255 STIRLING AVENUE, Winter Park, FL 32789
OFF MARKET

$2,800,100

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,635 sqft (on 0.31 acres)

255 STIRLING AVENUE, Winter Park, FL 32789

Est. Refi. Payment $19,933/mo*
Refinance Your Home
Currently Off Market - Sold Nov 24, 2025 for $2,835,000

Home Value

Trulia Estimate
$2.8M
Since last month
Decreased$24K (-0.9%)
Since last year
Decreased$450K (-13.8%)
Since last sale
Decreased$36K (-1.3%)
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 +95% in the last 10 years
MonthEstimated value
2026
September 2026$2.8M
August 2026$2.82M
July 2026$2.85M
June 2026$2.87M
May 2026$2.85M
April 2026$2.82M
March 2026$2.8M
February 2026$2.82M
January 2026$2.82M
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
1450 GLENCOE ROAD, Winter Park, FL
0.09
Single-Family Home
$1,589,000
12/29/25
4
3
2,785
1336 COLLEGE POINT, Winter Park, FL
0.13
Single-Family Home
$4,250,000
06/01/26
4
4
3,181
1391 RICHMOND ROAD, Winter Park, FL
0.14
Single-Family Home
$3,325,000
12/05/25
4
5.5
4,635
319 SANTIAGO DRIVE, Winter Park, FL
0.31
Single-Family Home
$1,900,000
02/20/26
4
4.5
3,515
1400 S PENNSYLVANIA AVENUE, Winter Park, FL
0.26
Single-Family Home
$1,300,000
01/02/26
4
3
2,310
1624 BARCELONA WAY, Winter Park, FL
0.34
Single-Family Home
$2,000,000
07/24/26
3
3
3,818
1820 ENGLEWOOD ROAD, Winter Park, FL
0.37
Single-Family Home
$3,020,000
10/02/25
5
5.5
4,263
1910 GLENCOE ROAD, Winter Park, FL
0.46
Single-Family Home
$3,150,000
06/29/26
4
5.5
3,788
1600 BARCELONA WAY, Winter Park, FL
0.31
Single-Family Home
$1,305,000
11/05/25
4
3.5
3,014

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
0.07
$3,157,800
5
5
4,264
Off Market
151 STIRLING AVENUE, Winter Park, FL 32789
0.07
$1,176,500
3
2
2,352
Off Market
1321 LAKEVIEW DRIVE, Winter Park, FL 32789
0.07
$1,776,600
4
3.5
4,287
Off Market
1341 COLLEGE POINT, Winter Park, FL 32789
0.06
$4,636,600
4
3.5
4,279
Off Market
1450 GLENCOE ROAD, Winter Park, FL 32789
0.09
$1,589,000
4
3
2,785
Recently Sold
1470 GLENCOE ROAD, Winter Park, FL 32789
0.11
$2,385,300
5
4.5
3,169
Off Market
1362 RICHMOND ROAD, Winter Park, FL 32789
0.13
$2,123,600
5
3.5
2,925
Off Market
1391 RICHMOND ROAD, Winter Park, FL 32789
0.14
$3,325,000
4
5.5
4,635
Recently Sold
1336 COLLEGE POINT, Winter Park, FL 32789
0.13
$4,250,000
4
4
3,181
Recently Sold
233 HAMPDEN PLACE, Winter Park, FL 32789
0.18
$1,091,300
5
3
2,813
Off Market
1274 RICHMOND ROAD, Winter Park, FL 32789
0.17
$1,013,200
5
3
2,906
Off Market

Local Information

  • Map ViewExplore the area around 255 STIRLING AVENUE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1982
0.31 acre lot
3,635 sqft
$770/sqft
2 Car Garage

About this House

What's unique:Beautiful fireplaceIncredible lakefront viewsClear water canalNature aboundsVenetian canal systemLakefront amenities
An incredible Winter Park Chain-of-Lakes opportunity on Lake Virginia with clear views of Rollins College. This transitionally designed home, situated in the highly coveted Virginia Heights, offers an opportunity like no other with proximity to Park Avenue coupled with the lakefront amenities through a Venetian canal system that uniquely connects five lakes and captures the quintessential Winter Park lifestyle. This four-bedroom three-and-a-half-bath home invites you into a two-story foyer surrounded by windows and natural light. The spacious kitchen features a mid-century tile backsplash, light cabinetry and a window out to the pool and lake. The main living space features a beautiful fireplace and back atrium that invites the stars and twinkling sunsets from the water. The separate dining room is spacious and there is an additional den or office space to round out the first floor. All bedrooms are upstairs and generously sized providing flexibility and the primary bedroom has the most incredible lakefront views. A clear water canal runs alongside the home and spills into lake Virginia adding to the ambiance of the backyard where nature abounds. Continue the existing renovation with your own style or build a house of your dreams. Impeccably located with shopping and dining at your fingertips as well as Rollins College. Fantastic schools with Audubon K-8 and Winter Park High. Don’t miss this one – call for your private tour.
255 STIRLING AVENUE, Winter Park, FL 32789 is a 4 bedroom, 4 bathroom, 3,635 sqft single-family home built in 1982. It last sold for $2,835,000 on Nov 24, 2025 (9% below the $3,100,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,800,100, with a rent estimate of $4,950/month.
Last check for updates: about 5 hours ago
Listed by Alison Mosley, (407) 304-6458
PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Frank Mosley, (407) 489-9508
PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Bought with: Ruth Harris, (407) 443-6349, COLDWELL BANKER REALTY, (407) 647-1211
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6346603
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 255 STIRLING AVENUE

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 3, Bedroom 4, Bathroom 2, Den, Dining Room, Foyer, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3635 Square Feet
Appliances & Utilities
Utilities: PublicAppliances: Dishwasher, Disposal, Dryer, Microwave, Refrigerator, WasherDishwasherDisposalDryerLaundry: InsideMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living RoomHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Tile, Hardwood
View
Has a ViewView: Water, Lake

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Balcony, Lighting, Private Mailbox, Rain GuttersFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Pool
Pool: In GroundPool
Frontage
WaterfrontWaterfront: Lake Front, Lake - Chain of Lakes, Lake Privileges, Lift - Covered, Skiing AllowedRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Public SewerWater Body: LAKE VIRGINIA

Days on Market

Cumulative Days on Market: 25

Property Information

Year Built
Year Built: 1982
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 072230890808090

Price & Status

Price
List Price: $3,100,000
Status Change & Dates
Off Market Date: Mon Oct 20 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: VIRGINIA HEIGHTS
School Information
Elementary School: Audubon Park K8Jr High / Middle School: Audubon Park K-8High School: Winter Park High

Building

Building Area
Building Area: 4580 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.31 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6346603Water ViewWater View: Water, LakeShowing Requirements: Appointment OnlyUniversal Property Id: US-12095-N-072230890808090-R-N

Price and Tax history

DateEventPrice
Nov 24, 2025
Source: Stellar MLS #O6346603
Sold
$2,835,000
Oct 21, 2025
Source: Stellar MLS #O6346603
Pending
$3,100,000
Oct 17, 2025
Source: Stellar MLS #O6346603
PriceChange
$3,100,000
Price decreased by 6%
Sep 25, 2025
Source: Stellar MLS #O6346603
Listed For Sale
$3,299,000
May 30, 2023
Source: N/A
Sold
$2,100,000

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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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 255 STIRLING AVENUE

  • What is 255 STIRLING AVENUE estimated to be worth?
    Trulia's estimated value for 255 STIRLING AVENUE in Winter Park, FL is $2,800,100.
  • What is the price history for 255 STIRLING AVENUE?
    255 STIRLING AVENUE in Winter Park, FL last sold for $2,835,000 in November 2025.
  • 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 255 STIRLING AVENUE have air conditioning?
    Yes, 255 STIRLING AVENUE in Winter Park, FL has air conditioning.
  • Does 255 STIRLING AVENUE have a pool?
    Yes, 255 STIRLING AVENUE in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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