Osprey, FL Homes

/43
$849,000 Pending
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229

Under contract-accepting backup offers. 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

Andrea Stultz

ENGEL + VOELKERS SARASOTA

(941) 883-9484

6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229
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/49
$3,495 total monthly price
- 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 $870,755

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 401, Osprey, FL 34229

/67
Est $585,714 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% Above List Price
- $307/SF
- 37 Days On Market
Last Sold Price $580,000

Last Listing Agent Rosalie Phillips Michael Saunders

/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
/38
$4,800 per month
- 4 Beds
- 3 Baths
- 2,290 Sq Ft
- House for Rent
956 Scherer Way, Osprey, FL 34229

Stunning 4-bedroom, fully furnished pool home backing directly to the tropical preserve of Oscar Scherer State Park in the highly desirable Woodlands at Rivendell. Enjoy privacy, serene views, and resort-style living within a beautifully maintained community featuring 400+ acres of lakes, walking trails, playground, and heated community pool. Prime location — walking distance to Pine View School

Chantelle Edalgo EXIT KING REALTY

956 Scherer Way, Osprey, FL 34229
/2
$505,025 Sold Mar 26, 2026

570 Crane Prairie Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,298 Sq Ft
- Built 2005
Last Sold Summary
- 1% Above List Price
- $220/SF
- 2 Days On Market
Current Estimated Value $499,668

Last Listing Agent Mickey Schweitzer MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC

570 Crane Prairie Way, Osprey, FL 34229

/2
Est $257,396 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
- 21% Below List Price
- $522/SF
- 0 Days On Market
Last Sold Price $325,000

Last Listing Agent Mark Lyda GENEROUS PROPERTY

/8
$2,850,000
- Land
- 0.39 Acre
- $7,307,692 per Acre
141 N Casey Key Rd, Osprey, FL 34229

Gulf-front vacant lot on Casey Key in Osprey. Buildable lot with County guidance. 107' Gulf frontage, cleared site ready for new construction. For buyers seeking to build a custom waterfront home, this Gulf-front vacant lot on Casey Key in Osprey offers a compelling opportunity in one of Sarasota County’s most sought-after coastal locations. The homesite is cleared and confirmed buildable based

Julie Larson

WHITE SANDS REALTY GROUP FL

(941) 263-0115

141 N Casey Key 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
$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 $737,746

Last Listing Agent Cathy Rustin FIRST LIGHT REAL ESTATE

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

/2
Est $220,369 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
- 17% Below List Price
- $445/SF
- 0 Days On Market
Last Sold Price $265,000

Last Listing Agent Jamie Mullis COLDWELL BANKER 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
/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
$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 $1,748,618

Last Listing Agent Mark Lyda GENEROUS PROPERTY

627 N MacEwen Dr, Osprey, FL 34229

/2
Est $93,745 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
- 4% Below List Price
- 104 Days On Market
Last Sold Price $98,000

Last Listing Agent David Babel BRIGHT REALTY

/43
$875,000
- 3 Beds
- 2 Baths
- 2,188 Sq Ft
599 Pine Ranch Rd E, Osprey, FL 34229

**EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers

Mark Lyda GENEROUS PROPERTY

599 Pine Ranch Rd E, 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
$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 $639,169

Last Listing Agent Linda Scheller COLDWELL BANKER REALTY

236 Hidden Bay Dr Unit 301, Osprey, FL 34229

/2
Est $273,910 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
- 9% Below List Price
- $264/SF
- 150 Days On Market
Last Sold Price $300,000

Last Listing Agent Peggy Olson PREMIER SOTHEBYS INTL REALTY

/57
$1,499,000 New Construction
- 3 Beds
- 3.5 Baths
- 2,913 Sq Ft
360 N Point Rd, Osprey, FL 34229

**DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen features

Mark Lyda GENEROUS PROPERTY

360 N Point Rd, 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
$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 $756,763

Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

779 Fordingbridge Way, Osprey, FL 34229

/2
Est $469,791 Not Listed For Sale

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

Last Sold Summary
- 6% Below List Price
- $308/SF
- 114 Days On Market
Last Sold Price $500,000

Last Listing Agent Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

/39
$879,000
- 3 Beds
- 3 Baths
- 2,622 Sq Ft
903 Tranquility Cir, Osprey, FL 34229

**IMPRESSIVE POOL/SPA HOME on a Desirable Corner Lot with Partial Water View** Custom-built by John Cannon and situated on an interior Cul De Sac in popular North Creek Estates, this 3-BED + Office/Den, 3 FULL BATH, 2-Car Garage residence affords wonderful privacy and features 2622sf of heated living area plus a spacious screened lanai with Heated Pool/Spa and ample covered seating area, for the

Mark Lyda GENEROUS PROPERTY

903 Tranquility Cir, 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
$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

/4
Not Listed For Sale

0 N Point Rd Unit MFRA4600038, Osprey, FL 34229
0 N Point Rd Unit MFRA4600038, Osprey, FL 34229

Last Sold Summary
- 52 Days On Market
Last Sold Price $850,000

Last Listing Agent Jennifer Arciniegas CUADRA GROUP LLC

/62
$1,695,000
- 3 Beds
- 3.5 Baths
- 4,241 Sq Ft
909 MacEwen Dr, Osprey, FL 34229

**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious

Mark Lyda GENEROUS PROPERTY

909 MacEwen Dr, 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
$1,065,000 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 $1,072,229

Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

1235 Yacht Harbor Dr, Osprey, FL 34229

/2
Not Listed For Sale

570 Blackburn Point Rd Unit C2, Osprey, FL 34229
- Built 2005
570 Blackburn Point Rd Unit C2, Osprey, FL 34229

Last Sold Summary
- 234 Days On Market
Last Sold Price $35,000

Last Listing Agent David Babel BRIGHT REALTY

/72
$550,000
- 2 Beds
- 2 Baths
- 1,932 Sq Ft
242 Hidden Bay Dr Unit 603, Osprey, FL 34229

Stunning, unobstructed views of the Intracoastal Waterway, Little Sarasota Bay, and the Gulf await from this beautiful Penthouse residence in Baypoint Vista, Osprey. Located within Hidden Bay, a gated and amenity rich community, this exceptional condo features 2 Bedrooms, 2 Bathrooms plus a versatile Den, an open floor plan, high ceilings, recessed lighting, a spacious kitchen, morning room,

Susan Retzke RE/MAX PALM

242 Hidden Bay Dr Unit 603, 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
$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 $1,002,108

Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC

142 Dory Ln, Osprey, FL 34229

/44
Est $1,095,666 Not Listed For Sale

3925 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,323 Sq Ft
- Built 2016
3925 Waypoint Ave, Osprey, FL 34229

Last Sold Summary
- 7% Below List Price
- $508/SF
- 42 Days On Market
Last Sold Price $1,180,000

Last Listing Agent Barry Bright BRIGHT REALTY

/73
$1,575,000
- 4 Beds
- 3 Baths
- 3,486 Sq Ft
20 Bayhead Ln, Osprey, FL 34229

A rare opportunity to own a significantly newer, custom-built residence inside the exclusive The Oaks Club Preserve, where most surrounding homes were built decades earlier. Completed in 2017 and set on a lakefront lot in a non-flood zone, this move-in-ready, hurricane-secure home offers a level of modern construction, privacy, and peace of mind seldom found in this exclusive community. In

Lielei Wahlmann EXP REALTY LLC

20 Bayhead Ln, 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
$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 $2,045,719

Last Listing Agent Mark Lyda GENEROUS PROPERTY

889 MacEwen Dr, Osprey, FL 34229

/65
Est $1,085,707 Not Listed For Sale

3937 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,314 Sq Ft
- Built 2016
3937 Waypoint Ave, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $519/SF
- 63 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Toni Turner Michael Saunders

Showing Results 41 - 80, Page 2 of 18

Florida Sarasota County Osprey

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