Thinking about trading Lake Michigan winters for Gulf sunsets? If you plan to sell your Chicago home first and then buy in Naples, timing and coordination matter. You want to avoid two mortgages, protect your cash, and still land the right home in Florida. In this guide, you’ll get a clear, step-by-step timeline, financing and logistics options, and Naples-specific tips so you can move with confidence. Let’s dive in.

Why sell-then-buy works

Selling first can be a smart path if you want to avoid carrying two mortgages and use your sale proceeds in Naples. It often puts you in a stronger position when you make an offer. You can move faster and negotiate with confidence.

The trade-off is coordination. Chicago and Naples have different market rhythms and seasonality. You may face a gap between closings or miss a listing if you wait too long after you sell. A plan for temporary housing, financing backstops, and agile decision-making helps you stay in control.

How long it really takes

Every move is unique, but most Chicago-to-Naples sell-then-buy plans fit one of these schedules:

• Standard timeline (8–12+ months): Lower stress, plan ahead, and maximize sale value before you buy in Naples.
• Compressed timeline (3–6 months): Higher coordination with faster decisions and possible temporary housing.
• True sell-then-buy: Close in Chicago, move to temporary housing in Naples, then shop aggressively for 1–3 weeks.

Use the timeline that fits your needs and risk tolerance.

Your Chicago sale plan

Pre-listing prep (2–8 weeks)

• Get clear on your numbers. Estimate net proceeds after commission, taxes, and closing costs.
• Prep the home. Declutter, deep clean, and make essential repairs. Simple cosmetic updates like fresh paint and curb appeal improvements can help.
• Consider a pre-listing inspection. Finding issues early reduces renegotiation risk later.
• Choose an experienced listing agent in your neighborhood who understands relocations.

Listing to contract

• Days on market vary by season and submarket. Spring and summer can move faster than winter. Expect anything from a few days in hot pockets to several weeks elsewhere.
• Negotiate terms that support your move. Ask about a rent-back so you can stay after closing, or set dates that align with your Naples purchase.

Contract to close (about 30–60 days)

• Keep communication tight with your buyer, attorney, and title company.
• Book movers early, especially during peak months.
• Line up storage and short-term housing in case dates do not align.

Start your Naples search early

Naples attracts many buyers from the Midwest, and inventory shifts with the season. Winter often brings more buyers and, in some cases, more high-end inventory. Single-story homes, hurricane-hardy construction, condo living, golf communities, and 55+ neighborhoods are common preferences.

What to expect when buying

• Finding the home: Desirable pockets can be competitive. Be ready to view quickly and decide with confidence.
• Contract to close: Often 30–45 days. Timing can vary based on loan type, condo or HOA document review, and insurance.
• Inspections: Plan for 7–15 days to complete inspections and negotiate repairs.

Local due diligence

• Flood zones and hurricane risk: Many coastal areas fall within FEMA flood zones. Your lender may require flood insurance. Wind mitigation features and hurricane protections can influence insurance terms.
• Condos and HOAs: Review financials and rules early. Some associations have reserve and insurance standards that affect financing.
• Seasonality: Winter is high season in Southwest Florida. Timing your search and travel can affect speed and selection.

Finance and timing tools

You have options if you need more flexibility between closings:

• Bridge loan or HELOC: Access short-term funds to write a strong offer before your Chicago sale closes. These products often have short terms and higher fees, and they typically require equity and strong credit.
• Rent-back and occupancy terms: In Chicago, consider a seller rent-back so you can stay a short period after closing. In Naples, you can ask for delayed possession or a seller rent-back, if acceptable to the seller.
• Contingencies: A home-sale contingency can work but may be less attractive in competitive Naples segments. Tight timelines and kick-out clauses can make it more acceptable.
• Appraisal and underwriting: Appraisals can add 1–3 weeks. Start pre-approval with a Florida lender early and keep your documents ready to help the process.

Insurance, taxes, and Florida paperwork

• Insurance: In Florida, wind and hurricane exposure matters. If the home is in a high-risk FEMA flood zone and you have a loan, you will likely need flood insurance. Wind mitigation inspections may help reduce premiums.
• Property taxes and homestead: Florida has no state income tax. If the Naples home will be your primary residence, the Collier County homestead exemption can reduce assessed value, and the Save Our Homes benefit can cap annual assessed-value increases for qualified homesteads. Check the Collier County Property Appraiser for requirements and deadlines.
• Residency tasks: New Florida residents are commonly expected to get a Florida driver license and register vehicles within a set period after establishing residency, often cited as within 30 days. Plan voter registration, mail forwarding, and utilities too.
• Title and closing: Use a trusted Florida title and closing agent. Verify all wiring instructions by phone using known contact details to avoid fraud.
• Hurricane season: June through November can disrupt moves and closings. Build flexibility into your schedule.

Move logistics Chicago to Naples

• Movers: Book early for spring, summer, and Naples high season. Confirm elevator access, building rules, and insurance if you are moving into a condo.
• Storage and shipping: If your dates do not line up, arrange storage near one city. Consider vehicle transport and pet travel plans.
• Temporary housing: Short-term rentals can be tight in high season. Keep backup options if your Naples closing slips.

Step-by-step timeline templates

Standard timeline (8–12+ months)

• 9–12 months out

  • Research Naples neighborhoods and communities that fit your lifestyle, including condos, golf communities, waterfront, or 55+ options.
  • Speak with a Naples-based agent and get a Florida mortgage pre-approval if financing.
  • Gather property documents, warranties, and permits for your Chicago home.
  • Start decluttering and schedule high-ROI repairs or cosmetic updates.

• 3–6 months before listing

  • Hire your Chicago listing agent and set a pricing strategy.
  • Stage and photograph the home.
  • Begin active Naples search with in-person or virtual tours.

• Listing period (up to 8 weeks)

  • Review offers and negotiate timing and possible rent-back.
  • Firm up your Naples financing plan, including bridge funds if needed.

• Contract to close in Chicago (about 30–60 days)

  • Coordinate dates so your Naples closing can follow.
  • If needed, arrange temporary housing or rent-back.

• After Chicago closes

  • Make a strong, non-contingent offer in Naples if your funds are available.
  • Allow 30–45 days to close in Naples, factoring in inspections, condo or HOA review, and insurance.

Compressed timeline (3–6 months)

• 3–4 months out

  • List in Chicago and launch an aggressive Naples search at the same time.
  • Consider a pre-listing inspection and a pricing strategy aimed at a quick sale.

• Rapid offer acceptance in Chicago

  • Target a quick close, often around 30 days.
  • Use sale proceeds or secure a bridge loan to make a non-contingent Naples offer.

• Trade-offs

  • Expect higher stress and possible temporary housing.
  • You may have less time to shop and may accept a less-preferred property.

True sell-then-buy after closing

• After your Chicago close
  • Relocate to Naples and use temporary housing for 1–3 weeks.
  • Tour homes daily and be prepared to write fast, strong offers.
  • Keep inspection vendors and insurance contacts ready so you can meet short timelines.

What to do between closings

• Use a rent-back in Chicago to stay in place while your Naples purchase closes, if the buyer agrees.
• Negotiate flexible occupancy with the Naples seller, if they will accept it.
• Line up a short-term rental, extended-stay hotel, or furnished monthly rental in Naples as a fallback.
• Store non-essentials and ship a smaller load so you can move quickly when your Naples home clears to close.

Make a stronger Naples offer

• Be pre-approved with a Florida lender and have proof of funds ready.
• Keep contingencies tight and timelines clear. If you must include a home-sale contingency, use a firm schedule and be ready with updates.
• Review condo or HOA documents early when possible, and consider insurance quotes and flood zone status before you commit.
• Schedule inspections quickly and respond to findings with clear repair asks or credits.

How we can help

You deserve a partner who understands both ends of this move. Our dual-market team supports high-end Chicago sellers and Naples buyers with one coordinated plan. We combine financial discipline, clear timelines, and concierge service so you can sell with confidence and buy smart in Southwest Florida.

Ready to map your Chicago-to-Naples timeline and next steps? Connect with Dominick Clarizio for a tailored plan and on-the-ground support in both markets.

FAQs

How does a sell-then-buy plan help my Naples offer?

• It frees your equity and can remove a home-sale contingency, which often strengthens your position in competitive Naples segments.

How long is contract to close in Naples?

• Many purchases close in about 30–45 days, depending on financing, insurance, inspections, and condo or HOA document review.

What is a rent-back and when should I use it?

• A rent-back lets you remain in the home after closing for a set period, which can bridge the gap between your Chicago sale and Naples purchase.

Do I need flood insurance in Naples?

• If your home is in a high-risk FEMA flood zone and you have a loan, your lender will likely require flood insurance, so check flood zone status early.

Is a home-sale contingency accepted in Naples?

• It can be, but it is often less attractive in competitive areas. Short timelines and kick-out clauses may help, but non-contingent offers are stronger.

What Florida tax benefits should I know about?

• Florida has no state income tax. If Naples will be your primary home, the Collier County homestead exemption and Save Our Homes benefit can reduce and cap assessed values subject to rules and deadlines.