1144 Sunset Dr, Winter Park, FL 32789
OFF MARKET

$2,450,200

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 4,777 sqft (on 0.29 acres)

1144 Sunset Dr, Winter Park, FL 32789

Est. Refi. Payment $16,956/mo*
Refinance Your Home
Currently Off Market - Sold Jun 22, 2021 for $1,650,000

Home Value

Trulia Estimate
$2.45M
Since last month
Increased$52K (+2.2%)
Since last year
Increased$136K (+5.9%)
Since last sale
Increased$805K (+48.8%)
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 +55% in the last 10 years
MonthEstimated value
2026
August 2026$2.45M
July 2026$2.4M
June 2026$2.45M
May 2026$2.42M
April 2026$2.42M
March 2026$2.41M
February 2026$2.39M
January 2026$2.33M
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
1361 PALMER AVE., Winter Park, FL
0.11
Single-Family Home
$1,825,000
10/16/25
5
3.5
3,558
1560 WOODLAND AVENUE, Winter Park, FL
0.20
Single-Family Home
$1,675,000
05/08/26
5
4.5
3,851
1420 PALMER AVENUE, Winter Park, FL
0.11
Single-Family Home
$1,300,000
11/06/25
4
3.5
2,953
715 VIA BELLA, Winter Park, FL
0.31
Single-Family Home
$2,078,500
12/11/25
5
4
4,328
1540 PALM AVENUE, Winter Park, FL
0.34
Single-Family Home
$1,860,000
03/26/26
5
3.5
3,423
1610 OAKHURST AVENUE, Winter Park, FL
0.14
Single-Family Home
$3,200,000
10/20/25
5
6
4,255
1300 MAYFIELD AVENUE, Winter Park, FL
0.14
Single-Family Home
$2,490,000
07/30/26
5
5.5
4,389
1781 PINE AVENUE, Winter Park, FL
0.34
Single-Family Home
$2,037,500
11/24/25
5
4.5
3,882
1640 MAYFIELD AVENUE, Winter Park, FL
0.12
Single-Family Home
$1,785,000
09/11/25
3
2.5
2,907
1661 WOODLAND AVENUE, Winter Park, FL
0.19
Single-Family Home
$1,300,000
05/15/26
3
3.5
3,215

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
1503 PALMER AVENUE, Winter Park, FL 32789
0.03
$1,315,400
4
3
2,688
Off Market
1520 PALMER AVENUE, Winter Park, FL 32789
0.07
$777,200
2
2
1,542
Off Market
1530 MAYFIELD AVENUE, Winter Park, FL 32789
0.02
$2,838,500
4
5
3,985
Off Market
1570 PALMER AVENUE, Winter Park, FL 32789
0.08
$1,640,000
4
3.5
3,048
For Sale
1600 PALMER AVENUE, Winter Park, FL 32789
0.08
$1,130,000
3
2.5
2,550
Recently Sold
1420 PALMER AVENUE, Winter Park, FL 32789
0.11
$1,300,000
4
3.5
2,953
Recently Sold
1597 OAKHURST AVENUE, Winter Park, FL 32789
0.10
$2,699,000
5
4.5
4,410
For Sale
1361 PALMER AVE., Winter Park, FL 32789
0.11
$1,817,200
5
3.5
3,558
Off Market
1611 MAYFIELD AVENUE, Winter Park, FL 32789
0.08
$1,880,100
6
5
3,266
Off Market
1351 MAYFIELD AVENUE, Winter Park, FL 32789
0.11
$850,000
3
2
1,466
Recently Sold
1660 PALMER AVENUE, Winter Park, FL 32789
0.12
$4,950,000
5
6.5
5,636
Recently Sold
1610 OAKHURST AVENUE, Winter Park, FL 32789
0.14
$3,187,200
5
6
4,255
Off Market

Local Information

  • Map ViewExplore the area around 1144 Sunset Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2008
Lot Size
0.29 acres
Living Area
4,777 sqft
Price/Sqft
$513
Parking
Garage

About this House

SHORT SALE...custom home redesigned and rebuilt in 2008 by Phil Kean Designs, Inc. for private client that never moved in. This home has never been lived in, clients were relocated prior to completion. Do not purchase another home in this price rangewithout seeing this one. Nothing has been left out of this home. Two master suites, one up and one down, designer kitchen with large attached prep area and butlers pantry with Sub-Zero refrigerator, two Wolf ovens and warming drawer, ice maker, two dishwashers, two ultra wine refrigerators and much more.... This home is NOW PRICED TO SELL.........PLEASE CONTINUE TO SHOW AND SUBMIT OFFERS DURING THE SHORT SALE PROCESS.....
1144 Sunset Dr, Winter Park, FL 32789 is a 5 bedroom, 5 bathroom, 4,777 sqft single-family home built in 2008. It last sold for $1,650,000 on Jun 22, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,450,200, with a rent estimate of $7,419/month.

Home Details for 1144 Sunset Dr

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace
Security
Security System

Property Information

Year Built
Year Built: 2008Year Updated: 2008
Property Type / Style
Property Type: Single Family Home

Exterior Features

Exterior Home Features
PatioPorchSprinkler System
Parking & Garage
GarageParking: Garage

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Jul 12, 2024
Source: Stellar MLS #O5939073
ListingRemoved
$1,600,000
Jun 22, 2021
Source: N/A
Sold
$1,650,000
May 11, 2021
Source: Stellar MLS #O5939073
Pending
$1,600,000
May 4, 2021
Source: Stellar MLS #O5939073
PendingToActive
$1,600,000
May 4, 2021
Source: Stellar MLS #O5939073
Pending
$1,600,000

Market trends in Winter Park

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$451K
$833MoM
Sale-to-List Price
98.0%
0.3%MoM
Price per sq ft
$287
$0MoM
Available listings
368
12MoM

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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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LGBTQ Local Legal Protections

Frequently asked questions about 1144 Sunset Dr

  • What is 1144 Sunset Dr estimated to be worth?
    Trulia's estimated value for 1144 Sunset Dr in Winter Park, FL is $2,450,200.
  • What is the price history for 1144 Sunset Dr?
    1144 Sunset Dr in Winter Park, FL last sold for $1,650,000 in June 2021.
  • 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 $451K. That is down $833 from the prior month.
  • Does 1144 Sunset Dr have air conditioning?
    Yes, 1144 Sunset Dr in Winter Park, FL has air conditioning.
  • How big is the lot at 1144 Sunset Dr?
    The lot at 1144 Sunset Dr in Winter Park, FL is about 0.29 acres (12,463 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 1144 Sunset Dr

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