1781 Windsor Dr, Winter Park, FL 32789
Property image
Property image
OFF MARKET

$1,182,700

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,444 sqft (on 0.26 acres)

1781 Windsor Dr, Winter Park, FL 32789

Est. Refi. Payment $8,424/mo*
Refinance Your Home
Currently Off Market - Sold May 14, 2021 for $805,000

Home Value

Trulia Estimate
$1.18M
Since last month
Increased$21K (+1.8%)
Since last year
Increased$65K (+5.8%)
Since last sale
Increased$379K (+47%)
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 +93% in the last 10 years
MonthEstimated value
2026
August 2026$1.18M
August 2026$1.18M
July 2026$1.16M
June 2026$1.18M
May 2026$1.17M
April 2026$1.18M
March 2026$1.16M
February 2026$1.16M
January 2026$1.12M
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
1681 WOODLAND AVENUE, Winter Park, FL
0.14
Single-Family Home
$750,000
11/19/25
3
2
2,422
1701 PALMER AVENUE, Winter Park, FL
0.26
Single-Family Home
$1,100,000
12/30/25
4
3
2,841
1571 LASBURY AVENUE, Winter Park, FL
0.20
Single-Family Home
$1,700,000
02/26/26
4
3
2,749
1822 YORKSHIRE DRIVE, Winter Park, FL
0.19
Single-Family Home
$557,000
07/31/26
3
3
1,620
1741 PALMER AVENUE, Winter Park, FL
0.26
Single-Family Home
$1,318,000
10/31/25
3
3
2,351
1680 PALMER AVENUE, Winter Park, FL
0.24
Single-Family Home
$795,000
04/30/26
3
2
1,893
1870 WALKER AVENUE, Winter Park, FL
0.18
Single-Family Home
$1,035,000
09/10/26
3
2.5
2,046
1661 WOODLAND AVENUE, Winter Park, FL
0.16
Single-Family Home
$1,300,000
05/15/26
3
3.5
3,215
1600 PALMER AVENUE, Winter Park, FL
0.27
Single-Family Home
$1,130,000
03/05/26
3
2.5
2,550
1673 MAYFIELD AVENUE, Winter Park, FL
0.32
Single-Family Home
$1,115,000
02/25/26
4
4
2,540

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
1771 WINDSOR DRIVE, Winter Park, FL 32789
0.02
$961,800
3
2.5
2,059
Off Market
1821 WINDSOR DRIVE, Winter Park, FL 32789
0.04
$984,300
4
2.5
2,188
Off Market
1851 WINDSOR DRIVE, Winter Park, FL 32789
0.07
$2,610,000
5
5.5
4,000
Off Market
890 N PHELPS AVENUE, Winter Park, FL 32789
0.11
$1,700,000
4
4
3,630
Recently Sold
785 N PHELPS AVENUE, Winter Park, FL 32789
0.10
$1,825,000
5
3.5
2,964
Recently Sold
1681 WOODLAND AVENUE, Winter Park, FL 32789
0.14
$750,000
3
2
2,422
Recently Sold
1880 WINDSOR DRIVE, Winter Park, FL 32789
0.11
$1,355,800
5
4
3,074
Off Market
1861 TAYLOR AVENUE, Winter Park, FL 32789
0.11
$1,650,000
5
6
3,116
Recently Sold
1770 OAKHURST AVENUE, Winter Park, FL 32789
0.16
$2,419,900
5
4.5
3,640
Off Market
1754 TAYLOR AVENUE, Winter Park, FL 32789
0.10
$2,569,999
5
4.5
3,670
For Sale
1810 TAYLOR AVE, Winter Park, FL 32789
0.11
$514,100
3
2
1,396
Off Market
1871 TAYLOR AVENUE, Winter Park, FL 32789
0.12
$1,500,000
4
4.5
3,401
Recently Sold

Local Information

  • Map ViewExplore the area around 1781 Windsor Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1951
0.26 acre lot
2,444 sqft
$484/sqft
Garage

About this House

Charming 4 bedroom/3 bath ranch style home located in the heart of Winter Park! Featuring more than 2,400 square feet of living space, step inside the foyer entry to find a beautifully updated home with hardwood and tile flooring, filled with natural light. To the left of the entry you will find a formal dining room with seamless access to the newly renovated kitchen equipped with beautiful quartz countertops, impressive white and grey cabinetry, island with additional sink, stainless steel appliances and counter top seating. A spacious living room with high ceilings is perfect for easy everyday living and entertaining. Step outside to enjoy the fabulous summer kitchen and outdoor entertaining space beneath a fully screened enclosure with an outdoor shower. A beautifully paved patio with fire pit seating overlooks the sparkling pool with fountain features. The master bedroom addition is generous in size complete with a seating area, an en suite with spa tub, separate shower with dual shower heads and large walk in closet. Split plan, the original master bedroom of the home features an en suite and a third and fourth bedroom with full bath complete the interior layout. Conveniently located just minutes away from shops and dining of all downtown Park Avenue, East End Market and Baldwin Park has to offer! Don't miss this opportunity to make this home yours today!
1781 Windsor Dr, Winter Park, FL 32789 is a 4 bedroom, 3 bathroom, 2,444 sqft single-family home built in 1951. It last sold for $805,000 on May 14, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,182,700, with a rent estimate of $4,268/month.

Home Details for 1781 Windsor Dr

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air

Exterior Features

Exterior Home Features
Roof: Composition
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1951Year Updated: 1980
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
Jul 12, 2024
Source: Stellar MLS #O5929843
ListingRemoved
$825,000
May 14, 2021
Source: N/A
Sold
$805,000
Mar 12, 2021
Source: Stellar MLS #O5929843
Pending
$825,000
Mar 12, 2021
Source: Stellar MLS #O5929843
Listed For Sale
$825,000
Oct 10, 2018
Source: N/A
Sold
$640,000

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
    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
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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
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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
    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

Frequently asked questions about 1781 Windsor Dr

  • What is 1781 Windsor Dr estimated to be worth?
    Trulia's estimated value for 1781 Windsor Dr in Winter Park, FL is $1,182,700.
  • What is the price history for 1781 Windsor Dr?
    1781 Windsor Dr in Winter Park, FL last sold for $805,000 in May 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 $455K. That is up $4.03K from the prior month.
  • Does 1781 Windsor Dr have air conditioning?
    Yes, 1781 Windsor Dr in Winter Park, FL has air conditioning.
  • Does 1781 Windsor Dr have a pool?
    Yes, 1781 Windsor Dr in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

154 pet-friendly rentals in Winter Park, FL

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Explore by feature - Air Conditioning

171 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

139 rentals with a pool in Winter Park, FL

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

Explore by feature - Outdoor Space

56 rentals with an outdoor space in Winter Park, FL

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