Old Naples, Florida Home Real Estate Listings
MLS® #: 224039753
- 71 18th AVE S
- NAPLES FL 34102
- $44,000,000
- 6 Beds | 4 Baths | 5,052 SqFt
- 0.95 Acres
- No damage to the house from hurricane Milton! Stunning Beachfront Property with 151 feet (.95 acres) of Beach frontage with views of the Naples Pier! ...
MLS® #: 226032729
- 275 Gulf Shore BLVD N
- NAPLES FL 34102
- $39,000,000
- Beds | Baths | SqFt
- 0 Acres
- Discover the exceptional opportunity to design and build a custom beachfront residence on this expansive Gulf-front property featuring approximately 1...
MLS® #: 226018147
- 23 6TH AVE N
- NAPLES FL 34102
- $27,900,000
- 6 Beds | 5.5 Baths | 5,945 SqFt
- 0.6 Acres
- Experience the pinnacle of beachfront luxury from this extraordinary Naples coastal estate, where timeless Bermuda-inspired architecture meets effortl...
MLS® #: 226035214
- 616 BOUGAINVILLEA RD
- NAPLES FL 34102
- $25,900,000
- 6 Beds | 10.5 Baths | 9,447 SqFt
- 0.52 Acres
- NOW COMPLETE! Commanding a rare western lakefront setting in the heart of Old Naples, this extraordinary new construction estate represents an excepti...
MLS® #: 226022104
- 1100 Gulf Shore BLVD S
- NAPLES FL 34102
- $25,000,000
- 6 Beds | 7 Baths | 6,978 SqFt
- 0.34 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. An exceptional opportunity to own a newly constructed estate on one of Olde...
MLS® #: 226024712
- 55 13th AVE S
- NAPLES FL 34102
- $22,995,000
- 6 Beds | 6 Baths | 6,143 SqFt
- 0.53 Acres
- This Gulf-front masterpiece offers an unparalleled blend of location, luxury, Gulf views, and resort-style living. Completely rebuilt in 2024 by Kukk ...
MLS® #: 225073939
- 285 Central AVE
- NAPLES FL 34102
- $17,950,000
- 5 Beds | 6.5 Baths | 6,822 SqFt
- 0.34 Acres
- Step into refined coastal living with this exceptional new construction home located just two blocks from the beach in the heart of Olde Naples. Desig...
MLS® #: 226034183
- 1963 Gulf Shore BLVD S
- NAPLES FL 34102
- $16,990,000
- 6 Beds | 6.5 Baths | 9,047 SqFt
- 0.52 Acres
- Quietly situated at the southernmost end of Gulf Shore Boulevard South, directly across from beach access, this exceptional Olde Naples estate is a tr...
MLS® #: 226031429
- 774 GOLF DR
- NAPLES FL 34102
- $14,500,000
- 5 Beds | 6.5 Baths | 6,882 SqFt
- 0.3 Acres
- Set within the prestigious South Golf Drive corridor in the heart of Old Naples, this newly completed estate embodies a rare level of architectural ex...
MLS® #: 226013404
- 264 8th AVE S
- NAPLES FL 34102
- $13,995,000
- 5 Beds | 6 Baths | 5,057 SqFt
- 0.26 Acres
- Steps from the shimmering Gulf waters, pristine white-sand beaches, and the vibrant charm of 5th Avenue South and 3rd Street South, 264 8th Avenue Sou...
MLS® #: 226029919
- 40 5th AVE S
- NAPLES FL 34102
- $13,500,000
- 5 Beds | 6.5 Baths | 7,635 SqFt
- 0.29 Acres
- One house from the sand. On Fifth Avenue South. Wrought-iron power gates, twin limestone staircases, a twenty-four-foot foyer. Mediterranean in spiri...
MLS® #: 223075606
- 626 S Golf DR
- NAPLES FL 34102
- $12,995,000
- 6 Beds | 6 Baths | 6,255 SqFt
- 0.37 Acres
- Just completed, this new home in Olde Naples with southern exposure is located just blocks to gulf beaches and the future Four Seasons Resort. Designe...
MLS® #: 226035032
- 501 7TH AVE N
- NAPLES FL 34102
- $12,900,000
- 5 Beds | 5.5 Baths | 5,449 SqFt
- 0.29 Acres
- Located on an oversized parcel in one of Old Naples’ most walkable residential enclaves, this newly constructed estate blends British West Indie...
MLS® #: 226002046
- 140 3rd AVE S
- NAPLES FL 34102
- $12,500,000
- 5 Beds | 7 Baths | 7,537 SqFt
- 0.34 Acres
- A landmark, custom built, Old Naples estate just four homes from the Gulf. Elevated and recently renovated, this exceptional residence offers over 7,5...
MLS® #: 225068377
- 273 10th AVE S
- NAPLES FL 34102
- $11,995,000
- 5 Beds | 6 Baths | 4,787 SqFt
- 0.2 Acres
- Just minutes from the world class shopping and dining on 3rd Street South &' Fifth Avenue South, this brand new, never lived in residence embod...
MLS® #: 225077098
- 349 2nd AVE N
- NAPLES FL 34102
- $10,999,000
- 4 Beds | 5 Baths | 5,017 SqFt
- 0.23 Acres
- This extraordinary custom-designed home is the epitome of luxurious living in downtown Naples. A true collaboration of the distinguished C&'E B...
MLS® #: 224028308
- 690 7th AVE N
- NAPLES FL 34102
- $10,895,000
- 5 Beds | 7 Baths | 4,998 SqFt
- 0.29 Acres
- Newly constructed Olde Naples cottage w 4,998 sf of living, southern exposure, built by award winning Calusa Construction. Interiors by award winning ...
MLS® #: 225056392
- 581 14th AVE S
- NAPLES FL 34102
- $10,499,000
- 4 Beds | 5.5 Baths | 4,534 SqFt
- 0.29 Acres
- A masterfully crafted collaboration between Jeffrey Fisher Home, renowned architect JMDG, and the highly respected Waterside Builders' this newly ...
MLS® #: 226032954
- 241 7TH AVE N
- NAPLES FL 34102
- $10,395,000
- 5 Beds | 6 Baths | 5,069 SqFt
- 0.32 Acres
- An extraordinary expression of luxury living in Olde Naples steps from the brand new Four Seasons Resort. This exceptional estate offers an enviable l...
MLS® #: 226019430
- 160 Broad AVE S
- NAPLES FL 34102
- $9,750,000
- 4 Beds | 5 Baths | 5,283 SqFt
- 0.26 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. Set just steps from the Gulf and the celebrated boutiques and restaurants o...
MLS® #: 224050004
- 12 Gulf Shore BLVD N
- NAPLES FL 34102
- $9,450,000
- Beds | Baths | SqFt
- 0.3 Acres
- Steps from the beautiful beaches of Downtown Naples and walking distance to 5th Ave and 3rd St restaurants. Here is your chance to build your dream ho...
MLS® #: 226031431
- 835 11TH AVE S
- NAPLES FL 34102
- $8,995,000
- 4 Beds | 5 Baths | 4,709 SqFt
- 0.17 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. Set along one of Old Naples’ quiet, palm-lined streets and just a sho...
MLS® #: 226028668
- 376 1ST AVE N
- NAPLES FL 34102
- $8,250,000
- 4 Beds | 4.5 Baths | 3,768 SqFt
- 0.23 Acres
- Ideally located in the heart of Olde Naples, just three blocks from the Gulf, this striking contemporary residence pairs innovative architectural desi...
MLS® #: 225052605
- 140 2nd AVE N
- NAPLES FL 34102
- $7,950,000
- Beds | Baths | SqFt
- 0.34 Acres
- Located on Naples'' most coveted and picturesque avenues, this oversized, southern-facing parcel offers a 100'' x 150'' footprint...
MLS® #: 226028046
- 1165 8TH ST S #302
- NAPLES FL 34102
- $7,695,000
- 4 Beds | 4.5 Baths | 4,378 SqFt
- 0 Acres
- Introducing Vela Bay, an intimate collection of four contemporary waterfront residences overlooking Naples Bay in the heart of Olde Naples. Designed f...
MLS® #: 226005784
- 739 5th AVE N
- NAPLES FL 34102
- $7,500,000
- 5 Beds | 8 Baths | 4,825 SqFt
- 0.24 Acres
- This 2022 custom-built home in Old Naples offers the perfect blend of luxury and resilience in an unbeatable location—just steps from NCH Baker ...
MLS® #: 226033005
- 185 North Lake DR
- NAPLES FL 34102
- $7,499,000
- 4 Beds | 5 Baths | 4,082 SqFt
- 0.33 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. Six doors from the Gulf, exceptional single-level living in the heart of Ol...
MLS® #: 226031758
- 180 7th AVE S
- NAPLES FL 34102
- $6,995,000
- 3 Beds | 4 Baths | 4,670 SqFt
- 0.34 Acres
- Old Florida charm meets modern sophistication in this beautifully updated Old Naples residence, located just over a block to the beach and 2 blocks to...
MLS® #: 225077814
- 405 7TH AVE N
- NAPLES FL 34102
- $6,950,000
- 4 Beds | 4.5 Baths | 4,092 SqFt
- 0.29 Acres
- Just steps from the Gulf, this exceptional coastal contemporary residence offers the perfect blend of refined style and relaxed Naples living. Designe...
MLS® #: 226011149
- 200 Golf DR
- NAPLES FL 34102
- $6,950,000
- 4 Beds | 4.5 Baths | 6,874 SqFt
- 0.29 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. O...
MLS® #: 225075505
- 2080 Gordon DR
- NAPLES FL 34102
- $6,900,000
- 3 Beds | 3.5 Baths | 3,033 SqFt
- 0.45 Acres
- In the private, gated enclave of Gordon Drive Estates a mere three doors from the sugar sand coastline, lies this meticulously maintained, custom home...
MLS® #: 226028042
- 1165 8TH ST S #202
- NAPLES FL 34102
- $6,795,000
- 4 Beds | 4.5 Baths | 4,378 SqFt
- 0 Acres
- Introducing Vela Bay, an intimate collection of four contemporary waterfront residences overlooking Naples Bay in the heart of Olde Naples. Designed f...
MLS® #: 226029571
- 1140 8th ST S
- NAPLES FL 34102
- $6,795,000
- 5 Beds | 5.5 Baths | 4,004 SqFt
- 0.17 Acres
- This exemplary home in a walk-to-beach-and-town location lives like brand new and is beautifully maintained. Built by Provident Beach Houses, this ele...
MLS® #: 226011370
- 1355 4th ST S
- NAPLES FL 34102
- $6,495,000
- 4 Beds | 5.5 Baths | 2,957 SqFt
- 0.17 Acres
- Completely reimagined and finished in 2025, this beautifully renovated Old Naples residence lives like a new home. Offering just under 3,000 square fe...
MLS® #: 226031105
- 135 7th ST N
- NAPLES FL 34102
- $6,495,000
- 4 Beds | 5 Baths | 4,730 SqFt
- 0.23 Acres
- BRAND-NEW 2026-BUILT LUXURY ESTATE—JUST COMPLETED AND NEVER LIVED IN—in the heart of OLDE NAPLES, about half a mile from the GULF BEACHES ...
MLS® #: 226020603
- 950 8th ST S
- NAPLES FL 34102
- $6,495,000
- 5 Beds | 4.5 Baths | 3,741 SqFt
- 0.17 Acres
- Ideally situated in the heart of downtown Naples, this completely remastered single-family residence embodies the essence of refined Florida living. T...
MLS® #: 225081202
- 745 12th AVE S 103
- NAPLES FL 34102
- $6,450,000
- 3 Beds | 4.5 Baths | 4,856 SqFt
- 0 Acres
- Steps from the boutique shopping and dining of Crayton Cove and offering nearly 5,000 square feet of living space, this 2019-built townhouse is an exc...
MLS® #: 226028669
- 788 7TH AVE N
- NAPLES FL 34102
- $6,450,000
- 4 Beds | 5.5 Baths | 3,939 SqFt
- 0.22 Acres
- Masterfully conceived and completed in 2025, this extraordinary Olde Naples residence represents the pinnacle of contemporary coastal design. Created ...
MLS® #: 226024974
- 742 11th AVE S
- NAPLES FL 34102
- $6,300,000
- 4 Beds | 5 Baths | 3,273 SqFt
- 0.23 Acres
- TWO EXCEPTIONAL OPPORTUNITIES. ONE EXTRAORDINARY ADDRESS. Perfectly positioned in the heart of Old Naples, this beautifully reimagined residence offer...
MLS® #: 226032568
- 844 8th ST S
- NAPLES FL 34102
- $6,290,000
- 4 Beds | 4.5 Baths | 3,495 SqFt
- 0.15 Acres
- In the heart of Old Naples, just three blocks from famed Fifth Avenue South and a short distance from the beach, this nearly new residence, constructe...
MLS® #: 226031870
- 560 9th AVE S
- NAPLES FL 34102
- $6,250,000
- 4 Beds | 4 Baths | 2,182 SqFt
- 0.44 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. Rare opportunity in the heart of Olde Naples. Ideally positioned between Fi...
MLS® #: 226031446
- 570 2nd AVE N
- NAPLES FL 34102
- $6,100,000
- 4 Beds | 3.5 Baths | 3,772 SqFt
- 0.18 Acres
- Five blocks to the beach in the heart of Olde Naples, this fully renovated residence delivers the rare combination of location, structural integrity, ...
MLS® #: 226028036
- 1165 8TH ST S #201
- NAPLES FL 34102
- $5,995,000
- 4 Beds | 4.5 Baths | 4,371 SqFt
- 0 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. Introducing Vela Bay, an intimate collection of four contemporary waterfron...
MLS® #: 226017050
- 545 13th AVE S
- NAPLES FL 34102
- $5,950,000
- 4 Beds | 5 Baths | 3,829 SqFt
- 0.24 Acres
- Discover an exquisite retreat in the heart of Olde Naples, just 2.5 blocks from 3rd Street South, featuring some of Naples’ most desirable shopp...
MLS® #: 226034533
- 444 3rd ST N
- NAPLES FL 34102
- $5,950,000
- 3 Beds | 3 Baths | 1,860 SqFt
- 0.36 Acres
- A beach bungalow in the heart of Old Naples, this charming three-bedroom, two-bath residence sits on an expansive 150-by-100-foot corner lot just thre...
MLS® #: 226033993
- 250 Golf DR
- NAPLES FL 34102
- $5,300,000
- 3 Beds | 4 Baths | 3,016 SqFt
- 0.35 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. A rare Old Naples opportunity offering 0.35 acres and 96 feet of frontage, ...
MLS® #: 226033966
- 244 11th AVE S
- NAPLES FL 34102
- $5,299,000
- 3 Beds | 2 Baths | 1,699 SqFt
- 0.17 Acres
- This Old Naples Dolphin Cottage was built in 1935 and has been meticulously restored to reflect the owner's love of historic Old Naples. The home is a...
MLS® #: 226031441
- 909 10th AVE S
- NAPLES FL 34102
- $5,195,000
- 3 Beds | 4.5 Baths | 3,550 SqFt
- 0.12 Acres
- In the heart of Olde Naples, this 2020-built courtyard residence blends timeless coastal architecture with refined, resort-style living just moments f...
MLS® #: 226032348
- 680 8th AVE S
- NAPLES FL 34102
- $4,995,000
- 3 Beds | 3 Baths | 3,050 SqFt
- 0.17 Acres
- Experience rare coastal charm and modern sophistication at the iconic Captain Parker House, ideally located within walking distance of 5th Ave S, 3rd ...
MLS® #: 225064774
- 1160 8th ST S
- NAPLES FL 34102
- $4,950,000
- 6 Beds | 4.5 Baths | 5,822 SqFt
- 0.17 Acres
- One or more photo(s) has been virtually staged, AI generated or rendered. Price significantly reduced and now priced to sell. Offering nearly 6,000 s...
MLS® #: 226014208
- 912 9th AVE S
- NAPLES FL 34102
- $4,950,000
- 4 Beds | 4.5 Baths | 3,385 SqFt
- 0.19 Acres
- (PRICE DECREASE 09/03/26: $5,195,000 - > $4,950,000) || Accented by the warm tones of morning-lit palms, this 2016 West Indies-style home by Jef...
MLS® #: 226009201
- 901 10th AVE S
- NAPLES FL 34102
- $4,900,000
- 4 Beds | 4.5 Baths | 3,538 SqFt
- 0.18 Acres
- Ideally positioned on a sun-filled corner lot in the heart of Old Naples, this exceptional 2020-built residence blends timeless coastal elegance with ...
MLS® #: 226031335
- 645 Broad AVE S
- NAPLES FL 34102
- $4,599,000
- 3 Beds | 3.5 Baths | 3,619 SqFt
- 0.17 Acres
- Between the Gulf of Mexico and Naples Bay, this coastal contemporary home captures the charm of Old Florida living. Just six blocks to the beach and N...
MLS® #: 226025231
- 888 10th AVE S
- NAPLES FL 34102
- $4,499,000
- 5 Beds | 5 Baths | 3,190 SqFt
- 0.2 Acres
- Exceptional Olde Naples living in the heart of it all. Ideally located just 5 blocks from Historic Fifth Avenue South, 8 blocks from Third Street Sout...
MLS® #: 226000909
- 680 Park ST
- NAPLES FL 34102
- $3,800,000
- Beds | Baths | SqFt
- 0.22 Acres
- Welcome to your future dream home site. Ideally located less than a one block walk from the fabulous 5th Ave South with its abundance of world class s...
MLS® #: 226012328
- 495 5th ST S 304
- NAPLES FL 34102
- $3,595,000
- 2 Beds | 2.5 Baths | 2,446 SqFt
- 0 Acres
- Set directly in the heart of Fifth Avenue South, this exceptional penthouse at 505 on Fifth offers a lifestyle rarely available in Naples—the en...
MLS® #: 226003779
- 340 12th AVE S 6
- NAPLES FL 34102
- $3,500,000
- 3 Beds | 3 Baths | 3,007 SqFt
- 0 Acres
- This elegant and expansive detached villa offers a rare lifestyle opportunity in the heart of Naples, just steps from the shops and restaurants of Thi...
MLS® #: 226014758
- 660 8th AVE S
- NAPLES FL 34102
- $3,295,000
- 5 Beds | 4 Baths | 2,320 SqFt
- 0.19 Acres
- Classic Olde Naples Cottage: Three blocks from Fifth Avenue South and six from the Gulf beaches, this renovated five-bedroom, four-bath home sits d...
MLS® #: 226034990
- 442 Central AVE S
- NAPLES FL 34102
- $3,250,000
- 2 Beds | 2 Baths | 1,000 SqFt
- 0.22 Acres
- This charming cottage-style residence on a .22-acre lot is just a 10 minute walk to the beach and presents an exceptional opportunity for investors an...
MLS® #: 226006431
- 395 7th AVE S
- NAPLES FL 34102
- $3,200,000
- Beds | Baths | SqFt
- 0.17 Acres
- 395 7th Avenue South offers a rare opportunity in the heart of Olde Naples to build your custom retreat. A short walk to Naples'' white sand be...
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Downing Frye Realty, Inc.
Naples People's Choice Award for 15 Years Straight !
"If you would like for me to do all of the research for you, please call me with your search criteria and I will email you all of the listings that specifically match your lifestyle requirements.
I have been selling Old Naples luxury real estate since 1978. I make it easy and enjoyable, while presenting you with all of the FACTS necessary to make an informed decision. There is a lot to take into consideration when buying Old Naples real estate in Naples, Florida to insure that you are not only buying the lifestyle that you are searching for but that the property does not have any ISSUES and that you are getting VALUE. Please take the time to read the About section to see my 35 year background in Custom Home Building, Development and Real Estate in Naples, Marco Island and Palm Beach, Florida
I bring this experience to each and every one of my buyers as their TRANSACTION BROKER. For discrete and professional service, please call me directly at 239-963-6590 to schedule a private viewing of any Old Naples home or condo real estate listings for sale in Naples, Florida."
