49 OSPREY POINT DRIVE, Osprey, FL 34229
Property image
Property image
FOR SALE
3D VIEW
0.4 ACRES

$2,399,000

Original price: $2,500,000
  • 4 Beds
  • 3.5 Baths
  • 3,953 sqft (on 0.40 acres)

49 OSPREY POINT DRIVE, Osprey, FL 34229

Est. Mortgage $15,780/mo*
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Home Highlights

Single-Family Home
Built in 1989
0.4 acre lot
$607/sqft
2 Car Garage
HOA $475/mo

Local Information

  • Map ViewExplore the area around 49 OSPREY POINT DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.
Last check for updates: about 8 hours ago
Listing Provided by: Jonathan Abrams, PLLC, (941) 232-2868
MICHAEL SAUNDERS & COMPANY, (941) 349-3444
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4671762
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 49 OSPREY POINT DRIVE

Interior Features

Interior Details
Number of Rooms: 5Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Great Room, Kitchen
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3953 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Public, Water ConnectedAppliances: Dishwasher, Range, Range Hood, RefrigeratorDishwasherLaundry: Inside,Laundry RoomRefrigerator
Heating & Cooling
Heating: Central,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Living RoomSpa: Heated, In Ground, OtherHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Hurricane Shutters/WindowsDoor: Outdoor Shower, Sliding DoorsFlooring: Concrete
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Concrete
View
No ViewView: Lake
Security
Security: Gated Community

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Enclosed, ScreenedVegetation: Mature LandscapingExterior: Outdoor Shower, StorageFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Workshop in Garage
Pool
Pool: Fiber Optic Lighting, In Ground, Salt WaterPool
Frontage
WaterfrontWaterfront: Bay/Harbor Front, Lake Front, Lake Privileges, Fishing PierRoad Surface Type: AsphaltOn Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 187Days on Market: 180+

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary,Custom
Building
Construction Materials: Block, Concrete, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 0142060007

Price & Status

Price
List Price: $2,399,000Price Per Sqft: $607

Active Status

MLS Status: Active

Location

Direction & Address
City: OSPREYCommunity: OAKS
School Information
Elementary School: Laurel Nokomis ElementaryJr High / Middle School: Sarasota MiddleHigh School: Venice Senior High

Agent Information

Listing Agent
Listing ID: A4671762

Building

Building Area
Building Area: 5227 Square Feet
Community rooms
Fitness Center

Community

Community Features: Bay/Harbor Front, Dock, Fishing, Water Access, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Restaurant, Tennis Court(s)Not Senior Community

HOA

HOA Name: The Oaks ClubHOA Phone: 941-966-2161Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $475/Monthly

Lot Information

Lot Area: 0.40 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4671762Water ViewWater View: LakeShowing Requirements: Appointment Only, ShowingTimeUniversal Property Id: US-12115-N-0142060007-R-N

Additional Information

HOA Amenities: Clubhouse,Fitness Center,Golf Course,Maintenance,Pickleball Court(s),Tennis Court(s)

Around this home

What Locals Say about Osprey

At least 46 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 87 % Say it's dog friendly

  • 85 % Say it's quiet

  • 84 % Say parking is easy

  • 75 % Say people would walk alone at night

  • 74 % Say there's wildlife

  • 67 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 41 % Say there are community events

  • 31 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Lindsey W.
    "It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
    4
    Flag
  • Mary V.
    "I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
    0
    Flag
  • Mary V.
    "Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
    3
    Flag
  • Bob T.
    "I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
    14
    Flag
  • Bob T.
    "Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
    1
    Flag
  • Larysathor
    "Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
    0
    Flag
  • Brenda F. D.
    "Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
    1
    Flag
  • Michelle C.
    "I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
    0
    Flag
  • nancybuscher
    "This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
    0
    Flag
  • info
    "Centrally located, minutes to beaches and shopping"
    1
    Flag
  • bookwoman39
    "Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
    0
    Flag
  • trishmainey1111
    "Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
    1
    Flag
  • Gail L.
    "I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
    0
    Flag

Market trends in Osprey

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$714K
$28.67KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
112
22MoM

Home Value

Trulia Estimate
$2.22M
Since last month
Increased$42K (+1.9%)
Since last year
Decreased$212K (-8.7%)
Since last sale
Increased$1M (+178%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +134% in the last 10 years
MonthEstimated value
2026
September 2026$2.22M
August 2026$2.18M
July 2026$2.19M
June 2026$2.19M
May 2026$2.19M
April 2026$2.28M
March 2026$2.28M
February 2026$2.27M
January 2026$2.36M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
325 OSPREY POINT DRIVE, Osprey, FL
0.07
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
25 SUGAR MILL DRIVE, Osprey, FL
0.16
Single-Family Home
$1,300,000
07/22/26
3
3.5
3,066
919 TRANQUILITY CIRCLE, Osprey, FL
0.33
Single-Family Home
$750,000
08/14/26
4
3.5
2,854
76 OSPREY POINT DRIVE, Osprey, FL
0.16
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
137 OSPREY POINT DRIVE, Osprey, FL
0.35
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
140 SUGAR MILL DRIVE, Osprey, FL
0.35
Single-Family Home
$1,325,000
06/16/26
4
4
3,286
449 WEBBS COVE, Osprey, FL
0.21
Single-Family Home
$2,470,000
08/27/26
4
3.5
5,287
67 SUGAR MILL DRIVE, Osprey, FL
0.27
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
903 TRANQUILITY CIRCLE, Osprey, FL
0.33
Single-Family Home
$780,000
08/25/26
3
3
2,622

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
38 OSPREY POINT DRIVE, Osprey, FL 34229
0.07
$2,880,600
4
5.5
3,974
Off Market
325 OSPREY POINT DRIVE, Osprey, FL 34229
0.07
$1,500,000
3
4.5
3,905
Recently Sold
75 OSPREY POINT DRIVE, Osprey, FL 34229
0.14
$1,595,000
4
4
4,001
For Sale
76 OSPREY POINT DRIVE, Osprey, FL 34229
0.16
$1,450,000
3
4.5
4,364
Recently Sold
340 OSPREY POINT DR, Osprey, FL 34229
0.10
$1,900,000
5
6
6,001
Recently Sold
410 BLUE GARDEN LANE LOT 6, Osprey, FL 34229
0.11
$699,000
-
-
-
For Sale
25 SUGAR MILL DRIVE, Osprey, FL 34229
0.16
$1,300,000
3
3.5
3,066
Recently Sold
442 WEBBS COVE, Osprey, FL 34229
0.20
$2,377,700
3
3.5
3,768
Off Market
601 FERNWALK LANE, Osprey, FL 34229
0.20
$3,716,400
4
5.5
5,453
Off Market
449 WEBBS COVE, Osprey, FL 34229
0.21
$2,470,000
4
3.5
5,287
Recently Sold
37 BAYHEAD LANE, Osprey, FL 34229
0.18
$699,900
3
2
2,168
Off Market

Price and Tax history

DateEventPrice
May 3, 2026
Source: Stellar MLS #A4671762
PriceChange
$2,399,000
Price decreased by 4%
Jan 29, 2026
Source: Stellar MLS #A4671762
PriceChange
$2,500,000
Price decreased by 4%
Nov 13, 2025
Source: Stellar MLS #A4671762
Listed For Sale
$2,595,000
Sep 1, 2025
Source: Stellar MLS #A4642364
ListingRemoved
$2,695,000
Jul 24, 2025
Source: Stellar MLS #A4642364
PriceChange
$2,695,000
Price decreased by 2%

LGBTQ Local Legal Protections

Jonathan Abrams, PLLC, MICHAEL SAUNDERS & COMPANY, (941) 349-3444
Agent Phone: (941) 232-2868

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Frequently asked questions about 49 OSPREY POINT DRIVE

  • What is the estimated monthly payment for 49 OSPREY POINT DRIVE?
    Based on a $2,399,000 list price with 20% down at today's rates, the estimated monthly payment for 49 OSPREY POINT DRIVE is approximately $15,654 (about $13,040 principal & interest, $2,539 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 49 OSPREY POINT DRIVE compare to homes in Osprey?
    49 OSPREY POINT DRIVE is listed at $2,399,000, about 236% above the $714K median sale price in Osprey.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See homes for sale in Osprey, FL.
  • What are the closest schools to 49 OSPREY POINT DRIVE?
    The closest schools to 49 OSPREY POINT DRIVE are Laurel Nokomis School (Pre-K/Elementary/Middle, rated 8/10), Venice Senior High School (rated 7/10).
  • Does 49 OSPREY POINT DRIVE have air conditioning?
    Yes, 49 OSPREY POINT DRIVE has air conditioning.
  • Does 49 OSPREY POINT DRIVE have a pool?
    Yes, 49 OSPREY POINT DRIVE has a pool.
49 OSPREY POINT DRIVE, Osprey, FL 34229 is a 4 bedroom, 4 bathroom, 3,953 sqft single-family home built in 1989. This property is currently available for sale and was listed by Stellar MLS on Nov 13, 2025. The MLS # for this home is MLS# A4671762.