301 Windward Pl, Oldsmar, FL 34677
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Property image
OFF MARKET

301 Windward Pl
Oldsmar, FL 34677

  • 2 Beds
  • 2 Baths
  • 879 sqft

$151,500

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $1,080/mo*
Refinance Your Home

$151,500

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $1,080/mo*
Refinance Your Home
2 Beds
2 Baths
879 sqft

Local Information

  • Map ViewExplore the area around 301 Windward Pl.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1984
Living Area
879 sqft
Price/Sqft
$172
Parking
None

About this House

Call to see this cute 2 Bedroom 2 bath downstairs with a great green view, like you have a backyard that you don't have to maintain. Gated East Lake Woodlands and the community has its own pool. Reserved parking right up front. Spacious main bedroom for queen size bed easily. Washer and Dryer provided in a outside laundry closet. Screened back lanai for great evening relaxing. Walk in the front door to the kitchen on the left and then the living / dining combination. Tiled for coolness. Bedrooms with beautiful vinyl flooring looks like wood.
301 Windward Pl, Oldsmar, FL 34677 is a 2 bedroom, 2 bathroom, 879 sqft condo built in 1984. It last sold for $80,000 on Dec 26, 2017. More recently, it was listed as a rental in May 2023 with an asking price of $1,800 per month. That rental listing was removed on June 11, 2023. It is currently off market. The Trulia Estimate is $151,500, with a rent estimate of $1,809/month.

Home Details for 301 Windward Pl

Interior Features

Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Laminate
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Property Information

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

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 3.54 acres

Price History for 301 Windward Pl

DatePriceEventSource
06/11/2023ListingRemovedZillow Rentals
05/25/2023$1,800Listed For RentZillow Rentals
05/25/2023ListingRemovedZillow Rentals
05/08/2023$1,800Listed For RentZillow Rentals
12/26/2017$80,000Sold
N/A
11/27/2017$89,900Listed For SaleAgent Provided
08/19/2002$71,000Sold
N/A

Market trends in Oldsmar

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$403K
$2.5KMoM
Sale-to-List Price
97.1%
0.1%MoM
Price per sq ft
$238
$4MoM
Available listings
193
1MoM
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Property Tax and Assessment

Year2024
Tax$2,649
Assessment$183,884
Home facts updated by county records

Comparable Sales for 301 Windward Pl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
106 Meadow Ln #106, Oldsmar, FL
0.08
Condo
$155,000
12/15/25
2
2
879
210 Martha Ln #210, Oldsmar, FL
0.28
Condo
$155,000
12/30/25
2
2
1,094
306 Martha Ln #42, Oldsmar, FL
0.28
Condo
$175,000
01/05/26
2
2
1,094
313 Martha Ln #4, Oldsmar, FL
0.28
Condo
$205,000
08/15/25
2
2
1,094
129 Cypress Ct #129, Oldsmar, FL
0.26
Condo
$152,000
04/03/26
2
2
1,054
107 Mary Dr #107, Oldsmar, FL
0.19
Condo
$179,000
05/15/26
2
2
1,094
106 Windward Pl, Oldsmar, FL
0.00
Condo
$124,100
04/01/26
2
2
879
226 Woodlake Wynde, Oldsmar, FL
0.41
Condo
$209,900
08/15/25
2
2
924
219 Cypress Ct #219, Oldsmar, FL
0.26
Condo
$175,000
05/01/26
2
2
1,054
213 Mary Dr #213, Oldsmar, FL
0.19
Condo
$172,500
09/25/25
2
2
1,094

Nearby homes

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Assigned Schools

These are the assigned schools for 301 Windward Pl.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Apartments for Rent

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Explore by feature - Pet Friendly

25 pet-friendly rentals in Oldsmar, FL

Explore by feature - Garage

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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

23 rentals with a washer/dryer in Oldsmar, FL

Explore by feature - Outdoor Space

7 rentals with an outdoor space in Oldsmar, FL

Homes for sale near 301 Windward Pl

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Off Market Homes Near 301 Windward Pl

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