4059 Waterview Loop, Winter Park, FL 32792
Master bedroom
Front bedroom
OFF MARKET

$410,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,647 sqft

4059 Waterview Loop, Winter Park, FL 32792

Est. Refi. Payment $2,929/mo*
Refinance Your Home
Currently Off Market - Sold Apr 1, 1990 for $104,500

Home Value

Trulia Estimate
$411K
Since last month
Decreased$6K (-1.4%)
Since last year
Increased$2K (+0.5%)
Since last sale
Increased$306K (+293.1%)
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 +85% in the last 10 years
MonthEstimated value
2026
November 2026$411K
October 2026$415K
September 2026$417K
August 2026$416K
July 2026$421K
June 2026$421K
May 2026$416K
April 2026$415K
March 2026$416K
February 2026$412K
January 2026$410K
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
4048 Waterview Loop, Winter Park, FL
0.04
Single-Family Home
$409,000
04/24/26
3
2
1,670
2009 SHADYHILL TERRACE, Winter Park, FL
0.15
Single-Family Home
$507,500
06/17/26
3
2
1,670
3720 JONQUIL LANE, Winter Park, FL
0.29
Single-Family Home
$445,000
06/01/26
3
2
1,647
1533 SPRINGTIME LOOP, Winter Park, FL
0.31
Single-Family Home
$410,000
09/23/26
3
2
1,192
1840 ASTER DRIVE, Winter Park, FL
0.53
Single-Family Home
$187,000
05/26/26
3
2
1,666
1816 MEADOWGOLD LANE, Winter Park, FL
0.23
Single-Family Home
$425,000
03/12/26
3
2.5
1,546
1280 GLADIOLAS DR, Winter Park, FL
0.33
Single-Family Home
$469,900
05/15/26
3
2
1,624
3641 OAK VISTA LANE, Winter Park, FL
0.38
Single-Family Home
$475,000
07/17/26
3
2
1,645
3641 HAWTHORNE LANE, Winter Park, FL
0.43
Single-Family Home
$440,000
11/02/26
3
2
1,622
1832 E CHERYL DRIVE, Winter Park, FL
0.34
Single-Family Home
$445,000
06/04/26
4
2
1,808

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
4051 Waterview Loop, Winter Park, FL 32792
0.02
$412,800
3
2
1,659
Off Market
4071 Waterview Loop, Winter Park, FL 32792
0.02
$495,700
4
3
1,983
Off Market
2122 Shadyhill Ter, Winter Park, FL 32792
0.02
$408,800
3
2
1,659
Off Market
2128 Shadyhill Ter, Winter Park, FL 32792
0.03
$478,700
3
2
1,891
Off Market
2114 SHADYHILL TERRACE, Winter Park, FL 32792
0.03
$496,900
3
2
1,626
Off Market
4064 Waterview Loop, Winter Park, FL 32792
0.03
$492,800
4
3
1,983
Off Market
4056 Waterview Loop, Winter Park, FL 32792
0.03
$492,400
4
3
1,983
Off Market
4087 Waterview Loop, Winter Park, FL 32792
0.03
$432,000
3
2
1,788
Off Market
4072 Waterview Loop, Winter Park, FL 32792
0.03
$480,600
4
3
2,197
Off Market
4048 Waterview Loop, Winter Park, FL 32792
0.04
$409,000
3
2
1,670
Recently Sold
4039 Waterview Loop, Winter Park, FL 32792
0.04
$496,800
3
2.5
1,884
Off Market
4080 Waterview Loop, Winter Park, FL 32792
0.04
$499,300
4
3
1,983
Off Market
2106 Shadyhill Ter, Winter Park, FL 32792
0.05
$526,000
4
2
1,983
Off Market
2134 Shadyhill Ter, Winter Park, FL 32792
0.05
$460,500
3
2
1,659
Off Market
4095 Waterview Loop, Winter Park, FL 32792
0.05
$537,400
4
2
2,197
Off Market
4088 Waterview Loop, Winter Park, FL 32792
0.05
$499,500
4
3
1,983
Off Market
4031 Waterview Loop, Winter Park, FL 32792
0.05
$427,900
3
2.5
1,715
Off Market
2127 Shadyhill Ter, Winter Park, FL 32792
0.06
$415,000
3
2
1,659
Off Market
4040 Waterview Loop, Winter Park, FL 32792
0.06
$391,700
3
2
1,648
Off Market
4032 Waterview Loop, Winter Park, FL 32792
0.06
$448,900
3
2
1,566
Off Market

Local Information

  • Map ViewExplore the area around 4059 Waterview Loop.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1990
1,647 sqft
$249/sqft
Garage

About this House

What's unique:Cozy fireplaceIndoor laundry roomSpacious family roomBreakfast nookDesirable split-bedroom floor plan
This beautiful 3br, 2ba, 2car garage home featuring volume ceilings is a split bedroom plan with walk-in closet in the master and fully equipped kitchen plus breakfast nook. The family room includes a fireplace and the screened lanai is accessed through sliding doors off the master, family room and living rooms. This wonderful, quiet community is close to shopping, recreation, as well as schools, and features a lake and tennis courts. Freshly painted inside and out, newly installed tile flooring, auto garage door and irrigation and security systems, a place you'll enjoy calling home.
4059 Waterview Loop, Winter Park, FL 32792 is a 3 bedroom, 2 bathroom, 1,647 sqft single-family home built in 1990. It last sold for $104,500 on Apr 1, 1990. More recently, it was listed as a rental in July 2026 with an asking price of $2,650 per month. That rental listing was removed on August 13, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $410,800, with a rent estimate of $2,606/month.

Home Details for 4059 Waterview Loop

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Interior Details
Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Stucco, Cement ConcreteFoundation Type: FootingLawn
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1990Year Updated: 1990
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 7492 sqft

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Aug 13, 2026
Source: Stellar MLS #O6425132
ListingRemoved
$2,650
Jul 17, 2026
Source: Stellar MLS #O6425132
Listed For Rent
$2,650
Jan 20, 2012
Source: N/A
ListingRemoved
$1,300
Jan 17, 2012
Source: N/A
Listed For Sale
$1,300
Apr 1, 1990
Source: N/A
Sold
$104,500

Market trends in Winter Park

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$465K
$10KMoM
Sale-to-List Price
98.0%
Price per sq ft
$280
$1MoM
Available listings
388
5MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Winter Park

At least 596 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 80 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
    Flag
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
    Flag
  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
    Flag
  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
    Flag
  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
    Flag
  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
    Flag
  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
    Flag
  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
    Flag
  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 4059 Waterview Loop

  • What is 4059 Waterview Loop estimated to be worth?
    Trulia's estimated value for 4059 Waterview Loop in Winter Park, FL is $410,800.
  • What is the price history for 4059 Waterview Loop?
    4059 Waterview Loop in Winter Park, FL last sold for $104,500 in April 1990.
  • Is Winter Park a buyer's or seller's market?
    Winter Park is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Park?
    The median sale price in Winter Park is $465K. That is up $10K from the prior month.
  • Does 4059 Waterview Loop have air conditioning?
    Yes, 4059 Waterview Loop in Winter Park, FL has air conditioning.
  • Does 4059 Waterview Loop have laundry facilities?
    Yes, 4059 Waterview Loop in Winter Park, FL has in-unit laundry.

Explore by feature - Pet Friendly

174 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

75 rentals with a garage in Winter Park, FL

Explore by feature - Air Conditioning

193 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

111 homes with a pool in Winter Park, FL

Explore by feature - Washer/dryer

219 rentals with a washer/dryer in Winter Park, FL

Explore by feature - Outdoor Space

60 rentals with an outdoor space in Winter Park, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 4059 Waterview Loop

Skip to last item
Skip to first item

Homes for sale near 4059 Waterview Loop

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