321 Windley Rd, Key Largo, FL 33037
Property image
Property image
OFF MARKET

$1,066,900

Trulia Estimate
as of Sep 2, 2026
  • 3 Beds
  • 2 Baths
  • 1,100 sqft
  • 3 Beds
  • 2 Baths
  • 1,100 sqft

321 Windley Rd, Key Largo, FL 33037

Home Highlights

Property Type
Single-Family Home
Living Area
1,100 sqft
Price/Sqft
$970

Local Information

  • Map ViewExplore the area around 321 Windley Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Available for 1-6 months. Charming, fully furnished 3-bedroom, 2-bathroom rental in Key Largo., located on the Bayside canal front. New flooring throughout, a modern updated kitchen, cozy living area, and comfortable bedrooms. a large screened-in patio with washer & dryer. freezer and ice maker. 6+ months rental will be considered.
321 Windley Rd, Key Largo, FL 33037 is a 3 bedroom, 2 bathroom, 1,100 sqft single-family home. It last sold for $225,000 on Mar 18, 2015 (3,362% above the $6,500 asking price). More recently, it was listed as a rental in December 2025 with an asking price of $3,900 per month. That rental listing was removed on January 27, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,066,900, with a rent estimate of $4,041/month.

Home Details for 321 Windley Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 6 Month

Interior Features

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

Exterior Features

Pool
Pool

Comparable Sales for 321 Windley Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
338 Windley Rd, Key Largo, FL
0.05
Single-Family Home
$1,100,000
11/05/25
3
2
1,248 sqft
955 Plantation Rd, Key Largo, FL
0.04
Single-Family Home
$775,000
03/26/26
3
2
1,660 sqft
4 Norwood Ave, Key Largo, FL
0.39
Single-Family Home
$440,000
10/21/25
3
2
1,066 sqft
1 N End Rd, Key Largo, FL
0.23
Single-Family Home
$650,000
11/17/25
3
2
1,500 sqft
8 N End Rd, Key Largo, FL
0.30
Single-Family Home
$665,000
08/14/26
3
2
1,306 sqft
15 Garden Cove Dr, Key Largo, FL
0.35
Single-Family Home
$718,000
09/29/25
3
2
1,196 sqft
32 S Andros Rd, Key Largo, FL
0.35
Single-Family Home
$665,000
08/28/26
3
2
1,291 sqft
949 Plantation Rd, Key Largo, FL
0.03
Single-Family Home
$995,000
06/01/26
4
3
1,502 sqft
239 Lower Matecumbe Rd #239, Key Largo, FL
0.14
Single-Family Home
$1,200,000
11/18/25
2
2
960 sqft
116 Long Key Rd, Key Largo, FL
0.25
Single-Family Home
$1,175,000
06/15/26
3
2
1,472 sqft

Nearby homes

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Rental Market Trends in Key Largo

Last updated Sep 2026
Trulia Rent Estimate$4,041/mo
Average rent
$3.9K
Available listings
125
View rental market trends in Key Largo, FL

Around this home

What Locals Say about Key Largo

At least 96 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 84 % Say parking is easy

  • 79 % Say car is needed

  • 78 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 72 % Say there's holiday spirit

  • 66 % Say it's quiet

  • 66 % Say they plan to stay for at least 5 years

  • 63 % Say it's walkable to restaurants

  • 55 % Say neighbors are friendly

  • 55 % Say kids play outside

  • 52 % Say there's wildlife

  • 47 % Say there are community events

  • 45 % Say it's walkable to grocery stores

  • 31 % Say streets are well-lit

  • 23 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Cn68dgn6hz
    "They have Dogs ism assuming they happy with the neighborhood as they are very much friendly is a very nice neighborhood "
    0
    Flag
  • Shaun Matthews
    "I drive everywhere I need to go. Golf carts are permissible in most neighborhoods. Everything is within a 5 min car ride. "
    0
    Flag
  • Dr.mahoney
    "We take care of each other in times of need hurricanes a good example. Animals are safe and people are friendly "
    0
    Flag
  • DC
    "Imagine living in a neighborhood where everyone knows each other and looks out for one another—where you can spend lazy afternoons lounging in beautiful parks or embark on thrilling marine adventures. Your kids will have a blast playing in sports leagues and attending top-notch schools. And the best part? The whole vibe is super chill and welcoming. That's the kind of community you'll find here!"
    0
    Flag
  • Carol Painter
    "Silver Shores is a beautiful 55 and older park! All yards are beautiful with grass, flowers, and trees! All the owners love it here!"
    0
    Flag
  • Deborah Clarke
    "Great neighbors, wonderful parks, beautiful sunsets, great church, great schools to choose from. The bond of our community. Every year our street throws an annual Keys Christmas Party. There is a sense of peace and connection knowing that you are safe and valued in your neighborhood. Everyone is so friendly, which makes it so inviting."
    0
    Flag
  • Karen M.
    "its a tourist spot area and very close to everything that you may need its a small city but very nice place"
    0
    Flag
  • Davius C.
    "It’s pretty dog friendly around here. I always see people walking their dogs. I have three of my own. The neighbors wave and say hi to my dogs while they are walking their dogs"
    0
    Flag
  • Diamonddegree
    "Private and secluded neighborhood at the beginning of the Florida keys. Great diving and snorkeling options "
    1
    Flag
  • Stuart G.
    "my commute is 20 miles but with traffic it takes anywhere from 35 minutes to 2 hours. just depends on the traffic "
    1
    Flag
  • Danlsteadman
    "Dogs are welcome at local restaurants with outside seating. Water bowls are available at these restaurants. "
    0
    Flag
  • Lmgkeys
    "Safe area. Surrounded by the water. Good schools. Great fishing and boating. Kayak and canoeing. Small island nearby."
    0
    Flag
  • Virgil R.
    "There are lots of kids here and watchful parents. So it’s safe for them to play outside and ride their bikes on the back streets. The fathers are outside and monitoring the speed people drive. "
    0
    Flag
  • Ruthrich41
    "We have allowed activities here so we get acquainted with a lot of people in our area and you get to know them and you make friends here we have 240 homes in our compound and a lot of good neighbours are very good friends are here"
    1
    Flag
  • Virgil R.
    "It’s next to the ocean and boat launches and public pools And Public parks where you can walk your dog play tennis do a fitness circuit and volleyball and it’s raining in downtown so it’s easy to leave there and get something to eat"
    1
    Flag
  • mdasca
    "This area is unique because it is close to Miami yet feels like worlds away. This community had neighbors that all have a passion for boating. There is no place in the world like the Florida keys!"
    0
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  • sherieann2008
    "This is one of the friendliest communities I have ever lived in. The neighbors all know each other and watch out for everyone. We are close to all of the entertainment and dining we want but have the quiet and privacy of a small community - the best of both worlds"
    0
    Flag
  • Lian A.
    "GATED COMMUNITY WITH DEEP WATER DOCKAGE - FAMILY FRIENDLY"
    0
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  • Kathy D.
    "Key Largo is known for its commuting ease from the Miami Dade area. It has a great Aquatic center, lots of dining options and, as with the rest of the Keys, is known for its water sports which include fishing, diving, kayaking, snorkeling, jet skies etc. The Keys are considered the Caribbean of the US. All the beauty and nice people, no passport."
    0
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  • Alicia O. L.
    "I have lived here for 7 years and absolutely love it!!!! A.L."
    1
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jan 27, 2026
Source: Zillow Rentals
ListingRemoved
$6,500
Dec 9, 2025
Source: Zillow Rentals
PriceChange
$6,500
Price increased by 67%
Dec 8, 2025
Source: Zillow Rentals
Listed For Rent
$3,900
Mar 18, 2015
Source: N/A
Sold
$225,000

Frequently asked questions about 321 Windley Rd

  • What is 321 Windley Rd estimated to be worth?
    Trulia's estimated value for 321 Windley Rd in Key Largo, FL is $1,066,900.
  • What is the price history for 321 Windley Rd?
    321 Windley Rd in Key Largo, FL last sold for $225,000 in March 2015.
  • Is Key Largo a buyer's or seller's market?
    Key Largo is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Key Largo?
    The median sale price in Key Largo is $1.4M. That is down $41.67K from the prior month.
  • Does 321 Windley Rd have air conditioning?
    Yes, 321 Windley Rd in Key Largo, FL has air conditioning.
  • Does 321 Windley Rd have a pool?
    Yes, 321 Windley Rd in Key Largo, FL has a pool.

Homes for rent near 321 Windley Rd

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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