1227 Golfside Dr, Winter Park, FL 32792
OFF MARKET

$794,900

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,804 sqft

1227 Golfside Dr, Winter Park, FL 32792

Est. Refi. Payment $5,713/mo*
Refinance Your Home
Currently Off Market - Sold Dec 8, 1993 for $129,000

Home Value

Trulia Estimate
$795K
Since last month
Increased$3K (+0.4%)
Since last year
Increased$40K (+5.3%)
Since last sale
Increased$667K (+517%)
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
September 2026$796K
August 2026$795K
July 2026$793K
June 2026$800K
May 2026$790K
April 2026$788K
March 2026$783K
February 2026$768K
January 2026$752K
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
1251 Golfside Dr, Winter Park, FL
0.05
Single-Family Home
$600,000
08/21/26
4
2
2,330
3065 LINDALE AVENUE, Orlando, FL
0.21
Single-Family Home
$1,100,000
09/24/25
3
3
2,806
2844 STANFIELD AVENUE, Orlando, FL
0.20
Single-Family Home
$950,000
12/11/25
3
2.5
2,486
1729 GOLFSIDE DRIVE, Winter Park, FL
0.31
Single-Family Home
$700,000
10/20/25
4
2
2,372
1317 MEDINAH COURT, Winter Park, FL
0.16
Single-Family Home
$755,000
02/26/26
4
2
2,015
3074 STANFIELD AVENUE, Orlando, FL
0.08
Single-Family Home
$735,000
10/15/25
3
2.5
1,936
1712 GOLFSIDE DRIVE, Winter Park, FL
0.27
Single-Family Home
$750,000
01/08/26
4
2
2,111
2781 STANFIELD AVENUE, Orlando, FL
0.27
Single-Family Home
$1,396,500
09/22/25
3
2.5
2,550
1507 GOLFSIDE DRIVE, Winter Park, FL
0.28
Single-Family Home
$610,000
09/19/25
3
2
2,003
1210 FAIRWAY DR, Winter Park, FL
0.36
Single-Family Home
$480,000
05/21/26
3
2
1,737

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
1129 GOLFSIDE DRIVE, Winter Park, FL 32792
0.06
$681,900
3
2
1,750
Off Market
5391 BRADY LANE, Orlando, FL 32814
0.09
$1,012,500
4
3.5
2,584
Off Market
3074 STANFIELD AVENUE, Orlando, FL 32814
0.08
$731,800
3
2.5
1,936
Off Market
3034 STANFIELD AVENUE, Orlando, FL 32814
0.06
$920,000
4
3.5
2,603
Recently Sold
5367 BRADY LANE, Orlando, FL 32814
0.11
$769,500
3
2.5
1,838
Off Market
1106 GOLFSIDE DRIVE, Winter Park, FL 32792
0.12
$700,000
5
4
2,765
Recently Sold
5374 ARDSDALE LANE, Orlando, FL 32814
0.08
$1,240,200
5
4
2,893
Off Market
1261 BURNING TREE LANE, Winter Park, FL 32792
0.07
$797,300
4
2
2,223
Off Market
5387 HIGH PARK LANE, Orlando, FL 32814
0.08
$1,292,900
4
3.5
3,198
Off Market
2983 STANFIELD AVENUE, Orlando, FL 32814
0.08
$1,146,300
4
3.5
3,366
Off Market
5343 BRADY LANE, Orlando, FL 32814
0.12
$740,000
3
2.5
1,838
Recently Sold
5327 BRADY LANE, Orlando, FL 32814
0.14
$793,300
3
2.5
1,779
Off Market

Local Information

  • Map ViewExplore the area around 1227 Golfside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1978
2,804 sqft
$283/sqft
Garage

About this House

Builder's personal home. Nothing was missed in this immaculate 2,804 SF Live area-Florida Custom home. It has been completely updated and renovated inside and out! Enjoy relaxing in rear & side yards with tranquil Stacked Stone Waterfall pool. Entertain using your Summer Kitchen on the rear patio which features a cozy wood burning fire pit and 1200 sqaure feet of "Trex" decking. The entire yard is lushly landscaped into a quiet Garden Paradise with full yard sprinkler system including drip system to all potted plants. No through traffic. Huge Oak tree canopy along entry road all the way past the home & continuing throughout the neighborhood. All conveniences within minutes without traveling major roads. Hospital, Schools, Major shopping, Restaurants and local Church's all close by. Only 5 minutes to world renowned downtown village of Winter Park.

Neighborhood Description

No thru traffic, huge Oak tree canopy along entry road all the way past our home and continuing thurout neighborhood. ALL conveniences within minutes without traveling major roads. Hospital, Schools, major shopping and restaurant and local church's all close by. (5) minutes to world reknown downtown village of Winter Park, Fl.
1227 Golfside Dr, Winter Park, FL 32792 is a 3 bedroom, 3 bathroom, 2,804 sqft single-family home built in 1978. It last sold for $129,000 on Dec 8, 1993. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $794,900, with a rent estimate of $3,849/month.

Home Details for 1227 Golfside Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
AtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Office, Recreation Room, Sun RoomWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: Stucco, Cement ConcreteGardenLawnPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1978Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Spanish

Building

Levels, Entrance, & Accessibility
Disabled Access

Community

Units in Building: 1

Lot Information

Lot Area: 8500 sqft

Price and Tax history

DateEventPrice
May 10, 2012
Source: Agent Provided
ListingRemoved
$399,900
May 4, 2012
Source: Agent Provided
Listed For Sale
$399,900
Dec 8, 1993
Source: N/A
Sold
$129,000

Market trends in Winter Park

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$455K
$4.03KMoM
Sale-to-List Price
98.1%
0.1%MoM
Price per sq ft
$281
$6MoM
Available listings
382
13MoM

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
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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
    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 1227 Golfside Dr

  • What is 1227 Golfside Dr estimated to be worth?
    Trulia's estimated value for 1227 Golfside Dr in Winter Park, FL is $794,900.
  • What is the price history for 1227 Golfside Dr?
    1227 Golfside Dr in Winter Park, FL last sold for $129,000 in December 1993.
  • 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 $455K. That is up $4.03K from the prior month.
  • Does 1227 Golfside Dr have air conditioning?
    Yes, 1227 Golfside Dr in Winter Park, FL has air conditioning.
  • Does 1227 Golfside Dr have a pool?
    Yes, 1227 Golfside Dr in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

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