21 Killarney Dr, Winter Park, FL 32789
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Property image
OFF MARKET

21 Killarney Dr
Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 5,077 sqft (on 0.39 acres)

$2,588,200

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $17,811/mo*
Refinance Your Home

$2,588,200

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $17,811/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,077 sqft
(on 0.39 acres)

Home Value

Trulia Estimate
$2.59M
Since last month
Decreased$10K (-0.4%)
Since last year
Increased$97K (+3.9%)
Since last sale
Increased$353K (+15.8%)
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 +585% in the last 10 years
MonthEstimated value
2026
August 2026$2.59M
July 2026$2.6M
June 2026$2.6M
May 2026$2.53M
April 2026$2.57M
March 2026$2.59M
February 2026$2.58M
January 2026$2.52M
2025
2024
2023
2022
2021
2020
2019
2018

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
600 OLOLU DRIVE, Winter Park, FL
0.53
Single-Family Home
$2,250,000
11/17/25
4
3.5
3,749
352 CAMBRIDGE BOULEVARD, Winter Park, FL
0.14
Single-Family Home
$640,000
06/05/26
5
3
1,917
Lot #20 KAROLINA AVE, Winter Park, FL
0.21
Single-Family Home
$956,809
12/18/25
4
3.5
2,662
1835 Karolina Ave, Winter Park, FL
0.35
Single-Family Home
$1,063,303
12/10/25
4
2.5
2,030
560 COUNTRY CLUB DRIVE, Winter Park, FL
0.69
Single-Family Home
$2,600,000
01/23/26
6
6
3,946
1840 BISCAYNE DRIVE, Winter Park, FL
0.34
Single-Family Home
$940,000
08/29/25
4
3
2,646
525 LAKEVIEW AVENUE, Winter Park, FL
0.65
Single-Family Home
$1,390,000
04/30/26
4
4.5
3,253
240 CAMBRIDGE BOULEVARD, Winter Park, FL
0.03
Single-Family Home
$490,000
12/30/25
3
2
1,630
1417 MILLER AVENUE, Winter Park, FL
0.87
Single-Family Home
$1,707,880
01/15/26
5
4
3,312
675 Overspin Dr, Winter Park, FL
0.47
Single-Family Home
$735,000
05/19/26
4
3.5
2,998

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
240 CAMBRIDGE BOULEVARD, Winter Park, FL 32789
0.03
$490,000
3
2
1,630
Recently Sold
218 ORANGE TERRACE DRIVE, Winter Park, FL 32789
0.07
$560,000
3
2
1,618
Recently Sold
2111 STAUNTON AVENUE, Winter Park, FL 32789
0.08
$403,500
3
1
1,292
Off Market
2112 STAUNTON AVENUE, Winter Park, FL 32789
0.11
$441,600
3
1
1,438
Off Market
1979 STAUNTON AVENUE, Winter Park, FL 32789
0.13
$225,900
1
1
736
Off Market
355 CAMBRIDGE BOULEVARD, Winter Park, FL 32789
0.13
$696,700
4
2.5
2,376
Off Market
1975 STAUNTON AVENUE, Winter Park, FL 32789
0.14
$367,500
3
2
1,200
Recently Sold
352 CAMBRIDGE BOULEVARD, Winter Park, FL 32789
0.14
$640,000
5
3
1,917
Recently Sold
2381 ROXBURY ROAD, Winter Park, FL 32789
0.15
$470,000
3
2
1,785
Recently Sold
259 ORANGE TERRACE DRIVE, Winter Park, FL 32789
0.15
$459,900
3
2
1,248
For Sale
260 ORANGE TERRACE DRIVE, Winter Park, FL 32789
0.16
$475,000
3
3
1,330
Recently Sold
2400 ROXBURY ROAD, Winter Park, FL 32789
0.17
$1,113,000
4
3.5
3,110
Off Market

Local Information

  • Map ViewExplore the area around 21 Killarney Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2018
Lot Size
0.39 acres
Living Area
5,077 sqft
Price/Sqft
$510

About this House

WINTER PARK LAKEFRONT LUXURY LIVING!!!! The newest addition to the active Winter Park Lakefront Luxury Home market has just arrived! This exquisite, large, lakefront pool home with covered boat dock is a breathtaking collaboration by Andy Katzman (RARE Builders) and John Drake (Green Apple Architecture). This 5077 sq ft 5 bedroom, 5 bath is the crowning Jewel of Lake Killarney! Offering not only superior function but also authentic modern/transitional aesthetic, with an incredibly well thought out floor plan, unique living areas, stunning high end finishes and great attention to detail. Remarkable marble, quartz, wood, and limestone throughout! This exceptional design with expansive use of glass and great attention to sight lines has resulted in an awe-inspiring bright, open and airy space with picturesque views of beautiful Lake Killarney from almost every main room in the house, and a floor plan that is flooded with natural light! Home boasts a tremendous kitchen, dining, family room combo that anchors the entire floor plan and leads out to the covered patio area overlooking the lake and out to the heated salt water pool, spa and outdoor kitchen, making this entire area a spectacular natural extension of the interior living space presenting one of the most beautiful Winter Park Lake views. Walk past the pool and across the yard to the private covered boat dock with lift. Take in the view, or take the boat out and enjoy lake life on one of Central Florida's best private lakes offering great water sports, fishing, cruising. Boat over to fantastic Winter Park dining, grocery, and shops on the other side of the lake! Home is prominently sited on a great lot and steals the show when viewed from the lake! In addition to a very well appointed chef's kitchen, a rare expansive butler's pantry with sink and dishwasher station, a wet bar, private second dining area, and a luxurious master suite with private access to the entire second floor balcony overlooking the pool and lake...you will love some of the less common additional spaces. Very rare large fitness room surrounded by glass with cathedral ceilings and unbelievable lake views. An inspiring home gym area! Good size second floor loft, a massive 5th bedroom (254 sq ft)/flex space/multi purpose room that offers hard to come by additional space for multiple potential applications. An additional office nook adjacent to master. All main bedrooms have direct access to full bathrooms! Full laundry room on both levels! Exterior of home is dramatic, refined and timeless. Beautiful architectural features such as the clever use of multiple arches and French doors, combined with brick, add considerable interest and appeal to this striking design! Eye catching contrasting dark tile roofs complete the composition! Green space in rear and large 3 car garage! This is a great opportunity to own a spectacular lakefront home in one of the most convenient locations in Winter Park. Minutes to Florida Hospital Orlando, and within 15 minutes of other community hospitals in Central Florida. Very close proximity to DT Orlando, Winter Park Village, Park Avenue shopping district and you are on and of I-4 in 2 minutes! WOW! WINTER PARK LAKEFRONT LIVING AT IT S BEST!
21 Killarney Dr, Winter Park, FL 32789 is a 5 bedroom, 5 bathroom, 5,077 sqft single-family home built in 2018. It last sold for $2,235,000 on May 4, 2021. It is currently off market. The Trulia Estimate is $2,588,200, with a rent estimate of $7,555/month.

Home Details for 21 Killarney Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDisposalDryer

Exterior Features

Exterior Home Features
Roof: Tile
Parking & Garage
Parking Spaces: 4Parking: Carport

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
May 4, 2021
Source: Stellar MLS #O5923090
Sold
$2,235,000
Feb 23, 2021
Source: Stellar MLS #O5923090
Pending
$2,495,000
Feb 17, 2021
Source: Stellar MLS #O5923090
Listed For Sale
$2,495,000
May 18, 2015
Source: N/A
Sold
$318,000

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
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Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
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  • 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
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  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
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  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
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  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
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  • 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."
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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
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  • 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
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  • 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
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  • 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
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  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
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  • 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
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  • 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
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  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
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  • 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
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  • 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
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  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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Homes for sale near 21 Killarney Dr

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Off Market Homes Near 21 Killarney Dr

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Frequently asked questions about 21 Killarney Dr

  • What is 21 Killarney Dr estimated to be worth?
    Trulia's estimated value for 21 Killarney Dr in Winter Park, FL is $2,588,200.
  • What is the price history for 21 Killarney Dr?
    21 Killarney Dr in Winter Park, FL last sold for $2,235,000 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 $451K. That is down $833 from the prior month.
  • How big is the lot at 21 Killarney Dr?
    The lot at 21 Killarney Dr in Winter Park, FL is about 0.39 acres (16,879 sq ft).
  • Does 21 Killarney Dr have parking?
    Yes, 21 Killarney Dr in Winter Park, FL has on-site parking.