Homes in ZIP Code 34229

/20
$190,000
- Land
- 20,908 Sq Ft
- $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
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/18
$1,850

Total Monthly Price
- 2 Beds
- 1 Bath
- 950 Sq Ft
- House for Rent
455 Pennsylvania Ave, Osprey, FL 34229

Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

455 Pennsylvania Ave, 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 $743,234

Last Listing Agent Cathy Rustin FIRST LIGHT REAL ESTATE

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

/98
Est $719,858 Not Listed For Sale

250 Hidden Bay Dr Unit A504, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
- Built 2017
250 Hidden Bay Dr Unit A504, Osprey, FL 34229

Last Sold Summary
- 17% Below List Price
- $399/SF
- 38 Days On Market
- Last Sold Price $865,000
- Jun 29, 2023
Last Listing Agent Frank Koziel, P.A. COLDWELL BANKER REALTY

/9
$2,850,000
- Land
- 16,988 Sq Ft
- $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
/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

Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! Sorry, no pets for renters. 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 for both everyday living and

Nancy Guerrero PMI SOUTHWEST FLORIDA

280 Hidden Bay Dr Unit 201, 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

/50
Est $1,086,362 Not Listed For Sale

3973 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,377 Sq Ft
- Built 2018
3973 Waypoint Ave, Osprey, FL 34229

Last Sold Summary
- 3% Above List Price
- $442/SF
- 84 Days On Market
- Last Sold Price $1,050,000
- Apr 01, 2024
Last Listing Agent Carlo Costantini DAVE JONES REALTY, LLC

/53
$1,100,000
- 5 Beds
- 3 Baths
- 3,912 Sq Ft
674 Clear Creek Dr, Osprey, FL 34229

Looking for a house within #1 US public school within a short distance? Discover this expansive 5-bedroom, 3-bathroom home with an oversized flex room, office, and almost 4,000 sq. ft. of living space, perfectly situated on a 9,017 sq. ft. lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2025), HVAC units (2019 & 2023), a new water heater (2022), fresh

Arkadiy Abdurakhmanov

United Realty Group Inc.

(941) 390-3801

674 Clear Creek Dr, Osprey, FL 34229
/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
$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

/53
Est $615,801 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% Above List Price
- $286/SF
- 38 Days On Market
- Last Sold Price $610,000
- Nov 23, 2023
Last Listing Agent Rory McDonald PREFERRED SHORE LLC

/79
$530,000
- 3 Beds
- 2.5 Baths
- 2,414 Sq Ft
562 Oak Bay Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees.The property welcomes you with a circular

Julianna Burns BERKSHIRE HATHAWAY HOMESERVICE

562 Oak Bay Dr, 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
$1,495,000 Sold Apr 14, 2026

554 Dove Pointe, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,501 Sq Ft
- Built 2002
Last Sold Summary
- $427/SF
- 2 Days On Market
Current Estimated Value $1,552,512

Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

554 Dove Pointe, Osprey, FL 34229

/15
Est $747,833 Not Listed For Sale

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

Last Sold Summary
- 7% Below List Price
- 375 Days On Market
- Last Sold Price $800,000
- Jun 28, 2024
Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

/62
$1,595,000
- 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
/46
$14,000 Per Month
- 4 Beds
- 6 Baths
- 9,081 Sq Ft
- House for Rent
854 MacEwen Dr, Osprey, FL 34229

Set on a quiet private cul-de-sac in The Oaks, this beautifully revitalized estate embodies the elegance of refined Florida living. Bright, open interiors and thoughtful updates create a welcoming flow from the chefs kitchen through the main living areas and out to the lanai, where sweeping golf course views frame the heated pool, spa, and fully equipped outdoor kitchen perfect for year-round

854 MacEwen Dr, 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

/41
Est $1,155,635 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
- 15% Below List Price
- $566/SF
- 11 Days On Market
- Last Sold Price $1,367,500
- Aug 31, 2023
Last Listing Agent Larry Brzostek RE/MAX

/63
$1,289,000
- 3 Beds
- 3.5 Baths
- 3,112 Sq Ft
156 Bishopscourt Rd, Osprey, FL 34229

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional

Joel Schemmel DOUGLAS ELLIMAN

156 Bishopscourt Rd, Osprey, FL 34229
/21
$2,300 Per Month
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Property for Rent
184 Explorer Dr Unit 184, Osprey, FL 34229

Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. 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 two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the

Claudia Dybala DALTON WADE INC

184 Explorer Dr Unit 184, 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
Est $743,774 Not Listed For Sale

402 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 3.5 Baths
- 2,887 Sq Ft
- Built 1995
402 Pine Ranch Rd E, Osprey, FL 34229

Last Sold Summary
- 24% Above List Price
- $208/SF
- 24 Days On Market
- Last Sold Price $600,000
- Apr 18, 2025
Last Listing Agent Ronnie Caron CARON REALTY INC

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

Under contract-accepting backup offers. 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

Susan Retzke RE/MAX PALM

242 Hidden Bay Dr Unit 603, Osprey, FL 34229
/27
$2,599 Per Month
- 2 Beds
- 2 Baths
- 1,500 Sq Ft
- Blackburn Bay Condos
2090 S Tamiami Trail Unit 303, Osprey, FL 34229

2090 S Tamiami Trail Unit 303, Osprey, FL 34229
/2
$4,000,000 Sold Apr 09, 2026

854 N Casey Key Rd, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 3,462 Sq Ft
- Built 1975
Last Sold Summary
- 16% Below List Price
- $1,155/SF
- 27 Days On Market
Last Listing Agent Charles Ruck POTTER TRINITY

854 N Casey Key Rd, 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
- Jun 09, 2023
Last Listing Agent Rosalie Phillips Michael Saunders

/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
/42
$5,900 Per Month
- 3 Beds
- 3 Baths
- 2,545 Sq Ft
- Condo for Rent
3603 N Point Rd Unit 602, Osprey, FL 34229

**FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite

Mark Lyda GENEROUS PROPERTY

3603 N Point Rd Unit 602, Osprey, FL 34229
/2
$155,000 Sold Apr 14, 2026

316 Tropic Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,151 Sq Ft
- Built 1979
Last Sold Summary
- 16% Below List Price
- $135/SF
- 36 Days On Market
Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

316 Tropic Dr, 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
- Jan 17, 2025
Last Listing Agent Mark Lyda GENEROUS PROPERTY

/72
$2,250,000
- 4 Beds
- 3.5 Baths
- 4,012 Sq Ft
433 E MacEwen Dr, Osprey, FL 34229

An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior

Mark Lyda GENEROUS PROPERTY

433 E MacEwen Dr, Osprey, FL 34229
/45
$3,250 Per Month
- 3 Beds
- 2 Baths
- 1,897 Sq Ft
- Annual Unfurnished 3 Bedroom 2 Bathroom Single Family Home in Osprey!
341 Bayshore Dr, Osprey, FL 34229

This fully renovated classic-style residence blends Old Florida charm with modern finishes and spacious living areas throughout. Featuring 3 Bedrooms and 2 Bathrooms, the home offers a functional layout designed for comfort and privacy. Conveniently located near Blackburn Boat Ramp with plenty of on-site parking.Just under 1900 sqft of living space, the kitchen flows seamlessly into the

341 Bayshore Dr, Osprey, FL 34229
/2
$362,500 Sold Apr 09, 2026

124 Revolution Way, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2016
Last Sold Summary
- 9% Below List Price
- $230/SF
- 47 Days On Market
Current Estimated Value $385,075

Last Listing Agent James Briley COLDWELL BANKER REALTY

124 Revolution Way, Osprey, FL 34229

/2
Est $632,696 Not Listed For Sale

610 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,431 Sq Ft
- Built 1995
610 Pine Ranch Rd E, Osprey, FL 34229

Last Sold Summary
- 3% Below List Price
- $267/SF
- 113 Days On Market
- Last Sold Price $650,000
- Apr 18, 2025
Last Listing Agent Kim Klee COLDWELL BANKER REALTY

/73
$2,395,000
- 3 Beds
- 3.5 Baths
- 4,519 Sq Ft
852 MacEwen Dr, Osprey, FL 34229

**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

Mark Lyda GENEROUS PROPERTY

852 MacEwen Dr, Osprey, FL 34229
/39
$6,950 Per Month
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
- Townhouse for Rent
101 Woodland Place, Osprey, FL 34229

Now AVAILABLE FOR LEASE PINE RUN Condominiums in OSPREY, Florida! 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed

Patrice Ivan WAGNER REALTY

101 Woodland Place, 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

/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
- Oct 07, 2024
Last Listing Agent Jamie Mullis COLDWELL BANKER REALTY

Showing Results 41 - 80, Page 2 of 18

Florida Sarasota County Osprey 34229

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