Sarasota's Premier Homes
One of the most popular communities provided by {{page_data.agentName}}

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
144
# of Listings
3
Avg # of Bedrooms
$532
Avg. $ / Sq.Ft.
$1,271,277
Med. List Price

Browse Osprey Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

144 Properties Found. Page 9 of 10.

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). 11,433 sq ft per survey;117 feet on US 41, 117 feet on Columbia, 102 feet on Shumard, and 96 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

*Open to discussing concessions with any reasonable offer* Sophisticated Office Condo in Prime Osprey Location – Act Now! Seize the opportunity to elevate your business in the prestigious Gulf Coast community of Osprey, FL. Positioned strategically on Tamiami Trail (US-41) between the cultural heart of Sarasota and the pristine beaches of Venice, this exceptional office condo places you in the epicenter of business and leisure. With seamless access to major highways, airports, and ports, your company will enjoy unmatched connectivity, opening doors to endless growth and networking potential. Osprey, nestled in the thriving Sarasota County, is renowned for its dynamic business ecosystem—fostering innovation, entrepreneurship, and economic vitality. This is more than just a location; it’s a chance to become part of a forward-thinking community dedicated to success. Surrounded by lush landscapes, serene waterways, and the nearby Gulf of Mexico, your team will thrive in an inspiring and sophisticated environment. Key Features: • Reception/Waiting Room that exudes professionalism • Spacious cubicles and 2 private offices for focused productivity • 1 Executive Conference Room, ideal for high-level meetings • Convenient kitchenette/breakroom for employee comfort • 1 In-suite restrooms for added convenience • Ample parking for your team and visitors • Quarterly HOA dues: $945 Don’t miss out on the chance to secure this stunning office space in one of the region’s most sought-after locations. The demand for spaces like this is high, and opportunities this exceptional won’t last long. Invest in your business’s future today—before it's gone!
#A4648348

OSPREY

436 S TAMIAMI TRAIL C4

None Beds

None Baths

1,272 Sq.Ft.

$374,900

MLS#: A4648348

New on site today
Welcome to Bay Street Village, a gated community in the heart of Osprey offering maintenance-free Florida living in an ideal Sarasota County location. This beautifully maintained condo features two bedrooms, two bathrooms, a versatile den, and a private extended one-car garage with interior access, creating a layout that is both functional and inviting. Inside, the open-concept living and dining areas are filled with natural light and flow seamlessly into the kitchen, making the space perfect for everyday living and entertaining. The kitchen is well appointed with stainless steel appliances including a double oven, generous counter space, a center island with seating, and a walk-in pantry. The primary suite offers a peaceful retreat with a walk-in closet and an ensuite bathroom featuring dual sinks, a makeup vanity, and a walk-in shower. With a split bedroom floorplan, the spacious guest bedroom and flexible den provide plenty of options for a home office, study, or additional guest space. Step out onto the screened lanai to enjoy calming water views and the soothing sound of the fountain, an ideal spot to relax and unwind. Bay Street Village offers resort-style amenities including a heated pool with a year round temperature of 85, fitness center, and clubhouse, all just steps away. Offering gated and secured access for both vehicles and pedestrians, each building includes four dedicated guest parking spaces for guests. The community is pet friendly and located directly across from Bay Street Park, which features a dog park and playground. Outdoor enthusiasts will love the easy access to the Legacy Trail right on Bay Street, perfect for biking, jogging, or leisurely walks. The location is truly exceptional. Osprey sits between Sarasota and Venice, offering convenient access to US 41 and I-75. Nokomis Beach is just 6.5 miles away, while the world-famous Siesta Key Beach is a short drive north. Nature lovers will appreciate being close to Oscar Scherer State Park, known for its hiking trails, wildlife, and kayaking opportunities. Shopping, dining, marinas, golf courses, and healthcare are all nearby, making everyday errands and weekend plans effortless. Pine View School for the Gifted, one of the area’s most highly regarded schools serving grades 2 through 12, is located just minutes away. A low monthly fee covers exterior maintenance, insurance, roof, landscaping, gated entry, water, trash, recycling, and community amenities. With no flood insurance required, this home works beautifully as a full-time residence, seasonal retreat, or investment opportunity. Bay Street Village offers the perfect blend of location, lifestyle, and low-maintenance living in one of Osprey’s most desirable communities.
#A4678068

OSPREY

172 EXPLORER DRIVE

2 Beds

2 Baths

1,449 Sq.Ft.

$350,000

MLS#: A4678068

One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and entertaining. Elegant tray ceilings, crown molding, and 9-foot ceilings enhance the first floor living space. The flooring is a beautiful wood look tile and LVP throughout the home. Upstairs, you’ll find both bedrooms, including the primary suite with a walk-in closet. As an extra bonus, there is a two-car garage. Enjoy the community pool, or your own private hot tub. Venture out to nearby Gulf beaches, shopping, dining, Oscar Sherer State Park and the Legacy Trail. Whether you’re looking for a year-round residence or a seasonal retreat, this home is the perfect fit. Don’t miss this opportunity—schedule your showing today!
#N6140508

OSPREY

1801 HIGHLAND ROAD

2 Beds

2 Baths

1,165 Sq.Ft.

$330,000

MLS#: N6140508

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

1,430 Sq.Ft.

$325,000

MLS#: A4658738

Welcome to Bay Street Village in Osprey, where maintenance-free Florida living awaits in this gorgeous gated community. This immaculate end-unit condo features 2 bedrooms, 2 bathrooms, and a 1-car garage. The garage is located beneath the unit and offers a private interior stairway leading to your second-floor residence. Enjoy an open-concept living and dining area perfect for entertaining that flows seamlessly into the beautiful kitchen, complete with a walk-in pantry, stainless steel appliances, and ample seating around a center island. The peaceful primary suite offers a walk-in closet and an ensuite bathroom with dual sinks, a makeup vanity, and a walk-in shower. Bay Street Village provides resort-style amenities, including a sparkling pool and a fitness center, along with plenty of guest parking. The community is dog-friendly, with a fantastic dog park just a short walk outside the gate. Outdoor enthusiasts will appreciate the easy access to the Legacy Trail right on Bay Street. Pine View School for the Gifted (grades 2-12) is conveniently located on the next street. Ideally situated, Osprey is just south of Sarasota and offers easy access to Nokomis Beach and the world-famous Siesta Key Beach.
#A4676420

OSPREY

100 NAVIGATION CIRCLE NA

2 Beds

2 Baths

1,135 Sq.Ft.

$305,000

MLS#: A4676420

Charming & Versatile Home Near the Beaches! This cute and cozy, well-maintained 3-bedroom, 2-bath residence offers exceptional flexibility including a private-entrance 1-bedroom, 1-bath suite plus den—perfect for an in-law suite, guest quarters, extra bedroom or home office setup. The home features durable tile and vinyl flooring throughout, updated bathrooms with newer showers, and a bright, comfortable layout. Enjoy Florida living year-round from the screened-in lanai overlooking a spacious backyard complete with a storage shed. Additional highlights include a metal roof, exterior paint completed last year, and peace of mind knowing the home did not flood. Home has been repiped, AC Changed in (2021) Metal Roof is (2014). Ideally located 6 miles to Siesta Key or 7 miles to Nokomis Beach, Boat launch at Blackburn only 3 miles away, shopping, dining, and everyday conveniences—this charming property offers comfort, versatility, and location all in one.
#A4677419

OSPREY

2043 CORDES STREET

3 Beds

2 Baths

1,186 Sq.Ft.

$299,000

MLS#: A4677419

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

$269,999

MLS#: A4623594

This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within the Pine Run community is also good with an abundance of trees and landscaping creating a private setting from your lanai off the livingroom. You will feel like you are living in a tree house! This condo has had extensive work done in the last 6 years including ELECTRIC ON-DEMAND TANKLESS HOT WATER HEATER, NEW CUSTOM KITCHEN WITH DOVE TAIL DRAWER CHERRY CABINETS, FLOORING, PAINT, LIGHT FIXTURES, NEW BATHROOMS AND PLUMBING. Unique frosted glass sliding doors in the dinette area open to washer dryer combo plus a pantry area! Crown molding in the living and dining area give an elegant feel to the rooms, The roof, maintained by the HOA was replaced about 3 years ago. Pine run is an active, vibrant community with small clubhouse with fitness room, pickle ball, tennis and other activities just waiting for you. Come take a look! If you are comparing other condo's, this one has much to like!
#A4671600

OSPREY

232 WOODLAND DRIVE 232

2 Beds

2 Baths

1,325 Sq.Ft.

$269,900

MLS#: A4671600

One or more photo(s) has been virtually staged. Welcome to 362 Pine Run Drive, a move-in ready, modern retreat nestled in the heart of Osprey, FL. This stunning 2-bedroom, 2-bathroom home offers 1,224 square feet of thoughtfully designed living space, set on an expansive 20-acre property. Revel in the tranquility of garden views and the glow of sunsets in the distance off the rear facing deck. Looking for a little more privacy? Access a large, private outdoor area from the kitchen or off of the main hallway. Soaring ceilings and abundant natural light fill the living areas and each room opens to inviting outdoor spaces, perfect for relaxation or entertaining. The home boasts a completely updated kitchen, featuring sleek finishes and high-end appliances, along with renovated bathrooms, new flooring throughout, new ceiling fans and lighting, ensuring a contemporary and stylish living experience. As part of a vibrant community, enjoy access to two sparkling pools, tennis and pickleball courts, a state-of-the-art fitness center, and a welcoming clubhouse. Outdoor enthusiasts will appreciate the fire pit and grill area, perfect for gatherings. Conveniently located near Publix, CVS, Ace Hardware, and a variety of dining options, this property offers the perfect blend of serene living and modern convenience. Experience the best of Osprey living at 362 Pine Run Drive.
#A4672574

OSPREY

362 PINE RUN DRIVE

2 Beds

2 Baths

1,224 Sq.Ft.

$235,000

MLS#: A4672574

Tranquil Coastal Living in Pine Run 244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown Sarasota. Step inside to discover light-filled spaces, a warm neutral palette, and a welcoming open layout. The kitchen stands out with stainless-steel appliances, a stylish glass backsplash, and playful custom cabinetry that adds personality and character. A cozy breakfast nook sits beside a large window overlooking lush greenery, creating the perfect spot to start your day. The spacious living and dining areas flow naturally toward a screened lanai with vaulted wood ceilings, where you can sip coffee in the morning or unwind at sunset to the sounds of nature. Both bedrooms are roomy and inviting, with the primary suite opening directly to the lanai for that indoor-outdoor lifestyle Florida is famous for. Pine Run offers resort-style amenities in a natural, park-like setting two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and kayak storage. With 20+ acres of native trees, walking trails, and tropical landscaping, this community feels worlds away yet sits moments from Tamiami Trail, dining, marinas, and the Gulf’s turquoise waters. Highlights: • 2 Bedrooms, 2 Bathrooms, 1,325 Sq Ft • Open, light-filled interior with stylish kitchen and breakfast nook • Vaulted, wood-ceiling lanai with peaceful treetop views • Primary suite with private lanai access • Full laundry, ample storage, and designated carport parking • Low-maintenance living with exceptional amenities • Minutes to Nokomis Beach, Casey Key, and downtown Sarasota Live easy. Breathe deep. Welcome home to Pine Run.
#A4667419

OSPREY

244 WOODLAND DRIVE 244

2 Beds

2 Baths

1,325 Sq.Ft.

$225,000

MLS#: A4667419

Located West of the Trail in Sorrento Shores, Osprey, this spacious 2BR/2BA villa with a den and oversized 1-car garage offers 1,578 sq. ft. of comfortable living space. A boating community with private dock access and a heated pool just steps away, it’s perfect for boaters, kayakers, or anyone seeking the coastal lifestyle. Features include hurricane-rated windows and doors, updated kitchen and baths with granite countertops, and a private walled courtyard ideal for entertaining. Home is currently being remodeled—ideal for investors or buyers ready to finish with their own touch. Sight-unseen (“blind”) offers will not be considered. No owner financing available.
#A4669327

OSPREY

106 VILLA DRIVE 106

2 Beds

2 Baths

1,578 Sq.Ft.

$199,000

MLS#: A4669327

Price reduced
AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais add more living space. Private Paved Patio 30x14 in the back yard . You’ll get more rest and relaxation. New attached work shed with lots of extra storage space. Attached laundry with washer and dryer plus more storage space. DOG-FRIENDLY zone up to 35 pounds. HERE ARE THE DETAILS: Open floor plan with kitchen, dining area and living room spaced perfectly. All kitchen appliances are FREE. New hurricane windows throughout. Master bedroom has 2 walk-in closets and attached sparkling bathroom with bathtub. The guest bedroom has a Murphy Bed and 1 walk-in closet. Plus the hallway has a full bath. Beautifully landscaped with night lighting. THE ARBORS provides a pool, pickleball court, clubhouse with many social events for you and your fun-loving, sun-loving neighbors: parties, annual flee market, bingo, poker nights, and more and more and more . . . . You will have A SHORT DRIVE TO Walmart, Publix, drug store, restaurants, places of worship, post office and ONLY 10 MINUTES TO NOKOMIS BEACH !! The HOA fee is a low $215/month.
#A4658930

OSPREY

238 PALM AIR DRIVE

2 Beds

2 Baths

1,152 Sq.Ft.

$193,000

MLS#: A4658930

Price reduced
GREAT NEW PRICE to live like you're on vacation every day in this beautiful one bedroom, one and a half bath, FIRST FLOOR condo in the popular community of Pine Run! Step inside and you'll find a welcoming, well-designed, floor plan that is beautifully decorated throughout. The primary bedroom has a beautiful UPDATED ensuite bathroom with a new hurricane window, dual closets and a private sliding patio door to the back lanai that lets the natural light in. The half bath is also UPDATED and has granite countertops. The UPDATED kitchen has plenty of cabinets for storage, beautiful granite countertops, a pass through counter to the dining area and a new hurricane impact sliding patio door letting in more natural light and opening to a cozy private patio. The screened-in lanai runs almost the entire length of the back of the condo and is a perfect space to enjoy the warm tropical breezes and views of the lush tropical landscaping. Lovely tile flooring in every room. Two pets are welcome here! A/C and water heater new in 2021. Plus you have your own brand new in 2025 stackable washer and dryer inside this unit. This condo comes with a covered one car carport and TWO outdoor storage closets; a perfect place to store your beach chairs and bicycle! Pine Run is a resort-style community in a fabulous location in Osprey with beautiful tropical landscaping and all kinds of amenities to enjoy from the two heated community pools, pickleball and tennis courts, club house with fitness room and outdoor kayak storage racks! During the season there are plenty of fun events to fill up your calendar. Close to Nokomis beach, in a great location between Sarasota and Venice where you will find delicious waterfront restaurants, boutique shoppes, festivals golfing, fishing, boating and more. This wonderful condo is ready right NOW for you to move in, relax and start having fun!
#N6140863

OSPREY

238 WOODLAND DRIVE 238

1 Beds

1 Baths

865 Sq.Ft.

$184,900

MLS#: N6140863

This home is located in the sought-after 55+ community of The Arbors. It offers a blend of comfort, updates, and a prime location between Sarasota and Venice. Featuring 2 bedrooms, 2 bathrooms, and a newly built carport, this home is designed for easy and comfortable living. The bright and airy living room welcomes you with abundant natural light, while the primary bedroom includes a spacious walk-in closet. French doors lead to the carport, and sliding doors open onto a lovely screened lanai, perfect for relaxing or entertaining. The home boasts fresh exterior paint, giving it a fresh and well-maintained look. A huge storage room sits under the carport, providing ample space for belongings and housing the laundry facilities for added convenience. The Arbors community boasts a range of amenities including a clubhouse, heated swimming pool, recreational area, boat and RV storage, a picnic pavilion, and a shuffleboard court. Residents can engage in numerous social activities or simply relish their peaceful retreat. This charming home is ideally situated just over a mile from the picturesque Casey Key, a short drive from Nokomis Beach, Venice Beach, and the vibrant Historic Downtown Venice. Surrounded by lush parks and natural beauty, the location offers a perfect blend of convenience and tranquility. For outdoor enthusiasts, the Legacy Trail is only about two miles away by bike, providing an exceptional opportunity for scenic rides and leisurely strolls. The property is also close to Sarasota Memorial Hospital, making it a practical choice for those seeking nearby healthcare options. This is a rare opportunity to own a well-maintained home in a friendly and vibrant community. Schedule your private tour today!
#A4672438

OSPREY

216 PALM AIR DRIVE

2 Beds

2 Baths

1,055 Sq.Ft.

$164,000

MLS#: A4672438

1 ... 7 8 9 10
Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service