Monroe, FL Homes

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
- 784 Sq Ft
17 Palm Dr, Key West, FL 33040

17 Palm Dr, Key West, FL 33040

/32
$1,099,000 Open Thu 2PM - 4PM
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
17137 Bonita Ln W, Summerland Key, FL 33042

Enjoy this ideal custom built Keys home located in beautiful Sugarloaf Shores! A very welcoming home with 3 bedrooms, 2 baths and a lovely enclosed porch with a captivating tong and groove ceiling. Attractive wood flooring throughout the living room, dining area and bedrooms with tile in the kitchen and baths. Two solid wide staircases lead up to the main entrance and another descending to

Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

17137 Bonita Ln W, Summerland Key, FL 33042
/58
$2,025,000 Sold May 13, 2025
- 1,292 Sq Ft
- $1567/SF
- 85 Days On Market
- 2 Beds
- 2 Baths
- Built 1988
22440 Jolly Roger Dr, Summerland Key, FL 33042

Experience the epitome of Florida Keys living in this stunning luxury waterfront home on Cudjoe Key. The back of the home has a South West Exposure, for endless ocean views and spectacular nightly sunsets. Constructed with poured concrete for unmatched durability and featuring a poured concrete floor, this home is a sanctuary of modern design and functionality. The property boasts impact-rated

Sandra Tuttle Island Welcome Real Estate

22440 Jolly Roger Dr, Summerland Key, FL 33042

/14
Est $441,761 Not Listed For Sale
- 1 Bed
701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

/15
$285,000
- Land
701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042

Spacious RV lot with nightly rentals allowed. 35' x 69' RV lot offers ample space for your outdoor living. Venture Out is a 24hr manned gated community with amentities including - Boat Ramp and fueling station, Marina store. Tennis, Pickleball, Bocce, Basketball courts and a playground for the little ones. This golf cart friendly and beautifully maintained property is the perfect balance of

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042
/11
$250,000 Sold May 12, 2025
- 672 Sq Ft
- $372/SF
- 5 Days On Market
- 2 Beds
- 1 Bath
- Built 1973
56 Palm Dr, Key West, FL 33040

Ready to buy n rebuild? Refurbish n rent? ROGO EXEMPTION in place!!Come check out this sweet little property located within a 15-minute drive to Key West.Neighborhood amenities include a tennis court and children's playground within it's green space just behind the infamous Baby's coffee!

Debora Bent Coastal Collection Real Estate

56 Palm Dr, Key West, FL 33040

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

/35
$875,000 Open Wed 1PM - 4PM
- 2 Beds
- 2 Baths
- 948 Sq Ft
22878 Privateer Dr, Summerland Key, FL 33042

Adorable 2 bed, 2 bath home with many new improvements! New impact windows and doors, new hardie-board siding installed on exterior of house, newer 60 foot concrete dock with cut-ins for a boat lift, roof replaced in October 2017 and newer hot water heater. All the heavy lifting has been done on this house located in sought after Cudjoe Key. Quick boating access to the Gulf and Atlantic,

Pamela Stangler Expert Realty LLC

22878 Privateer Dr, Summerland Key, FL 33042
/115
$12,250,000 Sold May 07, 2025
- 4,888 Sq Ft
- $2506/SF
- 44 Days On Market
- 7 Beds
- 6 Baths
- Built 2019
785 Sawyer Dr, Cudjoe Key, FL 33042

Welcome to Cypress Point, an exceptional and highly private, 7-Bed, 6-Bath, 4,888 Sq Ft oceanfront estate spanning almost a full acre on Cudjoe Key, where luxury and coastal beauty uniquely blend. This custom D'Asign Source built home is privately nestled behind an electric gate and boasts the finest finishes and amenities which include an oceanfront pool, outdoor theater, 6-hole golf green,

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

785 Sawyer Dr, Cudjoe Key, FL 33042

/2
Est $750,477 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
53 Gold Boullion Rd, Cudjoe Key, FL 33042

53 Gold Boullion Rd, Cudjoe Key, FL 33042

/40
$344,999
- 2 Beds
- 1 Bath
- 720 Sq Ft
701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

Step in to your new tropical paradise! This cozy 2 bedroom, 1 bathroom mobile home in Cudjoe Key offers affordable keys living. Enjoy all of the amenities that come with being located in the well known Venture Out community. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
/59
$860,300 Sold May 02, 2025
- 864 Sq Ft
- $996/SF
- 76 Days On Market
- 2 Beds
- 2 Baths
- Built 2000
701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

This home is BIG BOAT friendly and ready for you to move in. Turn key, fully furnished home located in the gated community of Venture Out on Cudjoe Key at Mile Marker 23. 2 Bedrooms and 2 Baths mid-rise sits on open water with an oversized massive 60' of concrete seawall. When you walk inside, you will feel like you are floating on the ocean with the large windows and picturesque ocean views. The

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

/69
Not Listed For Sale
- 1 Bed
- 1 Bath
- 420 Sq Ft
701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

/44
$997,000 Open Sat 11AM - 2PM
- 2 Beds
- 2 Baths
- 779 Sq Ft
701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

Welcome to your own piece of paradise in the heart of Cudjoe Key located in the gated community of Venture Out, where the island breeze and good vibes never stop!Live the island life in this turnkey 2 Bedroom, 2 Bath open water gem that's fully furnished and ready to rock your flip-flops off! Kick back on the oversized covered porch upstairs and catch the cool ocean vibes - it's your front-row

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
/39
$1,150,000 Sold Apr 29, 2025
- 1,528 Sq Ft
- $753/SF
- 330 Days On Market
- 3 Beds
- 2 Baths
- Built 2008
17215 Bonita Ln E, Summerland Key, FL 33042

This lovely, beautifully landscaped waterfront home, is located on a quiet street in the very desirable neighborhood of Sugarloaf Key. Move-in ready and equipped for easy Keys living. This CB constructed home features granite countertops , stainless appliances, impact windows, a large screened in porch and storage-up and down. All insurances under 5K and is assumable. With 3 bedrooms, one with a

Daniel Urban Century 21 Circle - Key West

17215 Bonita Ln E, Summerland Key, FL 33042

/2
Not Listed For Sale
BK 3 Lot 4 Antigua Ln, Ramrod Key, FL 33042

BK 3 Lot 4 Antigua Ln, Ramrod Key, FL 33042

/56
$295,000
- 1 Bed
- 1 Bath
- 368 Sq Ft
701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

Welcome to this well-maintained home located in the desirable all-age community of Venture Out on Cudjoe Key. This home offers more than meets the eye, featuring a spacious addition that includes a carpeted living area and a versatile flex room currently used as an extra sleeping space--ideal for guests or a home office.While the exterior is modest, the inside offers a comfortable, well-kept

Kimberly Didrichsons Bluescape Real Estate

701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
/2
$1,175,000 Sold Apr 24, 2025
- 1,470 Sq Ft
- $799/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 2016
16 Boulder Dr, Key West, FL 33040

Waterfront 3 bedroom 2 bath well maintained home.

Joe Bracciale Select Properties of NWFL

16 Boulder Dr, Key West, FL 33040

/66
Not Listed For Sale
- 2 Beds
701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

/60
$539,000
- 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

701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
/36
$330,000 Sold Apr 17, 2025
- 728 Sq Ft
- $453/SF
- 63 Days On Market
- 2 Beds
- 1 Bath
- Built 1983
701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

Welcome to your slice of paradise! This beautifully updated home is on the quiet, serene southwest side of the highly sought-after Venture Out Resort. With no neighbors behind you, you can enjoy added privacy and tranquility. The home is conveniently located next to the bathhouse for added convenience. Featuring two bedrooms and one bathroom, there is plenty of space to spread out and relax. The

Frank Griffiths Ocean Sotheby's International

701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

/3
$449,000
- Land
- 0.34 Acre
- $1,303,896 per Acre
Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

Oversized lot in gorgeous Sugarloaf Key with 15,000 Square feet ready for you to enter into the ROGO system. This sale comes with a ROGO Point Letter from Monroe County for 0 Disturbed Pine worth 24 points, giving you 44 points to enter into the ROGO system to build your dream home. Seller has done the Letter of Current Site Conditions with the County as well as engineering for a house, just

Pamela Stangler Expert Realty LLC

Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
/44
$650,000 Sold Apr 17, 2025
- 1,056 Sq Ft
- $616/SF
- 86 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
268 Spanish Main Dr, Summerland Key, FL 33042

Charming fishing bungalow located on oceanside Cudjoe Key just waiting to be yours. This waterfront haven features two bedrooms, two bathrooms and just under 1,100 square feet inside plus a permitted downstairs enclosure with plumbing and electric. Enjoy room for all to entertain in the open concept living area that seamlessly leads into the kitchen and dining. Waterside screened porch allows for

Ally Kelley Ocean Sotheby's International

268 Spanish Main Dr, Summerland Key, FL 33042

/2
Not Listed For Sale
- 1 Bed
- 1 Bath
- 520 Sq Ft
701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

/25
$775,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
180 Sugarloaf Dr, Summerland Key, FL 33042

This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000sqft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a quaint patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen, bonus screened porch and outdoor seating area. Whether you're looking for a full time

Jenny Perry Preferred Properties (KW)

180 Sugarloaf Dr, Summerland Key, FL 33042
/57
$1,375,000 Sold Apr 17, 2025
- 1,797 Sq Ft
- $765/SF
- 215 Days On Market
- 4 Beds
- 4 Baths
- Built 1972
468 Sawyer Dr, Summerland Key, FL 33042

Discover a Rare Gem in Cudjoe Gardens: Double Waterfront Lot with Private Boat BasinNestled in the Cudjoe Gardens costal community, this unique canal-front home boasts 4 bedrooms and 4 bathrooms, with an expansive upper deck offering stunning waterway views and breathtaking sunsets. The main house is ground level CBS construction and features terrazzo flooring throughout, capturing the true

Stacy Shahan Island Real Estate Company Florida Keys

468 Sawyer Dr, Summerland Key, FL 33042

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,110 Sq Ft
42 Beach Dr, Key West, FL 33040

42 Beach Dr, Key West, FL 33040

/42
$825,000
- 3 Beds
- 2 Baths
- 1,122 Sq Ft
22988 Port Royal Ln, Summerland Key, FL 33042

With unbeatable access to oceanside fishing, diving, and lobstering, this canal front home delivers the kind of location boaters rarely find. The west-facing canal sets the stage for vivid sunset views, while the spacious lot offers room for extra parking, trailered boats, or an RV. Inside, the home features three bedrooms, two bathrooms, granite countertops, stainless steel appliances, and

Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

22988 Port Royal Ln, Summerland Key, FL 33042
/36
$1,215,000 Sold Apr 09, 2025
- 1,440 Sq Ft
- $844/SF
- 23 Days On Market
- 3 Beds
- 2 Baths
- Built 2020
17246 Jamaica Ln, Summerland Key, FL 33042

This home has low cost transferable flood insurance of $735 a year. With being a new construction the home has low cost wind insurance of $1473 a year. The home is on the desirable subdivision of Sugarloaf Shores. A newly constructed home built in 2020 exceeds 180 wind load requirements. This property is a 3 bedroom 2 bath single family home on a canal with boat lift, floating dock, and a 20

Stephen Hachey

17246 Jamaica Ln, Summerland Key, FL 33042

/35
Not Listed For Sale
- 2 Beds
- 2 Baths
- 849 Sq Ft
701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

/44
$549,900
- 2 Beds
- 2 Baths
- 836 Sq Ft
701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

Transient 1 Day Rentals Allowed! Welcome to your tropical paradise! This charming 2 bedroom, 2 bathroom home in Cudjoe Key offers the perfect blend of comfort and island living. Enjoy the open-concept living and dining area, perfect for entertaining guests and take in all of the sunrise and sunset views from your porch! Take advantage of all the amenities that come with being located in the well

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
/39
$912,250 Sold Apr 03, 2025
- 1,344 Sq Ft
- $679/SF
- 43 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
22879 Blackbeard Ln, Summerland Key, FL 33042

Beautiful 3 bedroom 2 bathroom elevated island retreat on Cudjoe Key. This property features a private dock so you can keep your boat on site and enjoy immediate access to world class fishing and diving the stunning waters of the Florida Keys. Located just 25 minutes to Key West and 3 hours from Miami with grocery store, restaurants and bars close by. The exterior features hard plank siding and

Sandra Tuttle Island Welcome Real Estate

22879 Blackbeard Ln, Summerland Key, FL 33042

/17
Not Listed For Sale
- 2 Beds
- 1 Bath
- 770 Sq Ft
701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

/55
$925,000
- 2 Beds
- 1 Bath
- 806 Sq Ft
701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

Nightly Licensed Transient Rental!!!This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rent license. The floor plan makes the open water views as its main focus. Cook the catch of the day over looking the waters that you just caught that prized fish in. Sit back and watch

Bobby Coe RE/MAX Keys Connection (KW)

701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
/32
$1,830,000 Sold Apr 02, 2025
- 1,104 Sq Ft
- $1658/SF
- 77 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
17023 Allamanda Dr W, Summerland Key, FL 33042

Panoramic Sunset Paradise!Immerse yourself in breathtaking year-round sunsets from this stunning open-water estate on prestigious Sugarloaf Key. Nestled on an oversized, point lot with 282 feet of waterfront, this quiet, private island-like setting offers unmatched beauty and serenity while being minutes away from the vibrant lifestyle of Key West. Step into this 2-bedroom, 2-bathroom stilted

Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

17023 Allamanda Dr W, Summerland Key, FL 33042

/42
Not Listed For Sale
- 2 Beds
- 2 Baths
- 846 Sq Ft
18 Shore Dr, Key West, FL 33040

18 Shore Dr, Key West, FL 33040

/49
$985,000
- 2 Beds
- 2 Baths
- 888 Sq Ft
701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

Panoramic Ocean Views With Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
/40
$850,000 Sold Mar 31, 2025
- 1,312 Sq Ft
- $648/SF
- 59 Days On Market
- 2 Beds
- 2 Baths
- Built 1987
20914 7th Ave W, Summerland Key, FL 33042

Welcome to your perfect coastal retreat! This inviting 2-bedroom, 2-bath home plus office offers the ideal blend of comfort and convenience for boating enthusiasts. Nestled on the Oceanside with no bridges to navigate, it boasts a private 15,000 lb boatlift on 80 ft concrete dock a generous 4-ft draft making it a dream for those who love the water. Relax and unwind in the screened patio, perfect

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

20914 7th Ave W, Summerland Key, FL 33042

/41
Not Listed For Sale
- 2 Beds
- 2 Baths
- 860 Sq Ft
701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

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