Sarasota's Premier Homes
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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

<p>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.</p>
One of the most popular communities provided by Michael Graf
149
# of Listings
3
Avg # of Bedrooms
$397
Avg. $ / Sq.Ft.
$937,100
Med. List Price

Browse Osprey Real Estate Listings

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$250,000 - $500,000

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149 Properties Found. Page 7 of 10.

Clean, well built out and maintained office condo on US41 in Osprey. The unit features bright lighting, private offices, a reception area, and a conference room. Condo property is clean and presents a professional appearance with lots of on site parking.
#A4595920

OSPREY

430 S TAMIAMI TRAIL D1

None Beds

None Baths

1,272 Sq.Ft.

$395,000

MLS#: A4595920

Excellent location! Corner lot Zoned CG (Commercial General) with 117 feet of frontage on US 41 in Osprey, just north of Bay Street. Prime area of growth in Sarasota County next to Calico Corners, Bay St., Spanish Point restaurants, Sarasota crew and Super Walmart. Perfect opportunity for your own business or investment. Great accessibility on 3 sides for ingress and egress (US 41, Shumard, and Columbia). 10,469 sq ft: 117 feet on US 41, 116 feet on Columbia, 92.5 feet on Shumard, and 88 feet on North lot line. Vacant lot: no buildings on the property. Plat map and survey on attachments. There is a bus stop on the sidewalk on 41. Listing agent is owner.
#A4638654

OSPREY

51 N TAMIAMI TRAIL

None Beds

None Baths

0.24 acres

$395,000

MLS#: A4638654

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes, all brand new, and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, newly installed luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options. Membership is required with homeownership.
#A4662898

OSPREY

51 MAC EWEN DRIVE 14

1 Beds

1 Baths

595 Sq.Ft.

$350,000

MLS#: A4662898

Escape from the hustle and bustle of the real world to the charms of Hidden Bay. Located on 12 beautiful acres on Little Sarasota Bay, this gated community offers waterfront play and relaxation. Spend your perfect day at the amenity rich community clubhouse/pool or kayaking on Intracoastal waters. This lovely two-bedroom, two-bath home is roomy and bright, offering a den/office along with a screened in back porch that overlooks the wonderful sight of native Floridian landscaping. The natural light flows from room to room in more than 1,500 square feet of living space. The split-floorplan is thoughtfully arranged with the guest suite having direct access to the 2nd bathroom. Home includes new luxury vinyl flooring and stainless steel appliances. Additional community amenities include a social-rich clubhouse, tennis and pickleball courts, kayak racks/launch and a renovated fitness center. HOA fees include the maintenance of the roof and exterior of the building along with the water, basic cable and internet. Hidden Bay offers everything you need for a Florida lifestyle while residing close to award-winning beaches, Historic Spanish Pointe, Oscar Scherer State Park and The Legacy Trail. Enjoy all of the culture and arts that Sarasota has to offer by making this home yours!
#A4628192

OSPREY

294 HIDDEN BAY DRIVE 203

2 Beds

2 Baths

1,683 Sq.Ft.

$324,900

MLS#: A4628192

Location, Lifestyle, and Peace of Mind — All in One! Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low maintenance living. Step inside and be greeted by an inviting open-concept floor plan designed for modern living. Soaring ceilings, abundant natural light, and a thoughtful split-bedroom layout create the perfect blend of spaciousness and privacy. The heart of the home — a stunning chef’s kitchen — features granite countertops, stainless steel appliances, and a center island with seating, making it ideal for everyday meals or casual entertaining. Enjoy the convenience of an in-unit laundry room and the luxury of a primary suite retreat complete with a walk-in closet and a spa-inspired en-suite bath with dual vanities. Added bonuses include a whole-house water softener and a covered, screened patio overlooking lush gardens and swaying palm trees — your personal oasis. And for those with little ones or furry friends? The spacious side yard offers the perfect spot for play and relaxation. Resort-style living is yours with amenities including a heated pool, fitness center, and clubhouse. The attached garage with the longest driveway in the community, easily accommodating up to 4 cars, plus extra guest parking conveniently located right across the street. Even better — Bay Street Park, complete with a dog park and playground, is just steps away from the entrance. Unbeatable Sarasota/Venice Location! Ideally located between Sarasota and Venice, with easy access to US 41, I-75, Siesta Key, Nokomis Beach (just 6.5 miles!), the Legacy Trail, and Oscar Scherer State Park. Top-rated schools, golf courses, marinas, shopping, dining, and healthcare are all close by. With a low $460 monthly fee that covers exterior maintenance, insurance, roof, landscaping, gates, water, and amenities — and NO flood insurance required — this home is a smart choice for full-time living, a seasonal escape, or a savvy investment. Don’t miss your chance — schedule your private tour today!
#A4658738

OSPREY

116 NAVIGATION CIRCLE 106

3 Beds

2 Baths

1,511 Sq.Ft.

$319,000

MLS#: A4658738

Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minutes to the pristine shoreline of Nokomis Beach. This desirable gated community features a resort style heated pool, clubhouse and a fitness center designed to enhance your Florida life style. Enjoy local dining, shopping, and many arts and cultural attractions. This second floor meticulously maintained 2-bedroom/2-bathroom condo has an open floor plan and has an abundance of natural light. The kitchen is a chef's delight with rich dark wood cabinetry, granite countertops, stainless steel appliances, a walk-in pantry and a ample breakfast bar. The spacious dining area is adjacent and is perfect for casual dining or entertaining. The living room is comfortable for relaxing. Step onto a screened lanai; perfect for a peaceful morning or a wind down at the end of the day. Primary suite includes a walk-in, linen closet and an ensuite bathroom. Bathroom is complete with dual sinks, makeup vanity and a large shower. The second bedroom has a sizable closet and full bathroom nearby. The second bathroom comes complete with a shower/tub combo. The laundry room is conveniently located in the hallway near bedrooms. Included is an attached one car garage with an additional storage room. Perfect for full time residence, seasonal enjoyment or as an investment property.
#A4656830

OSPREY

4267 EXPEDITION WAY

2 Beds

2 Baths

1,219 Sq.Ft.

$310,000

MLS#: A4656830

Charming 2 Bedroom 2 Bath corner end unit( which provides extra natural light) condominium with attached 1 car Garage. Open floor plan, Kitchen features granite counter tops and stainless steel appliances, master bedroom suite has walk-in closet private bath with double vanity. Dining Room opens to enclosed balcony. Quality construction concrete block building with impact resistant glass windows, tile roof,and paver brick driveway. Bay Street Village is a Gated maintenance free complex featuring a Resort style Swimming Pool , fitness room, and Clubhouse This pet friendly complex is located across the street from Osprey Dog Park and easy access to the Legacy Trail great for biking, jogging, and leisurely walks. Fantastic location near shopping , dining, Oscar Scherer Park, and just a short drive to Siesta Key and Nokomis Beaches and A+ Pineview School is just 1 Minute away. A Great Place to spend the Season or a Lifetime. Welcome Home!!!
#A4648458

OSPREY

232 EXPLORER DRIVE 15

2 Beds

2 Baths

1,219 Sq.Ft.

$299,500

MLS#: A4648458

New on site 2 days ago
Nestled in a nature enthusiast’s haven is an architecturally stunning community. Located halfway between the cultural, shopping & culinary meccas of Sarasota & Venice you find the uniquely contemporary community of Pine Run. The community offers Tennis & Pickleball courts, Fitness center, two heated pools, Saunas and an exquisite club house. This ground floor unit offers dual zone A/C, in unit washer dryer, an abundance of natural light and is turnkey. The private courtyard and covered outdoor space is amazing for dining alfresco. Another unique characteristic of this residence is the rare amenity of a deeded, covered carport that offers ample extra storage. All this is located just minutes from some of the most stunning beaches in the world.
#N6140309

OSPREY

707 PINE RUN DRIVE

2 Beds

2 Baths

1,577 Sq.Ft.

$299,000

MLS#: N6140309

LIMITED SUPPLY LEFT IN PINE RUN - MOTIVATED SELLER - Your Opportunity To Add Your Personal Touch! Charming Coastal Retreat in the Heart of Osprey Welcome to 304 Pine Run Dr., a beautifully architecturally designed property nestled in the sought-after Pine Run community in Osprey, FL. Surrounded by lush tropical landscaping and just minutes from the Gulf Coast’s pristine beaches, this residence offers the perfect blend of tranquility and convenience. Step inside to discover an open and airy floor plan with abundant natural light, high ceilings, and tasteful finishes throughout. The owner has made major updates to the back entertaining room by increasing square feet. They also used hurricane windows and sliders along with heavy duty installation in the walls and ceiling. It's the only unit in Pine Run that offers this floor plan. The spacious living area flows seamlessly into the kitchen and dining spaces, making it perfect for entertaining. Enjoy cooking in the updated kitchen, featuring stainless steel appliances, modern cabinetry, and ample counter space. The primary suite serves as a private retreat with a generously sized walk-in closet and an en-suite bathroom. Additional bedrooms provide plenty of space for guests or a home office. Step outside to your private atriums, where you can unwind and take in the serene surroundings of this nature-inspired community. Pine Run residents enjoy access to an array of amenities, including two heated sparkling pools, pickleball courts, tennis courts, a fitness center, Saunas and a clubhouse. This location is ideal for outdoor enthusiasts, offering proximity to Oscar Scherer State Park, Legacy Trail, and the Gulf’s stunning beaches. Shopping, dining, and cultural attractions in Venice and Sarasota are just a short drive away. Whether you’re seeking a year-round residence or a seasonal getaway, this home offers an exceptional opportunity to embrace the coastal lifestyle. Don’t miss your chance—schedule your private showing today!
#A4636298

OSPREY

304 PINE RUN DRIVE

2 Beds

2 Baths

1,975 Sq.Ft.

$279,000

MLS#: A4636298

AMENITIES? YES! Reduced just in time for Snow Bird Season! You can have Floridas #1 Amenity a Boat Slip available to you 365 Days a year. Access to the Intracoastal and the Blue waters of the Gulf of Mexico in minutes. No association pool but you can put in your own! Nokomis Beach and the famous Drum Circle is 5 minutes away with shops and restaurants close by in downtown Venice. Take a look inside the Villa is completely updated. All new LVPF throughout, upgraded stainless appliances, granite counters and all new cabinets. Property Trends Open floor plan. Split bedroom floor plan with well appointed ensuites. Ready to buy now?
#TB8367998

OSPREY

208 VILLA DRIVE 208

2 Beds

2 Baths

1,389 Sq.Ft.

$275,000

MLS#: TB8367998

Welcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bath condo located in the sought-after Pine Run community. It is completely turnkey; all you need to bring are your clothes! This second-floor unit has been tastefully updated and comes equipped with everything you need to move right in, including all furniture, beds, bedding, all kitchenware, appliances, and even recreational items like beach chairs, coolers, and two bicycles. The 9-ft high ceiling gives you an open, airy feel. The unit has been updated throughout and re-plumbed for peace of mind. The two separate en-suite bedrooms are spacious and have their own patio decks and patio furniture for added privacy. The kitchen boasts solid wood cabinets, granite countertops, a cozy dinette area and it opens to a formal dining room, along with a comfortable living room that opens to a covered screened porch. Elegant upgrades include engineered hardwood scraped hickory flooring, designer light fixtures and fans, profiled baseboards and custom blinds. There’s ample storage with a deeded covered carport, two storage lockers and an easily accessible attic. Pine Run spans 20 acres of lush, tropical landscaping and offers an array of amenities to enhance your lifestyle. There are two heated pools, with one conveniently located just steps from the unit, pickle ball, tennis courts, walking trails, kayak rack storage for easy access to water adventures, and a main clubhouse with a fitness center for social gatherings. Situated just a mile from the iconic Casey Key Road and only two miles from Nokomis Beach, this condo offers the perfect blend of tranquility and convenience. Sarasota Airport is just 17 miles away, making travel a breeze. Across the street, you’ll find everything you need for daily living, including a Publix grocery store, hardware, salon, specialty retailers, fitness center, bike rental store & medical services. For dinner and entertainment take a leisurely stroll to the new Deep Lagoon restaurant or enjoy live music at the popular Casey Key Fish House and Tiki Bar. Six additional restaurants are within walking distance, offering a variety of dining options. The Legacy Bike Trail, area state parks and public beaches are all nearby. Whether you’re looking for a vacation retreat or a full-time residence, this condo offers everything you need to enjoy Florida living at its best. Do not miss out on this incredible opportunity to own a piece of paradise in one of the most desirable locations on the Gulf coast. Pine Run is nestled between Sarasota and Downtown Venice and is 7 miles away from the famous Siesta Key Beach, voted the #1 beach in the U.S.
#A4610314

OSPREY

207 WOODLAND DRIVE 207

2 Beds

2 Baths

1,483 Sq.Ft.

$269,999

MLS#: A4610314

This home was professionally inspected by a Contractor following Hurricanes Helene and Milton, and I’m pleased to report it sustained no damage from the storms. Welcome to this beautifully updated, spacious 2-story condo, boasting 2 bedrooms, 2.5 bathrooms, and updated modern finishes throughout. Nestled in a desirable community, you'll be just minutes from the beach, with easy access to Blackburn Point Road. The newly remodeled kitchen features sleek shaker-style cabinets, brand new stainless steel appliances (including a refrigerator, stove, dishwasher, and microwave), and stunning 3mm granite countertops. The open-concept living area is perfect for entertaining, with new water-resistant engineered laminate flooring throughout. Both bedrooms are generously sized with their own private patio, and the 2.5 bathrooms have been stylishly updated with new vanities, tile surrounds, and fixtures. You'll appreciate the convenience of washer/dryer hookups, with the existing unit in good shape. This 2 story condo is maintained by a well-managed HOA, which covers water, sewer, trash, and more. The property is connected to city utilities, ensuring worry-free living. Central A/C and hot water heater information will be provided upon request. Don't miss this opportunity to own a fully updated, move-in-ready, very unique condo in an incredible location! With its proximity to the beach, this property is perfect for those seeking a comfortable coastal lifestyle. Schedule your showing today!
#T3541882

OSPREY

758 PINE RUN DRIVE 758

2 Beds

2 Baths

1,184 Sq.Ft.

$256,500

MLS#: T3541882

Looking for an active lifestyle community within walking distance of the Intercoastal? Pine Run is the perfect location! Conveniently located between Sarasota and Venice in Osprey, this community is within walking distance of the famed Casey Key Fish House and Tiki Bar, plus many other restaurants, shopping areas, public boat launch, park and so much more! The Legacy Trail is also nearby! Pine Run offers two swimming pools, a small club house with fitness room, pickle ball and tennis courts, all in a wooded setting. This 2nd floor condo has been updated with a new kitchen with quartz counter tops and new stainless steel appliances. The A/C is brand new in 2025! Each of the two bedrooms have their own private balcony. The master suite with full bath, plus two closets! The living room and dining room feature sliding glass doors that lead to the screened balcony. The laundry closet is located in the kitchen and dinette area with washer and dryer included. There is a carport with one designated parking spot. Two exterior storage units
#A4660278

OSPREY

216 WOODLAND DRIVE 216

2 Beds

2 Baths

1,483 Sq.Ft.

$245,000

MLS#: A4660278

New on site 2 days ago
Hidden away in Osprey is the private oasis of Pine Run. You could not find a more natural setting and fantastic location, convenient to Sarasota, Venice and Gulf beaches. This immaculate, ground floor condo is being sold furnished so settling in will be easy. The updated kitchen with stainless appliances is large enough to incorporate dine-in eating, and a laundry closet with full size washer and dryer. A generously proportioned living/dining area leads to the private covered lanai with garden view. The master bedroom has a private en-suite bath and walk-in closet. Other outdoor spaces include a paved courtyard just off of the kitchen and a private interior courtyard with gazebo that can be accessed from the living room and master bedroom. Large sliders in every room allow lots of light in and you'll love the feel of sea breezes passing through when all are opened. Two exterior storage closets provide ample storage. Pine Run is a pet friendly haven for artists and the active; sitting on 20+ lushly vegetated acres, with 2 heated pools; clubhouse overlooking a lagoon teeming with wildlife; tennis; pickle ball; brick patio with fire pit; kayak storage; saunas and fitness room. The community's location is ideal: West of the Trail, near shopping/banking/medical services, parks, public beaches, nationally acclaimed Pine View School, and casual and fine dining. The Legacy Bike Trail and Blackburn Point Park with a kayak launch are minutes away and Nokomis Public Beach is a quick, convenient drive. The popular Casey Key Fish House & Tiki Bar and other waterfront dining, all within a short distance.
#A4663760

OSPREY

111 WOODLAND PLACE

2 Beds

2 Baths

1,474 Sq.Ft.

$245,000

MLS#: A4663760

Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens. Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and the tranquil beauty of Selby Gardens. How this property stands out: Low Taxes: Keep more money in your pocket with low property taxes, making this an affordable investment. No HOA: Enjoy the freedom to design and build your dream home without any restrictive's rules or fees. No CDD Fees: With no community development district fees, giving you more financial freedom in your new property. Perfectly positioned near some of Osprey’s most treasured landmarks, this land offers you a unique lifestyle. Imagine living just minutes from the serene shores of Sarasota Bay, where you can explore the historic Spanish Point or enjoy peaceful afternoons at Selby Gardens. Plus, you're close to the Legacy Trail for biking and hiking, and a short drive to Sarasota’s beaches, dining, and shopping. Whether you're an investor, builder, or homebuyer seeking the perfect place to bring your vision to life, this land offers endless possibilities. Don’t let this chance slip away—build your future in one of Florida’s most desirable and scenic locations! Claim your slice of paradise now—this opportunity won’t last!
#A4623594

OSPREY

456 WASHINGTON AVENUE

None Beds

None Baths

0.13 acres

$239,999

MLS#: A4623594

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