1416 BORDER DRIVE, Winter Park, FL 32789
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Property image
FOR SALE
NEW - 1 DAY AGO
3D VIEW

1416 BORDER DRIVE
Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,243 sqft

$675,000

Est. Mortgage $4,750/mo*
Get Pre-Qualified

$675,000

Est. Mortgage $4,750/mo*
Get Pre-Qualified
3 Beds
1 Bath
1,243 sqft

Home Highlights

HOA
None
Price/Sqft
$543
Climate Control
Central & Central Air
Listed
1 day ago

Local Information

  • Map ViewExplore the area around 1416 BORDER DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai, and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market, and the chain of lakes are all a short drive away. Property sold as is. Buyer to verify setbacks, utilities, impact fees, demolition requirements, and permitted building dimensions with the City of Winter Park.
Last check for updates: about 10 hours ago
Listing Provided by: Audra Wilks, (407) 252-8582
PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6434966
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 1416 BORDER DRIVE

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Primary Bathroom, Family Room, Florida Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1243 Square Feet
Appliances & Utilities
Utilities: Electricity Available, Electricity Connected, Public, Sewer Available, Sewer Connected, Street Lights, Water Available, Water ConnectedAppliances: NoneLaundry: Other
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Other
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Other
View
No View

Exterior Features

Exterior Home Features
Roof: MembraneVegetation: Trees/LandscapedExterior: Lighting, SidewalkFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo Garage
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 1Days on Market: 1

Property Information

Year Built
Year Built: 1956
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 322130942806030

Price & Status

Price
List Price: $675,000Price Per Sqft: $543
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINTER PARKCommunity: WINTER PARK VILLAGE
School Information
Elementary School: Dommerich ElemJr High / Middle School: Maitland MiddleHigh School: Winter Park High

Agent Information

Listing Agent
Listing ID: O6434966

Building

Building Area
Building Area: 1378 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 6857 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6434966Showing Considerations: See RemarksShowing Requirements: See Remarks, ShowingTimeUniversal Property Id: US-12095-N-322130942806030-R-N

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
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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
    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
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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
    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

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

Home Value

Trulia Estimate
$417K
Since last month
Decreased$14K (-3.2%)
Since last year
Increased$75K (+21.9%)
Since last sale
Decreased$8K (-1.8%)
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 +168% in the last 10 years
MonthEstimated value
2026
August 2026$417K
July 2026$431K
June 2026$345K
May 2026$339K
April 2026$335K
March 2026$338K
February 2026$340K
January 2026$347K
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
1414 BESSMOR ROAD, Winter Park, FL
0.05
Single-Family Home
$475,000
09/19/25
3
1
1,043
2779 SANBINA STREET, Winter Park, FL
0.25
Single-Family Home
$410,000
06/30/26
3
2
1,405
2889 ROUEN AVENUE, Winter Park, FL
0.31
Single-Family Home
$345,000
07/17/26
3
2
1,144
2190 TEMPLE DRIVE, Winter Park, FL
0.33
Single-Family Home
$675,000
11/28/25
3
2
1,442
2612 LAFAYETTE AVENUE, Winter Park, FL
0.14
Single-Family Home
$550,000
11/10/25
3
2.5
2,447
1816 AZALEA AVENUE, Winter Park, FL
0.27
Single-Family Home
$369,900
02/06/26
3
2
1,584
2973 SANBINA STREET, Winter Park, FL
0.39
Single-Family Home
$353,000
07/22/26
3
2
1,128

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
2435 CHANTILLY AVENUE, Winter Park, FL 32789
0.03
$1,613,300
4
4.5
3,055
Off Market
1416 BORDER DRIVE LOT 3, Winter Park, FL 32789
0.00
$675,000
-
-
-
For Sale
1414 BESSMOR ROAD, Winter Park, FL 32789
0.05
$459,400
3
1
1,043
Off Market
1414 BESSMOR ROAD LOT 3, Winter Park, FL 32789
0.05
-
-
-
-
Off Market
1404 BORDER DRIVE, Winter Park, FL 32789
0.02
$1,100,000
4
4
2,469
For Sale
2430 CHANTILLY AVENUE, Winter Park, FL 32789
0.06
$1,599,000
4
4
2,916
For Sale
1319 BESSMOR ROAD, Winter Park, FL 32789
0.04
$589,000
3
2
1,126
For Sale
1411 BORDER DRIVE, Winter Park, FL 32789
0.04
$1,903,400
4
5
4,638
Off Market
1402 BESSMOR ROAD, Winter Park, FL 32789
0.06
$442,400
4
1
1,100
Off Market
2421 MANDAN TRAIL, Winter Park, FL 32789
0.09
$990,900
3
3
2,310
Off Market
1320 BESSMOR ROAD, Winter Park, FL 32789
0.07
$1,299,200
5
3
2,577
Off Market

Price and Tax history

DateEventPrice
Aug 21, 2026
Source: Stellar MLS #O6434966
Listed For Sale
$675,000
Aug 21, 2026
Source: N/A
ListingRemoved
Jul 21, 2026
Source: N/A
PriceChange
$675,000
Price decreased by 10%
Jul 18, 2026
Source: N/A
PriceChange
$750,000
Price increased by 21%
Jul 6, 2026
Source: N/A
Listed For Sale
$620,000

LGBTQ Local Legal Protections

Audra Wilks, PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Agent Phone: (407) 252-8582

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Frequently asked questions about 1416 BORDER DRIVE

  • What is the estimated monthly payment for 1416 BORDER DRIVE?
    Based on a $675,000 list price with 20% down at today's rates, the estimated monthly payment for 1416 BORDER DRIVE in Winter Park, FL is approximately $4,788 (about $3,515 principal & interest, $1,198 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 1416 BORDER DRIVE compare to homes in Winter Park?
    1416 BORDER DRIVE in Winter Park, FL is listed at $675,000, about 50% above the $451K median sale price in Winter Park.
  • What do residents say about Winter Park?
    Residents describe Winter Park, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Winter Park, FL.
  • What are the closest schools to 1416 BORDER DRIVE?
    The closest schools to 1416 BORDER DRIVE in Winter Park, FL are Dommerich Elementary School (Pre-K, rated 10/10), Maitland Middle School (rated 6/10), Winter Park High School (rated 7/10).
  • Does 1416 BORDER DRIVE have air conditioning?
    Yes, 1416 BORDER DRIVE in Winter Park, FL has air conditioning.
  • Does 1416 BORDER DRIVE have laundry facilities?
    Yes, 1416 BORDER DRIVE in Winter Park, FL has laundry facilities.
1416 BORDER DRIVE, Winter Park, FL 32789 is a 3 bedroom, 1 bathroom, 1,243 sqft single-family home built in 1956. This property is currently available for sale and was listed by Stellar MLS on Aug 21, 2026. The MLS # for this home is MLS# O6434966.