Summerland Key, FL Homes

/2
Not Listed For Sale

3 Big Pine Ave, Big Pine Key, FL 33043
3 Big Pine Ave, Big Pine Key, FL 33043

Last Sold Summary
Last Sold Price $39,666

Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

/22
$679,000
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
19591 Navajo St, Summerland Key, FL 33042

INDIAN MOUNDS SPECIAL!!!! Two balconies with ocean views and a hot tub to enjoy them with!!! Just one block from the private community boat ramp, this elevated 2 bed, 2 bath home sits on a large oversized corner lot. There is plenty of room for parking your toys and a downstairs enclosure for additional storage. Hardibacker siding and a metal roof provide peace of mind.Upon entering, you'll find

Mike Kane

Internet Realty of the Florida Keys

(645) 230-1301

19591 Navajo St, Summerland Key, FL 33042
/33
$1,075,000 Sold Feb 20, 2026

17226 Jamaica Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1998
Last Sold Summary
- 10% Below List Price
- $861/SF
- 32 Days On Market
Current Estimated Value $1,173,673

Last Listing Agent Stephen Hachey

17226 Jamaica Ln, Summerland Key, FL 33042

/2
Not Listed For Sale

2 Big Pine Ave, Big Pine Key, FL 33043
2 Big Pine Ave, Big Pine Key, FL 33043

Last Sold Summary
Last Sold Price $39,666

Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

/36
$750,000
- Land
- 9.26 Acres
- $80,995 per Acre
0 Niles Rd, Summerland Key, FL 33042

Discover the perfect opportunity to build your dream home in the Lower Keys on this desirable parcel located on Summerland Key, FL. Set within a peaceful residential neighborhood, this property offers an inviting blend of tranquility and convenience—just minutes from US-1, local marinas, boat ramps, dining, beaches, and world-class fishing. Enjoy the relaxed island lifestyle, tropical breezes,

Javier Santana

Sunland Real Estate, LLC.

(786) 504-0768

0 Niles Rd, Summerland Key, FL 33042
/42
$635,000 Sold Feb 19, 2026

3231 Pompano St, Big Pine Key, FL 33043
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Built 1985
Last Sold Summary
- 2% Below List Price
- $735/SF
- 6 Days On Market
Current Estimated Value $641,572

Last Listing Agent Dawn McComish Lokation Real Estate

3231 Pompano St, Big Pine Key, FL 33043

/2
Not Listed For Sale

1 Big Pine Ave, Big Pine Key, FL 33043
1 Big Pine Ave, Big Pine Key, FL 33043

Last Sold Summary
Last Sold Price $39,666

Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

/53
$1,195,000
- 3 Beds
- 2 Baths
- 1,530 Sq Ft
29534 Geraldine St, Big Pine Key, FL 33043

Discover the perfect blend of island lifestyle and income potential in this well-appointed waterfront home located in a desirable Big Pine Key boating community with Commercial Fishing District zoning--a rare advantage allowing marine-based business use, boat storage, and added flexibility.Situated on a 18,000 sq ft double lot with 150' of canal frontage, this solid concrete, single-level home

Sandra Tuttle

Island Welcome Real Estate

(844) 697-1109

29534 Geraldine St, Big Pine Key, FL 33043
/17
$395,000 Sold Sep 22, 2025

10W Cooks Unit B, Cook Island Key, FL 33043
- 2 Beds
- 1 Bath
- 596 Sq Ft
- Built 1948
Last Sold Summary
- 12% Below List Price
- $663/SF
- 13 Days On Market
Current Estimated Value $425,000

Last Listing Agent Greg Gordon Island Home Realty Inc.

10W Cooks Unit B, Cook Island Key, FL 33043

/9
Not Listed For Sale

22819 Blackbeard Ln, Cudjoe Key, FL 33042
22819 Blackbeard Ln, Cudjoe Key, FL 33042

Last Sold Summary
- 543 Days On Market
Last Sold Price $200,000

Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

/51
$1,999,999 Under Contract
- 3 Beds
- 4 Baths
- 2,100 Sq Ft
23087 Sailfish Ln, Summerland Key, FL 33042

Designed for those who live by the tides, this extraordinary waterfront residence captures everything that defines the Florida Keys lifestyle. Situated on a rare 15,625 sq ft double lot with 175 feet of deep-water dockage, the home enjoys a premier location one in from open water, delivering sweeping open water views while remaining protected within a wide 50-foot canal. Architecturally striking,

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(786) 807-9315

23087 Sailfish Ln, Summerland Key, FL 33042
/54
$915,000 Sold Aug 19, 2025

29737 Newfound Blvd, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1978
Last Sold Summary
- 8% Below List Price
- $866/SF
- 33 Days On Market
Current Estimated Value $944,566

Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

29737 Newfound Blvd, Big Pine Key, FL 33043

/2
Not Listed For Sale

30919 Edward Rd Unit A & B, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,170 Sq Ft
- Built 1943
30919 Edward Rd Unit A & B, Big Pine Key, FL 33043

Last Sold Summary
- $316/SF
Last Sold Price $370,000

Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

/67
$1,449,900
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
17215 Bonita Ln E, Summerland Key, FL 33042

Completely reimagined and absolutely stunning, this beautifully remodeled home in Sugarloaf Shores showcases a full renovation, including a brand new dock. The beautiful 3 Bedroom 2 Bathroom home features commercial grade luxury vinyl floors, beautiful new finishes, custom cabinetry, new appliances, and fresh paint inside and out. Every detail was thoughtfully selected, creating a clean, modern

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(855) 798-4569

17215 Bonita Ln E, Summerland Key, FL 33042
/27
$1,900,000 Sold Jun 18, 2025

17022 Starfish Ln W, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,990 Sq Ft
- Built 1994
Last Sold Summary
- 14% Below List Price
- $955/SF
- 85 Days On Market
Current Estimated Value $1,977,344

Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

17022 Starfish Ln W, Summerland Key, FL 33042

/2
Not Listed For Sale

430 Les Rohde Dr, Ramrod Key, FL 33042
430 Les Rohde Dr, Ramrod Key, FL 33042

Last Sold Summary
Last Sold Price $180,000

Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

/64
$1,790,000
- 3 Beds
- 2 Baths
- 1,882 Sq Ft
30463 Hawk Ln, Big Pine Key, FL 33043

Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living.Outdoors, the home transforms into a

Sandra Tuttle

Island Welcome Real Estate

(844) 795-0878

30463 Hawk Ln, Big Pine Key, FL 33043
/60
$2,512,500 Sold Oct 31, 2025

1260 Sugarloaf Blvd, Summerland Key, FL 33042
- 4 Beds
- 3 Baths
- 2,886 Sq Ft
- Built 1991
Last Sold Summary
- 3% Below List Price
- $871/SF
- 60 Days On Market
Current Estimated Value $2,458,790

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

1260 Sugarloaf Blvd, Summerland Key, FL 33042

/2
Est $426,128 Not Listed For Sale

20874 4th Ave, Cudjoe Key, FL 33042
- Studio
20874 4th Ave, Cudjoe Key, FL 33042

Last Sold Summary
- 5% Below List Price
Last Sold Price $450,000

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

/16
$1,200,000
- 3 Beds
- 2 Baths
- 1,544 Sq Ft
715 Caribbean Dr E, Summerland Key, FL 33042

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

715 Caribbean Dr E, Summerland Key, FL 33042
/58
$2,025,000 Sold May 13, 2025

22440 Jolly Roger Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,292 Sq Ft
- Built 1988
Last Sold Summary
- 12% Below List Price
- $1,567/SF
- 85 Days On Market
Current Estimated Value $2,062,598

Last Listing Agent Sandra Tuttle Island Welcome Real Estate

22440 Jolly Roger Dr, Summerland Key, FL 33042

/2
Est $1,158,249 Not Listed For Sale

21034 Overseas Hwy, Cudjoe Key, FL 33042
- 3 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 2022
21034 Overseas Hwy, Cudjoe Key, FL 33042

Last Sold Summary
- 5% Below List Price
- $808/SF
Last Sold Price $1,100,000

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

/91
$1,200,000 Under Contract
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21855 Spain Blvd, Summerland Key, FL 33042

Imagine owning a pool home and 3.3 private acres in the Florida Keys - this rare opportunity is in Cudjoe Acres, an equestrian area just 20 miles from Key West, with two equestrian facilities just around the corner. The home sits on one secluded acre surrounded by a botanical garden of impressive plantings including rare palm trees, buttonwoods, orchids, dragon fruit cactus, fragrant Joe wood, a

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(645) 225-2307

21855 Spain Blvd, Summerland Key, FL 33042
/29
$495,000 Sold Feb 13, 2026

31525 Avenue A, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,278 Sq Ft
- Built 1958
Last Sold Summary
- 10% Below List Price
- $387/SF
- 229 Days On Market
Current Estimated Value $528,667

Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

31525 Avenue A, Big Pine Key, FL 33043

/2
Not Listed For Sale

1138 Basque Ln, Summerland Key, FL 33042
- 7,000 Sq Ft
1138 Basque Ln, Summerland Key, FL 33042

Last Sold Summary
- $10/SF
Last Sold Price $70,000

Last Listing Agent Jimmy Lane Island Life Realty Experts

/84
$1,290,000 Under Contract
- 2 Beds
- 2 Baths
- 1,596 Sq Ft
29653 Saratoga Ave, Big Pine Key, FL 33043

Looking for your piece of paradise in the Keys? You've found it! This property feels like a lush private resort. The exceptional features include pavers on deck and dock, heated/chilled pool, tiki hut and tiki bar, chef's outdoor kitchen, 10k boat lift, landscape irrigation with separate water meter, and landscape lighting. The entire yard is fenced and gated. The 1596 sq. ft. concrete block home

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(844) 638-3161

29653 Saratoga Ave, Big Pine Key, FL 33043
/32
$635,000 Sold Apr 25, 2025

2682 Koehns Ave, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1963
Last Sold Summary
- 2% Below List Price
- $509/SF
- 12 Days On Market
Current Estimated Value $650,937

Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

2682 Koehns Ave, Big Pine Key, FL 33043

/61
Est $2,784,138 Not Listed For Sale

20886 4th Ave W, Summerland Key, FL 33042
- 4 Beds
- 3 Baths
- 3,042 Sq Ft
- Built 2008
20886 4th Ave W, Summerland Key, FL 33042

Last Sold Summary
- 4% Below List Price
- $953/SF
- 66 Days On Market
Last Sold Price $2,900,000

Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

/19
$215,000
- Land
701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

Ian Calderwood

Bluescape Real Estate

(786) 761-5180

701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
/51
$975,000 Sold Aug 01, 2025

527 Heck Ave, Little Torch Key, FL 33042
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2023
Last Sold Summary
- 17% Below List Price
- $812/SF
- 101 Days On Market
Current Estimated Value $1,074,725

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

527 Heck Ave, Little Torch Key, FL 33042

/2
Est $821,000 Not Listed For Sale

164 Newfound Blvd, Big Pine Key, FL 33043
- Studio
164 Newfound Blvd, Big Pine Key, FL 33043

Last Sold Summary
- 721% Below List Price
Last Sold Price $100,000

Last Listing Agent Jimmy Lane Island Life Realty Experts

/39
$1,499,000
- 3 Beds
- 2 Baths
- 1,944 Sq Ft
20838 5th Ave W, Summerland Key, FL 33042

Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(786) 952-7261

20838 5th Ave W, Summerland Key, FL 33042
/41
$689,000 Sold Jun 27, 2025

29873 Journeys End Rd, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,184 Sq Ft
- Built 1991
Last Sold Summary
- 5% Below List Price
- $582/SF
- 104 Days On Market
Current Estimated Value $752,294

Last Listing Agent Heather Bennett Keller Williams Key West Compass Realty

29873 Journeys End Rd, Big Pine Key, FL 33043

/2
Est $479,667 Not Listed For Sale

2112 San Marco Dr, Big Pine Key, FL 33043
- Studio
2112 San Marco Dr, Big Pine Key, FL 33043

Last Sold Summary
- 734% Below List Price
Last Sold Price $57,500

Last Listing Agent Gladys Cornell RE/MAX

/37
$750,000
- 3 Beds
- 2 Baths
- 1,316 Sq Ft
29160 Primrose Ln, Big Pine Key, FL 33043

Welcome to Eden Pines! This well maintained 3BR/2B home sits on a generous very private 10,000 sq ft lot in Big Pine Key.Featuring a garage and tons of storage inside and out, fenced yard & room for a pool!Inside you will find 3BR, 2 updated baths and a smart layout with an open concept living.Step outside to a beautiful covered porch the perfect spot to enjoy your morning coffee watching the key

Michelle Howerton

Brenda Donnelly Real Estate LLC

(877) 521-8118

29160 Primrose Ln, Big Pine Key, FL 33043
/44
$1,550,000 Sold Feb 27, 2026

17094 Coral Dr, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,998 Sq Ft
- Built 1982
Last Sold Summary
- 14% Below List Price
- $776/SF
- 265 Days On Market
Current Estimated Value $1,691,320

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

17094 Coral Dr, Summerland Key, FL 33042

/2
Est $485,000 Not Listed For Sale

2120 San Marco Dr, Big Pine Key, FL 33043
- Studio
2120 San Marco Dr, Big Pine Key, FL 33043

Last Sold Summary
- 743% Below List Price
Last Sold Price $57,500

Last Listing Agent Gladys Cornell RE/MAX

/60
$487,500
- 2 Beds
- 1 Bath
- 667 Sq Ft
701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

Ian Calderwood

Bluescape Real Estate

(786) 981-9841

701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
/3
$49,000 Sold Jun 06, 2025

Lot 24 Vacant Land, Big Torch Key, FL 33042
- Land
Last Sold Summary
- 35% Below List Price
- 206 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 24 Vacant Land, Big Torch Key, FL 33042

/2
Est $944,955 Not Listed For Sale

31441 Ave F, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 854 Sq Ft
- Built 1980
31441 Ave F, Big Pine Key, FL 33043

Last Sold Summary
- 195% Below List Price
- $375/SF
Last Sold Price $320,000

Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

Showing Results 241 - 280, Page 7 of 18

Florida Monroe County Summerland Key

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Summerland Key, FL Homes

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