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Rare opportunity in The Highlands: Exceptional Privacy, Space and Potential! Discover the possibilities in this spacious, single-story, four-bedroom pool home in The Highlands, the ‘Crown-Jewel’ of The Meadows. Set on an expansive 100-foot-wide lot with no neighbors in sight and tranquil preserve views, this home offers exceptional privacy in a phenomenal location, just five minutes from 90+ restaurants and outstanding shopping! A highly sought-after floor plan features 3,000 square feet under air and 4,500 square feet under roof, including an expansive covered lanai ideal for Florida indoor-outdoor living. High ceilings, oversized windows and walls of sliding glass doors fill the home with natural light and showcase the beautiful, private setting. Offering four bedrooms, three-and-a-half baths, plus a flex room, it was thoughtfully designed for maximum privacy as the primary suite and guest bedrooms occupy separate wings. Outside, a large pool invites relaxation and entertaining, while the generous covered lanai provides ample space for alfresco dining and lounging, all overlooking a bountiful mango tree, queen palms and the peaceful preserve. Ready for updating, this home offers tremendous potential, an outstanding floor plan and valuable improvements, including a 2016 tile roof and hurricane-rated garage door, 2017 pool resurfacing, and two new A/C systems in 2025. All near all the fun The Meadows has to offer and five minutes to the UTC Mall, a world-class destination for shopping, dining, and entertainment. Set on 1,600 lush acres just 15 minutes from Downtown Sarasota, The Meadows combines resort living with the beauty of untouched nature. Enjoy 14 miles of scenic trails, an active social calendar, new fitness center, Junior Olympic pool, 10 pickleball courts, two 18-hole golf courses, and 15 Har-Tru tennis courts. Ideally located near award-winning beaches, cultural attractions, Nathan Benderson Park, Mote SEA Aquarium, Whole Foods, Trader Joe’s, and the upcoming Sarasota Orchestra and Legacy Bike Trail. A rare opportunity to create your dream Florida home in an exceptional setting! 2016 tile roof and hurricane-rated garage door, 2017 pool resurfacing, two new A/C systems in 2025, above floodplain in flood zone X.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1988
  • 0.34 Acre Lot
  • $20/yr HOA
  • 2 Car Garage
  • 1 day on Market

Open House

  • November 15, 2026
    1:00pm - 4:00pm

This open house information was last updated on 11/12/2026 12:51PM

  • Bedrooms
    3
  • Bathrooms
    3 full · 1 half
  • Year Built
    1988
  • Stories
    1.0
  • Construction Materials
    Block
  • Foundation
    Slab
  • Garage Spaces
    2.0
  • Parking Features
    Attached
  • Living Area
    3000.0
  • Interior Features
    Cathedral Ceiling(s), Eat-in Kitchen, Walk-In Closet(s), Vaulted Ceiling(s), Wet Bar, High Ceilings
  • Appliances
    Dryer, Dishwasher, Electric Water Heater, Refrigerator, Washer, Disposal, Electric Cooktop
  • Flooring
    Tile, Carpet
  • Furnished
    Unfurnished
  • Pool Features
    Gunite, In Ground, Private
  • Cooling
    Central Air
  • Heating
    Central

  • Acres
    0.34
  • Utilities
    Natural Gas Available
  • Water
    Public


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Frequently Asked Questions

How do I schedule a tour of 4403 Highland Oaks Cir?

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 4403 Highland Oaks Cir.

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 4403 Highland Oaks Cir?

Click Ask a Question to talk with our team. You already know it is a 3 bed, 3 bath, listed for $825,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Sarasota, and can even get you in to see the property quickly.

Are there any upcoming open houses for this property?

Yes—an open house is scheduled for . Let us connect you with our local expert before you go so they can help you prepare questions, highlight key features, and arrange a private tour if that time doesn't work.

How much is the monthly mortgage payment for 4403 Highland Oaks Cir?

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 4403 Highland Oaks Cir at around $5,333. 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 4403 Highland Oaks Cir?

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 Sarasota 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 4403 Highland Oaks Cir?

In most cases, yes. Whether 4403 Highland Oaks Cir is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Sarasota'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 4403 Highland Oaks Cir?

We can handle that for you. Our preferred local agent specializes in residentials in Sarasota 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 $825,000 with 3,000 sqft of space—that comes out to approximately $275 per square foot.

How long has this property been on the market?

4403 Highland Oaks Cir was listed on November 11, 2026, which means it's been on the market for 1 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 1988, making it approximately 38 years old.

What is the lot size of this property?

4403 Highland Oaks Cir sits on a 0.34-acre lot, which is 14,810 square feet.

What are the property taxes for 4403 Highland Oaks Cir?

The most recent public record shows annual property taxes for 4403 Highland Oaks Cir were approximately $7,658. 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 $20 paid annually.

This covers access to community features including: Playground, Fitness Center, Pool, Storage, Tennis Court(s), Trail(s), Park, Spa/Hot Tub, Basketball Court, RV/Boat Storage, Security, Golf Course, Recreation Facilities.

Is 4403 Highland Oaks Cir 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. Copyright 2026, Stellar MLS. All rights reserved.

Last Updated: November 12, 2026 at 01:17PM | Source: Stellar MLS | MLS#: A4712607