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Newest Homes for Sale in Cudjoe Key, FL

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  • /51

    $1,099,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    22953 John Silver Ln, Summerland Key, FL 33042

    Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment.

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (645) 241-8464

    22953 John Silver Ln, Summerland Key, FL 33042
  • /51

    $425,000

    • 2 Beds
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042

    Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile

    Justyn Ewald Expert Realty LLC

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042
  • /50

    $289,000

    • 1 Bed
    • 1 Bath
    • 340 Sq Ft

    701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042

    Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect Florida Keys getaway, ideal as a vacation rental investment, seasonal escape, or personal retreat. Turn-key and ready to enjoy or rent immediately, this property offers excellent income potential with nightly rentals allowed in

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
  • /46

    $1,269,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    116 Spanish Main Dr, Summerland Key, FL 33042

    Discover your personal sanctuary in the heart of Cudjoe Key, where authentic Florida Keys charm meets modern coastal luxury. This stunning 2-bedroom, 2-bathroom home has been thoughtfully updated to offer the ultimate waterfront lifestyle, just 21 miles from Key West's world-class dining and entertainment. The interior glows with natural light, highlighted by impact-resistant windows and elegant

    Lissete Cadwell, P.A. Hawks Cay Resort Sales LLC

    116 Spanish Main Dr, Summerland Key, FL 33042
  • /61

    $1,449,000

    • 2 Beds
    • 2 Baths
    • 1,372 Sq Ft

    21012 6th Ave, Summerland Key, FL 33042

    Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (645) 666-1284

    21012 6th Ave, Summerland Key, FL 33042
  • /48

    $1,499,000

    • 3 Beds
    • 2 Baths
    • 1,434 Sq Ft

    22939 Gasparilla Ln, Summerland Key, FL 33042

    Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete

    Donna Pezzi Keller Williams Key West Compass Realty

    22939 Gasparilla Ln, Summerland Key, FL 33042
  • /67

    $3,200,000

    New Construction
    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft

    270 E Caribbean Dr, Summerland Key, FL 33042

    Set against a spectacular open water backdrop with unforgettable sunset views modern, waterfront home was designed for both luxury living and serious boating. Built in 2022 with an exceptional design, the residence features solid concrete construction, polished concrete floors, impact-rated windows and doors, and a strong elevated build that delivers peace of mind in the Florida Keys

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-1469

    270 E Caribbean Dr, Summerland Key, FL 33042
  • /16

    $895,900

    $94K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Reduced over 100k for a quick sale. Boater's Paradise in Cudjoe Key under 1 million!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The

    Rayden Vega Casa Miami Real Estate

    22961 John Avery Ln, Summerland Key, FL 33042
  • /41

    $590,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    22920 Privateer Dr, Summerland Key, FL 33042

    Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, Summerland Key, FL 33042
  • /38

    $1,399,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    51 Drost Dr, Summerland Key, FL 33042

    Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 808-1276

    51 Drost Dr, Summerland Key, FL 33042
  • /61

    $639,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

    Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front home with 35 foot seawall. Located in a gated community with tons of amenities. New kitchen w/Caesar quartz countertops, full backsplash, new stainless steel appliances, Koehler sink, modern, white cabinets with an abundance of storage, including a large center Island. Open concept floor plan with open water

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
  • /70

    $2,800,000

    • 4 Beds
    • 3 Baths
    • 3,286 Sq Ft

    21640 Overseas Hwy, Summerland Key, FL 33042

    SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

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    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (855) 799-5158

    21640 Overseas Hwy, Summerland Key, FL 33042
  • /70

    $3,399,000

    • 3 Beds
    • 3 Baths
    • 3,056 Sq Ft

    21090 5th Ave, Cudjoe Key, FL 33042

    Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (866) 401-6074

    21090 5th Ave, Cudjoe Key, FL 33042
  • /51

    $1,725,000

    $174K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living. Large impact glass doors and windows frame ocean views and invite natural light into every room. Soaring, 26' ceilings enhance the open-concept layout with rich wood beams amplifying the

    Lauren Dunn Coldwell Banker Schmitt Islamorada

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • /6

    $499,000

    • Land
    • 6,969 Sq Ft
    • $3,118,750 per Acre

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042

    Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

    Lauren Dunn Coldwell Banker Schmitt Islamorada

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042
  • /2

    $45,000

    $5K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $281,250 per Acre

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042

    Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. worth 2 pts applying for Letter 2 additional lots available each for $50,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    (844) 484-2446

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042
  • /2

    $45,000

    $5K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $281,250 per Acre

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

    Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $50,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    (844) 526-4158

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042
  • /35

    $1,289,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    22777 Jolly Roger Dr, Cudjoe Key, FL 33042

    Stop dreaming and start packing. Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even have ample space for a chicken coop. A large saltwater pool is perfect for soaking up the sun and enjoying a peaceful

    Susan Halligan Live Local Realty of the Florida Keys

    22777 Jolly Roger Dr, Cudjoe Key, FL 33042
  • /33

    $249,000

    $30K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

    Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area. The home is clean and well cared for, offering a functional layout appropriate for full-time

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • /45

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    20868 5th Ave W, Summerland Key, FL 33042

    Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man

    Karen Haack Coldwell Banker Schmitt RE Co.

    20868 5th Ave W, Summerland Key, FL 33042
  • /42

    $1,325,000

    • 3 Beds
    • 2 Baths
    • 1,741 Sq Ft

    21025 3rd Ave, Summerland Key, FL 33042

    Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining.A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows

    Diane Corliss Coldwell Banker Schmitt RE Co.

    21025 3rd Ave, Summerland Key, FL 33042
  • /55

    $999,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    22978 Port Royal Ln, Summerland Key, FL 33042

    Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully

    Anne Press Lokation Real Estate

    22978 Port Royal Ln, Summerland Key, FL 33042
  • /69

    $3,500,000

    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    1083 Labat Ln, Cudjoe Key, FL 33042

    Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-0155

    1083 Labat Ln, Cudjoe Key, FL 33042
  • /2

    $50,000

    $125K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $312,500 per Acre

    0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042

    **PROPERTY DESCRIPTION** Oceanfront vacant lot in Cudjoe Key, FL (Block 14, Lot 1). Buildable residential parcel located in a platted subdivision, offering open water views and excellent investment potential. No ROGO permit currently in place; buyer must obtain allocation prior to building. Conveniently located near Key West with access to boating, fishing, and diving. Great opportunity to own

    Jaysen Larrieux LoKation

    0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042
  • /32

    $339,000

    $210K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

    Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
  • /58

    $277,500

    $18K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

    INCOME PRODUCING POWERHOUSE! Welcome to 'Conch Hideaway' #423, a proven tropical retreat and turnkey business in the premier Venture Out community. This charming 1BD/1BA home is a high-performing vacation rental that grossed $30,705 in 2025! INVESTMENT HIGHLIGHTS: Already live with rentals for 2026, this property has 27 days currently booked with $2,085.05 in gross revenue transferring to the

    Kate Baldwin Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
  • /38

    $965,000

    $84K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    288 Spanish Main Dr, Summerland Key, FL 33042

    PRICE REDUCED!! - UPDATED CANALFRONT HOME WITH 60' OF DOCKAGE Don't miss this exceptional opportunity to own a beautifully upgraded canalfront home in Cudjoe Key, offering 60 feet of seawall dockage and effortless access to the open water. This fully renovated 3-bedroom, 2-bath stilted home combines modern finishes with laid-back Florida Keys style, creating the ideal setting for full-time

    Richard Haskins Buy The Keys

    288 Spanish Main Dr, Summerland Key, FL 33042
  • /2

    $275,000

    • Land
    • 0 Sq Ft

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

    Seller Financing available.Builders and Developers take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

    Pamela Stangler Expert Realty LLC

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
  • /13

    $450,000

    $92K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $2,812,500 per Acre

    1147 Basque Ln, Cudjoe Key, FL 33042

    BUILDING & DOCK PERMITS IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water

    Brad Baker Key to the Keys Real Estate, Inc

    1147 Basque Ln, Cudjoe Key, FL 33042
  • /62

    $1,075,000

    • 4 Beds
    • 3 Baths
    • 2,448 Sq Ft

    165 Cutlass Ln, Summerland Key, FL 33042

    Discover your dream waterfront retreat in the Florida Keys. This canal-front home features 4 spacious bedrooms and 3 bathrooms with 2,448 sq. ft. of thoughtfully designed living space, perfect for accommodating family, guests, and entertaining. Enjoy expansive covered balconies on both levels, where you can relax and take in peaceful canal views and the laid-back island lifestyle. The generous

    Justyn Ewald Expert Realty LLC (HQ)

    165 Cutlass Ln, Summerland Key, FL 33042
  • /72

    $595,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

    Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
  • /12

    $495,000

    • Land
    • 2,078 Sq Ft
    • $10,376,420 per Acre

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

    Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

    Anay Ramos Miami New Realty

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
  • /33

    $469,000

    • 1 Bed
    • 2 Baths
    • 735 Sq Ft

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

    Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
  • /45

    $510,000

    $19K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

    MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

    Amanda Taylor Bluescape Real Estate

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
  • /64

    $1,080,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    22852 Buccaneer Ln, Summerland Key, FL 33042

    Experience the best of Keys living in this beautifully renovated waterfront home in sought-after Cudjoe Key--just minutes from local favorites like Square Grouper, 420 Lounge, and The Morning Joint. Boaters will appreciate the excellent access, complete with a concrete dock and 10,000 lb boat lift, making it easy to get on the water whenever you like. Privacy sets this property apart. The

    Agent Photo

    Austin Kimbler

    Expert Realty LLC (HQ)

    (645) 220-0519

    22852 Buccaneer Ln, Summerland Key, FL 33042
  • /27

    $375,000

    • 2 Beds
    • 1 Bath
    • 726 Sq Ft

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

    Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white

    Monika Rydzak EXP Realty LLC

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
  • /21

    $465,000

    • 1 Bed
    • 1 Bath
    • 799 Sq Ft

    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

    A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

    Rose Dell Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
  • /59

    $599,000

    New Construction $45K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

    Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 220-2833

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
  • /71

    $2,795,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,913 Sq Ft

    20920 5th Ave W, Summerland Key, FL 33042

    Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    (877) 939-4083

    20920 5th Ave W, Summerland Key, FL 33042
  • /43

    $1,799,000

    • 3 Beds
    • 3 Baths
    • 2,456 Sq Ft

    51 Sawyer Dr, Cudjoe Key, FL 33042

    Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (866) 618-8489

    51 Sawyer Dr, Cudjoe Key, FL 33042

Showing Results 1 - 40, Page 1 of 3

Frequently Asked Questions

What is the average home price in Cudjoe Key, FL?
Homes for sale in Cudjoe Key, FL have an average home price of $1,673,692.
Are home prices dropping in Cudjoe Key?
Yes, home prices in Cudjoe Key are down 35% in the last 12 months.
How many homes have sold over the last 12 months in Cudjoe Key, FL?
15 homes have sold in Cudjoe Key, FL over the last 12 months.
What are the most popular zip codes in Cudjoe Key, FL?
The most popular zip codes in Cudjoe Key, FL include 33042, 33040 and 33043.
How much do you need to make to afford a house in Cudjoe Key?
The median home price in Cudjoe Key is $1,463,000. If you put a 20% down payment of $292,600 and had a 30-year fixed mortgage with an interest rate of 6.51%, your estimated principal and interest payment would be $7,410 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $318K a year to afford the median home price in Cudjoe Key. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Cudjoe Key, FL?
Cudjoe Key, FL has highly rated public and private schools. Some of the best schools in Cudjoe Key based on Niche Grades are Sugarloaf School and Key West High School. Browse all the schools in Cudjoe Key, FL to learn more.

Home Trends in Cudjoe Key, FL

Housing Trends

Median Sale Price
$1,225,000
Median Single Family Sale Price
$1,325,000
Median 2 Bedroom Sale Price
$375,000
Average Price Per Sq Ft
$807
Number of Homes for Sale
10
Last 12 months Home Sales
15
Months of Supply
8.00
Median List Price
$1,463,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
13%
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