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Hilltop, Naples, Florida

Hilltop is an exclusive residential community in Naples, Florida, known for its elegant homes, beautifully landscaped streets, and peaceful surroundings. Offering a blend of luxury, privacy, and convenience, Hilltop attracts homebuyers seeking spacious residences in a prime Southwest Florida location.

Homes in Hilltop feature thoughtfully designed floor plans, high-end finishes, gourmet kitchens, expansive outdoor living areas, and lush tropical landscaping. Many properties include private pools, covered lanais, and generous lots that create an ideal setting for entertaining and year-round outdoor living.

Real Estate Statistics

Average Price $555K
Lowest Price $1.9K
Highest Price $5.2M
Total Listings 152
Avg. Days On Market 182
Avg. Price/SQFT $358

Property Types (active listings)


Hilltop Homes for Sale in Naples, FL

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1980 S Ocean Boulevard, Palm Beach

$200,000,000

1980 S Ocean Boulevard, Palm Beach

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # R11060793
204 E Jaffa N,

$100,000,000

204 E Jaffa N,

0 Beds 0 Baths 0 SqFt Commercial MLS® # B26068894
7 Ocean Lane, Palm Beach

$88,400,000

7 Ocean Lane, Palm Beach

5 Beds 8 Baths 9,410 SqFt Residential MLS® # R11139593
1355 S Flagler Drive #south Tower Duplex Ph, West Palm Beach

$70,000,000

1355 S Flagler Drive #south Tower Duplex Ph, West Palm Beach

7 Beds 10 Baths 13,904 SqFt Residential MLS® # R11155081
10203 Collins Avenue #2801, Bal Harbour

$69,500,000

10203 Collins Avenue #2801, Bal Harbour

6 Beds 8 Baths 8,993 SqFt Residential MLS® # A11931658
1260 N Lake Way, Palm Beach

$63,500,000

1260 N Lake Way, Palm Beach

6 Beds 8 Baths 7,034 SqFt Residential MLS® # R11133286
111 Via Del Lago, Palm Beach

$59,000,000

111 Via Del Lago, Palm Beach

9 Beds 12 Baths 12,000 SqFt Residential MLS® # B26077347
215 Bears Club Drive, Jupiter

$53,900,000

215 Bears Club Drive, Jupiter

6 Beds 12 Baths 15,075 SqFt Residential MLS® # R11168397
1426 N Ocean Boulevard, Palm Beach

$48,000,000

1426 N Ocean Boulevard, Palm Beach

7 Beds 8 Baths 6,747 SqFt Residential MLS® # B26047163
508 S Beach Road, Jupiter Island

$45,000,000

508 S Beach Road, Jupiter Island

5 Beds 8 Baths 8,551 SqFt Residential MLS® # B26031447
3501 N Ocean Boulevard, Gulf Stream

$42,000,000

3501 N Ocean Boulevard, Gulf Stream

5 Beds 8 Baths 5,970 SqFt Residential MLS® # B26019900
1355 S Flagler Drive #ph 2601, West Palm Beach

$39,500,000

1355 S Flagler Drive #ph 2601, West Palm Beach

4 Beds 6 Baths 8,066 SqFt Residential MLS® # R11128922
New
13920 Stirling Road, Southwest Ranches

$38,900,000

13920 Stirling Road, Southwest Ranches

8 Beds 13 Baths 23,442 SqFt Residential MLS® # B26085352
555 Ocean Boulevard, Golden Beach

$37,999,998

555 Ocean Boulevard, Golden Beach

8 Beds 11 Baths 9,618 SqFt Residential MLS® # F10539470
211 Bears Club Drive, Jupiter

$34,000,000

211 Bears Club Drive, Jupiter

5 Beds 8 Baths 10,796 SqFt Residential MLS® # B26080875
301 Plantation Road, Palm Beach

$32,000,000

301 Plantation Road, Palm Beach

7 Beds 11 Baths 7,063 SqFt Residential MLS® # B26080140
209 Commodore Drive, Jupiter

$30,000,000

209 Commodore Drive, Jupiter

9 Beds 14 Baths 24,320 SqFt Residential MLS® # R11104398
1355 S Flagler Drive #2203, West Palm Beach

$28,450,000

1355 S Flagler Drive #2203, West Palm Beach

4 Beds 6 Baths 5,743 SqFt Residential MLS® # R11163511
146 Bears Club Drive, Jupiter

$27,900,000

146 Bears Club Drive, Jupiter

6 Beds 10 Baths 10,401 SqFt Residential MLS® # B26080403
68 Isla Bahia Drive, Fort Lauderdale

$26,000,000

68 Isla Bahia Drive, Fort Lauderdale

6 Beds 10 Baths 8,327 SqFt Residential MLS® # B26074998
82719 Old Highway, Islamorada

$24,995,000

82719 Old Highway, Islamorada

7 Beds 11 Baths 10,182 SqFt Residential MLS® # A12091663
2330 Seven Oaks Lane, Palm Beach Gardens

$24,950,000

2330 Seven Oaks Lane, Palm Beach Gardens

7 Beds 13 Baths 17,440 SqFt Residential MLS® # B26076318
6001 Le Lac Road, Boca Raton

$24,950,000

6001 Le Lac Road, Boca Raton

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # B26070391
6001 Le Lac Road, Boca Raton

$24,950,000

6001 Le Lac Road, Boca Raton

7 Beds 9 Baths 10,914 SqFt Residential MLS® # B26041740
1100 S Flagler Drive #804, West Palm Beach

$24,950,000

1100 S Flagler Drive #804, West Palm Beach

4 Beds 6 Baths 4,906 SqFt Residential MLS® # B26033963
14880 Palmwood Road, Palm Beach Gardens

$24,900,000

14880 Palmwood Road, Palm Beach Gardens

7 Beds 11 Baths 10,398 SqFt Residential MLS® # B26040641
Playa Caletas, Canton De Garabito, Puntarenas,

$24,500,000

Playa Caletas, Canton De Garabito, Puntarenas,

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # B26043539
5 Grove Isle Drive #phs01, Coconut Grove

$23,500,000

5 Grove Isle Drive #phs01, Coconut Grove

4 Beds 6 Baths 7,027 SqFt Residential MLS® # A11989341
1355 S Flagler Drive #800, West Palm Beach

$23,500,000

1355 S Flagler Drive #800, West Palm Beach

4 Beds 6 Baths 5,355 SqFt Residential MLS® # B26005870
5 Via Flagler, Palm Beach

$23,495,000

5 Via Flagler, Palm Beach

4 Beds 6 Baths 6,437 SqFt Residential MLS® # B26074191
New Open House
13 Via Vizcaya, Palm Beach

$23,000,000

13 Via Vizcaya, Palm Beach

3 Beds 6 Baths 5,913 SqFt Residential
Thu, Oct 8th, 2026 @ 2pm - 4pm
MLS® # B26085543
3405 Olde Hampton Drive, Wellington

$23,000,000

3405 Olde Hampton Drive, Wellington

13 Beds 7 Baths 5,318 SqFt Residential MLS® # R11163167
369 Eagle Drive, Jupiter

$23,000,000

369 Eagle Drive, Jupiter

7 Beds 9 Baths 9,692 SqFt Residential MLS® # R11153115
New
97 Nurmi Drive, Fort Lauderdale

$22,900,000

97 Nurmi Drive, Fort Lauderdale

6 Beds 9 Baths 8,600 SqFt Residential MLS® # B26085009
1355 S Flagler Drive #2301, West Palm Beach

$22,875,000

1355 S Flagler Drive #2301, West Palm Beach

3 Beds 5 Baths 4,613 SqFt Residential MLS® # B26056288
13614 Rhone Circle, Palm Beach Gardens

$21,850,000

13614 Rhone Circle, Palm Beach Gardens

6 Beds 10 Baths 10,359 SqFt Residential MLS® # R11135823
232 Bears Club Drive, Jupiter

$21,500,000

232 Bears Club Drive, Jupiter

5 Beds 8 Baths 8,677 SqFt Residential MLS® # B26022087
17667 Se Federal Highway, Tequesta

$20,000,000

17667 Se Federal Highway, Tequesta

8 Beds 13 Baths 16,134 SqFt Residential MLS® # B26073493
1015 S Southlake Drive, Hollywood

$19,999,999

1015 S Southlake Drive, Hollywood

7 Beds 9 Baths 7,355 SqFt Residential MLS® # A12045486
New
3723a S Ocean Boulevard, Highland Beach

$19,950,000

3723a S Ocean Boulevard, Highland Beach

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # B26085026
New
3723 S Ocean Boulevard, Highland Beach

$19,950,000

3723 S Ocean Boulevard, Highland Beach

6 Beds 10 Baths 8,154 SqFt Residential MLS® # B26085036
New
409 N Atlantic Drive, Lantana

$19,950,000

409 N Atlantic Drive, Lantana

6 Beds 7 Baths 4,976 SqFt Residential MLS® # B26085270
2927 Rhone Drive, Palm Beach Gardens

$19,950,000

2927 Rhone Drive, Palm Beach Gardens

6 Beds 10 Baths 8,417 SqFt Residential MLS® # B26019572
New
12317 Banyan Road, North Palm Beach

$18,950,000

12317 Banyan Road, North Palm Beach

6 Beds 8 Baths 6,313 SqFt Residential MLS® # B26084452
13771 Le Bateau Isle, Palm Beach Gardens

$18,950,000

13771 Le Bateau Isle, Palm Beach Gardens

5 Beds 8 Baths 8,505 SqFt Residential MLS® # B26076191
13101 Monet Lane, Palm Beach Gardens

$18,900,000

13101 Monet Lane, Palm Beach Gardens

7 Beds 9 Baths 12,163 SqFt Residential MLS® # B26075022
1355 S Flagler Drive #1900, West Palm Beach

$18,850,000

1355 S Flagler Drive #1900, West Palm Beach

3 Beds 5 Baths 4,862 SqFt Residential MLS® # R11062658
2787 Calais Drive, Palm Beach Gardens

$18,595,000

2787 Calais Drive, Palm Beach Gardens

5 Beds 8 Baths 9,272 SqFt Residential MLS® # R11135826

Hilltop Homes for Sale in Naples, Florida | Complete Buyer's Guide

Discover Hilltop homes for sale in Naples, Florida. Explore neighborhood features, home prices, nearby amenities, and tips for buying a home in this centrally located Naples community.


Hilltop Homes for Sale in Naples, Florida

If you're searching for Hilltop homes for sale in Naples, Florida, you'll find a charming residential neighborhood offering a convenient location, established homes, and easy access to beaches, shopping, and dining. Hilltop appeals to buyers seeking an affordable entry into one of Southwest Florida's most desirable cities.

Located in central Naples, Hilltop features mostly single-family homes in a mature neighborhood that has continued to attract buyers looking for value and accessibility. Many properties date from the late 1960s through the 1980s, and some have been updated with modern kitchens, bathrooms, and outdoor living spaces. 

infographic-hilltop-naples-florida

Why Buy a Home in Hilltop?

Hilltop offers several advantages that make it attractive to homeowners, retirees, seasonal residents, and investors.

Excellent Central Location

Residents enjoy quick access to:

  • Downtown Naples

  • Gulf beaches

  • US-41 (Tamiami Trail)

  • Shopping centers

  • Restaurants

  • Medical facilities

The community sits east of US-41 and west of Goodlette-Frank Road, between Golden Gate Parkway and Pine Ridge Road, making it easy to reach many of Naples' most popular destinations. 

Established Neighborhood

Unlike many newer developments, Hilltop features:

  • Mature landscaping

  • Larger lots

  • Quiet residential streets

  • No high-rise buildings

  • Traditional Florida architecture

Many buyers appreciate the neighborhood's established character and long-standing residential feel.

Hilltop Real Estate Market

Hilltop is primarily composed of single-family homes.

Depending on availability, buyers may find:

  • Two-bedroom homes

  • Three-bedroom homes

  • Renovated residences

  • Homes with private pools

  • Attached garages

  • Spacious backyards

Inventory can be limited because the neighborhood is relatively small, and homes do not come on the market frequently. Recent listings have occasionally shown no active Hilltop properties, with nearby communities providing additional options. 

Browse Homes for Sale in Other Naples Neighborhoods

Home Prices

Home values vary depending on factors such as:

  • Home size

  • Interior updates

  • Lot dimensions

  • Pool features

  • Renovations

  • Market conditions

Recent sales in the neighborhood have included homes selling in the mid-$500,000s to around $600,000, while asking prices for available homes may differ depending on current inventory and upgrades. Because inventory changes frequently, buyers should check current MLS listings for the latest pricing. 

Community Amenities

Although Hilltop itself is a residential neighborhood without extensive private amenities, residents benefit from being close to many Naples attractions.

Nearby conveniences include:

  • Grocery stores

  • Fitness centers

  • Coffee shops

  • Medical offices

  • Local parks

  • Golf courses

  • Public beaches

  • Shopping plazas

Its location provides convenient access to everyday essentials as well as recreational opportunities.

Schools and Location

Families considering Hilltop appreciate its central Naples location and convenient access to schools, parks, and major roads.

Nearby educational opportunities may include:

  • Public elementary schools

  • Middle schools

  • High schools

  • Private schools

  • Charter schools

Prospective buyers should verify current school zoning with the local school district before purchasing.

Things to Do Near Hilltop

Living in Hilltop places residents close to many of Naples' most popular attractions.

Popular nearby activities include:

Beautiful Beaches

Naples is known for its white-sand Gulf beaches, perfect for:

  • Swimming

  • Sunsets

  • Paddleboarding

  • Shell collecting

Shopping

Nearby shopping destinations offer:

  • Boutique stores

  • National retailers

  • Grocery shopping

  • Home décor

  • Fashion

Dining

Residents can enjoy:

  • Seafood restaurants

  • Waterfront dining

  • Casual cafés

  • Fine dining

  • International cuisine

Outdoor Recreation

Outdoor enthusiasts can explore:

  • Parks

  • Nature preserves

  • Golf courses

  • Walking trails

  • Botanical gardens

Tips for Buying a Hilltop Home

Before purchasing a home in Hilltop, consider the following:

1. Get Pre-Approved

Mortgage pre-approval strengthens your offer and clarifies your budget.

2. Monitor New Listings

Because Hilltop has a limited number of homes, new listings can sell quickly.

3. Consider Renovated Homes

Many homes have been remodeled with updated kitchens, flooring, roofing, and energy-efficient features.

4. Review Insurance Costs

Florida homeowners should evaluate flood, wind, and homeowners insurance costs as part of their purchasing decision.

5. Work with a Local Real Estate Professional

An experienced local agent can provide neighborhood insights, market trends, and access to new listings as they become available.


Frequently Asked Questions

Are Hilltop homes in Naples expensive?

Pricing varies based on size, condition, and location. Hilltop has historically offered a more affordable option compared with many luxury Naples communities, though values fluctuate with market conditions. 

Is Hilltop close to the beach?

Yes. Hilltop is only a short drive from several Gulf Coast beaches, making it convenient for residents seeking coastal living. 

What types of homes are available?

Most properties are single-family homes with two or three bedrooms. Some homes feature pools, renovated interiors, and attached garages. 

Is Hilltop a good neighborhood?

Many buyers appreciate Hilltop for its central location, established homes, mature landscaping, and proximity to shopping, dining, and beaches.

Are there HOA fees?

Association requirements vary by property. Many Hilltop homes have no homeowners association fees, but buyers should verify this during the purchase process. 

Is Hilltop good for retirees?

Yes. Hilltop's quiet streets, central location, nearby healthcare, and access to beaches make it appealing to many retirees as well as seasonal residents.


Conclusion

Hilltop offers an attractive opportunity for buyers seeking a centrally located home in Naples, Florida. With established residences, convenient access to beaches, shopping, dining, and major roadways, the neighborhood continues to appeal to a wide variety of homebuyers.

Because available inventory can be limited, prospective buyers should monitor new listings and be prepared to act when a property that fits their needs becomes available.


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