2255 Chantilly Ave, Winter Park, FL 32789
OFF MARKET

2255 Chantilly Ave
Winter Park, FL 32789

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

$1,207,800

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $8,263/mo*
Refinance Your Home

$1,207,800

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $8,263/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,289 sqft
(on 0.26 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

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 History for 2255 Chantilly Ave

DatePriceEventSource
08/03/2021$779,000Sold
N/A
03/02/2017$600,000Sold
N/A
12/21/2016$609,000PriceChange
Agent Provided
12/07/2016$639,000PendingToActiveAgent Provided
12/01/2016$639,000PendingAgent Provided
11/17/2016$639,000PriceChange
Agent Provided
10/31/2016$649,000PriceChange
Agent Provided
10/05/2016$655,000PriceChange
Agent Provided
09/07/2016$670,000PriceChange
Agent Provided
07/18/2016$695,000PriceChange
Agent Provided
06/06/2016$705,000PriceChange
Agent Provided
04/25/2016$725,000PriceChange
Agent Provided
04/08/2016$749,000Listed For SaleAgent Provided
06/06/2013$615,000Sold
N/A
09/02/2012$665,000ListingRemovedAgent Provided
06/30/2012$665,000PriceChange
Agent Provided
05/10/2012$687,500Listed For SaleAgent Provided
07/14/2004$680,000Sold
N/A
03/18/2003$175,000Sold
N/A

Market trends in Winter Park

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$457K
$833MoM
Sale-to-List Price
97.0%
0.3%MoM
Price per sq ft
$284
$4MoM
Available listings
363
1MoM
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Property Tax and Assessment

Year2024
Tax$10,286
Assessment$1,049,123
Home facts updated by county records

Homeowner tools

Estimated monthly rent$6,408/mo
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Homes for rent near 2255 Chantilly Ave

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Comparable Sales for 2255 Chantilly Ave

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 Ave, Winter Park, FL
0.19
Single-Family Home
$1,270,000
10/30/25
4
3.5
3,349
1475 Hibiscus Ave, Winter Park, FL
0.11
Single-Family Home
$700,000
08/21/25
4
3
2,124
2030 Versailles Ave, Winter Park, FL
0.03
Single-Family Home
$2,175,000
11/24/25
4
4
3,461
2339 Lafayette Ave, Winter Park, FL
0.15
Single-Family Home
$1,650,000
06/30/25
4
5
3,379
1690 Oneco Ave, Winter Park, FL
0.33
Single-Family Home
$1,075,000
07/31/25
4
3
2,703
2632 Mandan Trl, Winter Park, FL
0.40
Single-Family Home
$750,000
03/16/26
4
2.5
2,441
1823 Sunset Dr, Winter Park, FL
0.30
Single-Family Home
$800,000
07/18/25
3
3.5
2,414
1685 Magnolia Ave, Winter Park, FL
0.24
Single-Family Home
$396,300
10/27/25
4
3
3,331
1612 Magnolia Ave, Winter Park, FL
0.22
Single-Family Home
$1,850,000
12/12/25
4
4
3,153

Nearby homes

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Assigned Schools

These are the assigned schools for 2255 Chantilly Ave.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Park

At least 594 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 79 % 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.
  • 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
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  • 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
    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
    Flag
  • 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
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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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  • Oviedohome
    "Need to drive to work. Can walk to local parks. Walking or biking other places does not feel so friendly even though there are restaurants and grocery stores nearby. There are two commuter train stations close by. "
    2
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Homes for sale near 2255 Chantilly Ave

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Off Market Homes Near 2255 Chantilly Ave

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2255 Chantilly Ave, Winter Park, FL 32789 is a 4 bedroom, 4 bathroom, 3,289 sqft single-family home built in 2004. This property is not currently available for sale. 2255 Chantilly Ave was last sold on Aug 3, 2021 for $779,000. The current Trulia Estimate for 2255 Chantilly Ave is $1,207,800.