554 Oak Bay Dr, Osprey, FL 34229
OFF MARKET

$466,100

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,749 sqft

554 Oak Bay Dr, Osprey, FL 34229

Est. Refi. Payment $3,064/mo*
Refinance Your Home
Currently Off Market - Sold Jul 5, 2022 for $440,000

Home Value

Trulia Estimate
$466K
Since last month
Increased$2K (+0.4%)
Since last year
Increased$5K (+1.1%)
Since last sale
Increased$27K (+6%)
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 +66% in the last 10 years
MonthEstimated value
2026
August 2026$467K
July 2026$465K
June 2026$475K
May 2026$473K
April 2026$473K
March 2026$471K
February 2026$473K
January 2026$470K
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
813 OAK POND DRIVE, Osprey, FL
0.10
Single-Family Home
$540,000
11/24/25
4
2
1,981
523 OAK BAY DRIVE, Osprey, FL
0.11
Single-Family Home
$540,000
08/07/26
4
2
2,399
566 OAK BAY DRIVE, Osprey, FL
0.05
Single-Family Home
$520,000
02/26/26
3
2
2,559
562 OAK BAY DRIVE, Osprey, FL
0.03
Single-Family Home
$511,500
06/17/26
3
2.5
2,414
597 OAK RIVER COURT, Osprey, FL
0.20
Single-Family Home
$685,000
04/24/26
4
2
2,111
563 PINE RANCH EAST ROAD, Osprey, FL
0.23
Single-Family Home
$665,000
11/06/25
3
2
2,346
619 OAK RIVER COURT, Osprey, FL
0.21
Single-Family Home
$620,000
08/28/26
3
2
2,047
571 PINE RANCH EAST ROAD, Osprey, FL
0.24
Single-Family Home
$620,000
05/20/26
5
2.5
2,746
594 PINE RANCH EAST ROAD, Osprey, FL
0.26
Single-Family Home
$625,000
11/07/25
3
2.5
2,298
5301 BARTOLOMEO STREET, Sarasota, FL
0.45
Single-Family Home
$665,000
01/26/26
3
2
1,918

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
562 OAK BAY DRIVE, Osprey, FL 34229
0.03
$511,500
3
2.5
2,414
Recently Sold
566 OAK BAY DRIVE, Osprey, FL 34229
0.05
$520,000
3
2
2,559
Recently Sold
813 OAK POND DRIVE, Osprey, FL 34229
0.10
$540,000
4
2
1,981
Recently Sold
523 OAK BAY DRIVE, Osprey, FL 34229
0.11
$540,000
4
2
2,399
Recently Sold
818 OAK POND DRIVE, Osprey, FL 34229
0.14
$571,900
4
2
1,975
Off Market
515 OAK BAY DRIVE, Osprey, FL 34229
0.13
$521,100
3
2
1,977
Off Market
825 OAK POND DRIVE, Osprey, FL 34229
0.14
$606,000
4
3
2,229
Off Market
590 OAK BAY DRIVE, Osprey, FL 34229
0.13
$530,300
3
2
1,892
Off Market
506 OAK BAY DRIVE, Osprey, FL 34229
0.17
$616,000
4
2.5
1,944
Off Market
502 OAK BAY DRIVE, Osprey, FL 34229
0.19
$511,900
3
2
2,116
Off Market
603 OAK BAY DRIVE, Osprey, FL 34229
0.19
$630,200
4
2
2,312
Off Market
522 PINE RANCH EAST ROAD, Osprey, FL 34229
0.21
$610,000
3
2
2,078
Off Market

Local Information

  • Map ViewExplore the area around 554 Oak Bay Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
1,749 sqft
$266/sqft
Garage

About this House

This single-family home is located at 554 Oak Bay Dr, Osprey, FL. 554 Oak Bay Dr is in Osprey, FL and in ZIP code 34229. This property has 4 bedrooms, 2 bathrooms and approximately 1,749 sqft of floor space. This property has a lot size of 10018 sqft and was built in 1999.
554 Oak Bay Dr, Osprey, FL 34229 is a 4 bedroom, 2 bathroom, 1,749 sqft single-family home built in 1999. It last sold for $440,000 on Jul 5, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $466,100, with a rent estimate of $2,740/month.

Home Details for 554 Oak Bay Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Other, Carpet
Interior Details
Number of Rooms: 7
Heating & Cooling
Air Conditioning

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: StuccoFoundation Type: Concrete
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1999Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price and Tax history

DateEventPrice
Jul 5, 2022
Source: N/A
Sold
$440,000
Dec 14, 1998
Source: N/A
Sold
$54,000

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

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 554 Oak Bay Dr

  • What is 554 Oak Bay Dr estimated to be worth?
    Trulia's estimated value for 554 Oak Bay Dr in Osprey, FL is $466,100.
  • What is the price history for 554 Oak Bay Dr?
    554 Oak Bay Dr in Osprey, FL last sold for $440,000 in July 2022.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Osprey?
    The median sale price in Osprey is $714K. That is up $28.67K from the prior month.
  • How big is the lot at 554 Oak Bay Dr?
    The lot at 554 Oak Bay Dr in Osprey, FL is about 0.23 acres (10,018 sq ft).
  • Does 554 Oak Bay Dr have a garage?
    Yes, 554 Oak Bay Dr in Osprey, FL has a garage.

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Off Market Homes Near 554 Oak Bay Dr

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