44 Westview Dr, Osprey, FL 34229
OFF MARKET

$545,600

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 2,616 sqft (on 0.28 acres)

44 Westview Dr, Osprey, FL 34229

Est. Refi. Payment $3,422/mo*
Refinance Your Home
Currently Off Market - Sold May 31, 1995 for $120,700

Home Value

Trulia Estimate
$546K
Since last month
Increased$10K (+1.8%)
Since last year
Increased$65K (+13.4%)
Since last sale
Increased$424K (+351.5%)
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 +32% in the last 10 years
MonthEstimated value
2026
August 2026$545K
July 2026$536K
June 2026$536K
May 2026$519K
April 2026$523K
March 2026$525K
February 2026$521K
January 2026$518K
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
106 RAPHAEL PLACE, Nokomis, FL
0.32
Single-Family Home
$255,000
01/12/26
3
2
1,839
116 1ST AVENUE, Nokomis, FL
0.46
Single-Family Home
$230,000
05/28/26
2
2
1,341
1728 S CREEK DRIVE, Osprey, FL
0.23
Single-Family Home
$730,000
10/24/25
3
2
2,320
570 CRANE PRAIRIE WAY, Osprey, FL
0.24
Single-Family Home
$505,025
03/26/26
3
2
2,298
157 LOOKOUT POINT DRIVE, Osprey, FL
0.21
Single-Family Home
$850,000
08/07/26
3
2
1,859
557 CRANE PRAIRIE WAY, Osprey, FL
0.32
Single-Family Home
$560,000
07/27/26
3
2
2,172
107 VAN DYCK DRIVE, Nokomis, FL
0.50
Single-Family Home
$335,000
12/23/25
2
2
1,333
1486 LANDVIEW LANE, Osprey, FL
0.32
Single-Family Home
$817,000
06/30/26
3
2
1,869
238 Lookout Point Dr, Osprey, FL
0.36
Single-Family Home
$800,000
05/01/26
3
2.5
2,676
510 LATITUDE LANE, Osprey, FL
0.44
Single-Family Home
$550,000
03/23/26
3
2
2,298

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
216 SHORELAND DRIVE, Osprey, FL 34229
0.03
$501,200
3
2
1,482
Off Market
0 / 19 WESTVIEW DRIVE LOT 2, Osprey, FL 34229
0.04
-
-
-
-
Off Market
108 PARK DRIVE, Osprey, FL 34229
0.06
$627,900
4
3
2,768
Off Market
1795 HIGHLAND ROAD, Osprey, FL 34229
0.09
$375,000
3
3
1,879
Recently Sold
1811 HIGHLAND ROAD, Osprey, FL 34229
0.09
$417,000
2
2
1,725
For Sale
1821 HIGHLAND ROAD, Osprey, FL 34229
0.10
$361,800
3
2
1,184
Off Market
1801 HIGHLAND ROAD, Osprey, FL 34229
0.11
$289,900
2
2
1,165
For Sale
1819 HIGHLAND ROAD, Osprey, FL 34229
0.11
$319,000
2
2.5
1,240
For Sale
1851 ISLAND WAY, Osprey, FL 34229
0.10
$3,314,100
5
5
5,233
Off Market
1862 ISLAND WAY, Osprey, FL 34229
0.14
$1,914,600
4
3
3,598
Off Market
1527 BUOY LANE, Osprey, FL 34229
0.17
$1,165,000
3
2.5
2,830
For Sale
53 LANDLUBBER LANE, Osprey, FL 34229
0.19
$842,200
4
3.5
2,557
Off Market

Local Information

  • Map ViewExplore the area around 44 Westview Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1986
Lot Size
0.28 acres
Living Area
2,616 sqft
Price/Sqft
$209
Parking
Garage

About this House

This single-family home is located at 44 Westview Dr, Osprey, FL. 44 Westview Dr is in Osprey, FL and in ZIP code 34229. This property has 2 bedrooms, 2 bathrooms and approximately 2,616 sqft of floor space. This property has a lot size of 0.28 acres and was built in 1986.
44 Westview Dr, Osprey, FL 34229 is a 2 bedroom, 2 bathroom, 2,616 sqft single-family home built in 1986. It last sold for $120,700 on May 31, 1995. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $545,600, with a rent estimate of $3,194/month.

Home Details for 44 Westview Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet
Interior Details
Number of Rooms: 5
Heating & Cooling
Air Conditioning
Fireplace & Spa
Hot Tub or Spa

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: OtherFoundation Type: Piling
Pool
Pool
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1986Year Updated: 2006
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
May 31, 1995
Source: N/A
Sold
$120,700

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 44 Westview Dr

  • What is 44 Westview Dr estimated to be worth?
    Trulia's estimated value for 44 Westview Dr in Osprey, FL is $545,600.
  • What is the price history for 44 Westview Dr?
    44 Westview Dr in Osprey, FL last sold for $120,700 in May 1995.
  • 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 44 Westview Dr have a pool?
    Yes, 44 Westview Dr in Osprey, FL has a pool.
  • How big is the lot at 44 Westview Dr?
    The lot at 44 Westview Dr in Osprey, FL is about 0.28 acres (12,371 sq ft).

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