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Positioned in the desirable community of Pepperwood and lovingly maintained by its original owner, this beautifully updated residence enjoys southern exposure and tranquil garden views, creating a light-filled and inviting atmosphere. Thoughtfully renovated and impeccably maintained, this two-bedroom, two-bath condominium offers an excellent Naples location, paired with comfortable indoor-outdoor living. Whether you are seeking a seasonal retreat, investment opportunity or full-time residence, this property presents exceptional value in a serene yet convenient setting. A screened lanai with tiled flooring and a ceiling fan provides covered outdoor living space overlooking lush, peaceful garden views, ideal for morning coffee or relaxing afternoons. Impact sliding doors and windows offer storm protection and added peace of mind. The residence includes one assigned carport space and extra storage for added convenience. Inside, porcelain tile flooring flows seamlessly throughout the main living areas and baths, enhancing durability and style. The updated kitchen is bright and functional, featuring white cabinetry, granite countertops, a tile backsplash, recessed lighting and a window above the sink that welcomes natural light. White Whirlpool appliances, including a range, dishwasher, microwave and refrigerator with icemaker complement the space, along with a breakfast counter and pantry for additional storage. The adjoining living and dining areas are open and comfortable, with direct access to the lanai for effortless indoor-outdoor living. The primary bedroom enjoys serene garden views and offers a walk-in closet for generous storage. The en-suite bath features a granite vanity with a full-width mirror and a floor-to-ceiling tiled walk-in shower with a glass enclosure. The guest bedroom includes a ceiling fan and is conveniently adjacent to a full bath with a shower-tub combination, providing comfort and privacy for visitors. A dedicated laundry room with overhead shelving, a washer and a dryer adds everyday convenience. Ideally just minutes from downtown Naples, Fifth Avenue South shopping and dining, and the stunning white sugar sand beaches along the Gulf, this Pepperwood residence combines updated finishes, southern exposure and a prime location for effortless Southwest Florida living. In a quiet, charming neighborhood designed in a circular layout ideal for morning strolls and evening walks, Pepperwood offers a community pool just a short distance from the unit, enhancing ease and enjoyment of everyday living. Just minutes from downtown Naples, Fifth Avenue South shopping and dining, and the stunning white sugar sand beaches along the Gulf, this residence combines updated finishes and an exceptional setting for effortless Southwest Florida living.

Highlights

  • Residential
  • Condominium
  • Built in 1984
  • $1,939/qtr HOA
  • 250 days on Market

  • Bedrooms
    2
  • Bathrooms
    2
  • Year Built
    1984
  • Stories
    1.0
  • Construction Materials
    Stucco, Cement Siding
  • Parking Features
    Driveway, Paved, Covered, Guest, Detached Carport
  • Living Area
    1118.0
  • Interior Features
    Walk-In Closet(s), Pantry, Breakfast Bar
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer, Disposal
  • Flooring
    Tile, Carpet
  • Furnished
    Unfurnished
  • Patio And Porch
    Patio
  • Security Features
    Smoke Detector(s)
  • Cooling
    Electric, Exhaust Fan
  • Heating
    Electric, Central, Exhaust Fan

  • Lot Features
    Zero Lot Line
  • Utilities
    Cable Available


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Frequently Asked Questions

How do I schedule a tour of 4955 Pepper Cir #B 106?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 4955 Pepper Cir #B 106.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 4955 Pepper Cir #B 106?

Click Ask a Question to talk with our team. You already know it is a 2 bed, 2 bath, listed for $259,999. We can talk through recent upgrades, potential seller motivation, how this condominium compares to others in Naples, and can even get you in to see the property quickly.

How do I get a virtual tour of 4955 Pepper Cir #B 106?

Yes! A virtual tour is available for 4955 Pepper Cir #B 106. Click here to view the full walkthrough and explore every room at your own pace. If you would like a guided virtual showing or have questions along the way, we can connect you with our local expert to walk you through it live.

How much is the monthly mortgage payment for 4955 Pepper Cir #B 106?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 4955 Pepper Cir #B 106 at around $1,661. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 4955 Pepper Cir #B 106?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Collier County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 4955 Pepper Cir #B 106?

In most cases, yes. Whether 4955 Pepper Cir #B 106 is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Naples's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 4955 Pepper Cir #B 106?

We can handle that for you. Our preferred local agent specializes in residentials in Naples and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $259,999 with 1,118 sqft of space—that comes out to approximately $233 per square foot.

How long has this property been on the market?

4955 Pepper Cir #B 106 was listed on March 05, 2026, which means it's been on the market for 250 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1984, making it approximately 42 years old.

What are the property taxes for 4955 Pepper Cir #B 106?

The most recent public record shows annual property taxes for 4955 Pepper Cir #B 106 were approximately $2,173. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is there an HOA fee for this property, and what does it cover?

This home has an HOA fee of $1,939 paid quarterly.

Is 4955 Pepper Cir #B 106 still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, Multiple Listing Service of Bonita SpringsEstero. All rights reserved.

Last Updated: November 10, 2026 at 02:15PM | Source: Multiple Listing Service of Bonita SpringsEstero | MLS#: 226009878