Summerland Key, FL City Guide | About Living in Summerland Key

Summerland Key

Located in Monroe County

33042

$1,526,483 Average Value

$887 Average Price per Sq Ft

62 Homes For Sale

Interested in learning more about homes in this area? Reach out to Austin Kimbler, an experienced agent in this area.

Agents Specializing in this Area

Emily Lombard

Ocean Sotheby's International Realty

(833) 447-1049

49 Total Sales

12 in Summerland Key

$399K - $2.9M Price Range

Emily Lombard
Sandra Tuttle

Island Welcome Real Estate

(786) 751-6441

163 Total Sales

128 in Summerland Key

$155K - $5.3M Price Range

Sandra Tuttle
Krissy Carnahan

Realty ONE Group Destination (ISL)

(786) 745-3395

26 Total Sales

1 in Summerland Key

$125,000 Price

Krissy Carnahan
Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 751-5529

562 Total Sales

358 in Summerland Key

$46K - $12.3M Price Range

Lisa Ferringo
Stacy Shahan

Island Real Estate Company Florida Keys

(813) 694-9962

31 Total Sales

28 in Summerland Key

$339K - $5.3M Price Range

Stacy Shahan
Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(844) 329-8954

13 Total Sales

1 in Summerland Key

$1,050,000 Price

Damian Vantriglia

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Schools

Source:

Sugarloaf School

Pre-K to 8th
Public

Key West High School

7th to 12th
Public

B+

Explore All Schools

Summerland Key Housing Trends

On average, homes in Summerland Key, FL sell after 119 days on the market compared to the national average of 54 days. The median sale price for homes in Summerland Key, FL over the last 12 months is $990,000, down 17% from the median home sale price over the previous 12 months.

Housing Trends

Median List Price

$1,295,000

Median Sale Price

$990,000

Median Single Family Sale Price

$1,150,000

Median Change From 1st List Price

10%

Last 12 months Home Sales

101

Median Home Sale Price YoY Change

-17%

Average Price Per Sq Ft

$887

Area Facts

Number of Homes

2,073

Number of Homes for Sale

Median Year Built

1987

Months of Supply

7.40

Average Single Family Home Size Sq Ft

1,525

Significantly below the national average

1,930

Average Townhouse Size Sq Ft

2,047

Median Lot Size Sq Ft

7,405

Open Houses

Saturday, Feb 28

Open Sat 12PM - 2PM
$1,250,000
- 3 Beds
- 2 Baths
- 1,544 Sq Ft
715 Caribbean Dr E
Experience the ultimate Florida Keys lifestyle at 715 Caribbean Drive East in Summerland Key. Located in a desirable boating and aviation community, this property offers rare access to a private neighborhood airstrip, ideal for pilots and aviation enthusiasts. Designed for boaters, the home features a 60-foot dock and a 15,000-lb boat lift, providing easy access to open water, nearby sandbars,

Christina Davis

Coldwell Banker Schmitt RE Co.

(844) 920-0831
Monday, Feb 23

Open Mon 11AM - 2PM
$1,569,999
- 4 Beds
- 3 Baths
- 2,136 Sq Ft
142 Peg Leg Ln
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
Sunday, Mar 1

Open Sun 11AM - 3PM
$2,069,000
- 3 Beds
- 2 Baths
- 1,849 Sq Ft
1733 Sunrise Dr
Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

Norman De la Cruz Florida Realty of Miami Corp

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Homes for Sale

$795,000

3 Beds
1 Bath
1,562 Sq Ft

360 W Shore Dr

Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

Brenda Thomas

Island Welcome Real Estate

(786) 949-3594

$615,000

2 Beds
2 Baths
912 Sq Ft

29951 Pine Channel Rd

*Back on Market & Ready for New Owners!* VA Assumable 2.625% interest rate for eligible Buyers! Total current payment $2864/mo! Inquire for more details.Welcome to your island escape! This beautifully updated 2 bedroom, 2 full bath stilted home offers the perfect blend of comfort, convenience, & coastal charm. Situated on a spacious lot in the heart of Big Pine Key, this property features a brand

Lindsay Ryan

EXP Realty LLC

(877) 412-3188

$1,325,000

3 Beds
2 Baths
1,494 Sq Ft

22974 Anne Bonny Ln

Welcome to 22974 Anne Bonny Lane in Cudjoe Key, a beautifully appointed, turn-key waterfront home designed for island living and ready for immediate enjoyment--whether as a full-time residence, second home, or income-producing vacation rental. This 3-bedroom, 2-bath coastal retreat is being offered fully furnished, with stylish furnishings purchased just two years ago, allowing a new owner to

Sandra Tuttle

Island Welcome Real Estate

(786) 869-3656

$1,699,000

2 Beds
2 Baths
1,980 Sq Ft

1607 Sunrise Dr

Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(855) 301-2387

$485,000

1 Bed
1 Bath
754 Sq Ft

701 Spanish Main Dr
Unit 182

Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

Ian Calderwood

Bluescape Real Estate

(786) 551-4336

$214,500

Land

701 Spanish Main Dr
Unit 658

RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

Ian Calderwood

Bluescape Real Estate

(786) 418-4615

$1,395,000

3 Beds
3 Baths
1,700 Sq Ft

16941 Driftwood Ln

There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key West,

Coby Taylor

Taylor & Assoc. RE, Inc.

(855) 606-6133

$975,000

2 Beds
2 Baths
960 Sq Ft

683 Blackbeard Rd
New 14 days ago

Located near a canal 'T', this oceanside property offers easy docking for larger boats and sailboats in the 50 ft. wide, flow-through canal, putting the Atlantic and back-country within easy reach. The rooftop deck is a wonderful vantage point for panoramic neighborhood and water views. Nestled in mature vegetation, the one-owner, custom-built, board and batten cedar home has been well-maintained

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(833) 982-0551

$625,000

2 Beds
1 Bath
850 Sq Ft

29961 Pine Channel Rd
New 5 days ago

Welcome to your perfect Florida Keys getaway in the heart of Big Pine Key. This charming 2-bedroom, 1-bath home offers an inviting open-concept layout that flows seamlessly between the living, dining, and kitchen areas. Natural light pours in through large windows, creating a bright, airy feel that complements the relaxed island setting.The kitchen features stainless steel appliances and a

Terrance Sullivan

Ocean Sotheby's International Realty

(833) 583-1227

$1,499,000

3 Beds
2 Baths
1,512 Sq Ft

823 Indies Rd

Fabulous sunset views over the salt ponds at this concrete 3 Bedroom 2 Bath home in Breezeswept Beach Estates. Located towards the end of a very quiet street this home offers a lot of privacy with beautiful views of the bird estuary in front and long views of the canal in the back. Boaters will appreciate the immediate ocean access with no bridges and easy turn around from the 60' step-down dock

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(305) 614-6847

$5,200,000

4 Beds
4 Baths
2,660 Sq Ft

17013 Coral Dr

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

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 882-3659

$3,750,000

3 Beds
2 Baths
1,851 Sq Ft

755 Sawyer Dr

In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

Terrance Sullivan

Ocean Sotheby's International Realty

(786) 204-2360

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Homes for Rent

$4,350 per month

3 Beds
2 Baths
1,290 Sq Ft

2635 Koehns Ave
Big Pine Key, FL

Discover this charming 3-bedroom, 2-bathroom furnished home. ALL UTILITIES ARE INCLUDED. The spacious, open floor plan features a gourmet kitchen with white quartz countertops and sleek, stainless-steel Bertazzoni appliances imported from Italy.Relax in the dining area, overlooking a screened-in patio with stunning views of the heated saltwater pool. The lush backyard is a tropical paradise,

Karen Liskey

Key Colony Beach Realty

(866) 729-5076

$12,500 per month

4 Beds
4 Baths
2,952 Sq Ft

21640 Overseas Hwy
Summerland Key, FL

Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

Dan Serban

Key West Luxury Real Estate Inc (KW)

(786) 442-3255

$2,700 per month

Coco Palms
2 Beds
2 Baths
900 Sq Ft

21585 Overseas Hwy
Cudjoe Key, FL

Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

$5,000 per month

3 Beds
3 Baths

27355 Guadaloupe Ln
Ramrod Key, FL

NEW CONSTRUCTION ANNUAL LEASE, AVAILABLE APRIL 13 bedroom, 3 bathroom 1500 sqft home with beautiful and spacious covered porch. Great canal boating access with wood dock and boat lift! Stainless steel appliances, quartz counter tops, and spacious bedrooms and living areas!Swimming pool to be installed summer of 2026, at no additional rent cost to tenant. First last and security required to move

Nick Boumerhi Meyer and Boumerhi Realty LLC

$5,537 - $15,000 per month

Little Torch Cottages
2 - 4 Beds
2-4 Baths
1,080+ Sq Ft

28501 Channel View Dr
Little Torch Key, FL

In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

$3,600 per month

2 Beds
2 Baths
1,056 Sq Ft

201 Cutthroat Dr
Summerland Key, FL

LONG TERM RENTAL AVAILABLESpacious and well maintained unfurnished 2-BD, 2-BTH Stilted home for rent in Cudjoe Key. It has stainless steel appliances (stove/oven is brand new), and the Main Bedroom has it's own porch.A large deck overlooks the canal and is perfect for an evening adult beverage. This property is situated at the corner of Cutthroat Dr. and Blackbeard Ln. and has a large concrete

Mark Peterson

$7,945 per month

Condo for Rent
3 Beds
2 Baths
1,431 Sq Ft

886 Loggerhead Ln
Unit ID1297829P
Summerland Key, FL

The advertised rate of $7,945/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 8, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

$4,900 per month

2 Beds
2 Baths
884 Sq Ft

27346 Martinique Ln
Summerland Key, FL

Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

Alicia Rufino Island Living Realty, LLC

$3,500 per month

House for Rent
2 Beds
2 Baths
912 Sq Ft

30612 23rd Ln
Big Pine Key, FL

Property Id: 2240886Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can relax in comfort. Enjoy the convenience of WiFi, AC, and a washing machine during your stay. The 2 bathrooms are equipped with all of the conveniences of home. Located between the Back Bay and the Ocean. Property sits on an acre lot, enjoy the breezy,

$5,357 per month

2 Beds
2 Baths
1,079 Sq Ft

53 Barry Ave
Summerland Key, FL

This is a 2 story furnished or unfurnished single family house with a private pool, fenced in yard, screened patio, 2 bedrooms, 2 bathrooms with showers, stainless steel appliances, hurricane windows, washer and dryer, tile and wood floors. You are also able to use the amenities at our property next door such as 24 hour community gym and sauna. marina with boat ramp, outdoor games, bbq, kayaks

Joseph Danieli AKT Realty LLC

$4,051 per month

Condo for Rent
2 Beds
2 Baths

29179 Rose Dr
Unit ID1307168P
Big Pine Key, FL

The advertised rate of $4,051/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 10, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

$3,800 per month

3 Beds
1.5 Baths
1,247 Sq Ft

29283 Coconut Palm Dr
Big Pine Key, FL

Ready to Rent beginning March 1st, 2026. This 3-bedroom, 1.5-bath home on Coconut Palm Drive is located in a quiet Big Pine Key neighborhood and features vaulted ceilings, crown molding, and an open-concept layout with great natural light. The property offers covered parking, a large downstairs storage area ideal for equipment or hobbies, and a fully fenced backyard for added privacy.

Lisa Cattran Engel & Volkers Marathon

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Source: Public Records

Property Mix - Square Feet

Summerland Key Has More Owners

Demographics

Total Population

11,851

Median Age

Population Density

54 ppl/acre

Population under 18

14.9%

Below the national average

23.8%

Population over 65

31.5%

Above the national average

19.1%

Finances

Median Household Income

$84,702

Above the national average

$79,601

Average Household Income

$105,481

Education and Workforce

High School Graduates

94.8%

Above the national average

89%

College Graduates

35.7%

Advanced Degrees

14.1%

% Population in Labor Force

61.1%

On par with the national average

64.9%

Weather

Annual Precipitation

41''

Average Winter Low Temperature

66°F

Average Summer High Temperature

91°F

Annual Snowfall

0''

Area Factors

Somewhat Bikeable

Bike Score®^®

27 / 100

Car-Dependent

Walk Score®^®

0 / 100

Source: Walk Score

Florida Monroe County

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Austin Kimbler

Expert Realty LLC (HQ)

Summerland Key

Summerland Key

Agents Specializing in this Area

Schools

Summerland Key Housing Trends

Housing Trends

Area Facts

Open Houses

Saturday, Feb 28

Open Sat 12PM - 2PM

Monday, Feb 23

Open Mon 11AM - 2PM

Sunday, Mar 1

Open Sun 11AM - 3PM

Homes for Sale

Homes for Rent

Distribution of Home Values

Average Home Value

Property Mix - Square Feet

Summerland Key Has More Owners

Demographics

Finances

Education and Workforce

Weather

Area Factors

Somewhat Bikeable

Car-Dependent

Summerland Key

Summerland Key

Agents Specializing in this Area

Schools

Summerland Key Housing Trends

Housing Trends

Area Facts

Open Houses

Saturday, Feb 28 Open Sat 12PM - 2PM

Monday, Feb 23 Open Mon 11AM - 2PM

Sunday, Mar 1 Open Sun 11AM - 3PM

Homes for Sale

Homes for Rent

Distribution of Home Values

Average Home Value

Property Mix - Square Feet

Summerland Key Has More Owners

Demographics

Finances

Education and Workforce

Weather

Area Factors

Somewhat Bikeable

Car-Dependent

Saturday, Feb 28

Open Sat 12PM - 2PM

Monday, Feb 23

Open Mon 11AM - 2PM

Sunday, Mar 1

Open Sun 11AM - 3PM