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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
144
# of Listings
3
Avg # of Bedrooms
$416
Avg. $ / Sq.Ft.
$951,486
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 10 of 10.

*AVAILABLE NOVEMBER 15, 2025 — PREVIEW BY APPOINTMENT ONLY* Currently occupied — showings available by appointment only. This beautifully updated 3-bedroom, 2-bathroom home, features a desirable split floor plan and a spacious 2-car garage. Offered unfurnished, with pool and yard maintenance included in the rent. HIGHLIGHTS: Open-concept layout designed for comfort, entertaining, and everyday functionality Generous screened lanai with private pool overlooking a serene natural preserve Located in a quiet, sought-after neighborhood perfect for families or professionals Zoned for top-rated schools, including Pine View School just 5 minutes away Easy access to Legacy Trail, parks, award-winning Gulf Coast beaches, shopping, dining, and more Conveniently located between Sarasota and Venice Enjoy peaceful Florida living in a home that balances privacy, location, and lifestyle. Don't miss your chance to make this your next home — schedule a private showing today!
#A4667570

OSPREY

603 PINE RANCH EAST ROAD

3 Beds

2 Baths

3,012 Sq.Ft.

$3,550

MLS#: A4667570

Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice features of the home: New Interior Paint! New Carpet! New Microwave! Irrigation System! Don't worry about maintaining the lawn/landscaping, that is included! Enjoy everything that surrounds you outside as well, such as the Legacy Trail just east of this home for walking, jogging, biking, rollerblading, strolling with your pets or whatever your outdoor activity of choice is. Just south of you is Oscar Scherer State Park for even more outdoor adventures. Just west of you is the beautiful Intracoastal Waterway & Gulf of Mexico with super soft white sandy beaches! You’re also in the company of the best schools around such as Pineview, next door to this neighborhood. Rivendell, a picturesque community known for its extensive green spaces, parks and 24 serene lakes!
#A4663790

OSPREY

1363 NEW FOREST LANE

2 Beds

2 Baths

2,307 Sq.Ft.

$3,000

MLS#: A4663790

ANNUAL/ GENTLY FURNISHED 4 BED/2.5 BATH. The home is gently furnished which will work perfectly for the family who has some furniture already. Available November1st - 9 month minimum - come stay here while your build your home. Master has a king bed with ensuite bathroom.- walk in shower, garden tub. Guest room has twin beds, 2nd guest room has a built in office and a Murphy bed. 4th bedroom is empty and could be an office or a bedroom w/ closet. There is a half bath near this room. The lanai is HUGE and has a nice tropical woods view. Centrally located - 14 minutes to the beach, 26 minutes to downtown Sarasota with all her cultural activities, 20 minutes to Venice, FL. Wifi and basic cable included. This is a non smoking house. A dog may be accepted with a pet fee. 1st month's rent, last month's rent and security needed at move in.
#A4668291

OSPREY

554 PINE RANCH EAST ROAD

4 Beds

2 Baths

2,064 Sq.Ft.

$3,000

MLS#: A4668291

***AVAILABLE NOVEMBER 2025 THRU JANUARY 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.
#A4589608

OSPREY

51 MAC EWEN DRIVE 1

1 Beds

1 Baths

623 Sq.Ft.

$2,500

MLS#: A4589608

Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment! As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows. But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh air, perfect for alfresco dining, outdoor games, or simply soaking up the sun. The screened porch provides a cozy haven for warm evenings or lazy mornings. Additional highlights include: Double garage for ample storage and parking Private and secure fenced yard Screened porch for bug-free relaxation Convenient laundry room Ample natural light throughout Don't miss this incredible opportunity to make this house your home!
#A4665305

OSPREY

305 BAY VISTA AVENUE

2 Beds

2 Baths

1,069 Sq.Ft.

$2,500

MLS#: A4665305

Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trail Osprey location with a Community pool. Close to beaches, restaurants and shopping.
#O6342686

OSPREY

1817 HIGHLAND ROAD

2 Beds

2 Baths

1,145 Sq.Ft.

$2,395

MLS#: O6342686

Take a look at this beautiful home, Clean and Move-In Ready, split plan featuring 3 bedrooms, 2 bathrooms, 1 car garage and approximately 1,462 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated. Applications are First Come First Serve basis. Possible Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!
#TB8434375

OSPREY

413 GLENWOOD AVENUE

3 Beds

2 Baths

1,462 Sq.Ft.

$2,249

MLS#: TB8434375

Stunning annual unfurnished 2 bed/2 bath ground floor condo located at Pine Run in Osprey, FL. Water, sewer/trash, lawn maintenance, washer/dryer, and pest control included. Available now for $2,200 a month. Application fee for each adult $50, association application fee of $50(10-day association approval process), $ 2,200 security deposit, and $100 administrative fee. 1 pet allowed (small to medium size) One-time non-refundable pet fee of $350. *Fico score over 600* Renters Insurance is required. Application is available on our website at aandrpropertymgmt.managebuilding.com This Beautiful community offers assigned parking, two heated swimming pools, pickleball courts, tennis courts, fitness center, and saunas. Offering close 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.
#A4664411

OSPREY

304 PINE RUN DRIVE 304

2 Beds

2 Baths

1,975 Sq.Ft.

$2,200

MLS#: A4664411

Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire stainless steel appliances. Recent renovations include updated flooring, a refreshed bathroom, and a fully fenced yard for added privacy. IMPACT WINOWS THROUGHOUT!! Enjoy outdoor living with both a side porch and a spacious rear deck—perfect for entertaining or relaxing in the Florida sunshine. The property sits on a 5,197 sq ft lot and includes central air conditioning and a separate laundry room. Located just minutes from world-renowned Gulf Coast beaches, this home blends comfort, style, and an unbeatable location. This home is located just south of Sarasota, just north of beautiful downtown Venice and minutes from the beaches! Your beach life is about to begin!
#A4660042

OSPREY

234 PATTERSON AVENUE

3 Beds

1 Baths

1,288 Sq.Ft.

$2,100

MLS#: A4660042

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