$3,250,000
5583 Jessamine Lane
Orlando, FL 32839
Listing updated: June 20, 2026 at 12:11 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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!!!
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveJun 20, 2026
- Listed$3,250,000Jun 20, 2026
- Price increased$3,250,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Lake Jessamine
- County
- Orange
- Year built
- 1961
- Living area
- 5,283 sq ft
- Price/sq ft
- $615
- Building area
- 6,403 sq ft (Public Records)
- Lot size
- 116,329 sq ft
- Lot category
- 2 to less than 5
- Flood zone
- X and AE
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $13,704 (2025)
- Parcel #
- 14-23-29-0000-00-054
- Zoning
- R-1AA
- MLS #
- O6414379
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Interior Details
- Bedrooms
- 5
- Full bathrooms
- 4
- Flooring
- Laminate, Tile
- Appliances
- Dishwasher, Dryer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Interior features
- Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Laundry
- Inside
- Stories / Levels
- Two
- Direction faces
- West
- Fireplace
- Yes
- In-law suite
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Boat, Guest, Oversized
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer to verify leasing restrictions with county.
- Approval process
- Buyer to verify leasing restrictions with county.
Exterior & Construction
- Construction materials
- Block, Concrete
- Roof
- Built-Up
- Foundation
- Slab
- Pool
- Private pool
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Canal/Lake For Irrigation, Public
- Utilities
- Cable Available, Electricity Available, Natural Gas Available, Water Available
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 19.1x27.9 |
| Dinette | First | 15.9x14.1 |
| Family Room | First | 10.6x17.7 |
| Dining Room | First | 29.6x19.3 |
| Kitchen | First | 16.1x17.7 |
| Primary Bedroom | First | 17.1x16.2 |
| Primary Bathroom | First | 13.2x11.3 |
| Laundry | First | 10.2x11.2 |
| Bathroom 2 | First | 5.3x8.2 |
| Bedroom 2 | Second | 14.9x12.5 |
| Bedroom 3 | Second | 118x15.4 |
| Office | Second | 10.2x8.5 |
| Bathroom 3 | Second | 10.5x11.2 |
| Balcony/Porch/Lanai | First | 29.8x13.8 |
Listing Details
- Listing date
- 2026-06-04
- On market date
- 2026-06-20
- Original list price
- $3,250,000
- Occupant type
- Owner
- MLS area
- 32839 - Orlando/Edgewood/Pinecastle
- Listing AOR
- Lake and Sumter
- Status changed
- 2026-06-20
- Tax legal description
- FROM CENTER OF SEC RUN E 318.9 FT FOR A POB TH E TO SE COR OF SW1/4 OF NE1/4 N 1 10 FT W TO A PT W OF POB S 110 FT TO POB IN SEC 14-23-29
Flood risk
See FEMA for this zone’s designation and insurance requirements.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
Heading east on I4, take exit 80 turning right onto 441. Turn left onto Holden Ave. Turn right onto Jessamine Ln. Turn left to stay on Jessamine Ln. It's at the end of the street.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
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.
Based on information submitted to the MLS GRID as of June 20, 2026 at 12:11 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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