144 Osprey Point Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

$3,695,300

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 5,178 sqft (on 0.53 acres)

144 Osprey Point Dr, Osprey, FL 34229

Est. Refi. Payment $23,180/mo*
Refinance Your Home
Currently Off Market - Sold Jan 19, 2022 for $3,000,000

Home Value

Trulia Estimate
$3.69M
Since last month
Increased$15K (+0.4%)
Since last year
Increased$108K (+3%)
Since last sale
Increased$695K (+23.2%)
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 +4% in the last 10 years
MonthEstimated value
2026
August 2026$3.7M
August 2026$3.68M
July 2026$3.68M
June 2026$3.75M
May 2026$3.73M
April 2026$3.71M
March 2026$3.77M
February 2026$3.72M
January 2026$3.71M
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
449 WEBBS COVE, Osprey, FL
0.19
Single-Family Home
$2,470,000
08/27/26
4
3.5
5,287
112 OSPREY POINT DRIVE, Osprey, FL
0.20
Single-Family Home
$2,315,000
10/30/25
6
5.5
8,621
133 Osprey Point Dr, Osprey, FL
0.08
Single-Family Home
$1,054,284
06/29/26
4
3
4,099
370 SUGAR MILL DRIVE, Osprey, FL
0.39
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
137 OSPREY POINT DRIVE, Osprey, FL
0.05
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
76 OSPREY POINT DRIVE, Osprey, FL
0.31
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
325 OSPREY POINT DRIVE, Osprey, FL
0.38
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
340 OSPREY POINT DR, Osprey, FL
0.43
Single-Family Home
$1,900,000
02/10/26
5
6
6,001
67 SUGAR MILL DRIVE, Osprey, FL
0.61
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
8900 FISHERMENS BAY DRIVE, Sarasota, FL
0.64
Single-Family Home
$3,485,000
09/29/25
4
3.5
4,158

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
148 OSPREY POINT DRIVE LOT 35, Osprey, FL 34229
0.03
-
-
-
-
Off Market
143 OSPREY POINT DRIVE, Osprey, FL 34229
0.04
$575,000
-
-
-
For Sale
137 OSPREY POINT DRIVE, Osprey, FL 34229
0.05
$1,285,000
4
3
3,303
Recently Sold
282 SHELL MIDDEN COURT, Osprey, FL 34229
0.12
$1,368,600
3
4.5
3,699
Off Market
216 OSPREY POINT DRIVE LOT 24, Osprey, FL 34229
0.15
$695,000
-
-
-
For Sale
230 OSPREY POINT DRIVE, Osprey, FL 34229
0.16
$2,329,700
3
3.5
3,586
Off Market
453 WEBBS COVE, Osprey, FL 34229
0.16
$1,670,600
3
3.5
3,953
Off Market
460 WEBBS COVE, Osprey, FL 34229
0.16
$2,638,200
3
4
5,479
Off Market
252 OSPREY POINT DRIVE, Osprey, FL 34229
0.19
$1,856,900
4
3.5
3,780
Off Market
449 WEBBS COVE, Osprey, FL 34229
0.19
$2,470,000
4
3.5
5,287
Recently Sold
442 WEBBS COVE, Osprey, FL 34229
0.19
$2,347,300
3
3.5
3,768
Off Market
101 OSPREY POINT DRIVE, Osprey, FL 34229
0.20
$4,790,000
4
5.5
5,087
For Sale

Local Information

  • Map ViewExplore the area around 144 Osprey Point Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2002
0.53 acre lot
5,178 sqft
$714/sqft
Garage

About this House

Beautifully positioned within Sarasota's elite country club The Oaks, this sophisticated, multi-level Key West-style home reflects the best in bespoke design. Driving into The Oaks, you'll instantly feel the privacy and attention to detail that sets this community apart from all others. Meandering roads under a canopy of native Oaks, Palms and Pines wind past exquisite single-family residences. The Oaks Bayside community is adjacent to Historic Spanish Point's nature preserve and the bayfront, affording the lucky residents of 144 Osprey Point Drive a prime protected location with striking sunset views. Master craftsmenship is evident throughout the home's three levels, with rich wood floors that connect main living spaces, soaring ceilings with exposed beams and a wraparound balcony that gives every member of the household views of the area's cherished wildlife. The gourmet kitchen is an epicurean delight with massive center island with bar seating and gas range; abundant cream cabinetry; wine refrigerator and breakfast nook overlooking the mangroves. Perfect for everyday living and entertaining, choose to dine indoors in the formal dining room, or opt for dinner under a blanket of stars on the open-air pool terrace with fully equppied and covered summer kitchen. Retreat to the master suite for the best in self-care with balcony access, marble spa bath and custom walk-in closet. Two additional guest suites allow the owner flexibility to covert one or both into a gym, office or den, and a secondary master suite with full kitchen and laundry boasts it's own wing. A drive-through motorcourt leads to two oversized garages with ample storage for all your automotive and recreational needs. A few homes down, a boat dock and kayak launch let you explore the area's mangrove tunnels and waterways. The Oaks is one of the most highly-regarded communities on Florida's Gulf Coast. Unrivaled amenities include two championship golf courses, a premier tennis program acknowledged by the International Tennis Federation, refined dining experiences, a wellness club that attends to body and spirit, croquet court, active social calendar and more. Owners within The Oaks Bayside are required to have a social or equity membership.
144 Osprey Point Dr, Osprey, FL 34229 is a 4 bedroom, 6 bathroom, 5,178 sqft single-family home built in 2002. It last sold for $3,000,000 on Jan 19, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,695,300, with a rent estimate of $7,475/month.

Home Details for 144 Osprey Point Dr

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningCooling System: CentralHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 2ElevatorFloors: Carpet, Hardwood
Interior Details
Number of Rooms: 8
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: Piling
Pool
Pool
Parking & Garage
GarageParking: Covered, Garage, Open

Property Information

Year Built
Year Built: 2002Year Updated: 2002
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.53 acres

Price and Tax history

DateEventPrice
Jan 19, 2022
Source: N/A
Sold
$3,000,000
Nov 22, 2021
Source: Stellar MLS #A4518503
Pending
$3,450,000
Sep 3, 2021
Source: Michael Saunders & Company
ListingRemoved
Mar 1, 2021
Source: Stellar MLS #A4492940
Listed For Sale
$3,450,000
Jan 13, 2006
Source: N/A
Sold
$2,744,000

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

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

LGBTQ Local Legal Protections

Frequently asked questions about 144 Osprey Point Dr

  • What is 144 Osprey Point Dr estimated to be worth?
    Trulia's estimated value for 144 Osprey Point Dr is $3,695,300.
  • What is the price history for 144 Osprey Point Dr?
    144 Osprey Point Dr last sold for $3,000,000 in January 2022.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • 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 recently sold homes in Osprey, FL.
  • Does 144 Osprey Point Dr have air conditioning?
    Yes, 144 Osprey Point Dr has air conditioning.
  • Does 144 Osprey Point Dr have a pool?
    Yes, 144 Osprey Point Dr has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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