211 Overlook Rd, Winter Park, FL 32789
Property image
Property image
OFF MARKET

$1,732,800

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 3,499 sqft (on 0.34 acres)

211 Overlook Rd, Winter Park, FL 32789

Est. Refi. Payment $12,023/mo*
Refinance Your Home
Currently Off Market - Sold Jul 16, 2018 for $700,000

Home Value

Trulia Estimate
$1.73M
Since last month
Increased$86K (+5.2%)
Since last year
Increased$195K (+12.6%)
Since last sale
Increased$1M (+148.6%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$1.74M
August 2026$1.73M
July 2026$1.65M
June 2026$1.69M
May 2026$1.76M
April 2026$1.67M
March 2026$1.67M
February 2026$1.65M
January 2026$1.63M
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
321 SYLVAN BOULEVARD, Winter Park, FL
0.08
Single-Family Home
$1,300,000
07/24/26
3
2.5
2,821
234 DETMAR DRIVE, Winter Park, FL
0.17
Single-Family Home
$1,400,000
06/25/26
4
5.5
3,609
446 ALBERTA DRIVE, Winter Park, FL
0.30
Single-Family Home
$1,600,000
04/22/26
4
2.5
3,263
185 SYLVAN BOULEVARD, Winter Park, FL
0.06
Single-Family Home
$2,500,000
03/06/26
4
4.5
3,138
501 HENKEL CIRCLE, Winter Park, FL
0.29
Single-Family Home
$1,905,000
04/10/26
5
4.5
3,746
516 HENKEL CIRCLE, Winter Park, FL
0.19
Single-Family Home
$2,925,000
03/24/26
5
6
4,143
250 CORTLAND AVENUE, Winter Park, FL
0.12
Single-Family Home
$920,000
07/22/26
3
2
2,114
1521 HARRIS CIRCLE, Winter Park, FL
0.18
Single-Family Home
$4,500,000
05/29/26
4
4.5
3,922
171 CORTLAND AVENUE, Winter Park, FL
0.08
Single-Family Home
$1,245,000
09/03/25
2
2
1,683
473 FLETCHER PLACE, Winter Park, FL
0.26
Single-Family Home
$3,000,000
05/15/26
5
5.5
4,296

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
193 OVERLOOK ROAD, Winter Park, FL 32789
0.01
$979,600
3
1.5
2,201
Off Market
140 CORTLAND AVENUE, Winter Park, FL 32789
0.03
$2,443,400
5
3.5
4,168
Off Market
104 CORTLAND AVENUE, Winter Park, FL 32789
0.04
$2,075,200
4
3
3,182
Off Market
224 OVERLOOK ROAD, Winter Park, FL 32789
0.04
$645,000
2
1.5
1,399
Recently Sold
225 SYLVAN BOULEVARD, Winter Park, FL 32789
0.05
$794,300
2
2
1,623
Off Market
185 SYLVAN BOULEVARD LOT 8, Winter Park, FL 32789
0.06
-
-
-
-
Off Market
185 SYLVAN BOULEVARD, Winter Park, FL 32789
0.06
$2,500,000
4
4.5
3,138
Recently Sold
254 SYLVAN BOULEVARD, Winter Park, FL 32789
0.07
$2,547,100
3
3
3,653
Off Market
171 CORTLAND AVENUE, Winter Park, FL 32789
0.08
$1,235,600
2
2
1,683
Off Market
321 SYLVAN BOULEVARD, Winter Park, FL 32789
0.08
$1,300,000
3
2.5
2,821
Recently Sold
1394 GROVE TERRACE, Winter Park, FL 32789
0.13
$1,560,700
4
3.5
2,958
Off Market
1415 GROVE TERRACE, Winter Park, FL 32789
0.13
$2,032,700
4
3
3,746
Off Market

Local Information

  • Map ViewExplore the area around 211 Overlook Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1936
Lot Size
0.34 acres
Living Area
3,499 sqft
Price/Sqft
$495
Parking
Garage

About this House

Wonderful two story character home in the heart of Winter Park on a quiet tree lined brick street. This adorable home has such great curb appeal and is in a wonderful part of Olde Winter Park-this cutie pie is pure potential! The interior offers five bedrooms, three and one-half baths, a formal living room, separate den and/or office, and family room. Master suite (downstairs) is overly spacious and features a wood burning fireplace and en suite, complete with a large soaking tub, shower, and expansive walk-in closet. Downstairs guest suite has private bath and could easily be enclosed to serve as a guest wing. Kitchen has been updated with stainless steel appliances, built-in oven, and pantry closet. Outdoor living space is extraordinary! Located on 0.34 acres the backyard is fantastic and has both an open deck and a covered patio that overlook the mature lawn and gardens. Hardwood floors, butler's pantry, bay windows, high ceilings, and more. Charming and delightful this house will make you feel right at home. This home is zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School.
211 Overlook Rd, Winter Park, FL 32789 is a 5 bedroom, 4 bathroom, 3,499 sqft single-family home built in 1936. It last sold for $700,000 on Jul 16, 2018. More recently, it was listed as a rental in May 2017 with an asking price of $3,950 per month. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,732,800, with a rent estimate of $6,500/month.

Home Details for 211 Overlook Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Wood
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1936Year Updated: 1985
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price and Tax history

DateEventPrice
Jul 16, 2018
Source: N/A
Sold
$700,000
May 21, 2018
Source: Agent Provided
PendingToActive
$749,900
May 21, 2018
Source: Agent Provided
Pending
$749,900
Mar 26, 2018
Source: Agent Provided
Listed For Sale
$749,900
May 18, 2017
Source: Agent Provided
ListingRemoved
$775,000

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
    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 211 Overlook Rd

  • What is 211 Overlook Rd estimated to be worth?
    Trulia's estimated value for 211 Overlook Rd in Winter Park, FL is $1,732,800.
  • What is the price history for 211 Overlook Rd?
    211 Overlook Rd in Winter Park, FL last sold for $700,000 in July 2018.
  • 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 211 Overlook Rd have air conditioning?
    Yes, 211 Overlook Rd in Winter Park, FL has air conditioning.
  • How big is the lot at 211 Overlook Rd?
    The lot at 211 Overlook Rd in Winter Park, FL is about 0.34 acres (14,975 sq ft).

Explore by feature - Pet Friendly

142 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

60 rentals with a garage in Winter Park, FL

Explore by feature - Air Conditioning

157 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

131 rentals with a pool in Winter Park, FL

Explore by feature - Washer/dryer

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

Explore by feature - Outdoor Space

56 rentals with an outdoor space in Winter Park, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 211 Overlook Rd

Skip to last item
Skip to first item

Homes for sale near 211 Overlook Rd

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