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155 Oakleigh Lane, MAITLAND


4 Beds
6 Baths
6,926 Sqft
2.24 Acres
3 Garages

One or more photo(s) has been virtually staged. Seller says SELL! PRICE REDUCTION on the shores of Lk Maitland & navigable on Winter Park Chain of Lakes, this CUSTOM Classic Georgian estate influenced by the old Georgia Governor's mansion! Over 160 Ft of Lake Maitland frontage & private Gated entrance, its own circular courtyard and water feature this oasis epitomizes Luxury Lakefront Living! Just shy of 7,000' of living space/over 10,000' of total area, enjoy 4 bedrooms/4 Full Baths and half baths for entertaining ease. Stunning DBL door entry to a magnificent 2 story Grand room which is second in importance only to the Water Views experienced from ALL Rooms. Functional and filled w/natural light, a Multi-Generational split floor plan which has 2 Master Suites on the first floor. Your special guest is accomodated in Master#2 on the opposite side of the home w/en suite bath & custom walk in closet.Upon entering you are greeted by REAL Hardwood flooring and Marble which showcases the expansive 2 Story Grand Room with coffered ceiling. A story book setting showcased by three sets of French doors w/arched trim draws your eyes to the majestic cypress trees, pool and lake beyond. Main Master BR has many features, its own fireplace, custom builtins, spa like master bath and 2nd circular staircase leading to a connected office above. Filled w/custom paneled hidden storage, a perfect getaway for the busy executive. Also on the first level a charming two story living room complete with marble fireplace & chandelier, an extra “flex” room (now used for exercising), Kitchen, Breakfast Nook, Laundry (with extensive cabinetry) and 2nd Master all on the main floor. Ascend the arched staircase to the two oversized additional bedrooms complete with their own baths. Upstairs stroll across one of the balconies to the loft which can function as a game room or home theatre, note the adjacent reading enclave and office access. These dual balconies span the width of the Grand room allowing you to traverse from one side of the home to the other all while enjoying the lake views. Throughout the home you will find customized built-ins with the craftsmanship of a master carpenter. The Molding and Trim work will amaze you, arched doorways and windows, 5 1/4” baseboards, trimmed columns and CROWN almost everywhere. You feel like you have stepped back in time to when pride of workmanship was exhibited with every building feature. Positioned with a Northern front entrance which takes advantage of natural light pouring through the arched windows and doorways from morning until sunset. Step outside onto the oversized terrace and experience an outdoor space that can handle any size party. Private Pool and deck flanked by Keystone Balustrades provide an area for water fun, sunning and a staircase leads to an abundant rear lawn and play space with an easy stroll to lake front activities. Private covered dock gives you direct access to all six of the Chains Lakes. Bring your favorite water toy and relax, it is safe and secure in the dock with new aluminum cradle boat hoist and electric screen enclosure. Combine that with ALL NEW Windows, new water softener, wallpaper removal and retexturing/paint of interior, new PEX piping & a Roof that has been updated with all new concrete pointe and all tiles which needed attention due to cracking or slippage have been repaired/replaced all in 21’-22’. TOTALLY UNIQUE this lakefront estate is a GEM and one of a kind… it just awaits your personal touches to create your own paradise.

155 Oakleigh Lane is in MAITLAND, FL. This Residential property for sale is currently being offered at $3,990,000. Built in 1959 this 4 bedroom, 6.00 bathroom Orange Residential property has been listed on for 161 days. 155 Oakleigh Lane is priced at $576.09 Per Square Foot, and is situated on 2.24 acres of land. Please contact your local Realtor® for more information on 155 Oakleigh Lane, MAITLAND, FL 32751. Property Listing Reference: MLS number: O6022997.

Essential Information
MLS® #O6022997
Full Baths4
Half Baths2
Square Footage6,926
Year Built1959
Sub-TypeSingle Family Residence
StyleCustom, Other, Traditional
Community Information
Address155 Oakleigh Lane
AreaMaitland / Eatonville
SubdivisionUNDER OAKS
Zip Code32751
# of Garages3
ViewTrees/Woods, Water
Is WaterfrontYes
Has PoolYes

Boat, Curb Parking, Driveway, Garage Door Opener, Ground Level, Guest, Off Street, On Street, Oversized

HeatingCentral, Electric, Zoned
CoolingCentral Air
# of Stories2
Interior Features

Built-in Features, Ceiling Fans(s), Coffered Ceiling(s), Crown Molding, High Ceilings, Master Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Wet Bar


Built-In Oven, Convection Oven, Dishwasher, Disposal, Exhaust Fan, Refrigerator, Water Softener


Gas, Living Room, Master Bedroom, Wood Burning

Lot DescriptionLevel, Oversized Lot, Paved
Exterior Features

Fence, French Doors, Irrigation System, Lighting, Other, Rain Gutters

School Information
ElementaryLake Sybelia Elem
MiddleMaitland Middle
HighWinter Park High
Other Information
Date ListedMay 9th, 2022
Days on Market161
Listing Details
Property History
Price Reduced from $4,199,000 to $3,990,000
Price Reduced from $4,499,000 to $4,199,000
Price Reduced from $4,800,000 to $4,499,000
Price Reduced from $5,200,000 to $4,800,000

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Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on December 1st, 2022 at 10:03pm EST.