Monroe, FL Homes

/47
$1,499,000
- 3 Beds
- 2 Baths
- 1,728 Sq Ft
17166 Wahoo Ln W, Summerland Key, FL 33042

This spacious 1,723 sq. ft. 3 Bedroom 2 Bath canal front Pool home is located in prestigious Sugarloaf Shores, an upscale community of waterfront homes just 15 miles from the magic of Key West. The resort-style home boasts a tropical waterfront pool with adjacent tiki bar to enjoy refreshments after a day out on the water. Boaters will appreciate the 100' of concrete dockage with davits on an

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 744-8525

17166 Wahoo Ln W, Summerland Key, FL 33042
Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/41
$650,000 Sold Jul 01, 2025
- 1,120 Sq Ft
- $580/SF
- 81 Days On Market
- 2 Beds
- 2 Baths
- Built 1984
22882 Buccaneer Ln, Summerland Key, FL 33042

Coastal Paradise: 2-Bedroom, 2-Bath Canal-Front Home with Direct Ocean AccessThis stunning 2-bedroom, 2-bath home offers the ultimate canal-front lifestyle, minutes from open water with no bridges to navigate, perfect for boating enthusiasts. Located on the coveted Oceanside, the property features a spacious 60-foot dock ready for your vessel, offering convenient and quick access to the

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

22882 Buccaneer Ln, Summerland Key, FL 33042

/4
Not Listed For Sale
0 Knockemdown Unit A11382026, Lower Keys, FL 33042

0 Knockemdown Unit A11382026, Lower Keys, FL 33042

/5
$350,000
- Land
25091 Overseas Hwy, Summerland Key, FL 33042

Attention all Commercial Fisherman and Marine Mechanics! Fantastic canal front commercial fishing district lot on Summerland Keys boasting 60' of road frontage with excellent highway visibility. 60' Concrete dock. Allowed uses include commercial fishing operations, boat repair and mechanic business and other home businesses.

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(855) 526-7517

25091 Overseas Hwy, Summerland Key, FL 33042
/44
$650,000 Sold Jun 30, 2025
- 828 Sq Ft
- $785/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 2002
701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

Turnkey Waterfront Vacation Rental with Ocean Views in Venture Out.Welcome to your Florida Keys escape--a fully furnished, income-producing 2-bedroom, 2-bath home ideally positioned on a wide canal with stunning ocean views and 35 feet of concrete seawall dockage. Located in the vibrant, gated community of Venture Out on Cudjoe Key, this well-maintained property is not just a serene coastal

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

/2
Est $2,240,262 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,360 Sq Ft
305 S Point Dr, Summerland Key, FL 33042

305 S Point Dr, Summerland Key, FL 33042

/26
$800,000
- 3 Beds
- 3 Baths
- 1,360 Sq Ft
23930 Overseas Hwy, Summerland Key, FL 33042

2 units for the price of one! What an amazing opportunity to buy in the Florida Keys market without breaking the bank. Live in one unit & rent the other.Legal WATERFRONT duplex on Summerland Key just 25 minunets to Key West. Upper unit has 2B and 1Bath spacious living and dining space that opens onto a large deck overlooking the canal. Luxury vinyl floors, new lighting, new paint, new ceiling

Michelle Howerton

Brenda Donnelly Real Estate LLC

(888) 431-6038

23930 Overseas Hwy, Summerland Key, FL 33042
/26
$239,000 Sold Jun 30, 2025
- Land
- 74 Days On Market
701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

Embrace the island lifestyle with this prime RV lot in Venture Out, a premier gated community on Cudjoe Key! Nestled in a quiet section of the park, this lot offers peak-a-boo ocean views and stunning sunsets from the rear of the property, making it the perfect tropical retreat. Whether you're looking for a personal getaway or a smart investment, this lot is a rare find--Venture Out is one of the

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

/2
Est $1,306,970 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,986 Sq Ft
22863 Bluegill Ln, Cudjoe Key, FL 33042

22863 Bluegill Ln, Cudjoe Key, FL 33042

/49
$1,749,000
- 3 Beds
- 2 Baths
- 1,667 Sq Ft
22865 Redfish Ln, Summerland Key, FL 33042

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 the generous spacing between homes, as well as having

Anneliese Dietrick

Coldwell Banker Schmitt Lower Keys (KW)

(305) 900-5290

22865 Redfish Ln, Summerland Key, FL 33042
/42
$1,900,000 Sold Jun 29, 2025
- 1,702 Sq Ft
- $1116/SF
- 17 Days On Market
- 3 Beds
- 2 Baths
- Built 2011
20867 5th Ave W, Cudjoe Key, FL 33042

Enjoy deep draft dockage, 2 Boat Lifts, Garage and Pool plus no steps to climb at this 3 Bedroom 2 Bath home located in Cudjoe Gardens, an upscale waterfront community of CBS constructed Above Flood ground level homes offering a neighborhood full service marina and waterfront restaurant and bar. Enter into the open Great Room where a wall of impact glass doors overlooks the pool and water. The

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

20867 5th Ave W, Cudjoe Key, FL 33042

/3
Est $372,500 Not Listed For Sale
0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

/40
$1,125,000
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

Welcome to your slice of paradise in one of the Lower Keys' most desirable communities--Sugarloaf Key! Here you'll enjoy island living with the convenience of being just 25 minutes from Key West, and close to popular restaurants, a weekly farmers market, and miles of scenic bike and walking paths.This waterfront home sits on a wide, aqua-colored canal with 100 feet of concrete dock--perfect for

Sandra Tuttle

Island Welcome Real Estate

(833) 952-2521

17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
/47
$1,100,000 Sold Jun 27, 2025
- 1,361 Sq Ft
- $808/SF
- 102 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
21014 7th Ave, Summerland Key, FL 33042

Nestled in one of the Lower Keys' most coveted boating communities, this meticulously renovated 3 bedroom 2 bathroom coastal retreat is more than just a home...it's a gateway to endless aquatic adventures. Situated on a deep-draft, flow-through canal with direct access to both the Atlantic and Gulf, this property is a dream for fishing, diving, and island-hopping enthusiasts. The brand-new

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

21014 7th Ave, Summerland Key, FL 33042

/15
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,010 Sq Ft
4 Shore Dr, Key West, FL 33040

4 Shore Dr, Key West, FL 33040

/43
$1,799,000
- 3 Beds
- 3 Baths
- 1,998 Sq Ft
17094 Coral Dr, Summerland Key, FL 33042

This beautifully appointed home is located in prestigious Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3 Bedroom 2 Bath 2,000 sq. ft. home a massive Great Room greets you highlighted by a true chef's Kitchen offering lots of custom cabinetry, stainless appliances, 2 wine coolers and large center island for friends

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 244-7125

17094 Coral Dr, Summerland Key, FL 33042
/42
$1,450,000 Sold Jun 23, 2025
- 1,425 Sq Ft
- $1018/SF
- 362 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
17177 Bonita Ln W, Summerland Key, FL 33042

Modern finishes and enviable boating at this Sugarloaf Shores pool home, nestled on over a quarter acre! Enjoy year-round temperate weather, this exceptional property comes equipped for enjoying the outdoors, offering a resort-style custom pool with heater, chiller, jetted spa, sitting ledge, sun deck, and paver pool deck! Just steps from the pool is a full-length, 100' concrete dock with davits,

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

17177 Bonita Ln W, Summerland Key, FL 33042

/2
Not Listed For Sale
13 Red Legs Ln, Cudjoe Key, FL 33042

13 Red Legs Ln, Cudjoe Key, FL 33042

/51
$1,099,000
- 3 Beds
- 3 Baths
- 1,920 Sq Ft
22841 Buccaneer Ln, Summerland Key, FL 33042

Welcome to ''Cayo Casa Cudjoe,'' a tropical haven where the island lifestyle seamlessly blends with world-class fishing. Nestled on a beautifully landscaped triple lot, this waterfront gem offers the ultimate escape. The heart of this angler's paradise are the 2 covered boat slips, each equipped with their own lift; your gateway to the best fishing, diving and boating in the Florida Keys. Whether

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 244-8373

22841 Buccaneer Ln, Summerland Key, FL 33042
/82
$1,800,000 Sold Jun 20, 2025
- 2,116 Sq Ft
- $851/SF
- 19 Days On Market
- 4 Beds
- 3 Baths
- Built 1999
17175 Allamanda Dr W, Summerland Key, FL 33042

Gorgeous Tropical Waterfront Oasis! No detail was overlooked in this stunning 4 BR, 3 BA luxury canal front estate in the prestigious Sugarloaf Shores. Tucked behind a privacy fence and surrounded by lush landscaping, this tropical retreat invites you to unwind in style. The expansive backyard is your personal oasis, featuring a massive heated concrete pool and a fully equipped 10' x 14' tiki

Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

17175 Allamanda Dr W, Summerland Key, FL 33042

/2
Not Listed For Sale
12 Red Legs Ln, Cudjoe Key, FL 33042

12 Red Legs Ln, Cudjoe Key, FL 33042

/51
$1,750,000
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21865 Spain Blvd, Summerland Key, FL 33042

Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

Matthew Sheehan Ocean Sotheby's International Realty

21865 Spain Blvd, Summerland Key, FL 33042
/59
$2,175,000 Sold Jun 20, 2025
- 2,192 Sq Ft
- $992/SF
- 41 Days On Market
- 3 Beds
- 2 Baths
- Built 2019
17346 Keystone Rd, Summerland Key, FL 33042

Welcome to this stunning 3-bedroom, 2-bathroom home perfectly situated on nearly half an acre, offering serene water views and direct canal access. Ideal for boaters and outdoor enthusiasts, the property features a concrete dock--your gateway to waterfront adventures.Step inside to an open floorplan designed for both comfort and entertaining. The heart of the home is a beautifully updated

Matthew Sheehan Ocean Sotheby's International Realty

17346 Keystone Rd, Summerland Key, FL 33042

/2
Not Listed For Sale
0 Crane Blvd, Sugarloaf Key, FL 33042

0 Crane Blvd, Sugarloaf Key, FL 33042

/42
$2,300,000
- 5 Beds
- 3 Baths
- 1,978 Sq Ft
94 Sacarma Dr, Cudjoe Key, FL 33042

Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

Michelle Blades Realty Executives Florida Keys Old Town

94 Sacarma Dr, Cudjoe Key, FL 33042
/27
$1,900,000 Sold Jun 18, 2025
- 1,990 Sq Ft
- $955/SF
- 85 Days On Market
- 3 Beds
- 2 Baths
- Built 1994
17022 Starfish Ln W, Summerland Key, FL 33042

SPECTACULAR OPEN WATER POINT & SUNSET VIEW. Enjoy waterfront living in this Classic 3 Bed/2 Bath wood frame home featuring vaulted ceilings and panoramic views overlooking Lower Sugarloaf Sound. Desirable SW exposure, 250' of protected waterfrontage providing quick boating access to both Atlantic and Gulf. Large ground level covered carport and patio plus secured storage room. Highly

Kieran Mahoney Century 21 Circle

17022 Starfish Ln W, Summerland Key, FL 33042

/2
Est $863,602 Not Listed For Sale
- Studio
17162 Starfish Ln W, Sugarloaf Shores, FL 33042

17162 Starfish Ln W, Sugarloaf Shores, FL 33042

/103
$1,895,000
- 4 Beds
- 3 Baths
- 2,353 Sq Ft
17176 Bonita Ln W, Summerland Key, FL 33042

Experience refined island living and world-class boating access in this exceptional Sugarloaf Shores residence. Situated on a generous 12,500 sq ft lot, this 2,353 sq ft, 4-bed, 3-bath, split-level home offers privacy, comfort, and thoughtfully designed indoor-outdoor living.Enjoy the beauty of mature tropical landscaping that surrounds the property, creating a serene atmosphere and lush privacy.

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

17176 Bonita Ln W, Summerland Key, FL 33042
/36
$1,225,000 Sold Jun 13, 2025
- 1,696 Sq Ft
- $722/SF
- 104 Days On Market
- 3 Beds
- 2 Baths
- Built 2023
165 Colson Dr, Cudjoe Key, FL 33042

Welcome Home! As you step inside of this Brand New contemporary coastal designed Florida Keys home, you will discover what you have been looking for in today's market. This property was built to last by using the finest available materials and sits on over a half-acre of land. The main great room features 15 ft. vaulted ceilings, an open concept living area with a combined high-end kitchen with a

Terry Garcia Keller Williams Key West Compass Realty

165 Colson Dr, Cudjoe Key, FL 33042

/2
Est $209,755 Not Listed For Sale
- Studio
951 Hawksbill Ln, Sugarloaf Key, FL 33042

951 Hawksbill Ln, Sugarloaf Key, FL 33042

/32
$1,689,000
- 3 Beds
- 2 Baths
- 2,144 Sq Ft
1151 Sugarloaf Blvd, Summerland Key, FL 33042

Truly unique and private estate property on the desired Sugarloaf Blvd. in Sugarloaf Shores. Ground level CBS house sits on 2 waterfront lots. Totaling over 1.3 acres of land and approx. 400 ft. of canal front. Amazing view up the canal to the open water. The large floor plan featuring 3 bedrooms, 2 baths, den/office and fireplace. Kitchen has stainless appliances, quartz countertops and lots of

Wendy Zintsmaster Truman & Co. (KW)

1151 Sugarloaf Blvd, Summerland Key, FL 33042
/58
$3,335,000 Sold Jun 13, 2025
- 2,950 Sq Ft
- $1131/SF
- 37 Days On Market
- 4 Beds
- 4 Baths
- Built 1956
23971 Henry St, Summerland Key, FL 33042

This newly renovated Oceanfront Pool home seamlessly blends luxury, privacy, and comfort while enjoying quick and easy ocean access on Summerland Key. Enter into the massive Great Room featuring 24-foot EURO retractable doors that open to sparkling ocean views and fill the space with lots of natural light. The Chef's Kitchen stands out with custom cabinetry, soft-close drawers, pull-out

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

23971 Henry St, Summerland Key, FL 33042

/8
Est $585,739 Not Listed For Sale
53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

/45
$1,950,000
- 2 Beds
- 2 Baths
- 1,281 Sq Ft
489 Sawyer Dr, Summerland Key, FL 33042

OCEANFRONT & CANALFRONT GEM-- A Rare Slice of ParadiseThis exceptional 17,560 sq. ft. property offers the best of both worlds with stunning open water views and protected canal frontage. The main home is a beautifully maintained 2 bedroom, 2 bath residence featuring 155 feet of sweeping ocean vistas, impact windows and sliding glass doors, and a layout designed to showcase breathtaking sunrises

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

489 Sawyer Dr, Summerland Key, FL 33042
/67
$3,550,000 Sold Jun 12, 2025
- 3,272 Sq Ft
- $1085/SF
- 68 Days On Market
- 5 Beds
- 5 Baths
- Built 2014
9 Bay Dr, Key West, FL 33040

This amazingly beautiful home is a true engineering masterpiece with open water views, 151 feet of seawall, a gorgeous pool, a boat ramp, covered garage and a floating dock for your water toys. Out of the 5 bedrooms, four are en suite, with three suites opening on to a spacious tiled terrace, to take in the 180 degree open water view and to soak up the sun in your own personal space. While the

Dan Serban Key West Luxury Real Estate Inc (KW)

9 Bay Dr, Key West, FL 33040

/2
Est $473,810 Not Listed For Sale
- Studio
20874 4th Ave, Cudjoe Key, FL 33042

20874 4th Ave, Cudjoe Key, FL 33042

/34
$1,380,000 Pending
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
22822 John Silver Ln, Summerland Key, FL 33042

Nestled in the serene and sought-after community of Cudjoe Key, this stunning Glen Gray Build two-story home offers the perfect blend of comfort, luxury, and coastal living. With three spacious bedrooms and two beautifully appointed bathrooms, this home is designed for both relaxation and entertaining, featuring exceptional outdoor spaces, waterfront access, and breathtaking ocean views.Key

Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

22822 John Silver Ln, Summerland Key, FL 33042
/73
$2,925,000 Sold Jun 10, 2025
- 1,472 Sq Ft
- $1987/SF
- 122 Days On Market
- 3 Beds
- 2 Baths
- Built 1991
17018 Wahoo Ln, Summerland Key, FL 33042

Welcome to the most exceptional home and premier lot currently available in the prestigious Sugarloaf Shores neighborhood. This property is a masterpiece of luxury, craftsmanship, and natural beauty, offering a lifestyle that truly must be experienced in person to be fully appreciated.Situated on an expansive 13,000+ square foot private point lot, this home boasts over 230 feet of crystal-clear

Coby Taylor Expert Realty LLC (HQ)

17018 Wahoo Ln, Summerland Key, FL 33042

/2
Not Listed For Sale
0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042

0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042

/114
$1,500,000 Under Contract
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
153 Galleon Ln, Summerland Key, FL 33042

Welcome home to this beautifully maintained waterfront retreat in the heart of the Florida Keys! Located on the highly sought-after Cudjoe Key, this spacious & elegant home blends casual island living with refined comfort, all custom-designed & cared for with exceptional pride & attention to detail.From the moment you arrive, you'll notice the peaceful, private setting of this stunning tropical

Lindsay Ryan EXP Realty LLC

153 Galleon Ln, Summerland Key, FL 33042

Showing Results 41 - 80, Page 2 of 18

Florida Monroe County Sugarloaf

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage