101 Oleander Cir, Key Largo, FL 33037
Property image
Property image
SOLD
AUG 21, 2026

$7,500,000

Last sold price
  • 7 Beds
  • 6 Baths
  • 4,460 sqft (on 1.62 acres)

101 Oleander Cir, Key Largo, FL 33037

Est. Refi. Payment $50,730/mo*
Refinance Your Home
Currently Off Market - Sold Aug 21, 2026 for $7,500,000 (3% below list price)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
30 Ocean Front Dr, Key Largo, FL
0.16
Single-Family Home
$7,000,000
05/01/26
4
3.5
3,778
555 Ocean Cay Dr, Key Largo, FL
0.40
Single-Family Home
$7,600,000
01/30/26
4
4
4,580
251 S Ocean Shores Dr, Key Largo, FL
0.40
Single-Family Home
$4,200,000
07/10/26
5
6.5
5,281
131 Marina Ave, Key Largo, FL
0.19
Single-Family Home
$1,900,000
10/17/25
5
3
2,567
158 Bahama Ave, Key Largo, FL
0.21
Single-Family Home
$3,000,000
03/24/26
4
3
2,334
215 Wildwood Cir, Key Largo, FL
0.10
Single-Family Home
$2,170,000
05/07/26
4
3
2,025
210 Wildwood Cir, Key Largo, FL
0.11
Single-Family Home
$1,293,750
05/27/26
4
2.5
2,093
202 Atlantic Blvd, Key Largo, FL
0.29
Single-Family Home
$2,300,000
12/18/25
4
4.5
1,260

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
Oleander Ave, Key Largo, FL 33037
0.04
-
-
-
-
Off Market
111 Oleander Cir, Key Largo, FL 33037
0.06
$3,482,200
3
3
1,936
Off Market
113 Oleander Cir, Key Largo, FL 33037
0.07
$4,182,500
4
4.5
2,507
Off Market
215 Wildwood Cir, Key Largo, FL 33037
0.10
$2,170,000
4
3
2,025
Recently Sold
210 Wildwood Cir, Key Largo, FL 33037
0.11
$1,293,750
4
2.5
2,093
Recently Sold
216 Wildwood Cir, Key Largo, FL 33037
0.13
$1,145,500
5
3
2,157
Off Market
309 Buttonwood Creek, Key Largo, FL 33037
0.14
-
-
-
-
Off Market
311 Buttonwood Cir, Key Largo, FL 33037
0.14
$1,899,000
2
3
1,064
For Sale
66 Seagate Blvd, Key Largo, FL 33037
0.11
$1,019,200
2
2
864
Off Market
64 Seagate Dr, Key Largo, FL 33037
0.12
$1,405,700
2
1.5
-
Off Market
301 Buttonwood Cir #A, Key Largo, FL 33037
0.13
$3,750,000
5
5
4,306
For Sale

Local Information

  • Map ViewExplore the area around 101 Oleander Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1959
1.62 acre lot
4,460 sqft
$1,682/sqft

About this House

Welcome to the iconic Key Largo Lighthouse, a one-of-a-kind oceanfront landmark set on 1.6 acres of lushly landscaped tropical paradise in Key Largo. With over 300 feet of seawalled waterfront, this private compound delivers an unmatched resort-style lifestyle in the Florida Keys. Surrounded by mature palms, the property offers an extraordinary array of amenities, including a private boat basin, pickleball court, working lighthouse, and a spectacular water-park-style infinity pool complete with a lazy river, grotto, hot tub, waterslide, and multiple cascading waterfalls. Designed for grand-scale entertaining or quality family time, the estate features three main buildings with accommodations for up to 20 guests. The main residence showcases a stunning great-room layout anchored by a chef's kitchen with a Wolf gas range, Sub-Zero refrigerator and six under-counter refrigerated drawers, full-size wine fridge, expansive pantry, and an oversized island ideal for gatherings. Additional living spaces include two separate units, each with full kitchens and bedrooms, along with three detached guest bedrooms with cabana baths, offering exceptional privacy and flexibility. Throughout the grounds, Old Chicago brick walkways, seven tiki huts, and thoughtfully designed lounging areas invite relaxation at every turn. Enjoy breathtaking ocean sunrises from the point and entertain under the cabana bar overlooking Pennekamp National Park, the Atlantic Ocean, and your private, secure boat basin—equipped with a boat lift, floating jet-ski lift, and kayak/paddleboard launch. The property is fully outfitted with impact windows and doors, a metal roof, and a standby generator capable of powering the entire estate, providing peace of mind year-round. This rare and irreplaceable oceanfront compound is the ultimate setting for unforgettable entertaining and luxurious island living. Simply too many impeccable details to capture—come see it in person and schedule your private showing toda
101 Oleander Cir, Key Largo, FL 33037 is a 7 bedroom, 7 bathroom, 4,460 sqft single-family home built in 1959. It last sold for $7,500,000 on Aug 21, 2026 (3% below the $7,750,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $5,879/month.
Last check for updates: about 1 hour ago
Listed by Timothy Lloyd, (954) 448-0781
Illustrated Properties, LLC
Bought with: Joy C Martin, (305) 394-7866, American Caribbean Real Estate, Christie's International Real Estate
Source: FLKMLS, MLS#618417

Home Details for 101 Oleander Cir

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Family Room
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 7Number of Bathrooms (full): 5Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4460 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: More Appliances, Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Freezer, Gas Appliances, Ice Maker, Wine Cooler, Stainless Steel Appliance(s)DishwasherDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Heat Pump,Ceiling Fans(s),DuctlessHas HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile
Levels, Entrance, & Accessibility
Accessibility: Accessible Full Bath, Grip-Accessible Features, Accessible Kitchen, Accessible Approach with RampFloors: Tile
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, DeckFencing: Fenced, PrivacyOther Structures: Gazebo, Guest HouseExterior: Bar, Built-in Barbecue, Chickee Hut, Lighting, Outdoor Kitchen, Outdoor Shower, Tennis Court(s)Has a Private Pool
Parking & Garage
No Attached GarageParking: RV Access/Parking,Storage
Pool
Pool: In Ground, Salt Water, DeckedPool
Frontage
WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: CBSNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00503800000000Additional Parcels Description: 00503800-000100

Price & Status

Price
List Price: $7,750,000Price Per Sqft: $1,682/sqft

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Key LargoCommunity: Key Largo Beach Addition (100.0)

Building

Building Area
Building Area: 4460 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 1.62 Acres

Offer

Listing Terms: Cash, Conventional

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 618417

Price and Tax history

DateEventPrice
Aug 21, 2026
Source: FLKMLS #618417
Sold
$7,500,000
Mar 19, 2026
Source: FLKMLS #618417
Contingent
$7,750,000
Feb 1, 2026
Source: Key West AOR #618417
Listed For Sale
$7,750,000
Apr 27, 2021
Source: FLKMLS #590864
Sold
$5,565,000
Mar 1, 2021
Source: FLKMLS #590864
Contingent
$5,999,000

Market trends in Key Largo

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.4M
$41.67KMoM
Sale-to-List Price
95.7%
0.4%MoM
Price per sq ft
$803
$38MoM
Available listings
241
14MoM

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Alicia O. L.
    "I have lived here for 7 years and absolutely love it!!!! A.L."
    1
    Flag

LGBTQ Local Legal Protections

MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.

Frequently asked questions about 101 Oleander Cir

  • What is the price history for 101 Oleander Cir?
    101 Oleander Cir in Key Largo, FL last sold for $7,500,000 in August 2026.
  • 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.
  • What do residents say about Key Largo?
    Residents describe Key Largo, FL as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Key Largo, FL.
  • Does 101 Oleander Cir have air conditioning?
    Yes, 101 Oleander Cir in Key Largo, FL has air conditioning.
  • Does 101 Oleander Cir have a pool?
    Yes, 101 Oleander Cir in Key Largo, FL has a pool.

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