1780 Windsor Dr, Winter Park, FL 32789
Property image
Property image
OFF MARKET

$799,900

Trulia Estimate
as of Sep 12, 2026
  • 3 Beds
  • 2 Baths
  • 1,824 sqft

1780 Windsor Dr, Winter Park, FL 32789

Home Highlights

Single-Family Home
1,824 sqft
$439/sqft
Garage

Local Information

  • Map ViewExplore the area around 1780 Windsor Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

This home is located in one of the most desirable areas of Winter Park. You will be walking distance the the Winter Park YMC and a short drive to Rollins College and the Park Ave shopping district. The home is on a large fenced lot with lawn maintenance included. The home has had some recent upgrades with new granite in the kitchen and new wood laminate in the master bedroom. The home has a nice enclosed porch with glass French doors overlooking the large backyard. There is a formal dining room, split plan bedrooms, and very large living room perfect for entertaining.
1780 Windsor Dr, Winter Park, FL 32789 is a 3 bedroom, 2 bathroom, 1,824 sqft single-family home. It last sold for $197,500 on Jul 1, 2011 (6,710% above the $2,900 asking price). More recently, it was listed as a rental in August 2024 with an asking price of $3,100 per month. That rental listing was removed on October 1, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $799,900, with a rent estimate of $3,337/month.

Home Details for 1780 Windsor Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Interior Features

Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central Air, Ceiling Fan

Exterior Features

Exterior Home Features
Lawn
Parking & Garage
GarageParking: Garage, On Site

Comparable Sales for 1780 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2002 Taylor Ave, Winter Park, FL
0.25
Single-Family Home
$300,000
08/19/26
3
2
1,468 sqft
1921 TAYLOR AVENUE, Winter Park, FL
0.19
Single-Family Home
$415,000
12/25/25
3
2
1,322 sqft
1871 BRYAN AVENUE, Winter Park, FL
0.17
Single-Family Home
$499,000
06/24/26
3
2
1,232 sqft
2042 YORKSHIRE DRIVE, Winter Park, FL
0.27
Single-Family Home
$475,000
02/06/26
3
2
1,573 sqft
1909 EDWIN BOULEVARD, Winter Park, FL
0.26
Single-Family Home
$425,000
04/30/26
3
2
1,355 sqft
524 BYRON ROAD, Winter Park, FL
0.30
Single-Family Home
$425,000
10/06/25
3
2
1,469 sqft
2007 Edwin Blvd, Winter Park, FL
0.33
Single-Family Home
$360,000
05/29/26
3
1.5
1,388 sqft
633 LANDER ROAD, Winter Park, FL
0.32
Single-Family Home
$421,000
04/29/26
3
2
1,400 sqft
1681 WOODLAND AVENUE, Winter Park, FL
0.17
Single-Family Home
$750,000
11/19/25
3
2
2,422 sqft
1822 YORKSHIRE DRIVE, Winter Park, FL
0.20
Single-Family Home
$557,000
07/31/26
3
3
1,620 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Winter Park

Last updated Sep 2026
Trulia Rent Estimate$3,337/mo
Average rent
$1.92K
$84MoM
Available listings
272
View rental market trends in Winter Park, FL

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
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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
    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
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  • 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
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  • 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
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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
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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

Price and Tax history

DateEventPrice
Oct 1, 2024
Source: Zillow Rentals
ListingRemoved
$2,900
Sep 5, 2024
Source: Zillow Rentals
PriceChange
$2,900
Price decreased by 6%
Aug 13, 2024
Source: Zillow Rentals
Listed For Rent
$3,100
Aug 18, 2023
Source: Zillow Rentals
ListingRemoved
Jun 28, 2023
Source: Zillow Rentals
PriceChange
$3,100
Price decreased by 3%

Frequently asked questions about 1780 Windsor Dr

  • What is 1780 Windsor Dr estimated to be worth?
    Trulia's estimated value for 1780 Windsor Dr in Winter Park, FL is $799,900.
  • What is the price history for 1780 Windsor Dr?
    1780 Windsor Dr in Winter Park, FL last sold for $197,500 in July 2011.
  • 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 1780 Windsor Dr have air conditioning?
    Yes, 1780 Windsor Dr in Winter Park, FL has air conditioning.
  • Does 1780 Windsor Dr have laundry facilities?
    Yes, 1780 Windsor Dr in Winter Park, FL has in-unit laundry.

Homes for rent near 1780 Windsor Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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