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414 E Caribbean Dr , Summerland, FL 33042

$3,495,000

4
beds
3 full · 1 half
baths
2,766
sqft
1970
year built

OCEANFRONT, CBS, POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful newly painted exterior, this elevated 4 bed 3.5 bath home offers 2,766 sq. ft. of beautifully designed living space where soaring ceilings and walls of glass frame endless turquoise water views. Rare 3 bedroom suites with ensuite bathrooms, and a 4th bedroom or office with ensuite half bath. The expansive open-concept living and entertaining areas create a seamless indoor-outdoor flow perfect for relaxing or hosting guests after a day on the water. Separate laundry room is a bonus. A rare concrete dock with a protected cut-in boat slip provides quick deep-water access to the Atlantic with no long canal commute--placing you minutes from world-class offshore fishing, reef diving, sandbars, and endless boating adventures. Step outside to your private oceanfront oasis featuring a sparkling pool and spa, expansive lounging decks, and a poolside kitchen designed for sunset entertaining and waterfront gatherings. Panoramic open-water views and ocean breezes create the perfect Keys atmosphere. Upstairs, the spacious primary suite offers stunning ocean views, a private balcony, and a peaceful retreat overlooking the Atlantic. Additional features include impact windows and doors, a metal roof, a chef's kitchen with granite countertops and stainless steel appliances, plus convenient access to the nearby Summerland Key Cove Airport for easy fly-in/fly-out travel in light aircraft. This rare offering combines luxury living, protected deep-water dockage, immediate ocean access, and unforgettable open-water views in one of the Florida Keys' most sought-after waterfront communities

Highlights

  • Residential
  • Single Family Residence
  • Built in 1970
  • 0.15 Acre Lot
  • Waterfront
  • 171 days on Market

  • Bedrooms
    4
  • Bathrooms
    3 full · 1 half
  • Year Built
    1970
  • Parking Features
    Open, Carport
  • Interior Features
    Cathedral Ceiling(s), Walk-In Closet(s), Granite Counters, Entrance Foyer
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Range, Disposal, Oven, Freezer, Wine Cooler, Stainless Steel Appliance(s)
  • Flooring
    Tile, Carpet
  • Furnished
    Unfurnished
  • Exterior Features
    Storage, Outdoor Kitchen, Built-in Barbecue
  • Patio And Porch
    Patio, Porch
  • Pool Features
    In Ground
  • Cooling
    Ceiling Fan(s), Central Air
  • Heating
    Central

  • Acres
    0.15
  • Water Front Features
    Ocean Front
  • Water Front
    Yes
  • View
    Ocean

  • Area
    08 - Summerland Key
  • County
    Monroe
  • City
    Summerland
  • Neighborhood
    Summerland Key Cove (25.0)
  • Zip Code
    33042

Ask a Question

Estimated Value

$3,515,220

Estimated Sales Price Range:

$3,269,154 - $3,761,285

Source: Constellation Data Labs

Price History

05/24/2026 Listed $3,495,000
Source: Florida Keys Board of REALTORS #620024
04/12/2022 Sold $3,350,000
Source: Florida Keys Board of REALTORS #599675
02/14/2022 Listed $3,495,000
Source: Florida Keys Board of REALTORS #599675

Source: MLS Data

Deed History

05/10/2022 Quit Claim Deed (non-arm's length) $0
04/13/2022 Warranty Deed $3,350,000
02/26/2015 Quit Claim Deed (non-arm's length) $0
02/26/2015 Warranty Deed $1,670,000
02/22/2006 Warranty Deed $950,000
03/19/2004 Quit Claim Deed (non-arm's length) $0
03/19/2004 Warranty Deed $950,000
12/31/1996 Warranty Deed $270,000
12/31/1996 Quit Claim Deed (non-arm's length) $100

Source: Public records via Constellation Data Labs

Mortgage History

06/29/2022 Coventional $1,500,000
03/03/2014 ARM (Adjustable Rate Mortgage as of August, 2009) $1,050,000
02/22/2006 Building or Construction Loan $1,924,000
04/08/2004 Unknown $47,000
03/19/2004 Unknown $712,500
12/31/1996 Coventional $201,750
12/31/1996 Coventional $201,750

Source: Public records via Constellation Data Labs

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Frequently Asked Questions

How do I schedule a tour of 414 E Caribbean Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 414 E Caribbean Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 414 E Caribbean Dr?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 3 bath, listed for $3,495,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Summerland, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 414 E Caribbean Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 414 E Caribbean Dr at around $21,702. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 414 E Caribbean Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Monroe County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 414 E Caribbean Dr?

In most cases, yes. Whether 414 E Caribbean Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Summerland's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 414 E Caribbean Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Summerland and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $3,495,000 with 2,766 sqft of space—that comes out to approximately $1,264 per square foot.

How long has this property been on the market?

414 E Caribbean Dr was listed on May 24, 2026, which means it's been on the market for 171 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1970, making it approximately 56 years old.

What is the lot size of this property?

414 E Caribbean Dr sits on a 0.15-acre lot, which is 6,534 square feet.

What are the property taxes for 414 E Caribbean Dr?

The most recent public record shows annual property taxes for 414 E Caribbean Dr were approximately $21,752. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 414 E Caribbean Dr still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

Search Nearby Postal Codes

Properties in 33042 Avg. Price $2M

Properties in 33043 Avg. Price $1M

IDX information is provided exclusively for consumers’ personal, non-commercial use, that it 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 MLS. Copyright 2026 Florida Keys Board of REALTORS®, Inc.