299 W 4TH AVENUE, Windermere, FL 34786
SOLD
JAN 8, 2026

$853,100

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,410 sqft (on 0.38 acres)

299 W 4TH AVENUE, Windermere, FL 34786

Est. Refi. Payment $6,125/mo*
Refinance Your Home
Currently Off Market - Sold Jan 8, 2026 for $862,000 (4% below list price)

Home Value

Trulia Estimate
$853K
Since last month
Decreased$8K (-0.9%)
Since last year
Increased$212K (+33%)
Since last sale
Decreased$9K (-1%)
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 +106% in the last 10 years
MonthEstimated value
2026
September 2026$853K
August 2026$861K
July 2026$869K
June 2026$873K
May 2026$867K
April 2026$860K
March 2026$855K
February 2026$859K
January 2026$861K
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
412 FOREST STREET, Windermere, FL
0.06
Single-Family Home
$765,000
07/30/26
5
2.5
2,539
635 BUTLER STREET, Windermere, FL
0.26
Single-Family Home
$975,000
10/20/25
3
3
2,353
316 E 5TH AVENUE, Windermere, FL
0.34
Single-Family Home
$1,050,000
05/21/26
4
3
2,412
111 MAIN STREET, Windermere, FL
0.26
Single-Family Home
$849,000
07/01/26
3
2
2,272
616 MAGNOLIA STREET, Windermere, FL
0.35
Single-Family Home
$830,000
10/27/25
4
2
2,582
735 OAKDALE STREET, Windermere, FL
0.42
Single-Family Home
$910,000
05/09/26
3
2.5
2,475
725 OAKDALE STREET, Windermere, FL
0.40
Single-Family Home
$1,000,000
08/28/26
3
2.5
2,795
65 OAKDALE STREET, Windermere, FL
0.39
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
720 MAIN STREET, Windermere, FL
0.36
Single-Family Home
$850,000
10/21/25
3
2
2,778

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
307 4TH AVENUE, Windermere, FL 34786
0.04
$1,209,900
4
3
3,190
Off Market
412 FOREST STREET, Windermere, FL 34786
0.06
$765,000
5
2.5
2,539
Recently Sold
526 BUTLER STREET, Windermere, FL 34786
0.17
$4,894,400
4
5
6,688
Off Market
226 FOREST STREET, Windermere, FL 34786
0.11
$778,200
3
2
1,532
Off Market
606 BUTLER STREET, Windermere, FL 34786
0.21
$2,650,800
3
2.5
3,469
Off Market
400 W 2ND AVENUE, Windermere, FL 34786
0.19
$884,100
3
2.5
2,346
Off Market
611 BUTLER STREET, Windermere, FL 34786
0.22
$775,000
3
2
1,774
For Sale
406 OAKDALE STREET, Windermere, FL 34786
0.19
$832,900
3
2
1,908
Off Market
409 W 2ND AVENUE, Windermere, FL 34786
0.21
$2,250,000
5
4.5
4,688
Recently Sold
628 BUTLER STREET, Windermere, FL 34786
0.26
$2,774,000
6
6
4,486
Off Market
628 FOREST STREET, Windermere, FL 34786
0.25
$700,000
1
1
750
For Sale

Local Information

  • Map ViewExplore the area around 299 W 4TH AVENUE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1984
0.38 acre lot
2,410 sqft
$358/sqft
3 Car Garage

About this House

What's unique:Island kitchenSecond-floor laundry roomGranite countertopsBeautiful curb appealNewly installed windowsSpacious primary suite
This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting. Step inside to original wood floors that extend throughout the main living areas, enriching the home with warmth and timeless appeal. The family room centers around a charming wood-burning fireplace, surrounded by newly installed windows (2020) that fill the space with natural light. French doors open to a large screened porch — an ideal spot for morning coffee, outdoor dining, or unwinding beneath the shade of mature trees. The island kitchen features granite countertops and generous workspace for cooking and entertaining. The first floor includes a full bedroom and bath, perfect for guests or a home office. Upstairs, the spacious primary suite offers a peaceful retreat, joined by two additional bedrooms and the convenience of a second-floor laundry room. New Septic and drain field 2020, A/C 2024, Well re-sleaved and new pump 2024. A partially air-conditioned, three-car garage provides excellent storage and space for vehicles, golf carts, or weekend adventure gear. Stroll or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience.
299 W 4TH AVENUE, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,410 sqft single-family home built in 1984. It last sold for $862,000 on Jan 8, 2026 (4% below the $895,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $853,100, with a rent estimate of $4,520/month.
Last check for updates: about 1 hour ago
Listed by Judy Black, (407) 810-1803
UPSIDE REAL ESTATE INC, (407) 308-5750
Amanda Black PA, (407) 616-0140
UPSIDE REAL ESTATE INC, (407) 308-5750
Bought with: Amanda Black PA, (407) 616-0140, UPSIDE REAL ESTATE INC, (407) 308-5750
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6357207
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 299 W 4TH AVENUE

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Balcony Porch Lanai, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2410 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Electricity ConnectedAppliances: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, WasherDishwasherDisposalDryerLaundry: Inside,Laundry Room,Upper LevelMicrowaveWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Wood BurningHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: French DoorsFlooring: Laminate, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Laminate, Hardwood
View
Has a ViewView: Trees/Woods

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Rear Porch, ScreenedVegetation: Bamboo, Fruit Trees, Oak TreesExterior: Private MailboxFoundation: CrawlspaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Other Parking: Garage Dimensions: 34x24No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Garage Door Opener,Garage Faces Side,Golf Cart Garage
Frontage
Waterfront: Lake PrivilegesResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Unimproved, DirtNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 35

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Craftsman
Building
Construction Materials: Wood SidingNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 172328933603200

Price & Status

Price
List Price: $895,000Price Per Sqft: $358/sqft
Status Change & Dates
Off Market Date: Fri Dec 12 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

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

Building

Building Area
Building Area: 3936 Square Feet

Community

Community Features: Golf Carts OK, Park, Playground, Restaurant, Tennis Court(s)Not Senior Community
Other
Playground

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.38 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, VA Loan

Energy

Energy Efficiency Features: Windows

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6357207Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-172328933603200-R-N

Additional Information

Golf Carts OKParkPlaygroundRestaurantTennis Court(s)

Price and Tax history

DateEventPrice
Jan 8, 2026
Source: Stellar MLS #O6357207
Sold
$862,000
Dec 13, 2025
Source: Stellar MLS #O6357207
Pending
$895,000
Nov 7, 2025
Source: Stellar MLS #O6357207
Listed For Sale
$895,000
Jan 2, 2025
Source: N/A
Sold
$650,000
Apr 22, 2019
Source: N/A
Sold
$425,000

Market trends in Windermere

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$856K
$41.5KMoM
Sale-to-List Price
96.8%
0.4%MoM
Price per sq ft
$297
$5MoM
Available listings
274
22MoM

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 299 W 4TH AVENUE

  • What is 299 W 4TH AVENUE estimated to be worth?
    Trulia's estimated value for 299 W 4TH AVENUE in Windermere, FL is $853,100.
  • What is the price history for 299 W 4TH AVENUE?
    299 W 4TH AVENUE in Windermere, FL last sold for $862,000 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 $856K. That is up $41.5K from the prior month.
  • Does 299 W 4TH AVENUE have air conditioning?
    Yes, 299 W 4TH AVENUE in Windermere, FL has air conditioning.
  • Does 299 W 4TH AVENUE have laundry facilities?
    Yes, 299 W 4TH AVENUE in Windermere, FL has in-unit laundry.

Explore by feature - Pet Friendly

59 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

72 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

92 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

85 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

99 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

21 rentals with an outdoor space in Windermere, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 299 W 4TH AVENUE

Skip to last item
Skip to first item

Homes for sale near 299 W 4TH AVENUE

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