Thinking about trading yard work for lake breezes and walkable streets? If you live in Highland Park and want less maintenance without leaving the 60035 lifestyle you love, condos and townhomes can be a smart move. You can unlock equity, simplify day-to-day upkeep, and stay close to shops, Metra, parks, and the lakefront. In this guide, you’ll learn where the best local options cluster, what HOA living really covers, how financing changes for condos, and a practical plan to sell and buy smoothly. Let’s dive in.
Why downsize within 60035
If you own a single-family home in Highland Park, you likely have meaningful equity. Local condo and townhome prices usually sit below the single-family median, which is why many owners use a condo or townhome to right-size. Public aggregator snapshots often show different numbers for 60035 because they include different property types and time frames. Since figures shift with seasons and inventory, plan to rely on a current MLS snapshot when you are ready to move.
Beyond price, the real win is lifestyle. You keep the community you know while trading exterior chores for low-maintenance living. Many buildings sit near Central Avenue and St. Johns Avenue, Ravinia and Braeside, or in the historic Fort Sheridan area, which means everyday conveniences can get closer as your space gets smarter.
Where you’ll find condos and townhomes
Downtown and St. Johns Avenue
In and around downtown Highland Park, you’ll find low- to mid-rise condominiums with elevator access, smaller footprints, and strong walkability to shops, dining, health services, and the Highland Park Metra stop. Explore the feel of the area through the city’s Downtown Highland Park overview. If you want car-light living and quick access to errands, this core is a top pick.
Ravinia and Braeside
Closer to the Ravinia and Braeside Metra stops, you’ll see more low-rise condo buildings and townhome clusters set along leafy streets. The seasonal rhythm of Ravinia Festival adds energy, while Metra access keeps Chicago trips simple. If you value quiet blocks with easy rail access, put this pocket on your tour list.
Fort Sheridan
Fort Sheridan offers a distinctive backdrop with refurbished historic structures, lakefront paths, and preserved open space. You’ll find a mix of condos and townhomes in a setting known for character and outdoor access. Buyers who want architecture with a story often prioritize this area.
Park Avenue West and nearby clusters
You’ll also see townhome-style condos along and near Park Avenue West and in planned developments around 60035. Expect attached homes with private entries, interior stairs, and garage parking. As of March 2026, public listings commonly show HOA dues ranging roughly from the mid-$300s to the upper-$600s per month, depending on amenities and what’s included. Always confirm current fees, inclusions, and any pending increases with association documents.
What HOA living changes day to day
Maintenance and services
For most associations, your monthly dues cover exterior upkeep, landscaping, snow removal, common-area utilities, and trash. That is the main time-saving benefit many downsizers want. Review the budget line items to confirm exactly what your dues include. The Community Associations Institute’s Illinois resources explain what to look for in owner associations and budgets. See CAI Illinois homeowner guidance.
Insurance split
Condo and townhome communities typically carry a master policy for the building or common elements, while you carry an HO-6 policy for your unit’s interior and personal property. Ask whether the master policy is replacement-cost or actual-cash-value, and whether loss-assessment coverage is recommended. This split affects both monthly costs and risk exposure. CAI’s guidance for Illinois homeowners outlines these best practices. Review the CAI Illinois homeowner guidance.
Rules and everyday limits
Associations often have rules for architectural changes, pets, rentals, and parking. These policies shape lifestyle, so request the current rules and check for pending changes before you commit. If you hope to rent seasonally in the future or have frequent guests, verify exactly what is allowed. CAI provides a helpful framework for understanding board processes and rulemaking in Illinois. See CAI Illinois homeowner guidance.
Reserves and special assessments
Healthy reserves help associations fund future capital projects without surprise assessments. Under the Illinois Condominium Property Act, boards must consider reserves and long-term planning when budgeting. As a buyer, ask for the most recent reserve study and the association’s special-assessment history before going firm on your offer. Review the relevant statute in the Illinois Condominium Property Act.
Documents to request early
Ask for these items as soon as your offer is accepted, and build time into attorney review to analyze them:
- Annual budget and year-to-date financials
- Most recent reserve study
- Board meeting minutes for the last 6 to 12 months
- Master insurance certificate and declarations
- Litigation statement and disclosure of any known building issues
- Rental policy, rules and regulations, and recorded declaration/bylaws
The CAI Illinois homeowner guidance aligns with these buyer due-diligence requests.
Financing condos and townhomes
Warrantability and project reviews
Many lenders complete project-level reviews for condos. Buildings with low owner-occupancy, high HOA delinquency, material litigation, limited reserves, or significant commercial space can be labeled non-warrantable, which may limit loan options or raise required down payments. Ask your lender to run a condo-project review early and to explain warrantable vs non-warrantable differences. For a plain-English overview, see this guide to warrantable vs non-warrantable condos.
Preapproval that fits your plan
If you plan to use FHA or VA financing, verify the building’s eligibility upfront. If you are considering buying before you sell, speak with your lender about short-term options like a bridge loan or HELOC and how those affect your debt-to-income ratio. You can review general info about bridge loans to understand how they work before you start.
Plan the sell-and-buy move
Timing strategies
- Sell first. This approach frees up equity and can simplify financing for the purchase. You might need temporary housing or a negotiated post-closing rent-back if your next home is not ready.
- Buy before you sell. You get stronger offers without a sale contingency, but you may need a bridge loan, HELOC, or substantial cash on hand. Expect higher short-term costs and more moving parts.
- Contingent offer. In slower or balanced markets, a home-sale contingency may be acceptable to some sellers. In competitive pockets, it can weaken your position. Your agent will help you match strategy to current 60035 conditions.
Understand selling costs
Plan for agent commissions and typical seller closing costs. Many sellers see total transaction costs land in the mid-single to low-double digits percent of the sale price once commissions, credits, and closing fees are tallied. Have your agent create a net-proceeds worksheet so you know how much equity you can apply to your next purchase.
Taxes when you sell
If your home was your primary residence and you meet the IRS ownership and use tests, you may be able to exclude up to $250,000 in gain if single or $500,000 if married filing jointly. Review the specifics in IRS Publication 523, and consult a tax professional for personalized guidance.
Staging, repairs, and prep
Downsizing usually includes editing belongings. Plan for decluttering, light repairs, and staging that highlights space and storage. A pre-listing inspection can surface issues early and reduce repair negotiations later. Small, targeted updates can make marketing more effective.
Your 60035 downsizing timeline and checklist
Use this local roadmap to keep the process calm and organized.
6 to 12 months before listing
- Define your target: true lock-and-leave condo or townhome with garage. Tour several buildings across price bands and neighborhoods.
- Meet with a lender for preapproval and ask about condo-project reviews and warrantability. If you may buy first, ask about bridge loans and HELOCs.
- Hire a local agent who understands both Highland Park single-family values and the condo/townhome micro-markets. Request a comparative market analysis and a preliminary net sheet.
30 to 90 days before listing or buying
- Declutter and donate or sell items. Arrange storage for keepsakes and seasonal gear.
- Schedule photography and staging. Consider a pre-listing inspection to limit surprises.
- For the purchase side, request HOA documents immediately after an accepted offer. Ask your lender to begin the project eligibility review as soon as possible.
Closing and move
- Try to align closing dates. Same-day or back-to-back closings reduce interim housing needs.
- If you need time, negotiate a short rent-back. If buying first, budget for bridge financing costs and timelines.
- Confirm your HO-6 condo insurance is active on purchase day, and verify how it dovetails with the building’s master policy.
Lifestyle value after the move
Transit and commuting
Highland Park sits on Metra’s Union Pacific North line with stations at Highland Park and Braeside, plus a seasonal Ravinia stop. That means convenient Chicago access without city upkeep. For system details and service patterns, review Metra’s Union Pacific North Line report.
Parks, trails, and lakefront
The Park District of Highland Park operates a wide network of parks, trails, golf, fitness, and lakefront amenities that support an active, lower-maintenance lifestyle. For a high-level snapshot of community assets and operations, see the Park District’s municipal profile. If you choose a walkable downtown location, everyday errands and dining often become a five-minute routine.
Schools snapshot for sellers and buyers
If school district context matters for your sale or purchase, note that much of Highland Park is served by North Shore School District 112 for elementary and middle grades and feeds into Township High School District 113. Learn more about District 112’s profile on the NSSD112 overview. Use neutral, factual criteria when evaluating attendance areas and verify boundaries through official district tools.
Next steps
Right-sizing in 60035 is about simplifying without giving up what you love about Highland Park. If you want a clear plan, a market-tested pricing strategy for your current home, and a curated tour of the best condos and townhomes for your lifestyle, let’s talk. Connect with Jimmy Styx to start your downsizing move with purpose, not pressure.
FAQs
What should I budget for HOA dues in Highland Park condos and townhomes?
- As of March 2026, public listings commonly show monthly dues in the ~$300 to ~$700 range, depending on amenities and what the association covers. Always confirm current figures and inclusions in the HOA budget and rules before you buy.
How do I know if a Highland Park condo is warrantable for financing?
- Ask your lender to run a condo-project review early. Flags like low owner-occupancy, high HOA delinquencies, litigation, or limited reserves can affect loan options. Learn the basics in this guide to warrantable vs non-warrantable condos.
Which documents should I request from an HOA before purchasing in 60035?
- Request the budget and financials, reserve study, board minutes, insurance certificate, litigation disclosures, rental policy, and recorded rules and bylaws. The CAI Illinois homeowner guidance outlines these due-diligence essentials.
Are there neighborhoods with more one-level living options in Highland Park?
- Yes. Downtown and the St. Johns Avenue corridor feature more elevator buildings with single-level condos. You can also find options in Ravinia/Braeside and select buildings in Fort Sheridan. Verify elevator access and entry steps during tours if mobility is a priority.
How does Metra access work if I downsize to downtown Highland Park?
- The Highland Park station on the Union Pacific North line puts you on a direct rail route to Chicago. Braeside serves the south side of town, and a seasonal Ravinia stop supports event travel. See service details in Metra’s Union Pacific North Line report.
Will I owe capital gains tax when I sell my current home in 60035?
- Many sellers who meet the IRS ownership and use tests may exclude up to $250,000 (single) or $500,000 (married filing jointly) of gain. Review IRS Publication 523 and consult a tax professional for advice tailored to your situation.
