Hemingway Place Homes in Naples, Florida
Hemingway Place is a private gated neighborhood of custom single-family homes in a convenient central Naples location. Mature shade trees, thoughtfully landscaped streets, distinctive architecture, and a limited number of residences give the community a quiet, established character that is increasingly difficult to find near the heart of Naples.
This is not a neighborhood built around a sprawling amenity campus or mandatory country club. Hemingway Place is centered on the homes themselves: gracious interiors, private pools, attractive yards, and a residential setting close to beaches, shopping, dining, healthcare, schools, and downtown Naples.
Gated Naples neighborhood • Custom estate-style homes • Private pools and lanais • Mature landscaping • Non-golf community • Central Naples setting • Limited inventory • Convenient beach and downtown access
A Small Community with a Distinct Identity
Hemingway Place feels different from many larger Naples developments. There is no through-traffic, the number of residences is limited, and the streets have a settled appearance shaped by mature landscaping and individually designed homes.
The community can be a strong fit for buyers who want gated privacy without the formality and ongoing membership expenses associated with a golf resort. Residents can enjoy the security and neighborhood standards of a private community while remaining free to choose their own clubs, fitness facilities, restaurants, beaches, and recreational activities.
Custom Home Character
Residences vary in architecture, room arrangement, outdoor living, finishes, renovations, landscaping, and garage configuration.
Private Naples Living
Gated entry, limited traffic, established trees, and private homesites create a calm residential environment.
Outdoor-Focused Design
Many homes are organized around pools, covered lanais, summer kitchens, gardens, and spacious entertaining areas.
Central Convenience
Beaches, Olde Naples, Waterside Shops, Artis–Naples, healthcare, schools, groceries, and restaurants are within practical reach.
Hemingway Place Home Designs
Homes in Hemingway Place are generally designed for buyers who appreciate generous living areas, privacy between bedrooms, quality construction, and a strong connection between the interior and the lanai. Because the residences were not all produced from one repeated plan, buyers will find meaningful differences from one property to another.
Features may include:
- Three or more bedrooms
- Private guest suites
- Home offices or dens
- Open great rooms
- Formal dining rooms
- Breakfast areas
- Chef-inspired kitchens
- Large center islands
- Walk-in pantries
- High, tray, or coffered ceilings
- Wide sliding glass doors
- Fireplaces
- Attached multi-car garages
- Private pools and spas
- Covered lanais
- Outdoor kitchens
- Courtyards or garden areas
A buyer planning to live in Naples throughout the year may prioritize storage, office space, garage capacity, storm protection, and shade. A seasonal owner may care more about guest separation, easy maintenance, a comfortable pool area, and the ability to secure the home while away.
Architecture That Does Not Feel Repeated
One of Hemingway Place’s strongest qualities is its architectural variety. Rooflines, entries, exterior finishes, windows, columns, courtyards, landscaping, and interior details may differ significantly.
This individuality gives the neighborhood personality, but it also means each property should be evaluated on its own merits. Square footage alone does not reveal construction quality, room proportions, natural light, renovation workmanship, outdoor privacy, mechanical condition, or the relationship between the house and its homesite.
Great Rooms and Entertaining Spaces
Many Hemingway Place residences are arranged around an open central living area connected to the kitchen, dining spaces, lanai, and pool. Large sliding doors can make the outdoor view part of the interior experience and allow gatherings to move naturally between the home and lanai.
When comparing floor plans, consider:
- Great-room width and furniture placement
- Ceiling height
- Kitchen visibility
- Dining-space flexibility
- Guest-bedroom separation
- Location of the home office
- Access to the lanai
- Natural light throughout the day
- Pool visibility
- Storage and closet space
Private Pools and Lanais
Outdoor living is often a defining part of a Hemingway Place home. Pools, covered lanais, summer kitchens, landscaped gardens, and screened enclosures give residents space to relax and entertain without depending on shared community amenities.
Outdoor features may include:
- Covered seating areas
- Outdoor dining spaces
- Private swimming pools
- Spas
- Screen enclosures
- Summer kitchens
- Built-in grills
- Fire features
- Water features
- Pool baths
- Landscape lighting
- Privacy hedges
- Courtyard gardens
Buyers should inspect the pool surface, tile, coping, deck, heating equipment, pumps, filtration system, spa components, screen enclosure, outdoor appliances, drainage, lighting, and surrounding landscaping.
Lanai Exposure Can Change Daily Living
The direction a pool and lanai face affects sunlight, shade, afternoon heat, water temperature, landscaping, and how often the outdoor space is used. Western exposure may provide stronger afternoon sun and evening light, while eastern exposure may offer softer mornings and more afternoon shade.
A second visit at a different time of day can reveal the true character of the outdoor area.
Homesites, Privacy, and Landscaping
Lot position matters in a small custom-home community. The distance between homes, mature plantings, wall placement, window orientation, driveway configuration, and lanai exposure can influence privacy and value.
Established landscaping can provide shade and screening, although buyers should also review:
- Tree condition
- Root systems
- Irrigation coverage
- Drainage
- Landscape maintenance
- Exterior lighting
- Privacy from neighboring lanais
- Visibility from the street
- Association landscaping requirements
Updated and Original Residences
Available Hemingway Place homes may range from carefully maintained original residences to substantially remodeled properties. An updated appearance can be attractive, but buyers should look beyond finishes and verify the age, quality, permits, warranties, and approval status of the work.
Renovations may include:
- Reconfigured kitchens
- New cabinetry
- Quartz or natural-stone countertops
- Modern appliances
- Updated primary bathrooms
- Walk-in showers
- New flooring
- Custom closets
- Updated lighting
- Impact-resistant windows and doors
- Newer roofing
- Updated HVAC systems
- Whole-house generators
- Pool renovations
- Outdoor kitchen improvements
- New landscaping
Buyers should request permits, invoices, contractor records, warranties, roof documentation, window specifications, HVAC dates, generator service information, pool records, and association approvals when applicable.
A Non-Golf Gated Lifestyle
Hemingway Place provides the privacy and standards of a gated community without requiring owners to join a golf club. This can appeal to buyers who prefer to choose their own recreational activities or who do not want club initiation fees, annual dues, food minimums, or membership assessments tied to home ownership.
Buyers comparing Naples Non-Golf Gated Resorts may find Hemingway Place especially appealing because of its limited size, custom homes, mature streetscape, and central location.
Central Naples Location
Hemingway Place offers access to a broad range of Naples destinations without placing residents directly in a busy commercial or tourist district. Its central position can reduce travel time for daily errands, dining, healthcare, school, shopping, cultural events, and beach visits.
Destinations within the broader area include:
- Fifth Avenue South
- Third Street South
- Olde Naples
- Naples beaches
- Waterside Shops
- Artis–Naples
- Mercato
- Restaurants and cafés
- Grocery stores
- Medical facilities
- Schools
- Fitness centers
- Parks
- Major Naples roadways
Travel time varies by season and time of day, so buyers should personally test routes to the destinations they expect to visit most often.
Near the Beach without Waterfront Maintenance
Hemingway Place is not a beachfront or boating community, but Gulf beaches and coastal attractions are within convenient reach. Buyers comparing Naples Waterfront Homes may prefer Hemingway Place when they want a private pool and central location without responsibility for docks, lifts, seawalls, canal depth, or marine maintenance.
Full-Time and Seasonal Ownership
The neighborhood can serve both full-time and seasonal homeowners. Permanent residents may appreciate home offices, garages, storage, privacy, outdoor living, and proximity to everyday services.
Seasonal residents may value gated access, established association management, private pools, low-density surroundings, and the ability to enjoy Naples without mandatory country club obligations.
Homeowners Association Review
Although Hemingway Place is smaller than many master-planned communities, buyers should still review the homeowners association thoroughly before purchasing.
Documents to examine may include:
- Declaration and covenants
- Association bylaws
- Rules and regulations
- Current operating budget
- Reserve information
- Recent meeting minutes
- Assessment history
- Insurance summaries
- Architectural guidelines
- Landscape standards
- Rental restrictions
- Pet policies
- Parking rules
- Gate and guest procedures
Association Fees and Responsibilities
Association expenses may support gated entry, common landscaping, private roads, lighting, management, insurance, reserves, or other neighborhood services. Buyers should verify the current fee and precisely what it covers.
Questions to ask include:
- How often are dues collected?
- Which services are included?
- Are individual yards owner maintained?
- Who maintains roads and gates?
- Are reserves adequately funded?
- Are assessments planned?
- Are capital contributions required at closing?
- What exterior maintenance standards apply?
- Are owners responsible for irrigation?
- Are landscaping changes regulated?
Architectural Guidelines
Exterior alterations may require association approval to protect the neighborhood’s appearance. Roofing, paint, windows, doors, pools, generators, fences, additions, driveways, exterior lighting, and landscaping may be regulated.
Before purchasing a home that needs improvements, buyers should confirm:
- Which renovations are allowed
- What approval process applies
- Whether deposits are required
- What contractor requirements apply
- Which work hours are permitted
- Whether prior alterations were approved
- Whether permits were properly closed
- How long architectural approval may take
Rental and Pet Policies
Buyers planning to rent should verify minimum lease periods, annual lease limits, tenant approval procedures, application fees, deposits, guest access, parking rules, and any ownership period required before leasing.
Pet policies may address the number, type, size, registration, leash requirements, waste removal, nuisance provisions, and use of neighborhood common areas.
Insurance and Storm Protection
Insurance should be investigated early because roof age, window protection, pool features, generators, prior claims, and building systems may affect premiums and availability.
Important considerations may include:
- Roof age and material
- Impact windows and doors
- Storm shutters
- Garage-door rating
- Wind-mitigation inspection
- Four-point inspection
- Flood-zone information
- Pool and screen-enclosure coverage
- Generator coverage
- Water-damage protection
- Prior claims
- Loss-assessment coverage
Home Inspection Priorities
A detailed inspection can help buyers identify current condition, deferred maintenance, and future ownership expenses. Depending on the age and construction of the home, buyers may wish to evaluate:
- Roof
- Attic and insulation
- HVAC systems
- Plumbing
- Electrical systems
- Water heater
- Windows and doors
- Appliances
- Pool and spa equipment
- Screen enclosure
- Outdoor kitchen
- Generator
- Drainage and grading
- Irrigation
- Exterior stucco
- Driveways and walkways
- Garage systems
- Termite or pest activity
- Interior moisture
Comparing Hemingway Place Homes
Pricing should reflect more than total square footage. Architecture, homesite size, privacy, renovation quality, ceiling height, garage capacity, outdoor living, roof age, storm protection, mechanical systems, and recent neighborhood sales can all affect market value.
Important comparison points include:
- Living area
- Bedroom and bathroom count
- Den or office
- Guest-suite arrangement
- Garage capacity
- Lot size and shape
- Pool and lanai orientation
- Privacy from neighboring homes
- Kitchen condition
- Bathroom updates
- Flooring
- Roof age
- Impact protection
- HVAC age
- Generator
- Outdoor kitchen
- Landscape quality
- Association expenses
- Recent Hemingway Place sales
- Comparable central Naples gated-community sales
Questions to Ask Before Buying
- What association fees are required?
- What services are included?
- Are reserves adequately funded?
- Are assessments planned or under discussion?
- What architectural restrictions apply?
- What rental rules apply?
- What pet restrictions apply?
- Were previous renovations approved and permitted?
- How old are the roof, HVAC systems, and water heater?
- Are the windows and doors impact rated?
- How old is the pool equipment?
- What is the lanai’s sun exposure?
- How private is the outdoor living area?
- What insurance information is available?
- Are there drainage or irrigation concerns?
- What road or gate responsibilities belong to the association?
- Which recent sales support the asking price?
- How does the home compare with nearby gated communities?
Why Buyers Choose Hemingway Place
- Intimate gated setting: Limited traffic and a small number of homes create a quiet neighborhood environment.
- Custom residences: Architectural variety provides more choice than a uniform production-home community.
- Private outdoor living: Pools, lanais, gardens, and summer kitchens support the Naples lifestyle.
- Central Naples convenience: Beaches, dining, shopping, healthcare, schools, and cultural attractions are within practical reach.
- No mandatory golf membership: Owners can enjoy a gated luxury setting without private-club obligations.
- Mature landscaping: Established trees and plantings add shade, privacy, and character.
- Full-time and seasonal appeal: The community can accommodate permanent residents and part-time Naples homeowners.
- Limited availability: The neighborhood’s small size can make listings relatively uncommon.
Buying or Selling in Hemingway Place
Hemingway Place should be compared with other boutique gated neighborhoods and the broader selection of Naples Homes for Sale. Buyers may favor the community when they want privacy, custom architecture, a private pool, central access, and fewer lifestyle obligations.
Those considering Naples Luxury Condos may find that Hemingway Place offers more interior space, garage capacity, private yards, and freedom from shared walls. Buyers also exploring Naples Golf Resorts should compare the benefits of club amenities with the simpler non-golf ownership experience available here.
Sellers should document renovations, permits, roof age, mechanical systems, impact protection, generator details, pool improvements, outdoor kitchens, landscaping, association approvals, and the home’s specific lot orientation and privacy features.
Current Hemingway Place homes for sale and active property search results are displayed below this community guide.
The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.