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.

/68
$2,985,000
- 3 Beds
- 2 Baths
- 2,232 Sq Ft
23941 Henry St, Summerland Key, FL 33042

Oceanfront retreat with sandy beach, protected dockage & direct access to the Ocean & Gulf.Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the

Stacy Shahan

Island Real Estate Company Florida Keys

(786) 686-4688

23941 Henry 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.

/66
$539,000
- 2 Beds
- 2 Baths
- 836 Sq Ft
701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

Ian Calderwood

Bluescape Real Estate

(786) 882-1915

701 Spanish Main Dr Unit 154, Cudjoe 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.

/58
$3,750,000
- 3 Beds
- 2 Baths
- 1,851 Sq Ft
755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

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

Terrance Sullivan

Ocean Sotheby's International Realty

(786) 465-7217

755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
/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.

/62
$750,000
- 3 Beds
- 2 Baths
- 1,410 Sq Ft
28151 Helen Ave, Summerland Key, FL 33042

Like new extra spacious open floor plan with efficient layout, ultra low insurances, and free public boat ramp nearby! This home features three large bedrooms and two full bathrooms with tiled showers, a huge eat-in stainless steel kitchen with room for an island or kitchen table, vinyl plank flooring throughout, all impact rated windows, metal roof, indoor laundry room, and spacious covered

Lindsay Ryan

EXP Realty LLC

(786) 952-7185

28151 Helen Ave, 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

/30
$750,000 Pending
- 3 Beds
- 2 Baths
- 1,062 Sq Ft
630 Barry Ave, Little Torch Key, FL 33042

Rarely does a property offer this much space and such rapid water access. Located near the end of a quiet, private street, this home sits on nearly three-quarters of an acre with 204.5 feet of canal frontage. The existing 3BD/2BA residence features a roof-covered deck built for sunset views, and while it needs some TLC, the value is in the land and the location. Build the outdoor oasis you've

Brenda Thomas

Island Welcome Real Estate

(786) 886-1075

630 Barry Ave, Little Torch 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)

/49
$799,000
- 2 Beds
- 2 Baths
- 912 Sq Ft
1672 Pandorea Ln, Big Pine Key, FL 33043

Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, an exceptional upgraded

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(888) 410-2419

1672 Pandorea 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)

/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

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(866) 827-7154

30374 Oleander Blvd, Big Pine Key, FL 33043
/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

/35
$599,000
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
27940 Lobster Tail Trail, Summerland Key, FL 33042

Discover one of the best waterfront buying opportunities in the Lower Keys! This spacious and well-maintained 3-bedroom, 2-bath manufactured home offers incredible value and lifestyle at just $625,000. Inside, you'll find an open floor plan with updated laminate floors, a bright kitchen, and a large primary suite featuring a big bedroom and a relaxing bath with a soaking tub.Outdoors, enjoy 46

Sandra Tuttle

Island Welcome Real Estate

(645) 218-8749

27940 Lobster Tail Trail, 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

/44
$2,295,000
- 3 Beds
- 2 Baths
- 1,900 Sq Ft
937 Gulf Dr, Summerland Key, FL 33042

High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout,

Sandra Tuttle

Island Welcome Real Estate

(645) 230-1994

937 Gulf Dr, Summerland Key, FL 33042
/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)

/34
$1,575,000
- 3 Beds
- 2 Baths
- 1,667 Sq Ft
22865 Redfish Ln, Summerland Key, FL 33042

The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

Anneliese Dietrick

Coldwell Banker Schmitt Lower Keys (KW)

(645) 241-6029

22865 Redfish Ln, Summerland 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

/38
$899,000
- 3 Beds
- 2 Baths
- 1,203 Sq Ft
153 Peg Leg Ln, Summerland Key, FL 33042

Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(833) 853-7147

153 Peg Leg Ln, 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

/43
$924,000
- 3 Beds
- 2 Baths
- 1,036 Sq Ft
420 W Indies Dr, Summerland Key, FL 33042

Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(645) 666-1028

420 W Indies Dr, Summerland Key, FL 33042
/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

/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

Miriam Novotny

Compass Florida, LLC

(786) 667-5744

20920 5th Ave W, Summerland 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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