2244 Shadowland Loop, Winter Park, FL 32792
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OFF MARKET

2244 Shadowland Loop
Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,142 sqft

$459,600

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,234/mo*
Refinance Your Home

$459,600

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,234/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,142 sqft

Home Value

Trulia Estimate
$460K
Since last month
$0 (0%)
Since last year
Decreased$11K (-2.4%)
Since last sale
Increased$60K (+14.9%)
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 +31% in the last 10 years
MonthEstimated value
2026
August 2026$460K
July 2026$464K
June 2026$460K
May 2026$462K
April 2026$462K
March 2026$469K
February 2026$466K
January 2026$463K
2025
2024
2023
2022
2021
2020

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
2224 SHADOWLAND LOOP, Winter Park, FL
0.03
Townhouse
$426,000
05/29/26
3
3
2,346
2380 SHADOWLAND LOOP, Winter Park, FL
0.04
Townhouse
$445,000
12/17/25
3
2.5
2,076
2232 SHADOWLAND LOOP, Winter Park, FL
0.02
Townhouse
$385,000
04/21/26
3
2.5
1,755
1537 BANTAM WAY, Winter Park, FL
0.06
Townhouse
$470,000
05/04/26
3
2.5
2,312
1522 BANTAM WAY, Winter Park, FL
0.09
Townhouse
$450,000
08/18/25
3
2.5
2,076
2393 Firstlight Way, Winter Park, FL
0.13
Townhouse
$450,000
07/16/26
3
3
2,378
2420 FIRSTLIGHT WAY, Winter Park, FL
0.09
Townhouse
$445,000
05/08/26
3
2.5
2,312
1375 MERRYDALE WAY, Winter Park, FL
0.07
Townhouse
$430,000
04/14/26
3
2.5
1,756
1471 BROAD WING LANE, Winter Park, FL
0.12
Townhouse
$448,000
09/23/25
3
2.5
2,010
1611 LITTLE WREN LANE, Winter Park, FL
0.11
Townhouse
$420,000
06/11/26
3
2.5
1,755

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
2260 SHADOWLAND LOOP, Winter Park, FL 32792
0.02
$470,700
3
2.5
2,308
Off Market
2232 SHADOWLAND LOOP, Winter Park, FL 32792
0.02
$385,000
3
2.5
1,755
Recently Sold
2224 SHADOWLAND LOOP, Winter Park, FL 32792
0.03
$426,000
3
3
2,346
Recently Sold
2380 SHADOWLAND LOOP, Winter Park, FL 32792
0.04
$445,000
3
2.5
2,076
Recently Sold
2464 FIRSTLIGHT WAY, Winter Park, FL 32792
0.06
$473,200
3
2.5
2,308
Off Market
2472 FIRSTLIGHT WAY, Winter Park, FL 32792
0.06
$423,600
3
2.5
2,076
Off Market
1306 MERRYDALE WAY, Winter Park, FL 32792
0.05
$421,100
3
2.5
2,002
Off Market
2448 FIRSTLIGHT WAY, Winter Park, FL 32792
0.07
$444,900
3
2.5
2,076
Off Market
2484 FIRSTLIGHT WAY, Winter Park, FL 32792
0.07
$408,700
3
2.5
1,755
Off Market
2444 FIRSTLIGHT WAY, Winter Park, FL 32792
0.07
$477,000
3
2.5
2,376
Off Market
1537 BANTAM WAY, Winter Park, FL 32792
0.06
$470,000
3
2.5
2,312
Recently Sold
1375 MERRYDALE WAY, Winter Park, FL 32792
0.07
$430,000
3
2.5
1,756
Recently Sold

Local Information

  • Map ViewExplore the area around 2244 Shadowland Loop.
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Living Area
2,142 sqft
Price/Sqft
$215
Parking
Attached Garage

About this House

Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood. The corner townhouse has huge living room with a high ceiling when you walk into the house, screen patio with the tile floor, one half bathroom downstairs. No CARPET IN THE PROPERTY, instead of the vinyl floor including upstairs and bedrooms, 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and shopping center. and upstairs floor. 3 Bedrooms upstairs with a big loft. Trey ceiling for the master bedrooms. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and shopping center and the best Trinity prep school.

owner pays HOA
2244 Shadowland Loop, Winter Park, FL 32792 is a 3 bedroom, 3 bathroom, 2,142 sqft townhouse. It last sold for $399,800 on Jul 27, 2021 (14,179% above the $2,800 asking price). More recently, it was listed as a rental in January 2022 with an asking price of $2,500 per month. That rental listing was removed on January 8, 2022. It is currently off market. The Trulia Estimate is $459,600, with a rent estimate of $2,948/month.

Home Details for 2244 Shadowland Loop

Property Information

Property Type / Style
Property Type: Townhouse

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DryerWasher
Heating & Cooling
Air ConditioningCooling System: Central Air

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Additional Information

Pool

Price and Tax history

DateEventPrice
Apr 1, 2025
Source: Stellar MLS #O6285898
ListingRemoved
$480,000
Mar 8, 2025
Source: Stellar MLS #O6285898
PriceChange
$480,000
Price decreased by 3%
Mar 2, 2025
Source: Stellar MLS #O6285898
Listed For Sale
$495,000
Jan 8, 2022
Source: Zillow Rental Manager
ListingRemoved
Jan 5, 2022
Source: Zillow Rental Manager
Listed For Rent
$2,500

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

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
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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
    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
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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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Explore by feature - Pet Friendly

144 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

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Explore by feature - Pool

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Homes for sale near 2244 Shadowland Loop

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Off Market Homes Near 2244 Shadowland Loop

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Frequently asked questions about 2244 Shadowland Loop

  • What is 2244 Shadowland Loop estimated to be worth?
    Trulia's estimated value for 2244 Shadowland Loop in Winter Park, FL is $459,600.
  • What is the price history for 2244 Shadowland Loop?
    2244 Shadowland Loop in Winter Park, FL last sold for $399,800 in July 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.
  • Does 2244 Shadowland Loop have air conditioning?
    Yes, 2244 Shadowland Loop in Winter Park, FL has air conditioning.
  • Does 2244 Shadowland Loop have a pool?
    Yes, 2244 Shadowland Loop in Winter Park, FL has a pool.