1414 BESSMOR ROAD, Winter Park, FL 32789
OFF MARKET

$459,700

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,043 sqft

1414 BESSMOR ROAD, Winter Park, FL 32789

Est. Refi. Payment $3,335/mo*
Refinance Your Home
Currently Off Market - Sold Sep 19, 2025 for $475,000

Home Value

Trulia Estimate
$460K
Since last month
Decreased$400 (-0.1%)
Since last year
Decreased$16K (-3.3%)
Since last sale
Decreased$16K (-3.3%)
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 +158% in the last 10 years
MonthEstimated value
2026
September 2026$459K
August 2026$460K
July 2026$458K
June 2026$454K
May 2026$454K
April 2026$450K
March 2026$454K
February 2026$491K
January 2026$489K
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
1416 BORDER DRIVE, Winter Park, FL
0.05
Single-Family Home
$425,000
06/25/26
3
1
1,243
2190 TEMPLE DRIVE, Winter Park, FL
0.28
Single-Family Home
$675,000
11/28/25
3
2
1,442
2779 SANBINA STREET, Winter Park, FL
0.30
Single-Family Home
$410,000
06/30/26
3
2
1,405
2889 ROUEN AVENUE, Winter Park, FL
0.37
Single-Family Home
$345,000
07/17/26
3
2
1,144
1441 PALM AVENUE, Winter Park, FL
0.46
Single-Family Home
$750,000
02/18/26
2
1
981
2612 LAFAYETTE AVENUE, Winter Park, FL
0.19
Single-Family Home
$550,000
11/10/25
3
2.5
2,447
2973 SANBINA STREET, Winter Park, FL
0.45
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
1414 BESSMOR ROAD LOT 3, Winter Park, FL 32789
0.00
-
-
-
-
Off Market
2301 CHANTILLY AVENUE, Winter Park, FL 32789
0.09
$1,451,100
4
4
3,350
Off Market
2417 CHANTILLY AVENUE, Winter Park, FL 32789
0.05
$1,579,000
4
3.5
2,718
For Sale
1402 BESSMOR ROAD, Winter Park, FL 32789
0.02
$438,000
4
1
1,100
Off Market
1320 BESSMOR ROAD, Winter Park, FL 32789
0.04
$1,295,000
5
3
2,577
Off Market
2503 VERSAILLES AVENUE, Winter Park, FL 32789
0.05
$2,100,000
5
4
4,026
Recently Sold
2415 VERSAILLES AVENUE, Winter Park, FL 32789
0.07
$1,863,900
4
3.5
3,954
Off Market
1319 BESSMOR ROAD, Winter Park, FL 32789
0.04
$589,000
3
2
1,126
For Sale
1416 BORDER DRIVE, Winter Park, FL 32789
0.05
$660,000
3
1
1,243
For Sale
1416 BORDER DRIVE LOT 3, Winter Park, FL 32789
0.05
$660,000
-
-
-
For Sale
2435 CHANTILLY AVENUE, Winter Park, FL 32789
0.07
$1,666,000
4
4.5
3,055
Off Market

Local Information

  • Map ViewExplore the area around 1414 BESSMOR ROAD.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1956
1,043 sqft
$441/sqft

About this House

Beautiful rehabbed Mid-century Bungalow in highly sought-after Winter Park Village. The house has been updated with new flooring, a new kitchen with stainless steel Samsung appliances, and much more. It has a huge bonus room that could be used as an Office, Family room, or Third Bedroom. The home is also a block away from the Via's and has the opportunity for redevelopment with many surrounding houses already being Rebuilt. Overall, this property has a lot of opportunities and would make a fantastic starter home, a great rental, a buy and hold, or a redevelopment now or in the future. Excellent investor opportunity.
1414 BESSMOR ROAD, Winter Park, FL 32789 is a 3 bedroom, 1 bathroom, 1,043 sqft single-family home built in 1956. It last sold for $475,000 on Sep 19, 2025 (10% above the $430,000 asking price). More recently, it was listed as a rental in December 2023 with an asking price of $2,300 per month. That rental listing was removed on December 18, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $459,700, with a rent estimate of $2,210/month.
Last check for updates: about 7 hours ago
Listed by Cristina Brandi, (407) 668-6782
SANMO REALTY, INC, (305) 967-6337
Bought with: Miranda Azer, (407) 312-6472, HOME WISE REALTY GROUP, INC., (407) 712-2000
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6145645
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 1414 BESSMOR ROAD

Interior Features

Interior Details
Number of Rooms: 5Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1043 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity AvailableAppliances: Dishwasher, Electric Water Heater, Microwave, Range, RefrigeratorDishwasherLaundry: InsideMicrowaveRefrigerator
Heating & Cooling
Heating: Central,Heat PumpHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Ceramic Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Ceramic Tile
View
No View

Exterior Features

Exterior Home Features
Roof: Other ShingleFencing: FencedExterior: OtherFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo Garage
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 4

Property Information

Year Built
Year Built: 1956
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 322130942805030

Price & Status

Price
List Price: $430,000
Status Change & Dates
Off Market Date: Tue Oct 24 2023

Active Status

MLS Status: Sold

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

Building

Building Area
Building Area: 1043 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 6860 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6145645Showing AttendedShowing Requirements: Appointment Only, Listing Agent Must AccompanyUniversal Property Id: US-12095-N-322130942805030-R-N

Price and Tax history

DateEventPrice
Sep 19, 2025
Source: N/A
Sold
$475,000
Aug 5, 2024
Source: Stellar MLS #O5953858
ListingRemoved
$340,000
Jun 12, 2024
Source: Stellar MLS #O6214050
Listed For Sale
$495,000
Dec 18, 2023
Source: Stellar MLS #O6161895
ListingRemoved
Dec 5, 2023
Source: Stellar MLS #O6161895
Listed For Rent
$2,300

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
    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
    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
    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
    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

LGBTQ Local Legal Protections

Frequently asked questions about 1414 BESSMOR ROAD

  • What is 1414 BESSMOR ROAD estimated to be worth?
    Trulia's estimated value for 1414 BESSMOR ROAD in Winter Park, FL is $459,700.
  • What is the price history for 1414 BESSMOR ROAD?
    1414 BESSMOR ROAD in Winter Park, FL last sold for $475,000 in September 2025.
  • 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 1414 BESSMOR ROAD have air conditioning?
    Yes, 1414 BESSMOR ROAD in Winter Park, FL has air conditioning.
  • Does 1414 BESSMOR ROAD have laundry facilities?
    Yes, 1414 BESSMOR ROAD in Winter Park, FL has laundry facilities.

Explore by feature - Pet Friendly

153 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

70 rentals with a garage in Winter Park, FL

Explore by feature - Air Conditioning

163 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

141 rentals with a pool in Winter Park, FL

Explore by feature - Washer/dryer

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

Explore by feature - Outdoor Space

55 rentals with an outdoor space in Winter Park, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 1414 BESSMOR ROAD

Skip to last item
Skip to first item

Homes for sale near 1414 BESSMOR ROAD

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item