28

Homes for Sale in Summerland Key, FL with 4-Bedrooms

Section Image Section Image
  • /43

    $888,000

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft

    25057 7th St, Summerland Key, FL 33042

    Welcome to your private retreat in the Lower Keys! Nestled on an expansive 20,000 sq ft lot, this meticulously maintained one-owner home offers the perfect blend of privacy, comfort, and Keys-style living. Backing up to a protected nature preserve, you'll enjoy uninterrupted sunset views from your master bedroom and upstairs balcony - with the added bonus of a natural windbreak and guaranteed

    Agent Photo

    Christopher Tanaka

    Coldwell Banker Schmitt RE Co.

    (786) 869-2251

    25057 7th St, Summerland Key, FL 33042
  • /89

    $3,695,000

    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    680 Elma Ave, Big Pine Key, FL 33043

    RARE west-facing private estate offering sunset views, owned bay bottom, and exceptional boating access. Welcome to Tarpon Cove, an exclusive retreat located in Big Pine Key, surrounded by the Florida Key Deer Preserve for unmatched privacy and natural beauty.The concrete residence has been meticulously reconstructed through a down-to-the-studs renovation, resulting in a 2023 effective age and is

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (877) 359-5426

    680 Elma Ave, Big Pine Key, FL 33043
  • /27

    $987,500

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft

    3962 No Name Rd, Big Pine Key, FL 33043

    Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    (888) 275-1086

    3962 No Name Rd, Big Pine Key, FL 33043
  • /48

    $675,000

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft

    31011 Avenue C, Big Pine Key, FL 33043

    This 4-bedroom, 2-bath, 1566 sq. ft. home in the Keys is a rare find for price! Features include a split bedroom floor plan, laundry room, a big sundeck, covered parking, ground-level storage enclosure, and convenient access from both Avenue C and Sands Rd. Local shops and amenities are nearby, with easy commutes to Marathon or Key West. The Big Pine Community Park, less than half a mile away,

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 856-6295

    31011 Avenue C, Big Pine Key, FL 33043
  • /43

    $763,000

    • 4 Beds
    • 2 Baths
    • 2,136 Sq Ft

    30374 Oleander Blvd, Big Pine Key, FL 33043

    If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provides ample space for family and guests with 4-bedrooms, 2-baths, a family room, laundry room and additional room that could be a 5th bedroom. Refreshing colors complement the space, and the tasteful furnishings are included with

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (866) 827-7154

    30374 Oleander Blvd, Big Pine Key, FL 33043
  • /72

    $2,995,000

    • 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

    (786) 667-5744

    20920 5th Ave W, Summerland Key, FL 33042
  • /62

    $5,200,000

    • 4 Beds
    • 4 Baths
    • 2,660 Sq Ft

    17013 Coral Dr, Summerland Key, FL 33042

    Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 882-3659

    17013 Coral Dr, Summerland Key, FL 33042
  • /32

    $975,000

    • 4 Beds
    • 3 Baths
    • 2,503 Sq Ft

    30451 Hibiscus Ln, Big Pine Key, FL 33043

    ONE-OF-A-KIND! Custom-built home '2010'on a large 125 X 250 property, 31,250 sq. ft. more than 1/2 acre. 4bd/3bth plus a bonus room for a total 2493 sqft. Perfect for 2 working professionals from home or a big family. Good size bedrooms. 2 are ensuite. Separate Kitchen Dining & Living Room and an extra room for office or hobbies, gym or guest. Concrete slab under house same size of house so lots

    Rose Dell Keller Williams Key West Compass Realty

    30451 Hibiscus Ln, Big Pine Key, FL 33043
  • /61

    $2,795,000

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft

    20844 4th Ave W, Summerland Key, FL 33042

    FISHERMAN'S DREAM! BIG BOATS WELCOME! DEEP WATER! LARGE WATERFRONT HOME in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of luxury and comfort. All new impact windows &

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • /66

    $2,795,000

    • 4 Beds
    • 5.5 Baths
    • 3,224 Sq Ft

    333 Indies Rd, Ramrod Key, FL 33042

    Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 51/2 bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis.This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a

    Greg MacLaren Internet Realty of the Florida Keys

    333 Indies Rd, Ramrod 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
  • /49

    $1,499,000

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft

    27372 W Indies Dr, Summerland Key, FL 33042

    Offered for the first time, this custom-built 4 bedroom, 3 bathroom waterfront residence on Ramrod Key showcases refined coastal design, exceptional craftsmanship, and magnificent ocean views. Completed in 2020, the two-story stilted home was thoughtfully designed to maximize light, views, and seamless indoor-outdoor living, with one master bedroom ensuite on each level for comfort and

    Sandra Dolowy KeyIsle Realty

    27372 W Indies Dr, Summerland Key, FL 33042
  • /49

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that showcase a breathtaking oceanfront setting. Situated on a double lot totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay—creating a rare and commanding presence along the shoreline.Broad covered

    Lauren Dunn Coldwell Banker Schmitt R.E.

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • /75

    $3,200,000

    • 4 Beds
    • 3 Baths
    • 2,812 Sq Ft

    16805 Tamarind Rd, Summerland Key, FL 33042

    OPEN WATER ELEGANCE on prestigious Southpoint, Sugarloaf Key. This exceptional 4-bedroom, 3-bath concrete waterfront residence captures breathtaking open water views from nearly every room and delivers the ultimate Florida Keys lifestyle.Positioned on a generous, beautifully landscaped lot with mature palms and established tropical greenery, the property welcomes you with a paved circular

    Lisa Swanson The Agency Florida Keys

    16805 Tamarind Rd, Summerland Key, FL 33042
  • /58

    $1,199,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3 Baths
    • 1,901 Sq Ft

    1547 Gardenia Ln, Big Pine Key, FL 33043

    Brand New Canal-Front Coastal Retreat in the Florida Keys....Welcome to this stunning new construction canal-front home, thoughtfully designed for comfort, durability, and modern island living. Situated on a 12,000 sq ft double lot, this elevated 4-bedroom, 3-bathroom residence offers 1,901 sq ft of living space and 9'6'' clearance under the home, providing peace of mind and ample storage

    Francesca Santiago Keller Williams Realty Professionals (KW)

    1547 Gardenia Ln, Big Pine Key, FL 33043
  • /82

    $3,699,000

    • 4 Beds
    • 3.5 Baths
    • 1,744 Sq Ft

    17183 Coral Dr, Summerland Key, FL 33042

    Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

    Jan Fritz Coldwell Banker Schmitt RE Co.

    17183 Coral Dr, Summerland Key, FL 33042
  • /57

    $1,900,000

    • 4 Beds
    • 3 Baths
    • 1,964 Sq Ft

    27385 Saint Lucie Ln, Summerland Key, FL 33042

    Tropical Keys Oasis -- Waterfront Luxury LivingCome experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the most

    Amedeo Belmonte William Raveis Florida LLC

    27385 Saint Lucie Ln, Summerland Key, FL 33042
  • /61

    $2,800,000

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft

    1553 Sunrise Dr, Big Pine Key, FL 33043

    Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large Porcelain floors and counter tops enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Four roomy suites

    Barbara Eads Barbara Eads Realty Inc.

    1553 Sunrise Dr, Big Pine Key, FL 33043
  • /74

    $2,995,000

    • 4 Beds
    • 4 Baths
    • 1,804 Sq Ft

    17385 Keystone Rd, Summerland Key, FL 33042

    Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. (24,662 sqft Upland & 12,477 submerged). These point lots are extremely limited and among the most

    Lisa Swanson The Agency Florida Keys

    17385 Keystone Rd, Summerland Key, FL 33042
  • /28

    $995,000

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

    27376 Tobago Ln, Summerland Key, FL 33042

    Nestled in Breezeswept Beach Estates, this fully remodeled canal-front home is the perfect Keys getaway. This 4-bed, 2-bath house features an open floor plan, vaulted ceilings, and a modern kitchen with granite countertops, new cabinets, and stainless steel appliances. The master suite offers a walk-in closet and spa-style bathroom, while the additional bedrooms provide plenty of space for family

    Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

    27376 Tobago Ln, Summerland Key, FL 33042
  • /20

    $1,295,000

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    29678 Enterprise Ave, Big Pine Key, FL 33043

    Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean,

    Thomas Carden Keys to the Coast Real Estate LLC

    29678 Enterprise Ave, Big Pine Key, FL 33043
  • /94

    $3,875,000

    • 4 Beds
    • 4 Baths
    • 2,766 Sq Ft

    414 Caribbean Dr E, Summerland Key, FL 33042

    Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft.

    Lisa Swanson The Agency Florida Keys

    414 Caribbean Dr E, Summerland Key, FL 33042
  • /53

    $1,710,000

    • 4 Beds
    • 2 Baths
    • 2,605 Sq Ft

    1481 Sugarloaf Blvd, Summerland Key, FL 33042

    Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy.Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring

    Jenna Stauffer Ocean Sotheby's International Realty

    1481 Sugarloaf Blvd, Summerland Key, FL 33042
  • /18

    $749,000

    • 4 Beds
    • 2.5 Baths
    • 1,924 Sq Ft

    1433 Sunset Rd, Big Pine Key, FL 33043

    Great price reduction on income producing CBS duplex in Big Pine Key. Good boating with direct access to Bogie Channel. Large lot with full seawall. Interior is cute and tidy and would be easy to rent or live in one side and generate extra income. Fully furnished.

    Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

    1433 Sunset Rd, Big Pine Key, FL 33043
  • /68

    $1,840,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 2,639 Sq Ft

    30985 Watson Blvd, Big Pine Key, FL 33043

    MODERN ISLAND RETREAT ON BOGIE CHANNEL - BIG PINE KEY, FLDiscover the epitome of Lower Keys living in this luxurious 4-bedroom, 3.5-bath CBS pool home, ideally positioned on Bogie Channel with direct BOATING access. Built in 2022 and offered furnished, this elevated residence combines modern design, coastal charm, and unmatched functionality. It's a rare find to own approximately .62 of an acre

    Donna Pezzi Keller Williams Key West Compass Realty

    30985 Watson Blvd, Big Pine Key, FL 33043
  • /59

    $1,529,999 Open Sat 11AM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,136 Sq Ft

    142 Peg Leg Ln, Cudjoe Key, FL 33042

    Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

    Alejandro Perez Amerifirst Realty

    142 Peg Leg Ln, Cudjoe Key, FL 33042
  • /53

    $2,300,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    30995 Watson Blvd, Big Pine Key, FL 33043

    FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent

    Banks Prevatt Coldwell Banker Schmitt RE Co.

    30995 Watson Blvd, Big Pine Key, FL 33043
  • /2

    $1,700,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft

    2211 San Sebastian Dr, Big Pine Key, FL 33043

    Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected deep water canal with excellent access to the Gulf and Atlantic. This 2000 sq ft home is situated in a quiet neighborhood and features an open living area design with chef's kitchen/ quartz counter tops, high ceilings, covered porch, custom railings, impact windows and doors, custom concrete heated and chilled

    Greg MacLaren Internet Realty of the Florida Keys

    2211 San Sebastian Dr, Big Pine Key, FL 33043

Home Trends in Summerland Key, FL

Housing Trends

Median Sale Price
$1,133,000
Median Single Family Sale Price
$1,164,000
Median Townhouse Sale Price
$1,750,000
Average Price Per Sq Ft
$910
Number of Homes for Sale
70
Last 12 months Home Sales
110
Months of Supply
7.60
Median List Price
$1,300,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-4%
How to Buy a Home How to Finance a Home How to Sell a Home