Osprey, FL homes for sale & real estate

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ABOUT THIS HOME
Osprey, FL Homes for Sale
One or more photo(s) has been virtually staged, AI generated or rendered. ONE OF A KIND HOME LAKE FRONT HOME! Welcome to a home where timeless elegance meets the natural beauty of Florida's Gulf Coast. Nestled within the highly sought-after Rivendell community in Osprey, this beautifully refreshed residence offers an exceptional combination of comfort, privacy, and lifestyle. Perfectly positioned on a tranquil lake with a picturesque preserve beyond, the peaceful setting creates a daily backdrop of breathtaking sunrises, abundant wildlife, and year-round outdoor enjoyment. From the moment you enter, soaring ceilings, abundant natural light, create an inviting atmosphere that feels both warm

$749,900

3 beds3 baths2,621 sq ft

1117 Mill Pond Ct, Osprey, FL 34229

Tranquil lake • New a/c system • Picturesque preserve

FOR SALE BY OWNER

ABOUT THIS HOME
Osprey, FL Homes for Sale
Opportunity Lot in Oaks Preserve at The Oaks Club . 56 acres with HOA approved plans to build a stunning home and a front yard of more than 300 feet. With no time requirements for building after purchase and the freedom to select a builder. Membership to The Oaks Club is required, and offers access to an exclusive array of amenities - including two championship 18-hole golf courses, 12 Har-Tru Hydro Grid tennis courts, a heated Junior Olympic pool, playground and professional croquet court. A magnificent, 42,000 sq. ft. clubhouse includes dining venues for every occasion and a variety of social activities. The ultimate backdrop for your country club lifestyle today.

$565,000

— beds— baths— sq ft

342 N Point Rd, Osprey, FL 34229

Hoa approved plans • 42 • Listed 2 days

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Osprey, FL Homes for Sale
Discover one of Osprey's best-kept secrets-The Cottages of Rivendell. Tucked away within The Woodlands of Rivendell, offers a lifestyle that is becoming increasingly rare. Towering oak trees create a tranquil, park-like setting, while charming front porches, white picket fences, and classic Old Florida architecture give the neighborhood its unmistakable character. This beautifully maintained 3/2 home welcomes you with an expansive great room featuring an elegant tray ceiling, creating a wonderful sense of openness. Enjoy peace of mind with numerous recent updates, including a new roof (2022), HVAC system (2025), water heater (2026), exterior paint (2026), a separate AC system for the garage

$595,000

3 beds2 baths1,731 sq ft

547 Meadow Sweet Cir, Osprey, FL 34229

Exterior paint • Clubhouse • Water heater

FOR SALE BY OWNER

ABOUT THIS HOME
Osprey, FL Homes for Sale
NEW ROOF, IMPACT WINDOWS & amp; DOORS, 3 NEW AIR CONDITIONERS, NEW MASTER BATH, NEW LIGHTING AND FLOORING

$1,000,000

3 beds3 baths1,869 sq ft

226 Saint James Park, Osprey, FL 34229

New lighting • New master bath • New flooring

ABOUT THIS HOME
Osprey, FL Homes for Sale
Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted. Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property feat

$630,000

4 beds2 baths2,186 sq ft

1036 Oak Meadow Ln, Osprey, FL 34229

Renovated floor plan • Community pool • New tile roof

Property at 299 Turquoise Ln, Osprey, FL 34229, 3 beds, 2 baths

$739,000

3 beds2 baths2,328 sq ft

299 Turquoise Ln, Osprey, FL 34229

Property at 916 Macewen Dr, Osprey, FL 34229, 5 beds, 7.5 baths

$1,900,000

5 beds7.5 baths5,986 sq ft

916 Macewen Dr, Osprey, FL 34229

Property at 329 Bay Vista Ave, Osprey, FL 34229, 2 beds, 2 baths

$419,000

2 beds2 baths1,346 sq ft

329 Bay Vista Ave, Osprey, FL 34229

Property at Undisclosed address, Osprey, FL 34229, 4 beds, 3 baths

$799,000

4 beds3 baths2,607 sq ft

Undisclosed address, Osprey, FL 34229

Property at 701 Pine Run Dr #701, Osprey, FL 34229, 1 bed, 1 bath

$172,000

1 bed1 bath586 sq ft

701 Pine Run Dr #701, Osprey, FL 34229

Property at 260 Hidden Bay Dr #402, Osprey, FL 34229, 3 beds, 2.5 baths

$775,000

3 beds2.5 baths1,950 sq ft

260 Hidden Bay Dr #402, Osprey, FL 34229

Property at 75 Osprey Point Dr, Osprey, FL 34229, 4 beds, 4 baths

$1,649,000

4 beds4 baths4,001 sq ft

75 Osprey Point Dr, Osprey, FL 34229

Property at 1495 Landview Ln, Osprey, FL 34229, 3 beds, 2 baths

$775,000

3 beds2 baths2,474 sq ft

1495 Landview Ln, Osprey, FL 34229

Property at 206 Four Knot Ln, Osprey, FL 34229, 3 beds, 2 baths

$1,790,000

3 beds2 baths2,411 sq ft

206 Four Knot Ln, Osprey, FL 34229

Property at 212 Washington Ave, Osprey, FL 34229, 3 beds, 2 baths

$420,000

3 beds2 baths1,478 sq ft

212 Washington Ave, Osprey, FL 34229

Property at 780 Sarabay Rd #16, Osprey, FL 34229, 2 beds, 2 baths

$425,000

2 beds2 baths1,574 sq ft

780 Sarabay Rd #16, Osprey, FL 34229

Property at 108 Woodland Pl #108, Osprey, FL 34229, 2 beds, 2 baths

$285,000

2 beds2 baths1,316 sq ft

108 Woodland Pl #108, Osprey, FL 34229

Property at 4213 Expedition Way #107, Osprey, FL 34229, 3 beds, 2 baths

$317,000

3 beds2 baths1,430 sq ft

4213 Expedition Way #107, Osprey, FL 34229

Property at 2309 Jessie Harbor Dr #2402, Osprey, FL 34229, 3 beds, 2.5 baths

$497,000

3 beds2.5 baths2,006 sq ft

2309 Jessie Harbor Dr #2402, Osprey, FL 34229

Property at 173 Navigation Cir #107, Osprey, FL 34229, 3 beds, 2 baths

$319,500

3 beds2 baths1,528 sq ft

173 Navigation Cir #107, Osprey, FL 34229

Property at 4429 Conchfish Ln, Osprey, FL 34229, 3 beds, 2 baths

$510,000

3 beds2 baths2,004 sq ft

4429 Conchfish Ln, Osprey, FL 34229

Property at 1361 New Forest Ln, Osprey, FL 34229, 3 beds, 2 baths

$535,000

3 beds2 baths2,074 sq ft

1361 New Forest Ln, Osprey, FL 34229

Property at 97 Sugar Mill Dr, Osprey, FL 34229, 5 beds, 5.5 baths

$1,950,000

5 beds5.5 baths4,885 sq ft

97 Sugar Mill Dr, Osprey, FL 34229

Property at 347 Bayshore Dr, Osprey, FL 34229, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths2,216 sq ft

347 Bayshore Dr, Osprey, FL 34229

Property at 480 Oriskany Ct, Osprey, FL 34229, 3 beds, 3.5 baths

$1,500,000

3 beds3.5 baths3,208 sq ft

480 Oriskany Ct, Osprey, FL 34229

Property at 156 Bishops Court Rd, Osprey, FL 34229, 3 beds, 3.5 baths

$1,289,000

3 beds3.5 baths3,112 sq ft

156 Bishops Court Rd, Osprey, FL 34229

Property at 1527 Buoy Ln, Osprey, FL 34229, 3 beds, 2.5 baths

$1,165,000

3 beds2.5 baths2,830 sq ft

1527 Buoy Ln, Osprey, FL 34229

Property at 759 Fordingbridge Way, Osprey, FL 34229, 4 beds, 3.5 baths

$715,000

4 beds3.5 baths2,950 sq ft

759 Fordingbridge Way, Osprey, FL 34229

Property at 313 Lookout Point Dr, Osprey, FL 34229, 4 beds, 4.5 baths

$5,999,999

4 beds4.5 baths5,337 sq ft

313 Lookout Point Dr, Osprey, FL 34229

Property at 570 Blackburn Point Rd #36, Osprey, FL 34229

$99,500

— beds— baths— sq ft

570 Blackburn Point Rd #36, Osprey, FL 34229

Property at 116 Woodland Pl #116, Osprey, FL 34229, 2 beds, 2 baths

$254,900

2 beds2 baths1,325 sq ft

116 Woodland Pl #116, Osprey, FL 34229

Property at 360 N Point Rd, Osprey, FL 34229, 3 beds, 3.5 baths

$1,495,000

3 beds3.5 baths2,913 sq ft

360 N Point Rd, Osprey, FL 34229

Property at 674 Clear Creek Dr, Osprey, FL 34229, 5 beds, 3 baths

$1,100,000

5 beds3 baths3,912 sq ft

674 Clear Creek Dr, Osprey, FL 34229

(954) 615-2180

Property at 4271 Expedition Way #103, Osprey, FL 34229, 2 beds, 2 baths

$260,000

2 beds2 baths1,135 sq ft

4271 Expedition Way #103, Osprey, FL 34229

Property at 5100 Jessie Harbor Dr #304, Osprey, FL 34229, 2 beds, 2 baths

$699,000

2 beds2 baths2,143 sq ft

5100 Jessie Harbor Dr #304, Osprey, FL 34229

Property at 447 N Shore Dr, Osprey, FL 34229, 3 beds, 2 baths

$499,000

3 beds2 baths1,874 sq ft

447 N Shore Dr, Osprey, FL 34229

Property at 42 W Oak St, Osprey, FL 34229, 2 beds, 1 bath

$55,000

2 beds1 bath1,000 sq ft

42 W Oak St, Osprey, FL 34229

Property at 110 Woodland Pl #110, Osprey, FL 34229, 2 beds, 2 baths

$215,000

2 beds2 baths1,325 sq ft

110 Woodland Pl #110, Osprey, FL 34229

Property at 320 Tropic Dr, Osprey, FL 34229, 2 beds, 2 baths

$185,000

2 beds2 baths1,199 sq ft

320 Tropic Dr, Osprey, FL 34229

Property at 4296 Expedition Way #104, Osprey, FL 34229, 2 beds, 2 baths

$299,990

2 beds2 baths1,135 sq ft

4296 Expedition Way #104, Osprey, FL 34229

Property at 742 Harms Dr, Osprey, FL 34229, 3 beds, 2 baths

$499,900

3 beds2 baths1,293 sq ft

742 Harms Dr, Osprey, FL 34229

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Based on information submitted to the MLS GRID as of Sun Aug 09 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Osprey, FL

Cities

Neighborhoods
Zip Codes

Southbay Yacht & Racquet Club homes for sale
$1,597,500
Rivendell homes for sale
$655,000
Palmer Ranch homes for sale
$445,000
Stoneybrook Golf & Country Club homes for sale
$315,000
Sarabay Acres homes for sale
$437,000
Oaks homes for sale
$1,175,000

Osprey, FL real estate trends

All Home Types trends in Osprey, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$580,653

-25.6% YoY | May 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

May 2026

Growth

% YoY

Osprey, FL

$580,653

-25.6%

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236

Deals*

4.8

Satisfaction

1068

Homes closed*

* Data from the last year

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