-in lanai featuring roll-down sun protection and westerly exposure, ideal for relaxing sunsets or entertaining guests. Recent updates include new roof and paint from July 2023 (transferable warranty) and a new air conditioner in May 2024. Well for irrigation. Woodlands at Rivendell is in Osprey near the top-rated Pine View School, the Legacy Trail, shopping, dining, Casey Key, kayaking, boating, and the beautiful Gulf beaches. In a preferred X flood zone with low HOA dues (only $721 semi-annually), and no CDD fees.

OSPREY

1036 OAK MEADOW LN

4 Beds

2 Baths

2,186 Sq.Ft.

$585,000

MLS#: A4669695

Price reduced

NEW PRICE • REAL OPPORTUNITY • SELLER READY.
This is your chance to secure a West of the Trail pool home in the coveted Bay Acres community at an exceptional value.
Welcome to Bay Acres—a quiet coastal enclave where classic Florida charm meets everyday livability. Positioned on a generous corner lot with a circular driveway, this 3-bedroom, 3-bath residence delivers space, privacy, and flexibility rarely found at this price point.
Inside, the split floor plan is both functional and inviting, ideal for full-time living, hosting guests, or multigenerational needs. The heart of the home opens effortlessly through large double doors to an oversized screened pool retreat, creating that true indoor-outdoor lifestyle everyone wants but few homes actually deliver. Morning coffee, evening swims, weekend gatherings—this backyard was made for it.
Each bedroom is thoughtfully placed for privacy, while the layout easily adapts to a home office, guest suite, or extended family living. The corner-lot setting enhances natural light, adds breathing room, and boosts curb appeal with mature Florida landscaping. Home was re-Plumbed 2 years ago. Bay Acres offers a rare West of the Trail lifestyle near the Intracoastal, with optional HOA membership providing access to the community dock—perfect for boating enthusiasts. You’re minutes to Nokomis Beach, Venice, Siesta Key, Pine View School, shopping, dining, and U.S. 41, making this location as practical as it is desirable. With a significant price improvement already in place, this home now represents one of the best opportunities in Bay Acres. Bring your vision, and make this coastal pool home your own.

OSPREY

315 BAYSHORE DRIVE

3 Beds

3 Baths

2,384 Sq.Ft.

$549,900

MLS#: A4671634

#A4662424

OSPREY

455 N SHORE DRIVE

2 Beds

2 Baths

1,229 Sq.Ft.

$549,000

MLS#: A4662424

New on site 3 days ago

Developer potential awaits with this exceptional opportunity to purchase just over one acre that was previously platted as 7 lots. Location has great proximity to many amenities and Pineview School. There have been some new homes built in the immediate area. Property would be ideal to replat to original 7 lots and build smaller and more affordable spec homes. There are existing older improvements on the property which have not been included in the value of the land. Survey is available.

OSPREY

34 WASHINGTON AVENUE

None Beds

None Baths

1.07 acres

$549,000

MLS#: A4677765

Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been successfully used as an investment property with substantial rental income. Recent updates include: interior renovation, new roof and pool cage rescreened (2021), pool pump (2022), HVAC (2023), water heater, well pump, and garage door opener (2024), plus automated pool cleaner and septic flush (2025). Enjoy the spacious layout, modern finishes, and resort-style outdoor living with a heated pool and screened lanai. The location is ideally situated between downtown Sarasota and Venice, with a short drive to area beaches, parks, restaurants, and shopping. Oscar Scherer State Park is directly across the street, offering birdwatching and nature trails. The Legacy Trail (Osprey Junction Trailhead) is just 3 minutes away, making this a very bike-friendly area. With no HOA and ample parking, you can bring your boat, RV, or other recreational toys-there's plenty of room to store them comfortably on the property. This property is the perfect combination of updated comfort, natural beauty, and an unbeatable location. Ideal as a full-time residence, seasonal retreat, or income-producing investment.

OSPREY

742 HARMS DRIVE

3 Beds

2 Baths

1,293 Sq.Ft.

$545,000

MLS#: A4666421

This lot and location really stands out! Set back on a quiet street, on a beautifully landscaped oversized lot, and a huge lawn in the backyard with a preserve as the backdrop, this well maintained, light-filled residence offers a rare combination of elegance, security, privacy, efficiency, value, and Florida lifestyle.

This is a rare opportunity… one of the least expensive maintenance-free homes in top-rated Osprey, and also in a renowned, upscale community - The Woodlands at Rivendell. Beautiful and quiet, yet 'everything' is minutes away,

The open floor plan features double tray ceilings, crown molding, and built-ins that create a comfortable, sophisticated atmosphere. Seamless indoor outdoor living, with 15 feet of sliding glass doors opening onto a covered patio and lanai. Enjoy nature views and stunning sunsets that are visible throughout the living area. Step through the stylish entryway and you're greeted by sunlight flooding in through custom-made plantation shutters. Large diagonal tile floors flow throughout the main living areas while cherry hardwood flooring adds elegance to the bedrooms and den. The open kitchen features expansive Corian countertops and plenty of wood cabinets for storage. There are two breakfast bars and newer high-quality appliances - all, except the Bosch dishwasher, have been replaced in the last few years. The kitchen has an RO drinking water system, and the whole home provides bottle-quality water with a Kinetico Water Softener, Activated Carbon Water filtration, and a UV light system. The dining areas bump-out design streams sunlight into the dining and kitchen areas. The master suite is a tranquil retreat, featuring a bump-out with bay windows and glass sliders to the lanai and 2 walk-in closets The ensuite bathroom has a large walk-in shower, soaking tub, and a dual sink vanity. The 2nd bedroom also has bay windows, so the room is bright with plenty of closet space, and there is a full bath just outside the bedroom door. The spacious home office features a decorative archway and dual sliding pocket doors - it could easily be converted to a nursery or 3rd bedroom. Save money with your own private irrigation well and a new 6 zone Irrigation Controller. Landscaping care is provided for only $114/mo through the Woodlands HOA. The entire HVAC (Heat & AC) unit, including a UV light to prevent bacterial growth, was replaced 4/26/22. It has been regularly maintained with a service contract and major wear components were replaced this summer . The 50-gallon electric dual element (for quick heating) water heater was replaced 2/20/23. The oversized 2 car garage features an extra refrigerator/freezer, large utility sink, wall cabinets, and pull-down stairs with plywood flooring overhead provides additional attic storage. Located between Sarasota and Venice, Rivendell offers a beautifully maintained neighborhood, designed to embrace the Florida lifestyle on close to 400 acres of parks, lakes and nature trails. Nature enthusiasts will also appreciate the close proximity to a number of recreational areas, including Oscar Scherer State Park, Myakka River State Park, Bay Street Dog Park, the Legacy Trail system, and numerous other parks for kayaking, biking, and hiking. The #1 rated grade school in FL, and #18 in the USA, (Pine View), shopping, restaurants, medical facilities, beaches, restaurants, public boat launches, golf, parks, the Legacy trail and more… it’s all right here!

OSPREY

827 PLACID LAKE DRIVE

2 Beds

2 Baths

1,875 Sq.Ft.

$544,700

MLS#: TB8412007

New on site 4 days ago

Welcome home! This GULF ACCESS, WATERFRONT condo is ready for its new owners. Fully updated, this 2 BED, 2 BATH residence with a 1 CAR GARAGE is ideally positioned at the END OF A CANAL, offering privacy, open water views, and MILLION-DOLLAR SUNSET VIEWS every night. Located within a GATED community spanning approximately 11 acres, this home delivers both serenity and an active Florida lifestyle.
Lush tropical landscaping leads to a private side entrance with an additional parking space, in addition to your one-car garage—making this one of the most special and uniquely positioned units in all of Blackburn. This intimate building of only four units sits at the end of the community marina, placing you just steps from your boat and offering a front-row seat to breathtaking sunsets. A BONUS LANAI DOOR provides direct sidewalk access, making trips to the pool, marina, or clubhouse quick and convenient.
Designed for effortless coastal living, this condo has been thoughtfully updated with FRESH NEUTRAL PAINT, LUXURY VINYL PLANK FLOORING installed in 2023, 5” BASEBOARDS, CROWN MOLDING throughout (including the lanai), PLANTATION SHUTTERS throughout (excluding sliders), and STAINLESS STEEL APPLIANCES, including a NEW MAYTAG DISHWASHER (Oct 2025). The primary suite offers exceptional storage with THREE CLOSETS, including a BONUS WALK-IN CLOSET located within the primary bathroom. Additional upgrades include REMOTE-CONTROL CEILING FANS, an EPOXIED (granite-style) garage and lanai floor, and a ONE-CAR GARAGE with BUILT-IN OVERHEAD STORAGE SHELVING.
This FINANCIALLY SOUND community offers boat slips available to rent behind the unit and a resort-style amenity package including a POOL, CLUBHOUSE, FITNESS ROOM, TENNIS COURT, PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, and beautifully maintained grounds. Residents also enjoy an active social calendar featuring water aerobics, monthly happy hours, bingo and game nights, monthly girls’ nights out, pickleball club, book club, and more.
Spend your days boating to the jetty, visiting nearby tiki bars, or beaching the boat at Snake Island—this is true FLORIDA WATERFRONT LIVING. Conveniently located near US-41, with easy access to numerous beaches, Downtown Sarasota, Downtown Venice, I-75, Sarasota Memorial Hospital Venice Campus, and all the Florida charm you could imagine.
Call today to schedule your private showing and experience this exceptional waterfront lifestyle firsthand.

OSPREY

1102 JESSIE HARBOR DRIVE 1102

2 Beds

2 Baths

1,425 Sq.Ft.

$475,000

MLS#: C7519762

PENTHOUSE CONDO IN WATERFRONT COMMUNITY!
Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for soaking up the Florida sunshine and enjoying great views.
The gourmet kitchen is a chef’s dream, offering granite countertops, wood cabinetry, stainless steel appliances, and a cozy eat-in area for casual dining. The expansive master suite boasts a private balcony, two walk-in closets, double vanities, a soaking tub, and a separate shower for ultimate relaxation.
Additional highlights include a wet bar for entertaining and three separate balconies for outdoor living. Enjoy resort-style amenities such as tennis courts, pickleball, shuffleboard, a heated pool, clubhouse, walking paths, a workout facility, and a convenient kayak launch for endless waterfront adventures. Bring your own boat and take advantage of your separately available assigned boat dock area!
When you’re ready to explore, you’ll find yourself just 10 minutes from several Gulf Coast beaches, thousands of acres of parks and preserves, and world-class shopping, dining, and fishing. Quick connections to Sarasota’s vibrant arts scene, the new Mote Marine Aquarium, Spanish Point, the Legacy Trail, and Oscar Scherer State Park are all just minutes away. All of this and you will just be 5 minutes from I-75 where the rest of the world awaits you.
Take the elevator to your nearby 2 assigned parking spots under the building.
Don’t miss your chance to own this exceptional penthouse—schedule your private showing today!

OSPREY

7303 JESSIE HARBOR DRIVE 7303

3 Beds

2 Baths

1,883 Sq.Ft.

$474,900

MLS#: D6142543

Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.

OSPREY

32 BAY AVENUE

2 Beds

2 Baths

2,148 Sq.Ft.

$463,000

MLS#: N6140978

PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in Florida, or for anyone looking to downsize without sacrificing comfort or style. Residents enjoy the best of the Florida lifestyle, with close proximity to beautiful beaches-just 2 stoplights away. Additionally, the community is near parks, arts venues, shopping, and restaurants, making it perfect for both active living and peaceful retreat. This home has been thoughtfully updated with new porcelain "wood-look" tile throughout most of the living space, a renovated guest bathroom featuring a walk-in shower, fresh interior paint, and a new roof installed in 2021. The neighborhood is located in one of Sarasota County's top school districts, with Pine View School just a few minutes away. Just a short walk up the street, the community clubhouse offers a generously sized pool, perfect for swimming and social gatherings. Whether you're seeking tranquil relaxation or active outdoor adventures, this exceptional property and community provide the perfect balance.
Notice- Some photos of the property have been Virtually Staged.

OSPREY

508 MEADOW SWEET CIRCLE

2 Beds

2 Baths

1,604 Sq.Ft.

$455,000

MLS#: A4664579

PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool

Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.
Walking distance to Casey Key Mainland (Chef Rolfs), private community Shoreland Park & Oscar Scherer State Park. Minutes away from COSTCO, Publix, Target, Richard's, YMCA Potter Park, waterfront dining (Casey Key Fish House & Tiki bar - waterfront , Spanish Point restaurant & Tiki Bar. The townhouse is close to Laurel Rd and Sarasota Memorial Hospital.

Property is managed by owner. Timely response to accommodate your needs.

Summary of amenities:

PARKING: 2-CAR TANDEM GARAGE
HOA PRIVATE COMMUNITY
1 BLOCK FROM INTERCOASTAL

SCREENED BALCONY
CEILING FANS
VAULTED CEILING
CENTRAL AIR

UPGRADED TALL CABINETS
GRANITE COUNTERTOP
STAINLESS STEEL APPLIANCES
CONVECTION RANGE/OVEN/AIRFRYER
MICROWAVE
DISHWASHER
IN-SINK DISPOSAL
SMART REFRIGERATOR

DINING ROOM & FAMILY ROOM
MASTER BEDROOM WITH WALK-IN CLOSET
MASTER BATH
GUEST BEDROOM
ADDITIONAL STORAGE IN LOWER FLOOR OR GARAGE
AIR CONDITIONING
WASHER/DRYER
SPRINKLER SYSTEM

COMMUNITY SWIMMING POOL WITH LOUNGE CHAIRS + USE OF CASEY KEY MAINLAND POOL
WALK/BIKE TO TOP RATED PINEVIEW SCHOOL, WALLMART, POST OFFICE, LEGACY BIKE TRAIL
CLOSE TO SIESTA KEY, NOKOMIS BEACH, VENICE BEACH, OSCAR SCHERER STATE PARK
HUGE FURNISHED BONUS ROOM ON FIRST FLOOR
OUTDOOR GRILL

OSPREY

1811 HIGHLAND ROAD

2 Beds

2 Baths

1,725 Sq.Ft.

$433,000

MLS#: TB8443161

Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions

Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining.

Enjoy cooking in the stylish open kitchen, complete with granite countertops and ample cabinet space. Luxury vinyl flooring runs throughout the home, adding durability and a sleek, contemporary feel.

With no HOA, CDD, or deed restrictions, this property provides true freedom and flexibility—bring your boat, RV, or other recreational vehicles with ease. The generous lot offers plenty of room for parking and outdoor enjoyment.

Don’t miss this rare opportunity to own a centrally located, low-maintenance home in a highly desirable area!

OSPREY

352 GLENWOOD AVE

3 Beds

2 Baths

1,300 Sq.Ft.

$429,500

MLS#: N6138982

Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the post office and two Tiki bars. You can launch your kayak from the private waterfront park on a protected bay with dockage for boats up to 22 feet. There is a waiting list for the dockage. Bay Acres is a non-deed-restricted neighborhood. You can park your RV or commercial vehicles on your property. Major updates include new roof, 3 years old, exterior paint 3 years, New HVAC this year, a Water treatment system recently installed and a rescreened lanai. Some interior updates have been done, but most need personal touches. This house has a new neighbor owned fence at the back of the lot and no fence at either side. The lot is large enough for a pool.

OSPREY

524 SARABAY ROAD

3 Beds

2 Baths

1,760 Sq.Ft.

$424,000

MLS#: A4676179

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