416 Windward Pl, Oldsmar, FL 34677
SOLD
DEC 29, 2025

$153,600

Trulia Estimate
  • Studio
  • 879 sqft

416 Windward Pl, Oldsmar, FL 34677

Est. Refi. Payment $1,120/mo*
Refinance Your Home
Currently Off Market - Sold Dec 29, 2025 for $160,000

Home Value

Trulia Estimate
$154K
Since last month
Decreased$800 (-0.5%)
Since last year
Decreased$4K (-2.2%)
Since last sale
Decreased$4K (-2.5%)
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 +95% in the last 10 years
MonthEstimated value
2026
September 2026$156K
August 2026$157K
July 2026$159K
June 2026$160K
May 2026$157K
March 2026$158K
February 2026$159K
January 2026$160K
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 WINDWARD PLACE, Oldsmar, FL
0.00
Condo
$124,100
04/01/26
2
2
879
106 MEADOW LANE #106, Oldsmar, FL
0.08
Condo
$155,000
12/15/25
2
2
879
106 Meadow Ln, Oldsmar, FL
0.09
Condo
$155,000
12/17/25
2
2
875
103 MEADOW LANE #103, Oldsmar, FL
0.08
Condo
$125,000
03/24/26
2
2
879
108 LAKEVIEW PLACE #108, Oldsmar, FL
0.15
Condo
$170,000
04/09/26
2
2
1,094
118 LAKEVIEW WAY #118, Oldsmar, FL
0.13
Condo
$145,000
08/17/26
2
2
1,148
143 LAKESIDE DRIVE #143, Oldsmar, FL
0.10
Condo
$214,500
11/14/25
2
2
1,094
143 Lakeside Dr, Oldsmar, FL
0.10
Condo
$214,900
11/17/25
-
1,094
141 LAKEVIEW WAY, Oldsmar, FL
0.18
Condo
$150,000
08/05/26
2
2
1,094

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
109 LAKESIDE COURT #73, Oldsmar, FL 34677
0.04
$189,000
2
2
1,094
Off Market
105 LAKESIDE COURT ELW VI UNIT 5, Oldsmar, FL 34677
0.04
$230,000
2
2
1,150
For Sale
106 WINDWARD PLACE, Oldsmar, FL 34677
0.00
$179,950
2
2
879
Foreclosure
204 WINDWARD PLACE #36, Oldsmar, FL 34677
0.00
$188,000
2
2
879
For Sale
112 WINDWARD PLACE #12, Oldsmar, FL 34677
0.00
$161,800
2
2
879
Off Market
305 WINDWARD PLACE #305, Oldsmar, FL 34677
0.00
$120,600
1
1
644
Off Market
115 WINDWARD PLACE #15, Oldsmar, FL 34677
0.00
$180,000
2
2
879
For Sale
106 LAKESIDE COURT, Oldsmar, FL 34677
0.07
$145,000
2
2
1,094
For Sale
147 LAKESIDE DRIVE, Oldsmar, FL 34677
0.10
$190,900
2
2
1,148
Off Market
143 LAKESIDE DRIVE #143, Oldsmar, FL 34677
0.10
$210,500
2
2
1,094
Off Market
149 LAKESIDE DRIVE #149, Oldsmar, FL 34677
0.10
$168,400
2
2
1,148
Off Market
138 LAKESIDE DRIVE #138, Oldsmar, FL 34677
0.10
$195,100
2
2
1,094
Off Market

Local Information

  • Map ViewExplore the area around 416 Windward Pl.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1984
879 sqft
$182/sqft

About this House

2nd floor end unit condo has newer carpet and linoleum. Comfortable lifestyle with livingroom/diningroom combination and breakfast bar to eat-in kitchen with granite countertops and newer appliances. Kitchen with plenty of cabinets and counterspace plus window to keep it light and bright. Split bedroom plan, guest suite with pocket door for privacy. Master with walk in closets, linen closet and large vanity area and walk in shower. Sliders from master bedroom and living area outto screen enclosed lanai where washer and dryer are located. This is a non smoking residence. Water, sewer, trash and basic cable is included in the rent. Heated community pool nearby.
416 Windward Pl, Oldsmar, FL 34677 is a studio, 879 sqft condo built in 1984. It last sold for $160,000 on Dec 29, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $153,600, with a rent estimate of $1,644/month.

Home Details for 416 Windward Pl

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Property Information

Year Built
Year Built: 1984Year Updated: 1984
Property Type / Style
Property Type: Condo

Exterior Features

Exterior Home Features
Exterior: StonePatio
Pool
Pool
Parking & Garage
Parking: None

Price & Status

Price
Price Per Sqft: $182/sqft

Community

Units in Building: 1

Price and Tax history

DateEventPrice
Dec 29, 2025
Source: N/A
Sold
$160,000
May 18, 2005
Source: N/A
Sold
$105,000

Market trends in Oldsmar

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$372K
$42.48KMoM
Sale-to-List Price
97.9%
0.2%MoM
Price per sq ft
$239
$13MoM
Available listings
178
4MoM

Around this home

What Locals Say about Oldsmar

At least 195 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 90 % Say there are sidewalks

  • 90 % Say car is needed

  • 87 % Say parking is easy

  • 79 % Say it's quiet

  • 77 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 74 % Say streets are well-lit

  • 68 % Say kids play outside

  • 66 % Say there's wildlife

  • 64 % Say yards are well-kept

  • 63 % Say it's walkable to restaurants

  • 60 % Say they plan to stay for at least 5 years

  • 58 % Say it's walkable to grocery stores

  • 57 % Say neighbors are friendly

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Mike Rood
    "Oldsmar is a safe community with lots of outdoor opportunities for fun. There are a lot of welcoming neighbors. "
    0
    Flag
  • Alexandruivan1982
    "Close to everything. Safe, clean, pools available. Lots of parks, great schools. Lots of activities: ice skating, ymca, oldsmar rec center has many classes. "
    0
    Flag
  • Cancion14590
    "A little bit further drive to most of my destinations, but totally worth it for the safety and surroundings"
    3
    Flag
  • William G. I.
    "Dog owners would love this area just don't be like everyone else in my apartment complex and not pick up dog poo"
    2
    Flag
  • Smithlouise58
    "We don’t have public transportation except for a taxi service who is very reasonable. We are within 15 minutes of all the beaches. We are convenient to shopping and Drs. "
    0
    Flag
  • Asia7412
    "Dog owners would love how much green grass there is and how good the sidewalks are. But I would prefer if they keep the area clean"
    2
    Flag
  • Awasenda18
    "Great place to live. Lots of families and very pet friendly. Close to beaches. Very safe neighborhood overall. "
    1
    Flag
  • Nicholas.balan
    "very closed and private great atmosphere and well maintained. People always walk their dogs and the grass and sidewalks as well as the parks are well maintained"
    0
    Flag
  • Sheila C.
    "I have been here 17years. Very family friendly. Safe to walk at night. Great restaurants and shops within walking distance. "
    1
    Flag
  • Sam L.
    "Close to Tampa and Cleawater but far enough also. Close to stores, restaurants, and theater. Lots of local shops and farmers market."
    0
    Flag
  • Dave B.
    "Ice rink and sports fields.. Publix and good food places to take the family. Close to Tampa and Beaches ."
    0
    Flag
  • Krista L.
    "There are nice sidewalks and in my family's subdivision has an HOA so the yards have to be maintained. "
    0
    Flag
  • Kathy.gasparini1963
    "ELW is a short commute to any part of the county. Very good location! Tampa road to Memorial will take you to the airport in 25 minutes. We have lived here for 25 years. That is how much we love it! "
    2
    Flag
  • Noelle V.
    "Lots of neighbors with great dogs. Can walk to dog park to play or just take a nice stroll in the neighborhood. Love it. "
    1
    Flag
  • OldsmarRocks!
    "A family friendly neighborhood where everybody keeps their homes and yards in great condition. The area is convenient to lots of shopping options and a 15 minute ride to Tampa airport."
    0
    Flag
  • Tregas
    "The walking distance to great parks, a beautiful secluded town beach on Tampa Bay, and a golf cart neighborhood all less than 12 miles from the Tampa International Airport make this a highly sought after neighborhood with no HOA fees"
    0
    Flag
  • Shawnluv
    "Dog friendly community. Everyone here is friendly and looks out for one another. It's a private circle. A good mixture of ages and the families with kids are never a problem (ie kids running around being mischievous and loud)."
    0
    Flag
  • Tracyhami
    "everything the dogs are well taken care of they have walking areas and parks around the area. it is a pet lover's paradise "
    0
    Flag
  • Kittyharlott
    "Oldsmar is a great area to walk dogs. Forest lake are is the best. Shopping and restaurants are near. "
    0
    Flag
  • Charles p.
    "I love Oldsmar I've lived here all my life my kids have gone to East Lake High School love the area wouldn't live anywhere else"
    0
    Flag
  • Aidenkai200
    "I've lived here for 9 years and I love it so much and wanting to renovate it to make it super nice and warm and comfortable"
    0
    Flag
  • Matty
    "Very friendly neighborhood that is also very pet friendly. Everyone knows the dogs names in the neighborhood."
    0
    Flag
  • Judi
    "Love the neighborhood because it is equally close to beaches, major highways, healthy grocery stores and airport! "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 416 Windward Pl

  • What is 416 Windward Pl estimated to be worth?
    Trulia's estimated value for 416 Windward Pl in Oldsmar, FL is $153,600.
  • What is the price history for 416 Windward Pl?
    416 Windward Pl in Oldsmar, FL last sold for $160,000 in December 2025.
  • Is Oldsmar a buyer's or seller's market?
    Oldsmar is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Oldsmar?
    The median sale price in Oldsmar is $372K. That is down $42.48K from the prior month.
  • Does 416 Windward Pl have a pool?
    Yes, 416 Windward Pl in Oldsmar, FL has a pool.

Explore by feature - Pet Friendly

34 pet-friendly rentals in Oldsmar, FL

Explore by feature - Garage

18 rentals with a garage in Oldsmar, FL

Explore by feature - Air Conditioning

71 rentals with air conditioning in Oldsmar, FL

Explore by feature - Pool

50 rentals with a pool in Oldsmar, FL

Explore by feature - Washer/dryer

65 rentals with a washer/dryer in Oldsmar, FL

Explore by feature - Outdoor Space

11 rentals with an outdoor space in Oldsmar, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 416 Windward Pl

Skip to last item
Skip to first item

Homes for sale near 416 Windward Pl

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item