Homes in ZIP Code 34229

/69
$749,000
- 3 Beds
- 3 Baths
- 2,267 Sq Ft
471 Park Trace Blvd, Osprey, FL 34229

Welcome to your dream home! This stunning, custom-built 3 bedroom, 3 bathroom residence perfectly blends luxury, comfort, and location for the ideal Florida lifestyle. This home is nestled in a highly sought-after neighborhood offering peace, privacy, and a vibrant community feel with low HOA fees. It is situated on an over-sized corner lot, with exceptional lake-views, and just moments from

Bill Cantrell FLORIDA HOME TEAM LLC

471 Park Trace Blvd, Osprey, FL 34229
/32
$1,750 per month
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
- Condo for Rent
1847 Highland Rd Unit 1865 Shoreland, Osprey, FL 34229

Spacious Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants. Right across Oscar Scherer State Park. Shoreland Park is down the street, where you can launch your kayak.

1847 Highland Rd Unit 1865 Shoreland, Osprey, FL 34229
/2
$395,000 Sold Jun 16, 2025
- Land
- 0.52 Acre
- $759,615 per Acre
- 30 Days On Market
109 Burney Rd, Osprey, FL 34229

Build your dream home on this HALF ACRE lot situated on a quiet dead-end street with no neighboring homes on 3 sides. This property offers a rare sense of seclusion and tranquility, perfect for those seeking a peaceful retreat. The property includes a well-maintained home with two bedrooms, one and a half bathrooms, an outdoor shower, three large sheds, two extra-long driveways, perfect for

Lori Madden MANGROVE REALTY ASSOCIATES

109 Burney Rd, Osprey, FL 34229

/41
Est $1,142,380 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,416 Sq Ft
3932 Waypoint Ave, Osprey, FL 34229

3932 Waypoint Ave, Osprey, FL 34229

/68
$1,970,000
- 4 Beds
- 4 Baths
- 3,286 Sq Ft
140 Sugar Mill Dr, Osprey, FL 34229

**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The Impressive

Mark Lyda GENEROUS PROPERTY

140 Sugar Mill Dr, Osprey, FL 34229
/21
$2,299 per month
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Condo for Rent
4248 Expedition Way Unit 4248, Osprey, FL 34229

Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Welcome home to this beautiful 3-bedroom, 2-bathroom condo in the sought after gated community of Bay Street Village! Neutral paint, ceiling fans throughout, tile flooring in the main living areas and carpet in the bedrooms make decorating a breeze!

Colbey Mason RYNTAL

4248 Expedition Way Unit 4248, Osprey, FL 34229
/2
$720,000 Sold Jun 16, 2025
- 2,320 Sq Ft
- $310/SF
- 130 Days On Market
- 4 Beds
- 3 Baths
- Built 2005
518 Luminary Blvd, Osprey, FL 34229

Discover the perfect blend of comfort and sophistication in this meticulously maintained home located in the highly desirable Willowbend community. The striking architecture of the Ashley floor plan, complete with a rare three-car garage with epoxy floor, enhances the property’s curb appeal. Enjoy peace of mind with hurricane impact-rated doors, windows and sliders throughout the residence. Step

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

518 Luminary Blvd, Osprey, FL 34229

/63
Est $1,064,931 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,115 Sq Ft
3929 Waypoint Ave, Osprey, FL 34229

3929 Waypoint Ave, Osprey, FL 34229

/68
$998,000 Open Sun 2PM - 4PM
- 4 Beds
- 3 Baths
- 3,438 Sq Ft
766 Shadow Bay Way, Osprey, FL 34229

Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized pool with a generously sized spa and ambient lighting, perfect for evening

Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

766 Shadow Bay Way, Osprey, FL 34229
/18
$1,850 per month
- 2 Beds
- 1 Bath
- 950 Sq Ft
- House for Rent
455 Pennsylvania Ave, Osprey, FL 34229

Available ~ Contact for current infoNO PETS ~ NO SMOKING Unique property has a style all its own, including native wildflower/herbal garden and beach gear. Nestled away in the ole' Florida fishing Village of Osprey is this quaint quiet FULLY FURNISHED TURN KEY 2/1 offers:~Upgraded kitchen fully equipped with all the necessary essentials, ~Stainless steel appliances

455 Pennsylvania Ave, Osprey, FL 34229
/2
$725,000 Sold Jun 13, 2025
- 2,678 Sq Ft
- $271/SF
- 75 Days On Market
- 4 Beds
- 3 Baths
- Built 2005
608 Crane Prairie Way, Osprey, FL 34229

One or more photo(s) has been virtually staged. Exceptional Opportunity on this Newly Priced Gem with stunning views and privacy! Discover your dream home in this stunning 2,678 square foot Wyndham model by Lee Wetherington, one of the largest in the maintenance-free community of Willowbend in Osprey. The owner has added improvements in excess of $150K since their purchase and has been lovingly

Linda Williams GULF SHORES REALTY

608 Crane Prairie Way, Osprey, FL 34229

/67
Est $574,412 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,890 Sq Ft
52 Bishops Court Rd Unit 113, Osprey, FL 34229

52 Bishops Court Rd Unit 113, Osprey, FL 34229

/34
$1,450,000 Open Sat 1PM - 4PM
- 5 Beds
- 3.5 Baths
- 3,481 Sq Ft
296 Pine Ranch Trail, Osprey, FL 34229

**THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of

Deborah Frederick ASHTON LAKES REALTY INC

296 Pine Ranch Trail, Osprey, FL 34229
/29
$3,995 per month
- 2 Beds
- 2 Baths
- 1,678 Sq Ft
- House for Rent
76 Bishops Court Rd Unit 116, Osprey, FL 34229

Date Available 5/15//25 end of lease 10/30/25 Luxury turnkey furnished Georgian Style Villa in beautiful, secure, gated Oaks Preserve within The Oaks Club in Osprey FL. Nestled among the live oaks and palms and native vegetation with lovely flowering annuals and perennials, this villa is one of twelve townhome and villa condominium units of the Bishopscourt Townhomes. Both en-suite bedrooms are

Fred Beles CAPITAL REAL ESTATE ENTERPRISE

76 Bishops Court Rd Unit 116, Osprey, FL 34229
/2
$235,000 Sold Jun 13, 2025
- 1,223 Sq Ft
- $192/SF
- 144 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
109 Woodland Place, Osprey, FL 34229

Welcome to 109 Woodland Place, a serene retreat nestled within the lush, natural surroundings of the Pine Run community in Osprey, Florida. This charming 2-bedroom, 2-bathroom condominium offers 1,223 square feet of thoughtfully designed living space, seamlessly blending comfort with the beauty of its environment. As you enter, you’ll be greeted by soaring ceilings and an open floor plan that

Derek Edwards KELLER WILLIAMS ON THE WATER S

109 Woodland Place, Osprey, FL 34229

/39
Est $400,995 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
103 Explorer Dr Unit A-2, Osprey, FL 34229

103 Explorer Dr Unit A-2, Osprey, FL 34229

/38
$815,000
- 3 Beds
- 2 Baths
- 2,443 Sq Ft
901 Reflection Way, Osprey, FL 34229

LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of thoughtfully designed living space, this 3-Bedroom + Office/Den, 2-Bath residence is MOVE-IN READY

Mark Lyda GENEROUS PROPERTY

901 Reflection Way, Osprey, FL 34229
/49
$2,995 per month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Condo for Rent
127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229
/2
$685,000 Sold Jun 12, 2025
- 2,203 Sq Ft
- $311/SF
- 5 Days On Market
- 3 Beds
- 3 Baths
- Built 2000
385 N Point Rd Unit 503, Osprey, FL 34229

Experience luxury coastal living in this 5th-floor condo, offering breathtaking water and Preserve views that rival those of higher floors. This residence in Meridian at The Oaks Preserve features 3 bedrooms, 3 full baths, and a dining room, all enhanced with new furnishings. Offered turnkey, all it needs is for you to move in and start living a carefree lifestyle on Florida’s gorgeous Gulf

Steve Abbe COLDWELL BANKER REALTY

385 N Point Rd Unit 503, Osprey, FL 34229

/2
Est $330,428 Not Listed For Sale
- 2 Beds
19 Westview Dr, Osprey, FL 34229

19 Westview Dr, Osprey, FL 34229

/62
$965,000
- 2 Beds
- 2 Baths
- 2,310 Sq Ft
13 Bayhead Ln, Osprey, FL 34229

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

Mark Lyda GENEROUS PROPERTY

13 Bayhead Ln, Osprey, FL 34229
/48
$2,350 per month
- 3 Beds
- 2.5 Baths
- 1,655 Sq Ft
- Townhouse for Rent
4209 Expedition Way Unit 102, Osprey, FL 34229

This lovely 3 bedroom, 2 1⁄2 bath townhome. This unfurnished unit has (2) Separate Single car garages-Storage and Parking. Located Close to Beaches, Shopping and Dining. Like New, Freshly Painted, Built in 2016. The kitchen has granite, nice cabinets, and stainless appliances. Beautiful Water View w/ fountain! Large open kitchen, dining and living room. All bedrooms are upstairs and are great

Tim Weller EXIT KING REALTY

4209 Expedition Way Unit 102, Osprey, FL 34229
/2
$1,700,000 Sold Jun 12, 2025
- 2,315 Sq Ft
- $734/SF
- 108 Days On Market
- 3 Beds
- 3 Baths
- Built 1972
525 S Shore Dr, Osprey, FL 34229

This redesigned mid-century styled 3-bedroom Bayfront home has been fully remastered with entertaining in mind. The stunning outdoor oasis says it all, with a panoramic view pool cage, a large, covered area, outdoor kitchen, and an amazing pool and spa featuring a stone waterfall and propane-fueled fire sconces. The pool cage was recently rescreened with no see um screen. Inside, the split

Andree Huffine COLDWELL BANKER REALTY

525 S Shore Dr, Osprey, FL 34229

/4
Not Listed For Sale
0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

/79
$1,500,000
- 4 Beds
- 3.5 Baths
- 3,464 Sq Ft
402 Walls Way, Osprey, FL 34229

Welcome to timeless elegance and modern comfort in The Oaks Clubside. This stunning 4-bedroom plus den/office, 3.5-bath home, built in 2014 by Todd Johnson Homes, blends country modern style with refined sophistication. Situated on an oversized .64-acre corner lot, this courtyard-style residence is designed for effortless Florida living. Step through grand double wood doors into an inviting space

Steve Abbe COLDWELL BANKER REALTY

402 Walls Way, Osprey, FL 34229
/87
$7,000 per month
- 3 Beds
- 2 Baths
- 2,143 Sq Ft
- Condo for Rent
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

This beautiful 5th Floor condo located in Blackburn Harbor Residences is now available for Season 2026! There are breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and 2 bathrooms. As you step inside the

Chrissie Cummings JENNETTE PROPERTIES INC

5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
/2
$3,525,000 Sold Jun 06, 2025
- 5,279 Sq Ft
- $668/SF
- 124 Days On Market
- 5 Beds
- 5 Baths
- Built 2007
275 Lookout Point Dr, Osprey, FL 34229

This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida’s Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property. The custom John Cannon home features a grand double

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

275 Lookout Point Dr, Osprey, FL 34229

/44
Est $1,145,632 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,323 Sq Ft
3925 Waypoint Ave, Osprey, FL 34229

3925 Waypoint Ave, Osprey, FL 34229

/69
$1,200,000
- 5 Beds
- 4 Baths
- 3,938 Sq Ft
820 Placid Lake Dr, Osprey, FL 34229

***carpet was professionally cleaned 3/26/25*** Discover this beautiful, expansive 5-bedroom, 4-bathroom home offering 3,938 sq. ft. of living space on a 10,548 sq. ft. lot. Designed for both comfort and elegance, this residence features an open-concept floor plan with crown molding throughout, custom solid wood-designed cabinets, induction oven, a glass tile backsplash, stainless steel

Ali Marks LOYD ROBBINS & CO. LLC

820 Placid Lake Dr, Osprey, FL 34229
/43
$6,000 per month
- 3 Beds
- 2 Baths
- 2,374 Sq Ft
- Condo for Rent
14041 Bellagio Way Unit 218, Osprey, FL 34229

If you're looking for a place that offers a rent to own opportunity, now is your chance! Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from the newly reopened Midnight Pass beach, and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space

Kelli Eggen COLDWELL BANKER REALTY

14041 Bellagio Way Unit 218, Osprey, FL 34229
/2
$640,000 Sold Jun 04, 2025
- 2,234 Sq Ft
- $286/SF
- 15 Days On Market
- 3 Beds
- 3 Baths
- Built 2003
519 Habitat Blvd, Osprey, FL 34229

This exquisite three-bedroom, three-bath-plus-den home by Lee Wetherington Homes exemplifies intelligent design and beauty in the community of Willowbend. The Savannah floor plan is a rare great room plan with one of the few natural gas fireplaces in the neighborhood. This is the focal point of the home with stacked flagstone and a beautiful mantel flanked in shelving. The residence features an

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

519 Habitat Blvd, Osprey, FL 34229

/65
Est $1,126,088 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,314 Sq Ft
3937 Waypoint Ave, Osprey, FL 34229

3937 Waypoint Ave, Osprey, FL 34229

/28
$199,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
218 Palm Air Dr, Osprey, FL 34229

You’ll be impressed with this delightful double wide from the moment you enter featuring 2 spacious bedrooms and 2 updated bathrooms with a total of 1120 Sq Feet built in 1979 with large shed and enclosed lanai. Being sold Furnished and Turnkey. The kitchen was totally remodeled in 2020 an island was added with new appliances in and it flows into the dining area and living room creating a large

Carlos Saramago EXIT KING REALTY

218 Palm Air Dr, Osprey, FL 34229
/41
$2,400 per month
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Condo for Rent
4214 Frontier Ln Unit 102, Osprey, FL 34229

Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Welcome to this lovely, fully furnished, 2-bedroom, 2-bathroom condo in Osprey! This condo is ready to welcome your entire family, complete with bright and airy spaces, spacious bedrooms, and a coastal vibe perfect for the ideal Florida lifestyle! Not

Colbey Mason RYNTAL

4214 Frontier Ln Unit 102, Osprey, FL 34229
/2
$1,197,000 Sold May 30, 2025
- 3,321 Sq Ft
- $360/SF
- 20 Days On Market
- 3 Beds
- 5 Baths
- Built 1991
223 Saint James Park, Osprey, FL 34229

Luxury Clubside Living at The Oaks – featuring Elegance and Comfort! Stunning Clubside residence in the upscale Oaks Club, offering the perfect blend of estate charm and modern luxury. Nestled among grand oak trees with partial lake and full golf course views, this beautifully upgraded home offers 3,321 sq ft of refined living space in one of Sarasota’s most exclusive communities. You’re

John Hockenberry RE/MAX ALLIANCE GROUP

223 Saint James Park, Osprey, FL 34229

/22
Est $307,695 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
101 Navigation Cir Unit 101, Osprey, FL 34229

101 Navigation Cir Unit 101, Osprey, FL 34229

/61
$1,395,000
- 3 Beds
- 3 Baths
- 2,545 Sq Ft
3603 N Point Rd Unit 702, Osprey, FL 34229

**MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer

Mark Lyda GENEROUS PROPERTY

3603 N Point Rd Unit 702, Osprey, FL 34229
/25
$2,250 per month
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Townhouse for Rent
184 Explorer Dr, Osprey, FL 34229

The unit is available for rent from July 15 ,2025.The minimum rental period is 3 months. The monthly rent is $2250. The tenant is responsible for electricity and internet costs. NO PETS! INCLUDED IN THE LEASE : Water, sewer. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling

Claudia Dybala DALTON WADE INC

184 Explorer Dr, Osprey, FL 34229
/2
$904,900 Sold May 30, 2025
- 2,705 Sq Ft
- $335/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 1989
336 Pine Ranch Rd E, Osprey, FL 34229

Nestled on a rare one-acre private oasis, this stunning lakefront home in Osprey offers the perfect blend of tranquility and convenience. With mature landscaping, majestic pine trees, and abundant wildlife, this is a true sanctuary—yet you're just minutes from Pine View School (Ranked #18 in the nation), Siesta Key Beach, The Legacy Trail, and US-41. Near I-75, centrally located between Venice

Marco Guadagnini PREFERRED SHORE LLC

336 Pine Ranch Rd E, Osprey, FL 34229

/40
Est $336,653 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
163 Explorer Dr Unit 103, Osprey, FL 34229

163 Explorer Dr Unit 103, Osprey, FL 34229

Showing Results 41 - 80, Page 2 of 18

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