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Price Reduced Homes for Sale in Summerland Key, FL

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  • /34

    $799,000

    $91K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,638 Sq Ft

    27 Lake Dr N, Summerland Key, FL 33042

    Welcome to the Mango Cottage on Summerland Key! Tucked away on a quiet dead-end street, this 3 bedroom, 1 bath canal front CBS home combines the laid back Florida Keys lifestyle with excellent boating access and a few features you simply don't find everywhere. Surrounded by multiple mature fruit trees, including several mango trees! This property has a distinctly tropical feel from the moment you

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    27 Lake Dr N, Summerland Key, FL 33042
  • /38

    $640,000

    Open Sat 11AM - 2PM $49K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    711 State Rd Unit 4A, Little Torch Key, FL 33042

    A Classic Keys Boating Cottage! Exceptional value for a 3 bedroom 2 bath waterfront home in the Lower Keys! With 60' of seawall, enjoy easy boating access to nearby hot spots in the gulf and ocean side. The State Road 4a boat ramp is just a few doors away which is so convenient to launch your boat. Plenty of parking out front and room for a pool. Featuring laminate floors, a dedicated laundry

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    711 State Rd Unit 4A, Little Torch Key, FL 33042
  • /22

    $899,000

    $51K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 902 Sq Ft

    24923 Park Dr, Summerland Key, FL 33042

    Tropical Waterfront Living in the Florida Keys!Welcome to 24923 Park Drive in beautiful Summerland Key, where laid back Florida Keys living meets ultimate waterfront lifestyle. This charming canal-front property offers an opportunity to create your own paradise in one of the Keys' most desirable boating communities.Positioned along a wide protected canal, the property features

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    24923 Park Dr, Summerland Key, FL 33042
  • /33

    $565,000

    $34K PRICE DROP Pre-Foreclosure
    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    30354 Palm Dr, Big Pine Key, FL 33043

    Private Lower Keys opportunity! Nestled behind a lush hedge of mature Areca palms, this 2BR/2BA CBS home offers privacy, solid construction, and endless potential. Recent improvements include a 2018 post-Irma roof and storm shutters. The fully fenced 6,250 sq. ft. lot provides ample space for a pool, outdoor living, or tropical gardens, with a storage shed already in place. Enjoy a peaceful

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    30354 Palm Dr, Big Pine Key, FL 33043
  • /71

    $509,000

    $16K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile homenestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft

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    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
  • /10

    $474,000

    $25K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $1,394,118 per Acre

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

    Welcome to the lowest priced waterfront lot with an active building permit and DEP and Army Corp mitigation fees paid on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
  • /32

    $1,150,000

    $149K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,774 Sq Ft

    30525 Winifred St, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in POOL offers the perfect blend of comfort, space, and island living. Situated on an oversized 21,438 fenced in corner lot with a private gated entrance, the property provides exceptional privacy and a peaceful setting surrounded by tropical beauty. Plenty of space for your RV, Boat Trailer and more. It's a

    Joyce Craul Expert Realty LLC (HQ)

    30525 Winifred St, Big Pine Key, FL 33043
  • /28

    $699,000

    $139K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    3856 Donna Rd, Big Pine Key, FL 33043

    Own Your Own Private Boat Ramp. Major Price Improvement from original Listing, Priced to SELL, Motivated Seller, Bring all Offers. Sportsman Paradise. 2 Bedroom House with Permitted Concrete BOAT RAMP, concrete sea wall, concrete fish cleaning table with Permitted Downstairs Bathroom. Real short idle to open water. Back country fishing, lobster diving/snorkel and stone crabs right in your back

    Alan Ballas Alan Ballas Realty

    3856 Donna Rd, Big Pine Key, FL 33043
  • /20

    $500,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    27910 Porgie Path, Summerland Key, FL 33042

    Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping.

    27910 Porgie Path, Summerland Key, FL 33042
  • /68

    $1,199,900

    $200K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,312 Sq Ft

    3746 Park Ave, Big Pine Key, FL 33043

    SELLER WILL GIVE A $20,000.00 BUYER CLOSING CREDIT! Welcome to your private paradise in the Lower Keys! This beautifully updated 2-bedroom, 2-bathroom two-story home offers the ultimate island escape with unmatched privacy -- no direct neighbors on any side, just peaceful surroundings, tropical landscaping, and the charm of the native Key Deer. Designed for true Florida Keys living, the outdoor

    Cabot Brown Compass Florida - Miami Beach

    3746 Park Ave, Big Pine Key, FL 33043
  • /44

    $1,019,000

    Open Sat 10AM - 12PM $81K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    29555 Enterprise Ave, Big Pine Key, FL 33043

    Accessibility elevator! Welcome to your Lower Keys retreat where comfort, and coastal living come together beautifully along with the convenience of an interior elevator. Situated on the desirable boating canal system of Pine Channel Estates, this 3 bedroom, 2 bath home is designed for those who appreciate the water based lifestyle.Inside, soaring vaulted ceilings create an open and airy

    Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

    29555 Enterprise Ave, Big Pine Key, FL 33043
  • /73

    $2,799,000

    New Construction $501K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,886 Sq Ft

    23950 Overseas Hwy, Summerland Key, FL 33042

    Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Keys. Recognizable by its signature pink façade and blue metal roof, this exceptional Summerland Key residence captures the spirit of island living while offering the quality, comfort, and peace of mind of modern CBS construction.

    TEAM Walters Gloria, Rachel and Michae Ocean Sotheby's International Realty

    23950 Overseas Hwy, Summerland Key, FL 33042
  • /30

    $600,000

    $75K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft

    29188 Tulip Ln, Big Pine Key, FL 33043

    Nestled at the quiet end of a peaceful street, this beautifully maintained home is all about the blend of island charm, privacy, and modern comfort. No HOA. Unique architecture, surrounded by graceful Areca palms and bordered by county land on two sides, the property feels like a serene tropical oasis. Step inside to find soaring cathedral ceilings that create a bright, airy atmosphere throughout

    Steven Koleno Beycome of Florida, LLC

    29188 Tulip Ln, Big Pine Key, FL 33043
  • /42

    $980,000

    $170K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft

    750 W Indies Dr, Summerland Key, FL 33042

    This three bedroom , two bathroom home sits on an expansive 12,200 square foot piece of property in the highly sought after Breezeswept Beach Estates neighborhood on Ramrod Key. Upstairs there are two bedrooms and one bath, and a large kitchen and living room. Downstairs is a one bedroom, one bathroom bungalow with a complete kitchen!The exterior of the property has several updates,

    Mary Conklin Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    750 W Indies Dr, Summerland Key, FL 33042
  • /5

    $145,000

    $80K PRICE DROP
    • Land
    • 0 Sq Ft

    29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043

    ROGO-exempt 2,250 sq ft parcel in the Florida Keys. Bring your vision to life and build a home in Big Pine Key without the typical ROGO delays. Start building now - no wait time! Mobile home, modular home or single family residence.The lot is located within Breezy Estates RV Park, a well-maintained community with amenities including a pool, clubhouse, laundry, landscaping, and basic

    Steven Koleno Beycome of Florida, LLC

    29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
  • /21

    $899,000

    $151K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,418 Sq Ft

    1540 Lantana Ln, Big Pine Key, FL 33043

    Bring your boats to this beautifully furnished canal front home. This home is secluded on a large corner lot with 190 ft. of concrete seawall. Large and open living, dining, and kitchen areas. Lovely updated kitchen and bathes. New beautiful floors, along with impact windows, doors, and metal roof. Enjoy swimming in the above ground pool, relaxing on the deck, cocktails at the bar, or meeting the

    Andrea Lennon Vylla Home

    1540 Lantana Ln, Big Pine Key, FL 33043
  • /42

    $805,000

    $44K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    27416 Martinique Ln, Summerland Key, FL 33042

    Discover the relaxed vibe of the Lower Keys and uncover your sense of 'Place'. This tropical home on Ramrod Key is not just 4 walls, it is a canvas to create your most prized and cherished, Florida Keys memories. Located in the sought after Breezeswept Beach Estates neighborhood. This waterfront home offers concrete dock and 60 feet on the water and a super Kayak /SUP swim-out launch. Wide open

    Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

    27416 Martinique Ln, Summerland Key, FL 33042
  • /56

    $1,125,000

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 960 Sq Ft

    29565 Flying Cloud Ave, Big Pine Key, FL 33043

    Waterfront retreat with excellent boating access in the heart of Big Pine Key! Home has 15k boat lift, fish cleaning table and clear deep canal. This elevated home features a private dock, canal frontage, and plenty of room for boats, trailers outdoor entertaining and out door showers. Open-concept living areas, abundant natural light, and spacious porches create the perfect Keys getaway or

    Frank Kowalski Metro Dade Realty, Inc.

    29565 Flying Cloud Ave, Big Pine Key, FL 33043
  • /42

    $799,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 984 Sq Ft

    937 Loggerhead Ln, Summerland Key, FL 33042

    Opportunities like this are hard to find in the Lower Keys--this fully renovated 3-bedroom, 2-bath home sits on a generous half-acre lot in the highly desirable Sugarloaf Key area, offering space, privacy, and modern upgrades throughout. Designed for easy coastal living, the home features durable Hardie board siding, a long-lasting metal roof, tile flooring throughout, and an energy-efficient

    Richard Haskins Buy The Keys

    937 Loggerhead Ln, Summerland Key, FL 33042
  • /49

    $779,000

    $41K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,076 Sq Ft

    1817 Watson Blvd, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this 2-bedroom, 2-bath canal-front ranch style home offers a rare opportunity to enjoy the Florida Keys lifestyle while investing for exceptional future potential. Situated on an oversized 1 1/2 lot with direct boating access out to open water in 3 mins, this property is a true waterfront gem. The existing home provides comfortable island living with abundant

    Paul Rogers Coldwell Banker Schmitt RE Co.

    1817 Watson Blvd, Big Pine Key, FL 33043
  • /42

    $699,000

    $86K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,224 Sq Ft

    31033 Hibiscus Dr, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized DOUBLE LOT with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Or you may just want to demo the house and build your Keys Dream Home on two

    Karen Haack Coldwell Banker Schmitt RE Co.

    31033 Hibiscus Dr, Big Pine Key, FL 33043
  • /49

    $749,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    19543 Navajo St, Cudjoe Key, FL 33042

    3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

    Pamela Stangler Expert Realty LLC

    19543 Navajo St, Cudjoe Key, FL 33042
  • /33

    $239,000

    $10K 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 gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room.The property is currently occupied by a long-term

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • /41

    $799,000

    $170K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,277 Sq Ft

    29544 Independence Ave, Big Pine Key, FL 33043

    LOCATION and PRICE is the KEY to this charming, one level coastal retreat. 75' canal-frontage, 2 bedrooms, 2 full baths plus a bonus all-season sunroom. Property is furnished with many upgrades. Generous and impressive living space is perfect for entertaining and family gatherings. Grab a siesta or your favorite beverage while overlooking the canal from the sunroom or on the covered patio. Pine

    Jennifer Sylvia Keller Williams Key West Compass Realty

    29544 Independence Ave, Big Pine Key, FL 33043
  • /34

    $1,469,000

    New Construction $80K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft

    27374 Guadaloupe Ln, Summerland Key, FL 33042

    *Construction process underway. Expected completion November/December 2026Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    27374 Guadaloupe Ln, Summerland Key, FL 33042
  • /4

    $1,999,000

    $751K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,020 Sq Ft

    32029 Marginella Dr, Big Pine Key, FL 33043

    Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? Look no further than this exceptional offering nestled in the heart of the Natural Florida Keys. Situated on the private and secluded No Name Key, just a stone's throw away from Big Pine Key, this nearly 2-acre property presents

    Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

    32029 Marginella Dr, Big Pine Key, FL 33043
  • /3

    $99,000

    $36K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $291,176 per Acre

    19617 Date Palm Dr, Sugarloaf Key, FL 33042

    PRICED TO SELL. Now only $99,000 and the least expensive southernmost lot for sale in The Florida Keys!Best priced lot in popular Upper Sugarloaf Key and priced for immediate sale! Take advantage of this opportunity to develop this larger 150 x 100 Tier III platted lot (infill lot located in a developed subdivision with adequate infrastructure). With its prime location and desirable

    Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

    19617 Date Palm Dr, Sugarloaf Key, FL 33042
  • /77

    $2,499,000

    $401K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,700 Sq Ft

    29581 Richard Rd, Big Pine Key, FL 33043

    Spectacular Open-Water Retreat with Unmatched Sunset ViewThis exceptional open-water property offers breathtaking western-facing sunset views and premier ocean access with no bridges--perfect for boating enthusiasts. Enjoy privacy and natural beauty bordering the Florida Key Deer Preserve.The property features over 200 feet of concrete seawall, a 35' x 15' boat basin making it ideal for

    Diane Corliss Coldwell Banker Schmitt RE Co.

    29581 Richard Rd, Big Pine Key, FL 33043
  • /3

    $205,000

    $10K PRICE DROP
    • Land
    • 7,840 Sq Ft
    • $1,138,889 per Acre

    27334 Saint Lucie Ln, Big Pine, FL 33042

    Rare opportunity to own a canal-front property in the desirable Breezeswept Beach Estates community on Ramrod Key. Please note that the property currently has an unresolved issue involving the lot-line adjustment and the configuration of the parcel. The buyer will be responsible for investigating, resolving, and assuming all costs associated with this matter after closing. The asking price has

    Gilberto Imery Gilvan Realty Corp

    27334 Saint Lucie Ln, Big Pine, FL 33042

Home Price Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,170,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$924,500
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$922
Number of Homes for Sale
29
Last 12 months Home Sales
110
Months of Supply
4.40
Median List Price
$1,269,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-1%
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