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Osprey

One of the most popular communities provided by The Graf Group of Coldwell Banker

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 The Graf Group of Coldwell Banker

130

# of Listings

2

Avg # of Bedrooms

$518

Avg. $ / Sq.Ft.

$1,136,271

Med. List Price

Browse Osprey Real Estate Listings

Under $250,000

$250,000 - $500,000

15 Properties Found. Page 1 of 1.

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental.
Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower.
Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool.
Short-term rentals are permitted, offering flexibility and excellent investment potential.
Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar.
Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

OSPREY

51 MACEWEN DRIVE 5

1 Beds

1 Baths

595 Sq.Ft.

$235,000

MLS#: A4689838

Withing the prestigious The Oaks Golf and Country Club, at the Windsor Lodge, this second-floor, maintenance-free, lakeside efficiency features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted.
As an investment, as a weekend get-away or for visiting family and friends:
Enjoy the country club lifestyle at The Oaks Club, a private, member-owned club in Osprey, Florida. Mandatory membership required with purchase as first time buyers at The Oaks. Amenities include two championship 18-hole golf courses, twelve tennis courts, four pickleball courts, a state-of-the-art Fitness/WellFit Center, croquet courts, clubhouse with three restaurants, banquet facilities, and an active social calendar.

OSPREY

51 MACEWEN DRIVE 11

1 Beds

1 Baths

623 Sq.Ft.

$235,000

MLS#: A4679180

FURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beauty and modern living. This two-bedroom, two-bath condo is nestled within the serene 20+ acres of lush native Florida landscape. As you step inside, you'll be greeted by a spacious and inviting living area, thoughtfully designed to maximize comfort and functionality. The condo offers two well-appointed bedrooms, each offering ample space. Pine Run is a vibrant community that offers a variety of amenities for your enjoyment. Take a dip in one of the two community pools, perfect for cooling off on a sunny Florida day. Stay active and engage in friendly competition on the tennis courts or try your hand at pickleball. For those who enjoy the beach, you'll be delighted to discover that the condo is less than half a mile away from the Gulf of Mexico. Spend your days basking in the warm sun, strolling along the sandy shores, or indulging in water activities. Pine Run is not just a place to live, it's a lifestyle. With its picturesque surroundings, abundant amenities, and proximity to the Gulf of Mexico, this condo offers the perfect blend of tranquility and convenience.

OSPREY

110 WOODLAND PLACE 110

2 Beds

2 Baths

1,325 Sq.Ft.

$225,000

MLS#: A4696738

Tucked away in the charming community of Pine Run, this uniquely designed two-story condo offers the perfect blend of privacy, comfort, and Florida lifestyle living in the heart of Osprey. This spacious 2-bedroom, 2-bath residence features a layout offering the primary suite on the first floor—ideal for ease of living and added privacy. The main level offers an inviting living and dining area filled with natural light, creating a warm and welcoming space for both relaxing and entertaining. The primary bedroom retreat provides generous space, ample closet storage, and a well-appointed en-suite bath. Upstairs, you’ll find a loft that is designed to be the second bedroom and full bath, perfect for guests, a home office, or seasonal visitors. The two-story design enhances privacy while maintaining an open and airy feel throughout. Pine Run is truly a hidden gem, known for its lush, mature landscaping and tranquil setting. Residents enjoy a peaceful, maintenance-free lifestyle just minutes from Gulf beaches, waterfront dining, shopping, and the cultural attractions of Sarasota. Whether you’re searching for a full-time residence or a seasonal retreat, this condo offers the ideal combination of comfort, location, and relaxed coastal living.

OSPREY

211 WOODLAND DRIVE 211

2 Beds

2 Baths

1,223 Sq.Ft.

$200,000

MLS#: A4684191

One or more photo(s) has been virtually staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and lighting. The possibilities are endless as this space can be kept for leisure or used to build an additional home. The seller invested $28,000 in fundamental upgrades, includin g: New subflooring and moisture barrier, Laminate flooring throughout main living areas and bathrooms, and Fresh carpeting in bedrooms and the Florida Room. The interior features an open floor plan with two bedrooms. The primary suite includes dual walk-in closets and a ensuite bath. This home is light and bright with a comfortable Florida Room—perfect for morning coffee or evening relaxation. A large outdoor shed offers abundant storage and includes a washer and dryer. This desirable lot is located in the pet-friendly section of the park. Monthly dues include an impressive list of amenities: access to the clubhouse, heated community pool, lawn service, water, garbage pickup, sewer, cable TV, and internet. The Seller recently spent $28,000 on a new sub floor, new moisture barrier, New laminate flooring in kitchen, dining, great room, bathrooms, and hallway. New carpet in both bedrooms and Florida room. There’s even an on-site storage area for your boats, RVs, or kayaks for a small fee! The location is unbeatable—close to Casey Key, the Legacy Trail, Walmart, shopping, restaurants and the Nokomis and Siesta Key Beaches. You’re also just a short drive from historic downtown Venice and the lively attractions of downtown Sarasota. The community also offers an active clubhouse, heated pool, dog run, shuffleboard, exercise area, and regular social events.

OSPREY

320 TROPIC DRIVE

2 Beds

2 Baths

1,199 Sq.Ft.

$195,000

MLS#: A4692490

Price reduced

**Pine View School** NO HOA** Custom House-Separate Guest House- Separate RV/Boat** Discover an exceptional opportunity to create your custom dream home in the heart of Osprey — one of Sarasota County’s most desirable coastal communities. This buildable vacant homesite offers the perfect canvas to design a private retreat tailored to your lifestyle, all while enjoying the charm, convenience, and natural beauty of Florida’s Gulf Coast. With over 7,000 square feet of buildable area on the ground level alone, the possibilities are truly expansive. Whether you envision a sprawling single-story estate or a multi-level architectural masterpiece, there is ample room to bring your vision to life. The generous footprint allows space for:
A luxurious primary residence.
A private ADU (Accessory Dwelling Unit) for guests or extended family Dedicated RV parking or a custom RV garage
Outdoor living areas, pool, and entertaining spaces. The property is graced with mature trees, providing natural shade, character, and the opportunity to design a home that blends seamlessly with the surrounding landscape. The established greenery enhances privacy and creates a serene setting that feels tucked away, yet connected. Location is everything — and this homesite delivers. Conveniently located near nationally recognized schools, the area is highly sought after for its top-tier education and strong community appeal. Residents enjoy easy access to nearby beaches, parks, boating, golf, shopping, and dining throughout Osprey, Nokomis, and Sarasota. Build without compromise. Design without limits. This is your opportunity to secure a prime homesite in Osprey and create the Florida lifestyle you’ve always imagined. Renderings are available. One of the closest buildable lots in the proximity of Pine View School!

OSPREY

14 OLD VENICE ROAD

None Beds

None Baths

0.48 acres

$175,000

MLS#: A4682477

This slip will house a boat with the maximum dimensions of 27.5'L x 11'W x 11.5'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is also an onsite boat detailing company, independent mechanic, as well as boat transporter. The marina is centrally located between Sarasota and Venice on Little Sarasota Bay. It is just minutes from Midnight Pass...the highly anticipated new opening project being reviewed by Sarasota County. Open seven days a week

OSPREY

570 BLACKBURN POINT ROAD 43

None Beds

None Baths

N/A

$115,000

MLS#: A4672823

Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in right away and make some upgrades as needed. YOU and your fellow homeowners will own the company that owns the park. it's a Co-Op park for over-55 owner residents. Therefore, everybody takes pride in keeping it wonderfully maintained and reasonably priced with low HOA dues. Better take a look before the bidding war starts.

OSPREY

348 TROPIC DRIVE

2 Beds

2 Baths

864 Sq.Ft.

$109,900

MLS#: A4668240

The slip can hold a boat with the maximum dimensions of 32.5L x 9'W x 9'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is also an onsite boat detailing company, independent mechanic, as well as boat transporter. The marina is centrally located between Sarasota and Venice on Little Sarasota Bay. It is just minutes from Midnight Pass...the highly anticipated new opening project being reviewed by Sarasota County. Open seven days a week

OSPREY

570 BLACKBURN POINT ROAD 13

None Beds

None Baths

N/A

$109,000

MLS#: A4674344

Price reduced

A rare opportunity in Osprey, FL — two adjacent residential lots, each approximately 5,916 sq ft, available individually or together for nearly 12,000 sq ft of combined space. Purchase one lot and build your ideal Florida home, or secure both lots and create either two separate residences or one expansive estate with room for your vision to unfold.

Positioned in one of Sarasota County’s most desirable areas, this location places you just minutes from Pine View School, one of the highest-ranked public schools in Florida. Outdoor recreation is unmatched with the Legacy Trail nearby for biking, walking, and running, and Oscar Scherer State Park offering 1,400 acres of hiking, kayaking, birding, and natural Florida beauty.

You’re also perfectly situated for beach lovers — enjoy quick access to Nokomis Beach, Venice Beach, and the world-renowned Siesta Key Beach, celebrated for its powder-soft quartz sand and turquoise Gulf waters.

Everyday conveniences are close at hand with shopping, dining, parks, and grocery options just minutes away, all while the lots remain tucked within a peaceful residential setting.

Build one home or two — the flexibility, location, and lifestyle make this an exceptional opportunity in the heart of Osprey. ADJACENT LOT FOR SALE TOO: MLS#N6144088 PID# 0143070065

OSPREY

GLENWOOD AVENUE

None Beds

None Baths

0.14 acres

$75,000

MLS#: N6144086

Price reduced

A rare opportunity in Osprey, FL — two adjacent residential lots, each approximately 5,916 sq ft, available individually or together for nearly 12,000 sq ft of combined space. Purchase one lot and build your ideal Florida home, or secure both lots and create either two separate residences or one expansive estate with room for your vision to unfold.

Positioned in one of Sarasota County’s most desirable areas, this location places you just minutes from Pine View School, one of the highest-ranked public schools in Florida. Outdoor recreation is unmatched with the Legacy Trail nearby for biking, walking, and running, and Oscar Scherer State Park offering 1,400 acres of hiking, kayaking, birding, and natural Florida beauty.

You’re also perfectly situated for beach lovers — enjoy quick access to Nokomis Beach, Venice Beach, and the world-renowned Siesta Key Beach, celebrated for its powder-soft quartz sand and turquoise Gulf waters.

Everyday conveniences are close at hand with shopping, dining, parks, and grocery options just minutes away, all while the lots remain tucked within a peaceful residential setting.

Build one home or two — the flexibility, location, and lifestyle make this an exceptional opportunity in the heart of Osprey. ADJACENT LOT AVAILABLE FOR SALE TOO: MLS# N6144086 PID# 0143070064

OSPREY

GLENWOOD AVENUE

None Beds

None Baths

0.14 acres

$75,000

MLS#: N6144088

Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 9.5W x 6.5H. With valet boat service, full-time staff, wash, fuel, and pump-out stations, fish cleaning tables, a bait and tackle shop, maintenance racks, picnic tables, restrooms, an on-site restaurant, deli, and ship store, its a boaters dream. Call ahead for splash, fueling, and even have your deli order waiting when you arrive. Enjoy quick access to Midnight Pass and the Venice Inlet, along with the peace of mind that comes from hurricane-safe indoor storage that could even reduce your insurance costs. Skip the storm prep, protect your investment, and enjoy effortless boating with first-class service at Osprey Harbor Village.

OSPREY

570 BLACKBURN POINT ROAD 11

None Beds

None Baths

N/A

$42,500

MLS#: A4658755

This slip will house a boat with the maximum dimensions of 35.5' length, 10' width and 6' height This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is also an onsite boat detailing company, independent mechanic, as well as boat transporter. The marina is centrally located between Sarasota and Venice on Little Sarasota Bay. It is just minutes from Midnight Pass...the highly anticipated new opening project being reviewed by Sarasota County. Open seven days a week

OSPREY

570 BLACKBURN POINT ROAD 26

None Beds

None Baths

N/A

$36,000

MLS#: A4680901

Welcome to OSPREY HARBOR VILLAGE. This boat rackominium was built as a category 3 hurricane-rated building. Store your boat out of the sun and protected from the harsh Florida weather. This 3rd-level rack measures 28'L x 12'W x 8.5'H and can accommodate a boat with dimensions of 28'L x 11'W x ~6.5'H (measure height from the keel to the highest fixed point on the boat). This rackominium features concierge service with onsite fuel, work racks, wash down service, engine flushing, bait shop (deli, drinks, fishing tackle, bait, store, etc.) There is also a pump-out station, fish cleaning tables, restrooms, and professional full-time and friendly staff! Here's how it works...Call ahead and have your boat "splashed" and fueled, arrive and enjoy your day on the water, return to the dock and the staff pulls your boat, flushes the engine(s), washes the outside, and places it back in your OWN rack for next time! Osprey Harbor Village is very close to Midnight Pass, the Venice Inlet out to the gulf, and near to many boatable restaurants and picnic islands! Take the stress out of boating. Stop trailering your boat to the ramp, and buy a boat rack out of the elements with always the prospects of future appreciation on your investment! Buy today.

OSPREY

570 BLACKBURN POINT ROAD LNG42

None Beds

None Baths

N/A

$35,900

MLS#: A4677438

Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Plus, HOA is prepaid thru the end of 2025! Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 32.5Lx10Wx6H. With valet boat service, full-time staff, wash, fuel, and pump-out stations, fish cleaning tables, a bait and tackle shop, maintenance racks, picnic tables, restrooms, an on-site restaurant, deli, and ship store, it's a boater's dream. Call ahead for splash, fueling, and even have your deli order waiting when you arrive. Enjoy quick access to Midnight Pass and the Venice Inlet, along with the peace of mind that comes from hurricane-safe indoor storage that could even reduce your insurance costs. Skip the storm prep, protect your investment, and enjoy effortless boating with first-class service at Osprey Harbor Village.

OSPREY

570 BLACKBURN POINT ROAD 38

None Beds

None Baths

N/A

$32,500

MLS#: A4681400

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