321 Stirling Ave, Winter Park, FL 32789
OFF MARKET

$4,057,100

Trulia Estimate
  • 5 Beds
  • 5.5 Baths
  • 5,500 sqft (on 0.32 acres)

321 Stirling Ave, Winter Park, FL 32789

Est. Refi. Payment $28,241/mo*
Refinance Your Home
Currently Off Market - Sold Aug 17, 1998 for $244,500

Home Value

Trulia Estimate
$4.06M
Since last month
Increased$129K (+3.3%)
Since last year
Increased$519K (+14.7%)
Since last sale
Increased$4M (+1,559.3%)
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 +189% in the last 10 years
MonthEstimated value
2026
August 2026$4.06M
August 2026$4.03M
July 2026$3.93M
June 2026$3.88M
May 2026$3.91M
April 2026$3.81M
March 2026$3.85M
February 2026$3.83M
January 2026$3.71M
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
1221 RICHMOND ROAD, Winter Park, FL
0.18
Single-Family Home
$5,125,000
06/24/26
5
5.5
5,164
1391 RICHMOND ROAD, Winter Park, FL
0.08
Single-Family Home
$3,325,000
12/05/25
4
5.5
4,635
255 STIRLING AVENUE, Winter Park, FL
0.07
Single-Family Home
$2,835,000
11/24/25
4
3.5
3,635
1336 COLLEGE POINT, Winter Park, FL
0.20
Single-Family Home
$4,250,000
06/01/26
4
4
3,181
319 SANTIAGO DRIVE, Winter Park, FL
0.25
Single-Family Home
$1,900,000
02/20/26
4
4.5
3,515
1820 ENGLEWOOD ROAD, Winter Park, FL
0.36
Single-Family Home
$3,020,000
10/02/25
5
5.5
4,263
215 SALVADOR SQUARE, Winter Park, FL
0.24
Single-Family Home
$1,000,000
11/03/25
4
3.5
2,565
1450 GLENCOE ROAD, Winter Park, FL
0.15
Single-Family Home
$1,589,000
12/29/25
4
3
2,785
1600 BARCELONA WAY, Winter Park, FL
0.24
Single-Family Home
$1,305,000
11/05/25
4
3.5
3,014
1742 BARCELONA WAY, Winter Park, FL
0.36
Single-Family Home
$1,480,000
09/19/25
5
7
3,626

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
1331 LAKEVIEW DRIVE, Winter Park, FL 32789
0.02
$3,158,600
5
5
4,264
Off Market
1321 LAKEVIEW DRIVE, Winter Park, FL 32789
0.03
$1,640,400
4
3.5
4,287
Off Market
1362 RICHMOND ROAD, Winter Park, FL 32789
0.06
$2,095,700
5
3.5
2,925
Off Market
255 STIRLING AVENUE, Winter Park, FL 32789
0.07
$2,835,000
4
3.5
3,635
Recently Sold
1391 RICHMOND ROAD, Winter Park, FL 32789
0.08
$3,325,000
4
5.5
4,635
Recently Sold
1274 RICHMOND ROAD, Winter Park, FL 32789
0.11
$1,005,800
5
3
2,906
Off Market
1341 COLLEGE POINT, Winter Park, FL 32789
0.13
$4,538,400
4
3.5
4,279
Off Market
151 STIRLING AVENUE, Winter Park, FL 32789
0.14
$1,174,900
3
2
2,352
Off Market
1450 GLENCOE ROAD, Winter Park, FL 32789
0.15
$1,589,000
4
3
2,785
Recently Sold
1470 GLENCOE ROAD, Winter Park, FL 32789
0.15
$2,369,000
5
4.5
3,169
Off Market
451 FAIRFAX AVE., Winter Park, FL 32789
0.16
$879,000
3
3
2,227
Recently Sold
233 HAMPDEN PLACE, Winter Park, FL 32789
0.19
$1,100,900
5
3
2,813
Off Market

Local Information

  • Map ViewExplore the area around 321 Stirling Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2017
Lot Size
0.32 acres
Living Area
5,500 sqft
Price/Sqft
$738
Parking
Garage

About this House

Stunning high end new construction/equipped 5 bedroom pool/spa/outdoor kitchen home with mother-in-law suite and basement, and exquisite landscaping by Signature Landscape. The house is across the street from Lake Virginia which can be see from the Master bedroom/balcony, and is a short walk to downtown Park Avenue, Winter Park.
321 Stirling Ave, Winter Park, FL 32789 is a 5 bedroom, 6 bathroom, 5,500 sqft single-family home built in 2017. It last sold for $244,500 on Aug 17, 1998. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,057,100, with a rent estimate of $6,668/month.

Home Details for 321 Stirling Ave

Interior Features

Interior Details
BasementAtticIn-law unitTypes of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation RoomWet Bar
Heating & Cooling
Heating: Forced Air, Electric, GasCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: Stucco, Wood, Brick, Cement ConcreteGardenLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 2017Year Updated: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Spanish

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price and Tax history

DateEventPrice
Aug 17, 1998
Source: N/A
Sold
$244,500
Jun 20, 1996
Source: N/A
Sold
$235,000

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
    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
    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
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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 321 Stirling Ave

  • What is 321 Stirling Ave estimated to be worth?
    Trulia's estimated value for 321 Stirling Ave in Winter Park, FL is $4,057,100.
  • What is the price history for 321 Stirling Ave?
    321 Stirling Ave in Winter Park, FL last sold for $244,500 in August 1998.
  • 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 321 Stirling Ave have air conditioning?
    Yes, 321 Stirling Ave in Winter Park, FL has air conditioning.
  • Does 321 Stirling Ave have a pool?
    Yes, 321 Stirling Ave in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

143 pet-friendly rentals in Winter Park, FL

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132 rentals with a pool in Winter Park, FL

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58 rentals with an outdoor space in Winter Park, FL

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Off Market Homes Near 321 Stirling Ave

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