Homes in ZIP Code 34229

/55
$699,000 Pending
- 4 Beds
- 3 Baths
- 2,540 Sq Ft
146 Willow Bend Way, Osprey, FL 34229

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 146 Willow Bend Way, a custom-built residence by Vision Homes in the sought-after community of Park Trace Estates. Nestled on a large lot with a pod view, this residence combines generous living spaces with a split floor plan suited for both family and guests. Featuring four bedrooms, three full

Maria Rocha

KELLER WILLIAMS ON THE WATER S

(941) 206-2984

146 Willow Bend Way, Osprey, FL 34229
/49
$3,495 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
$925,000 Sold Apr 10, 2025

280 Hidden Bay Dr Unit 401, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,166 Sq Ft
- Built 2024
Last Sold Summary
- $427/SF
- 31 Days On Market
Current Estimated Value $875,834

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 401, Osprey, FL 34229

/53
Est $604,248 Not Listed For Sale

4421 Conchfish Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,133 Sq Ft
- Built 2017
4421 Conchfish Ln, Osprey, FL 34229

Last Sold Summary
- 1% Below List Price
- $286/SF
- 38 Days On Market
Last Sold Price $610,000

Last Listing Agent Rory McDonald PREFERRED SHORE LLC

/43
$874,900
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229

Enjoy sweeping Intercoastal water views with glimpses of the Gulf from this beautifully upgraded top-floor, end-unit residence filled with natural light, privacy, & coastal elegance. The interior features Luxury vinyl plank flooring, plantation shutters, crown molding, and higher ceilings unique to the top floor. The chef’s kitchen offers Bosch and JennAir appliances, a Liebherr split

Andrea Stultz

ENGEL + VOELKERS SARASOTA

(941) 883-9484

6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229
/33
$2,500 per month
- 2 Beds
- 2 Baths
- 1,394 Sq Ft
- House for Rent
119 Villa Dr, Osprey, FL 34229

Live the ultimate waterfront lifestyle in this beautifully maintained 2-bedroom, 2-bath canal-front home with direct boating access to the Intracoastal and the Gulf. Inside, you’ll find tile flooring throughout for a clean, cohesive look and easy maintenance. The beautifully updated kitchen features modern finishes, ample cabinetry, and generous counter space, all flowing seamlessly into the open

Jaime Barcelo GULF COAST REALTY & MANAGEMENT

119 Villa Dr, Osprey, FL 34229
/2
$727,500 Sold Feb 12, 2026

260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
- Built 2019
Last Sold Summary
- 17% Below List Price
- $336/SF
- 257 Days On Market
Current Estimated Value $790,668

Last Listing Agent Cathy Rustin FIRST LIGHT REAL ESTATE

260 Hidden Bay Dr Unit B 305, Osprey, FL 34229

/15
Est $736,333 Not Listed For Sale

148 Osprey Point Dr, Osprey, FL 34229
148 Osprey Point Dr, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- 375 Days On Market
Last Sold Price $800,000

Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

/20
$190,000
- Land
- 0.48 Acre
- $395,833 per Acre
14 Old Venice Rd, Osprey, FL 34229

**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

Mousa Wakileh

COLDWELL BANKER REALTY

(941) 770-3716

14 Old Venice Rd, Osprey, FL 34229
/48
$5,600 per month
- 3 Beds
- 2 Baths
- 2,306 Sq Ft
- House for Rent
124 Turquoise Ln, Osprey, FL 34229

Impressive three-bedroom, two-bathroom home with heated pool designed for both comfortable family living and grand-scale entertaining. High-speed internet is now included. Ideally situated on a quiet cul-de-sac in Emerald Woods at The Oaks, this gated, beautifully landscaped community features serene lakes throughout and offers a prime location just minutes from Siesta Key and the Gulf of Mexico.

Cody Smith RENT SARASOTA

124 Turquoise Ln, Osprey, FL 34229
/2
$1,750,000 Sold Oct 27, 2025

627 N MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4.5 Baths
- 3,857 Sq Ft
- Built 2000
Last Sold Summary
- 10% Below List Price
- $454/SF
- 1 Day On Market
Current Estimated Value $1,734,198

Last Listing Agent Mark Lyda GENEROUS PROPERTY

627 N MacEwen Dr, Osprey, FL 34229

/41
Est $1,131,674 Not Listed For Sale

3932 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,416 Sq Ft
- Built 2017
3932 Waypoint Ave, Osprey, FL 34229

Last Sold Summary
- 17% Below List Price
- $566/SF
- 11 Days On Market
Last Sold Price $1,367,500

Last Listing Agent Larry Brzostek RE/MAX

/74
$1,695,000
- 3 Beds
- 3.5 Baths
- 3,066 Sq Ft
25 Sugar Mill Dr, Osprey, FL 34229

METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite

Mark Lyda GENEROUS PROPERTY

25 Sugar Mill Dr, Osprey, FL 34229
/32
$3,595 per month
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Condo for Rent
280 Hidden Bay Dr Unit 202, Osprey, FL 34229

Be the first to call this brand-new condo in Edgewater at Hidden Bay home. The kitchen showcases a sleek, modern design, complemented by solid wood cabinetry and quartz countertops, creating an ideal space for both everyday living and effortless entertaining. Appliances include a stainless-steel refrigerator, microwave, range, and dishwasher. Large windows bring in an abundance of natural light

Nancy Guerrero PMI SOUTHWEST FLORIDA

280 Hidden Bay Dr Unit 202, Osprey, FL 34229
/2
$650,000 Sold Jul 03, 2025

236 Hidden Bay Dr Unit 301, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
- Built 1997
Last Sold Summary
- 13% Below List Price
- $310/SF
- 246 Days On Market
Current Estimated Value $639,960

Last Listing Agent Linda Scheller COLDWELL BANKER REALTY

236 Hidden Bay Dr Unit 301, Osprey, FL 34229

/67
Est $576,854 Not Listed For Sale

52 Bishops Court Rd Unit 113, Osprey, FL 34229
- 2 Beds
- 2.5 Baths
- 1,890 Sq Ft
- Built 1984
52 Bishops Court Rd Unit 113, Osprey, FL 34229

Last Sold Summary
- 1% Below List Price
- $307/SF
- 37 Days On Market
Last Sold Price $580,000

Last Listing Agent Rosalie Phillips Michael Saunders

/49
$1,175,000 Pending
- 3 Beds
- 2.5 Baths
- 2,735 Sq Ft
219 Keel Way, Osprey, FL 34229

Under contract-accepting backup offers. **IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including elegant Bolivian woodwork, beautiful tile floors throughout,

Mark Lyda GENEROUS PROPERTY

219 Keel Way, Osprey, FL 34229
/35
$3,795 per month
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Condo for Rent
280 Hidden Bay Dr Unit 203, Osprey, FL 34229

This second-story unit in Edgewater at Hidden Bay is ready for move-in and is furnished or unfurnished. The apartment includes 3 bedrooms, 2 bathrooms, modern finishes, and steady natural light throughout. The kitchen provides ample cabinet storage, a breakfast bar, quartz countertops, and all major appliances, including a stainless-steel refrigerator, microwave, dishwasher, and range. The open

Nancy Guerrero PMI SOUTHWEST FLORIDA

280 Hidden Bay Dr Unit 203, Osprey, FL 34229
/2
$780,000 Sold May 08, 2025

779 Fordingbridge Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,154 Sq Ft
- Built 2002
Last Sold Summary
- 1% Below List Price
- $362/SF
- 6 Days On Market
Current Estimated Value $743,624

Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

779 Fordingbridge Way, Osprey, FL 34229

/2
Est $262,922 Not Listed For Sale

51 MacEwen Dr Unit 20, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 623 Sq Ft
- Built 1990
51 MacEwen Dr Unit 20, Osprey, FL 34229

Last Sold Summary
- 19% Below List Price
- $522/SF
- 0 Days On Market
Last Sold Price $325,000

Last Listing Agent Mark Lyda GENEROUS PROPERTY

/82
$1,295,000
- 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 a

Deborah Frederick ASHTON LAKES REALTY INC

296 Pine Ranch Trail, Osprey, FL 34229
/36
$3,795 per month
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
- Condo for Rent
280 Hidden Bay Dr Unit 201, Osprey, FL 34229

WOW WOW WOW. This is a must see. Impressive upscale living!! Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space

Nancy Guerrero PMI SOUTHWEST FLORIDA

280 Hidden Bay Dr Unit 201, Osprey, FL 34229
/2
$163,000 Sold Mar 06, 2026

334 Tropic Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,143 Sq Ft
- Built 1978
Last Sold Summary
- 7% Below List Price
- $143/SF
- 2 Days On Market
Last Listing Agent Laura Guess-Fox COLDWELL BANKER REALTY

334 Tropic Dr, Osprey, FL 34229

/2
Est $237,195 Not Listed For Sale

51 MacEwen Dr Unit 13, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 595 Sq Ft
- Built 1990
51 MacEwen Dr Unit 13, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $445/SF
- 0 Days On Market
Last Sold Price $265,000

Last Listing Agent Jamie Mullis COLDWELL BANKER REALTY

/75
$2,100,000
- 4 Beds
- 5.5 Baths
- 4,346 Sq Ft
538 Dove Pointe, Osprey, FL 34229

**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

Mark Lyda GENEROUS PROPERTY

538 Dove Pointe, Osprey, FL 34229
/24
$6,000 per month
- 3 Beds
- 3.5 Baths
- 2,570 Sq Ft
- House for Rent
32 Bayhead Ln, Osprey, FL 34229

Stunning 3 bedroom, 3 1⁄2 bath professionally redesigned home in the Oaks Preserve. This exceptional property features a spacious chef’s kitchen with top-of-the-line appliances, a large prep island, quartz countertops throughout, and an open concept for ease in entertaining. The family/gathering has a panoramic view overlooking the lanai, lake and fountain. and lake with a fountain. The Owners’

Christian Higgins ANDRE LECLAIR PROPERTIES LLC

32 Bayhead Ln, Osprey, FL 34229
/2
$1,065,000 Sold Feb 20, 2026

1235 Yacht Harbor Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,698 Sq Ft
- Built 1984
Last Sold Summary
- 9% Below List Price
- $395/SF
- 30 Days On Market
Current Estimated Value $1,142,686

Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

1235 Yacht Harbor Dr, Osprey, FL 34229

/2
Est $92,636 Not Listed For Sale

570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229
- Studio
570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229

Last Sold Summary
- 5% Below List Price
- 104 Days On Market
Last Sold Price $98,000

Last Listing Agent David Babel BRIGHT REALTY

/62
$850,000
- 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
/31
$4,500 per month
- 3 Beds
- 2 Baths
- 2,367 Sq Ft
- House for Rent
1355 Southbay Dr, Osprey, FL 34229

Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three-bedroom two bath pool home is located in an active community with unmatched amenities such as an active social atmosphere, heated community pool, playground, fitness room, tennis, pickleball courts, and fishing. All for you to enjoy! Walk, bike or take your golf cart to restaurants, shopping or the

Sharon Lewis GOLF & BAY PROPERTIES LLC

1355 Southbay Dr, Osprey, FL 34229
/2
$1,050,000 Sold Jul 22, 2025

142 Dory Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,531 Sq Ft
- Built 1984
Last Sold Summary
- 12% Below List Price
- $415/SF
- 32 Days On Market
Current Estimated Value $981,176

Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC

142 Dory Ln, Osprey, FL 34229

/2
Est $1,388,162 Not Listed For Sale

5345 Trails Bend Ct, Sarasota, FL 34238
- 3 Beds
- 3 Baths
- 3,071 Sq Ft
- Built 2020
5345 Trails Bend Ct, Sarasota, FL 34238

Last Sold Summary
- $454/SF
- 0 Days On Market
Last Sold Price $1,395,000

Last Listing Agent Sara Leicht SARASELLSSARASOTA.COM

/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
/31
$1,995 per month
- 3 Beds
- 2 Baths
- 1,334 Sq Ft
- Townhouse for Rent
1755 Highland Rd, Osprey, FL 34229

Spacious duplex in Osprey with a bonus room! This Townhouse boasts 2 bedrooms and a bonus room downstairs that can be used as an office, playroom or even additional bedroom. The unit features a single car garage, washer and dryer hook ups, a screened in patio out front, an oversized living room. This community is located off us highway 41 south, right across the street from beautiful Oscar

Jennifer . STOCKTON REALTY ADVISORS LLC

1755 Highland Rd, Osprey, FL 34229
/2
$2,100,000 Sold Jan 30, 2026

889 MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 3,235 Sq Ft
- Built 1994
Last Sold Summary
- 9% Below List Price
- $649/SF
- 41 Days On Market
Current Estimated Value $2,209,120

Last Listing Agent Mark Lyda GENEROUS PROPERTY

889 MacEwen Dr, Osprey, FL 34229

/2
Est $275,316 Not Listed For Sale

153 Navigation Cir Unit 106, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2014
153 Navigation Cir Unit 106, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $264/SF
- 150 Days On Market
Last Sold Price $300,000

Last Listing Agent Peggy Olson PREMIER SOTHEBYS INTL REALTY

/63
$1,250,000
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
409 N Point Rd Unit 601, Osprey, FL 34229

**FANTASTIC GULF AND BAY VIEWS FROM THIS UPDATED 6TH-FLOOR CORNER RESIDENCE** This spacious, light-filled corner unit offers nearly 2,600 sq. ft. of living space and features 3 bedrooms plus a study/den, 3 full baths, two elevator banks, two assigned second-level parking spaces, and climate-controlled storage. Located behind the secure gates of The Oaks Preserve Country Club, this residence

Mark Lyda GENEROUS PROPERTY

409 N Point Rd Unit 601, Osprey, FL 34229
/27
$1,950 per month
- 2 Beds
- 2 Baths
- 1,184 Sq Ft
- Condo for Rent
758 Pine Run Dr Unit 758, Osprey, FL 34229

Welcome to your beautifully updated coastal retreat! This spacious 2-story condo offers 2 bedrooms, 2.5 bathrooms, and a fresh modern design throughout. Perfectly situated in a desirable community just minutes from the beach and with easy access to Blackburn Point Road, this home combines style, comfort, and convenience. Step inside to find a newly remodeled kitchen featuring shaker-style

Jaime Barcelo GULF COAST REALTY & MANAGEMENT

758 Pine Run Dr Unit 758, Osprey, FL 34229
/2
$1,405,000 Sold Jul 11, 2025

282 Shell Midden Ct, Osprey, FL 34229
- 3 Beds
- 4.5 Baths
- 3,699 Sq Ft
- Built 1992
Last Sold Summary
- 17% Below List Price
- $380/SF
- 128 Days On Market
Current Estimated Value $1,478,213

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

282 Shell Midden Ct, Osprey, FL 34229

/2
Est $458,859 Not Listed For Sale

19 Westview Dr, Osprey, FL 34229
- 2 Beds
- Built 1990
19 Westview Dr, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $308/SF
- 114 Days On Market
Last Sold Price $500,000

Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

Showing Results 41 - 80, Page 2 of 18

Florida Sarasota County Osprey 34229

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