2 OAKDALE STREET, Windermere, FL 34786
SOLD
JAN 9, 2026

$1,595,200

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,152 sqft (on 0.40 acres)

2 OAKDALE STREET, Windermere, FL 34786

Est. Refi. Payment $11,175/mo*
Refinance Your Home
Currently Off Market - Sold Jan 9, 2026 for $1,160,000 (3% below list price)

Home Value

Trulia Estimate
$1.59M
Since last month
Increased$50K (+3.2%)
Since last year
Increased$647K (+68%)
Since last sale
Increased$439K (+37.8%)
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 +181% in the last 10 years
MonthEstimated value
2026
August 2026$1.6M
August 2026$1.6M
July 2026$1.55M
June 2026$1.19M
May 2026$1.19M
April 2026$1.19M
March 2026$1.19M
February 2026$1.19M
January 2026$1.18M
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
76 OAKDALE STREET, Windermere, FL
0.19
Single-Family Home
$1,060,000
09/11/25
3
1.5
2,011
20 OAKDALE STREET, Windermere, FL
0.06
Single-Family Home
$1,400,000
09/04/26
3
2.5
2,188
65 OAKDALE STREET, Windermere, FL
0.17
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
111 MAIN STREET, Windermere, FL
0.26
Single-Family Home
$849,000
07/01/26
3
2
2,272
416 MAGNOLIA STREET, Windermere, FL
0.52
Single-Family Home
$820,000
03/06/26
2
1.5
2,115
299 W 4TH AVENUE, Windermere, FL
0.51
Single-Family Home
$862,000
01/08/26
4
3
2,410
414 E 5TH AVENUE, Windermere, FL
0.63
Single-Family Home
$1,050,000
05/14/26
3
2
2,521
316 E 5TH AVENUE, Windermere, FL
0.60
Single-Family Home
$1,050,000
05/21/26
4
3
2,412

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
20 OAKDALE STREET, Windermere, FL 34786
0.06
$1,400,000
3
2.5
2,188
Recently Sold
19 MAIN STREET, Windermere, FL 34786
0.06
$2,792,500
4
3
2,331
Off Market
33 MAIN STREET, Windermere, FL 34786
0.10
$1,572,000
4
2
2,130
For Sale
57 OAKDALE STREET, Windermere, FL 34786
0.15
$1,231,200
3
2
1,637
Off Market
65 OAKDALE STREET, Windermere, FL 34786
0.17
$1,046,700
4
2
2,191
Off Market
2807 BUTLER BAY DRIVE N, Windermere, FL 34786
0.18
$2,487,600
5
4.5
4,876
Off Market
76 OAKDALE STREET, Windermere, FL 34786
0.19
$1,052,600
3
1.5
2,011
Off Market
50 FOREST STREET, Windermere, FL 34786
0.21
$7,422,100
6
5.5
7,388
Off Market
81 OAKDALE STREET, Windermere, FL 34786
0.21
$2,200,000
5
4.5
4,284
Recently Sold
84 OAKDALE ST, Windermere, FL 34786
0.21
$1,750,000
4
5
3,519
Recently Sold
7 1ST COURT, Windermere, FL 34786
0.23
$2,789,300
4
3
3,149
Off Market

Local Information

  • Map ViewExplore the area around 2 OAKDALE STREET.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1959
0.4 acre lot
2,152 sqft
$539/sqft
2 Car Garage

About this House

CANAL FRONTAGE ON 2 SIDES! Extremely RARE in the TOWN OF WINDERMERE, a single story 3/2 in a CUL-DE-SAC, on a PAVED STREET with a DOCK and CANALS ON 2 SIDES giving DIRECT ACCESS to LAKE DOWN AND WASEON BAY and the ENTIRE BUTLER CHAIN BEYOND. This lovingly maintained home is move-in ready, ready for your personal touches, or the ideal lot for your waterfront dream home. Extensive landscaping with abundant flowering plants and a covered front porch provide a warm welcome to this spacious ranch home. A foyer divides the kitchen and living spaces from the bedroom wing. The kitchen features solid surface countertops, wood cabinets and a breakfast nook with views of Lake Down. A large formal dining room and living room offer ample space for hosting holidays and entertaining family and friends. An absolutely enormous family room with wood plantation shutters is anchored by a beautiful wood burning fireplace and views of the canals. The spacious bedrooms feature vaulted ceilings and California closet organizers. The primary suite has an en-suite bathroom and sliding doors to a large, covered patio in the rear. The primary bath and hall bath have been beautifully updated. The large rear and side yards are also heavily landscaped with wood paths, mature cypress trees and unparalleled views of the canals. There is a COVERED DOCK in the rear. This is a NATURAL GAS home with hookups for the GRILL, DRYER and TANKLESS WATER HEATER. One of the 2 car garage bays currently houses a SAUNA. ROOF REPLACED in 2019, A/C in 2016. This is what Windermere living is all about - a large cul-de-sac waterfront lot on the Butler Chain of Lakes and a short distance to the shops and events in downtown Windermere.
2 OAKDALE STREET, Windermere, FL 34786 is a 3 bedroom, 2 bathroom, 2,152 sqft single-family home built in 1959. It last sold for $1,160,000 on Jan 9, 2026 (3% below the $1,195,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,595,200, with a rent estimate of $4,513/month.
Last check for updates: about 20 hours ago
Listed by Christopher Bauman, (407) 928-6231
REVEL REALTY LLC, (407) 876-6448
Bought with: Steve Healy, (407) 230-1441, CORCORAN PREMIER REALTY, (407) 965-1155
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6356935
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 2 OAKDALE STREET

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dinette, Dining Room, Family Room, Foyer, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2152 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Water ConnectedAppliances: Dishwasher, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, WasherDishwasherDryerLaundry: Gas Dryer Hookup,In GarageMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Electric,Heat PumpHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Family Room, Masonry, Wood BurningHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Shutters, Window TreatmentsDoor: Sliding DoorsFlooring: Carpet, Laminate, Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Laminate, Tile, Hardwood
View
Has a ViewView: Water, Canal, Lake

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Rear PorchVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation SystemFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Guest,Open
Frontage
WaterfrontWaterfront: Canal - Saltwater, Freshwater Canal Access, Lake Privileges, Lift - CoveredResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 3

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Block, Wood SidingNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 082328194801100

Price & Status

Price
List Price: $1,195,000Price Per Sqft: $539/sqft
Status Change & Dates
Off Market Date: Mon Dec 01 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINDERMERECommunity: DAVIS SHORES
School Information
Elementary School: Windermere ElemJr High / Middle School: Gotha MiddleHigh School: Olympia High

Building

Building Area
Building Area: 3328 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.40 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6356935Water ViewWater View: Water, Canal, LakeShowing Requirements: Appointment Only, ShowingTimeUniversal Property Id: US-12095-N-082328194801100-R-N

Price and Tax history

DateEventPrice
Jan 9, 2026
Source: Stellar MLS #O6356935
Sold
$1,160,000
Dec 1, 2025
Source: Stellar MLS #O6356935
Pending
$1,195,000
Nov 28, 2025
Source: Stellar MLS #O6356935
Listed For Sale
$1,195,000

Market trends in Windermere

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
296
11MoM

Around this home

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 Windermere

At least 271 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 80 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

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

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
    0
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
    0
    Flag
  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
    0
    Flag
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
    Flag
  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
    0
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
    0
    Flag
  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
    5
    Flag
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
    3
    Flag
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
    0
    Flag
  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
    2
    Flag
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
    0
    Flag
  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
    2
    Flag
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
    Flag
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
    Flag
  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
    Flag
  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
    0
    Flag
  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
    0
    Flag
  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
    Flag
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
    Flag
  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
    1
    Flag
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
    Flag
  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
    Flag
  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
    1
    Flag
  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
    0
    Flag
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
    1
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2 OAKDALE STREET

  • What is 2 OAKDALE STREET estimated to be worth?
    Trulia's estimated value for 2 OAKDALE STREET in Windermere, FL is $1,595,200.
  • What is the price history for 2 OAKDALE STREET?
    2 OAKDALE STREET in Windermere, FL last sold for $1,160,000 in January 2026.
  • Is Windermere a buyer's or seller's market?
    Windermere is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windermere?
    The median sale price in Windermere is $814K. That is up $92.5K from the prior month.
  • Does 2 OAKDALE STREET have air conditioning?
    Yes, 2 OAKDALE STREET in Windermere, FL has air conditioning.
  • Does 2 OAKDALE STREET have laundry facilities?
    Yes, 2 OAKDALE STREET in Windermere, FL has in-unit laundry.

Explore by feature - Pet Friendly

58 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

74 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

93 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

91 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

94 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

22 rentals with an outdoor space in Windermere, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 2 OAKDALE STREET

Skip to last item
Skip to first item

Homes for sale near 2 OAKDALE STREET

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