101 OSPREY POINT DRIVE, Osprey, FL 34229
Property image
Property image
FOR SALE
3D VIEW
0.93 ACRES

$4,790,000

  • 4 Beds
  • 5.5 Baths
  • 5,087 sqft (on 0.93 acres)

101 OSPREY POINT DRIVE, Osprey, FL 34229

Est. Mortgage $31,460/mo*
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Home Highlights

Single-Family Home
Built in 1985
0.93 acre lot
$942/sqft
3 Car Garage
HOA $950/mo

Local Information

  • Map ViewExplore the area around 101 OSPREY POINT DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.
Last check for updates: about 6 hours ago
Listing Provided by: Joel Schemmel, (941) 587-4894
DOUGLAS ELLIMAN, (941) 867-6199
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4694716
Also Listed on Stellar MLS, Douglas Elliman.
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 101 OSPREY POINT DRIVE

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Dining Room, Family Room, Kitchen, Library, Living RoomWet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5087 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Propane, Public, Sewer Connected, Sprinkler Well, Street Lights, Water ConnectedAppliances: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine RefrigeratorDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Living Room, Other Room, Master Bedroom, Wood BurningSpa: In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window Treatments, Hurricane ShuttersDoor: French DoorsFlooring: Brick/Stone, Ceramic Tile, Parquet
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Brick Stone, Ceramic Tile, Parquet
View
Has a ViewView: Water, Lake
Security
Security: Gated Community, Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Front Porch, Rear PorchVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation System, Lighting, Private MailboxFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Other Parking: Garage Dimensions: 22x35No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Circular Driveway,Driveway,Garage Door Opener,Garage Faces Side,Off Street
Pool
Pool: Gunite, In GroundPool
Frontage
WaterfrontWaterfront: Lake FrontRoad Surface Type: Paved, AsphaltOn Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 98Days on Market: 107

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Custom,Traditional
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 0142050008

Price & Status

Price
List Price: $4,790,000Price Per Sqft: $942

Active Status

MLS Status: Active

Media

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: A4694716

Building

Building Area
Building Area: 6841 Square Feet
Community rooms
Fitness Center

Community

Community Features: Buyer Approval Required, Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Pool, Special Community Restrictions, Tennis Court(s)Not Senior Community

HOA

HOA Fee Includes: 24-Hour Guard, Community Pool, Manager, Private Road, SecurityHOA Name: Asset Management/ Hope RootHOA Phone: 813-607-2220Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $950/Monthly

Lot Information

Lot Area: 0.93 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4694716Water ViewWater View: Water, LakeShowing Advance Notice: 24Showing AttendedShowing Considerations: No SignShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0142050008-R-N

Additional Information

HOA Amenities: Clubhouse,Fitness Center,Gated,Handicap Modified,Pool,Recreation Facilities,Security,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 July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM

Home Value

Trulia Estimate
$4.24M
Since last month
Increased$15K (+0.3%)
Since last year
Decreased$426K (-9.1%)
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 +186% in the last 10 years
MonthEstimated value
2026
August 2026$4.25M
August 2026$4.24M
June 2026$4.29M
May 2026$4.56M
April 2026$4.41M
February 2026$4.4M
January 2026$4.38M
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
112 OSPREY POINT DRIVE, Osprey, FL
0.05
Single-Family Home
$2,315,000
10/30/25
6
5.5
8,621
449 WEBBS COVE, Osprey, FL
0.14
Single-Family Home
$2,470,000
08/27/26
4
3.5
5,287
370 SUGAR MILL DRIVE, Osprey, FL
0.20
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
76 OSPREY POINT DRIVE, Osprey, FL
0.14
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
340 OSPREY POINT DR, Osprey, FL
0.35
Single-Family Home
$1,900,000
02/10/26
5
6
6,001
325 OSPREY POINT DRIVE, Osprey, FL
0.30
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
137 OSPREY POINT DRIVE, Osprey, FL
0.17
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
67 SUGAR MILL DRIVE, Osprey, FL
0.44
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
140 SUGAR MILL DRIVE, Osprey, FL
0.46
Single-Family Home
$1,325,000
06/16/26
4
4
3,286

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
112 OSPREY POINT DRIVE, Osprey, FL 34229
0.05
$6,449,000
6
5.5
8,621
For Sale
460 WEBBS COVE, Osprey, FL 34229
0.10
$2,638,200
3
4
5,479
Off Market
442 WEBBS COVE, Osprey, FL 34229
0.11
$2,347,300
3
3.5
3,768
Off Market
76 OSPREY POINT DRIVE, Osprey, FL 34229
0.14
$1,450,000
3
4.5
4,364
Recently Sold
75 OSPREY POINT DRIVE, Osprey, FL 34229
0.14
$1,595,000
4
4
4,001
For Sale
453 WEBBS COVE, Osprey, FL 34229
0.13
$1,670,600
3
3.5
3,953
Off Market
449 WEBBS COVE, Osprey, FL 34229
0.14
$2,470,000
4
3.5
5,287
Recently Sold
137 OSPREY POINT DRIVE, Osprey, FL 34229
0.17
$1,285,000
4
3
3,303
Recently Sold
370 SUGAR MILL DRIVE, Osprey, FL 34229
0.20
$2,189,000
5
5.5
4,783
Recently Sold
143 OSPREY POINT DRIVE, Osprey, FL 34229
0.19
$575,000
-
-
-
For Sale
282 SHELL MIDDEN COURT, Osprey, FL 34229
0.19
$1,368,600
3
4.5
3,699
Off Market

Price and Tax history

DateEventPrice
May 26, 2026
Source: Stellar MLS #A4694716
Listed For Sale
$4,790,000
Mar 25, 2026
Source: Stellar MLS #A4664424
ListingRemoved
$5,000,000
Sep 17, 2025
Source: Stellar MLS #A4664424
Listed For Sale
$5,000,000
Jun 11, 2025
Source: Stellar MLS #A4639897
ListingRemoved
$5,300,000
Mar 23, 2025
Source: Stellar MLS #A4639897
Listed For Sale
$5,300,000

LGBTQ Local Legal Protections

Joel Schemmel, DOUGLAS ELLIMAN, (941) 867-6199
Agent Phone: (941) 587-4894

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Frequently asked questions about 101 OSPREY POINT DRIVE

  • What is the estimated monthly payment for 101 OSPREY POINT DRIVE?
    Based on a $4,790,000 list price with 20% down at today's rates, the estimated monthly payment for 101 OSPREY POINT DRIVE is approximately $31,000 (about $25,856 principal & interest, $5,069 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • 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 101 OSPREY POINT DRIVE?
    The closest schools to 101 OSPREY POINT DRIVE are Laurel Nokomis School (Pre-K/Elementary/Middle, rated 8/10), Venice Senior High School (rated 7/10).
  • What is 101 OSPREY POINT DRIVE estimated to be worth?
    Trulia's estimated value for 101 OSPREY POINT DRIVE is $4,243,800.
  • Does 101 OSPREY POINT DRIVE have air conditioning?
    Yes, 101 OSPREY POINT DRIVE has air conditioning.
  • Does 101 OSPREY POINT DRIVE have a pool?
    Yes, 101 OSPREY POINT DRIVE has a pool.
101 OSPREY POINT DRIVE, Osprey, FL 34229 is a 4 bedroom, 6 bathroom, 5,087 sqft single-family home built in 1985. This property is currently available for sale and was listed by Stellar MLS on May 26, 2026. The MLS # for this home is MLS# A4694716.