CENTURY 21 Edge
$3,250,0005 bd4 ba5,283 sqft$615 /sqft≈$20,058 /mo all-in ↓

5583 JESSAMINE LANE, ORLANDO, FL, 32839

Active122 days on marketListed Jun 20, 2026MLS #O6414379

WaterfrontPrivate poolSingle Family ResidenceLAKE JESSAMINE

About this home

5583 JESSAMINE LANE

Welcome to your new dream home! Experience the rare blend of luxury, privacy, and lakefront living with this extraordinary pool home on Lake Jessamine, situated on 2.67 acres with NO HOA. Tucked away on a cul-de-sac behind a gated entry, this remarkable property offers the feeling of a private retreat while still placing you in the heart of Orlando. A long driveway and manicured landscaping create a stunning first impression as you arrive. A spacious two-car garage awaits at the end of the driveway, as well as an in-law suite complete with a kitchenette, to provide the perfect setup for guests or older relatives. Beyond the entry, the home immediately welcomes you with soaring ceilings, dramatic windows flooding the space with natural light, and elegant finishes throughout. A striking accent wall in the foyer sets the tone, while a peaceful koi pond and sanctuary area create the perfect setting for quiet mornings and tranquil reflection. The cozy living room centers around a beautiful fireplace, creating a warm atmosphere for evenings spent with loved ones. Remodeled in 2019 and with new plumbing in 2026, the kitchen is truly the heart of the home and a dream for any culinary enthusiast. Thoughtfully designed with a wraparound breakfast bar, oversized island, crown-molded cabinetry, subway tile backsplash, and top-of-the-line appliances, every detail was curated for both beauty and functionality. A gas range with custom hood and pot filler, spacious walk-in pantry, and abundant storage make entertaining and every day living feel equally effortless. Just behind the kitchen, a wine storage wall adds a elevated design feature perfect for showcasing your collection.The primary suite, located on the first floor, provides private access to the outdoor living area and a spacious walk-in closet with custom storage(2026) and plantation shutters that create the perfect setting to get ready for the day in. The en suite bathroom features a gorgeous freestanding tub, oversized walk-in shower with rain shower head, and a dual sink vanity. Upstairs, a breathtaking floating staircase with floor-to-ceiling windows leads to additional bedrooms and a home office space, ideal for remote work or creative pursuits. Additional bedrooms provide plenty of storage, natural light, and space so everyone in the family can feel at home. Step outside and discover your own private lakeside paradise! The resort-style pool and spa overlook Lake Jessamine, creating an unforgettable backdrop that you'll never grow tired of. A covered patio provides the perfect setting for al fresco dining, while the fenced backyard offers room for four-legged friends and play. Head out onto the lake from your private dock and covered boat lift for endless days on the water. Recent upgrades provide peace of mind, including a new roof in 2019, new exterior & interior paint in 2026, updated electrical and plumbing systems in 2026, and a recently upgraded seawall. Just minutes from I-4, you’ll have quick access to downtown, Orlando International Airport, theme parks, and world-class shopping and dining destinations including Mall at Millenia, Florida Mall, and Costco. This property is more than a home, it’s a private lakefront estate offering luxury, convenience, and the ultimate Florida lifestyle all in one extraordinary setting. Don't miss out on this amazing, well cared for home in an ideal location, schedule your private showing TODAY!!!

Facts & features

The home at a glance

5

Bedrooms

4

Bathrooms

5,283

Sqft

2.67 ac

Lot size

2

Garage

1961

Year built

Two

Levels

$615

Per sqft

Private poolWaterfrontFireplaceWater viewPets allowed

Inside

FlooringLaminate · Tile
AppliancesDishwasher · Dryer · Ice Maker · Microwave · Range · Range Hood · Refrigerator · Washer · Wine Refrigerator
InteriorBuilt-in Features · Cathedral Ceiling(s) · Ceiling Fan(s) · Crown Molding · Eating Space In Kitchen · High Ceilings · Living Room/Dining Room Combo · Open Floorplan · Primary Bedroom Main Floor · Skylight(s) · Split Bedroom · Stone Counters · Thermostat · Vaulted Ceiling(s) · Walk-In Closet(s)
LaundryInside
CoolingCentral Air
HeatingCentral

Outside & construction

RoofBuilt-Up
ConstructionBlock · Concrete
FoundationSlab
ViewWater
FacesWest
ParkingBoat · Guest · Oversized
ExteriorIrrigation System

Community & fees

Taxes (2025)$13,704/yr
PetsYes

Utilities & systems

UtilitiesCable Available · Electricity Available · Natural Gas Available · Water Available
WaterCanal/Lake For Irrigation · Public

The numbers

What it really costs

Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.

$20,058 /mo · 10% down Conventional, 30-yr fixed at 6%

Principal & interest$17,537
PMI (est., until 20% equity)$1,219
Property tax — 2025 actual bill$1,142
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $325,000Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.

These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $325,000
Interest rate6.00%
Loan term

Estimated payment

$20,058/mo

Principal & interest$17,537
PMI (est., until 20% equity)$1,219
Property taxes (actual bill)$1,142
Est. insurance$160

Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.

Value check

Is the price right?

The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.

List $3.3M
$1.7MedgeAI estimate $1,987,038 · range $1.8M–$2.2M$3.4M

vs edgeAI estimate

+63.6%

$/sqft vs Orlando actives

$615 vs $237

Days on market

122 vs 61 typical

Where $615/sqft sits among the 400 Orlando actives

159
139
65
12
9
16 · this home
$135–215$215–295$295–375$375–455$455–535$535+

The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.

Where it sits

Inside Holden Avenue

Drive times from this address

Downtown Orlando≈ 10 min
Orlando Int’l Airport (MCO)≈ 17 min
Universal Orlando≈ 20 min
Walt Disney World≈ 30 min

Estimated driving times, typical traffic. Data © OpenStreetMap contributors.

Get to know Orlando. See the full Orlando guide →

Holden Avenue — neighborhood snapshot

Population

4,167

Median age

43

Median income

$63,123

Median home value

$338,260

Avg household

3

Households w/ children

414

For the school run

Orange County School District

ElementaryPineloch Elementary★★★★★
HighOak Ridge High★★★★★
MiddleMemorial Middle★★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Orlando market

Seller’s marketLeans seller — 4.7 months of inventoryBuyer’s market

$400K → $395K

Orlando median sold, yr/yr

97.1%

Sale-to-list ratio (12 mo)

210 of 400

Orlando actives have cut their price

Median sold price, Orlando, trailing 36 months (3-month rolling) · live MLS data.

This home is listed 3728% above the ORLANDO 32839 median. See the full Orlando market guide →

Paper trail

This home's history

Jun 20, 2026Listed at $3,250,000 · 122 days on market since
1961Built · LAKE JESSAMINE

Reality check

What actually sold near 5583 JESSAMINE LANE

Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.

5143 CRANES POINT COURTSold · May ’26

$3,000,000

5143 CRANES POINT COURT

5 bd · 4.5 ba · 5,168 sqft · $580/sqft · 12 DOM

5475 LAKE JESSAMINE DRIVESold · Jul ’26

$1,575,000

5475 LAKE JESSAMINE DRIVE

4 bd · 3.5 ba · 4,388 sqft · $359/sqft · 18 DOM

5339 OAK TERRACE DRIVESold · Jul ’26

$1,250,000

5339 OAK TERRACE DRIVE

4 bd · 4 ba · 4,157 sqft · $301/sqft · 0 DOM

Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.

Your home team

The pros in your corner

Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Shawn Headley

Your agent

Shawn Headley

Realtor · CENTURY 21 Edge

Tours, negotiation, and every question about 5583 JESSAMINE LANE — start here.

Andrew Acosta

Your lender

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Pre-approval, rates, and the real monthly number for 5583 JESSAMINE LANE — before you fall in love.

See it in person

Schedule a tour

Live availability from Shawn's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.

Straight answers

5583 JESSAMINE LANE FAQs

What would the monthly payment be for 5583 JESSAMINE LANE?+

With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $20,058/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.

What are the property taxes on 5583 JESSAMINE LANE?+

The most recent tax bill on record (2025) was $13,704. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.

Are pets allowed at 5583 JESSAMINE LANE?+

The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.

How does the price compare to other homes in Orlando?+

At $3,250,000, this home is listed about 755% above the Orlando median of $379,900. The market section on this page shows how the area is trending.

Which schools are assigned to 5583 JESSAMINE LANE?+

Pineloch Elementary (elementary), Oak Ridge High (high), Memorial Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.

The brief

Three things that matter here

01Positioned at the premium end

$3,250,000 runs 3728% above the ORLANDO 32839 median — but at 5,283 sqft it's also nearly 3 times the size of the typical Orlando listing.

02Waterfront living

This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.

03Time on market is leverage

122 days on market against a Orlando median of 61 — sellers in this position are usually ready to negotiate.

Listing courtesy of DENIZ REALTY PARTNERS LLC · Joseph Davis. MLS #O6414379.

IDX information is 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.

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