320 Cortland Ave, Winter Park, FL 32789
Property image
Property image
OFF MARKET

$2,862,200

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 4,321 sqft (on 0.65 acres)

320 Cortland Ave, Winter Park, FL 32789

Est. Refi. Payment $20,022/mo*
Refinance Your Home
Currently Off Market - Sold Mar 21, 2017 for $1,375,000

Home Value

Trulia Estimate
$2.86M
Since last month
Increased$77K (+2.8%)
Since last year
Increased$251K (+9.6%)
Since last sale
Increased$1M (+108.4%)
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 +114% in the last 10 years
MonthEstimated value
2026
August 2026$2.87M
August 2026$2.86M
July 2026$2.79M
June 2026$2.87M
May 2026$2.86M
April 2026$2.81M
March 2026$2.82M
February 2026$2.81M
January 2026$2.77M
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
446 ALBERTA DRIVE, Winter Park, FL
0.12
Single-Family Home
$1,600,000
04/22/26
4
2.5
3,263
321 SYLVAN BOULEVARD, Winter Park, FL
0.10
Single-Family Home
$1,300,000
07/24/26
3
2.5
2,821
234 DETMAR DRIVE, Winter Park, FL
0.20
Single-Family Home
$1,400,000
06/25/26
4
5.5
3,609
409 Balmoral Rd, Winter Park, FL
0.64
Single-Family Home
$1,325,000
05/08/26
4
3.5
3,651
1571 LASBURY AVENUE, Winter Park, FL
0.37
Single-Family Home
$1,700,000
02/26/26
4
3
2,749
473 FLETCHER PLACE, Winter Park, FL
0.16
Single-Family Home
$3,000,000
05/15/26
5
5.5
4,296
405 LAKEWOOD DRIVE, Winter Park, FL
0.29
Single-Family Home
$6,500,000
07/31/26
4
3
4,208
1521 HARRIS CIRCLE, Winter Park, FL
0.28
Single-Family Home
$4,500,000
05/29/26
4
4.5
3,922
185 SYLVAN BOULEVARD, Winter Park, FL
0.23
Single-Family Home
$2,500,000
03/06/26
4
4.5
3,138
516 HENKEL CIRCLE, Winter Park, FL
0.31
Single-Family Home
$2,925,000
03/24/26
5
6
4,143

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
360 CORTLAND AVENUE, Winter Park, FL 32789
0.04
$2,741,800
4
6
4,240
Off Market
311 CORTLAND AVENUE, Winter Park, FL 32789
0.03
$784,800
2
2
1,382
Off Market
446 ALBERTA DRIVE, Winter Park, FL 32789
0.12
$1,600,000
4
2.5
3,263
Recently Sold
250 CORTLAND AVENUE, Winter Park, FL 32789
0.06
$920,000
3
2
2,114
Recently Sold
1310 ALOMA AVENUE, Winter Park, FL 32789
0.05
$807,000
4
2.5
2,533
Off Market
1219 Verdant Glade Pl, Winter Park, FL 32792
0.11
$636,300
3
3.5
2,002
Off Market
345 SYLVAN BOULEVARD, Winter Park, FL 32789
0.07
$1,044,000
4
2.5
2,011
Off Market
425 ALBERTA DRIVE, Winter Park, FL 32789
0.14
$2,692,300
3
2
2,310
Off Market
281 BREWER AVENUE, Winter Park, FL 32789
0.13
$1,800,000
5
4.5
4,029
For Sale
321 SYLVAN BOULEVARD, Winter Park, FL 32789
0.10
$1,300,000
3
2.5
2,821
Recently Sold
1333 ALBERTA DRIVE, Winter Park, FL 32789
0.14
$5,178,000
3
3.5
3,738
Off Market
450 LAKEWOOD DRIVE, Winter Park, FL 32789
0.18
$2,500,000
5
5
4,572
For Sale

Local Information

  • Map ViewExplore the area around 320 Cortland Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
0.65 acre lot
4,321 sqft
$662/sqft
Garage

About this House

Stunning Olde World Masterpiece Estate completely remodeled by Bill Felkel! Walk to Park Ave. 4 bedrooms, 3.5 baths plus 2 offices. Casa Floresta-featured in WP Magazine and Orlando Home & Leisure. Designed by WP''s notable architect Harold Hair in 1937. 2010 Parade of Homes Winner! Four lots in the heart of WP. Enter into the picturesque courtyard with sections of reclaimed New Orleans iron and fountain. Cozy living room and wine closet and bar. Plaster walls, wood floors and authentic Spanish Saltillo tile floors (clay from river beds in Mexico). Breathtaking dining room-20 ft cathedral ceilings and wood burning fireplace. Relax in family rooms with hand-painted beams reproduced from Knowles Chapel and slate floors with floor to ceiling windows. Well appointed and gracious kitchen. Subzero, Thermador natural gas cooktop, 2 dishwashers. Bosch washer and dryer. Granite counters. Beautiful master bedroom, custom closet and spacious master bath with dual vanities, jetted tub, separate shower. Tranquil backyard setting with tons of entertaining areas. Saltwater/heated pool with hand-painted Mexican tile. Reclaimed Chicago brick pavers. Outdoor living room designed by Tom Lamar. Vintage barrel roof tiles to match home. Hand-painted Mexican tile sink. Hand cast fireplace, stone interior. Wood fired pizza oven. Hand-painted tresses (elements of Biltmore Hotel). Chandelier is original to the home. Hand forged iron encasing window, custom iron S-stops on shutters designed from Casa Feliz. Historic meets modern.
320 Cortland Ave, Winter Park, FL 32789 is a 4 bedroom, 4 bathroom, 4,321 sqft single-family home built in 1940. It last sold for $1,375,000 on Mar 21, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,862,200, with a rent estimate of $7,125/month.

Home Details for 320 Cortland Ave

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood, Slate
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyMicrowaveRefrigerator
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1940Year Updated: 1990
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.65 acres

Price and Tax history

DateEventPrice
Mar 21, 2017
Source: N/A
Sold
$1,375,000
Dec 21, 2016
Source: Agent Provided
Pending
$1,399,000
Jul 27, 2016
Source: Agent Provided
Listed For Sale
$1,399,000
Jun 15, 2016
Source: Agent Provided
ListingRemoved
$1,399,000
Jun 8, 2016
Source: Agent Provided
PriceChange
$1,399,000
Price decreased by 2%

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
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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
    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
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LGBTQ Local Legal Protections

Frequently asked questions about 320 Cortland Ave

  • What is 320 Cortland Ave estimated to be worth?
    Trulia's estimated value for 320 Cortland Ave in Winter Park, FL is $2,862,200.
  • What is the price history for 320 Cortland Ave?
    320 Cortland Ave in Winter Park, FL last sold for $1,375,000 in March 2017.
  • 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 320 Cortland Ave have air conditioning?
    Yes, 320 Cortland Ave in Winter Park, FL has air conditioning.
  • Does 320 Cortland Ave have a pool?
    Yes, 320 Cortland Ave in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

145 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

162 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

130 rentals with a pool in Winter Park, FL

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160 rentals with a washer/dryer in Winter Park, FL

Explore by feature - Outdoor Space

53 rentals with an outdoor space in Winter Park, FL

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Off Market Homes Near 320 Cortland Ave

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