2255 Chantilly Ave, Winter Park, FL 32789
Property image
Property image
OFF MARKET

$1,230,300

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,289 sqft (on 0.26 acres)

2255 Chantilly Ave, Winter Park, FL 32789

Est. Refi. Payment $8,487/mo*
Refinance Your Home
Currently Off Market - Sold Aug 3, 2021 for $779,000

Home Value

Trulia Estimate
$1.23M
Since last month
Increased$6K (+0.5%)
Since last year
Increased$28K (+2.3%)
Since last sale
Increased$448K (+57.5%)
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 +88% in the last 10 years
MonthEstimated value
2026
August 2026$1.23M
August 2026$1.23M
July 2026$1.22M
June 2026$1.23M
May 2026$1.2M
April 2026$1.21M
March 2026$1.2M
February 2026$1.19M
January 2026$1.18M
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
1440 Place Vendome, Winter Park, FL
0.03
Single-Family Home
$1,250,000
01/06/26
5
4
3,800
2401 LAFAYETTE AVENUE, Winter Park, FL
0.19
Single-Family Home
$1,270,000
10/30/25
4
3.5
3,349
2030 VERSAILLES AVENUE, Winter Park, FL
0.03
Single-Family Home
$2,175,000
11/24/25
4
4
3,461
1340 PLACE PICARDY, Winter Park, FL
0.17
Single-Family Home
$1,500,000
06/29/26
3
3.5
3,459
2632 MANDAN TRAIL, Winter Park, FL
0.40
Single-Family Home
$750,000
03/16/26
4
2.5
2,441
2408 LAFAYETTE AVENUE, Winter Park, FL
0.19
Single-Family Home
$1,395,000
06/30/26
4
3.5
2,838
1685 Magnolia Ave, Winter Park, FL
0.24
Single-Family Home
$396,300
10/27/25
4
3
3,331
1612 MAGNOLIA AVENUE, Winter Park, FL
0.22
Single-Family Home
$1,850,000
12/12/25
4
4
3,153
2607 Lafayette Ave, Winter Park, FL
0.36
Single-Family Home
$1,000,000
04/01/26
4
3.5
2,770
2423 VIA SIENNA, Winter Park, FL
0.26
Single-Family Home
$2,080,000
06/26/26
4
3.5
3,472

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
1531 PLACE PICARDY, Winter Park, FL 32789
0.04
$1,928,700
4
4
3,964
Off Market
2030 VERSAILLES AVENUE, Winter Park, FL 32789
0.03
$2,175,000
4
4
3,461
Recently Sold
1470 PLACE PICARDY, Winter Park, FL 32789
0.08
$1,602,900
5
5
4,227
Off Market
1421 PLACE PICARDY, Winter Park, FL 32789
0.07
$2,671,900
5
5
4,882
Off Market
2301 CHANTILLY AVENUE, Winter Park, FL 32789
0.08
$1,444,000
4
4
3,350
Off Market
1400 PLACE PICARDY, Winter Park, FL 32789
0.10
$2,527,100
5
5.5
4,338
Off Market
2343 VERSAILLES AVENUE, Winter Park, FL 32789
0.11
$1,865,000
4
3.5
3,307
For Sale
1443 HIBISCUS AVENUE, Winter Park, FL 32789
0.11
$838,800
3
2.5
1,994
Off Market
1361 PLACE VENDOME, Winter Park, FL 32789
0.12
$1,559,600
4
4
3,578
Off Market
2415 VERSAILLES AVENUE, Winter Park, FL 32789
0.14
$1,861,500
4
3.5
3,954
Off Market
2329 LAFAYETTE AVENUE, Winter Park, FL 32789
0.14
$1,536,600
5
4.5
2,992
Off Market
1350 PLACE VENDOME, Winter Park, FL 32789
0.14
$1,898,300
4
3.5
4,049
Off Market

Local Information

  • Map ViewExplore the area around 2255 Chantilly 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
2004
Lot Size
0.26 acres
Living Area
3,289 sqft
Price/Sqft
$374
Parking
Garage

About this House

Spacious, gracious and priced to sell! Don't miss this remarkable four bedroom custom- designed Winter Park beauty! Lovely wood floors, tall ceilings, gorgeous crown molding, beautiful architectural trim, and a rear-entry garage are just a few of the many special features of this home. The kitchen is fabulous with its large breakfast room, black granite countertops, stainless steel appliances and custom cabinetry. This kitchen is a chef's dream and overlooks the family room with a great view of the large back yard. This entire space is ideal for family gatherings and any and all entertaining. Adjacent to the kitchen and leading into the formal dining room is a very functional butler's pantry. The downstairs master bedroom has new wood floors, a walk-in closet, and French Doors leading to the covered patio. The master bath has dual sinks, a Jacuzzi tub and the convenience of a separate shower. Three additional bedrooms, two baths, and a bonus room comprise the second story. On the exterior, a columned front porch and a second story balcony give this house great curb appeal! The short distance to downtown Winter Park and the ever popular Park Avenue makes this an ultra-convenient locations. "A" rated schools - Dommerich Elementary, Maitland Middle, and Winter Park High.
2255 Chantilly Ave, Winter Park, FL 32789 is a 4 bedroom, 4 bathroom, 3,289 sqft single-family home built in 2004. It last sold for $779,000 on Aug 3, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,230,300, with a rent estimate of $7,991/month.

Home Details for 2255 Chantilly Ave

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Types of Rooms: Dining RoomCeiling Fan
Appliances & Utilities
DishwasherMicrowave

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: StuccoGardenPatioPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2004Year Updated: 2004
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Aug 3, 2021
Source: N/A
Sold
$779,000
Mar 2, 2017
Source: N/A
Sold
$600,000
Dec 21, 2016
Source: Agent Provided
PriceChange
$609,000
Price decreased by 5%
Dec 7, 2016
Source: Agent Provided
PendingToActive
$639,000
Dec 1, 2016
Source: Agent Provided
Pending
$639,000

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
    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
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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 2255 Chantilly Ave

  • What is 2255 Chantilly Ave estimated to be worth?
    Trulia's estimated value for 2255 Chantilly Ave in Winter Park, FL is $1,230,300.
  • What is the price history for 2255 Chantilly Ave?
    2255 Chantilly Ave in Winter Park, FL last sold for $779,000 in August 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 2255 Chantilly Ave have air conditioning?
    Yes, 2255 Chantilly Ave in Winter Park, FL has air conditioning.
  • How big is the lot at 2255 Chantilly Ave?
    The lot at 2255 Chantilly Ave in Winter Park, FL is about 0.26 acres (11,225 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 2255 Chantilly Ave

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