1166 OAKS BOULEVARD

$ 1,799,000
1166 OAKS BOULEVARD, Winter Park
  • Updated On:
  • September 16, 2025
  • Property Size
  • 2,860 ft2
  • Bathrooms
  • 3.5
  • Bedrooms
  • 4
  • Rooms
  • 10

Description

Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space.

Relax on the charming front covered porch, the perfect spot to enjoy your morning coffee. Step inside to find meticulous attention to detail—from stunning wide white oak floors to exquisite custom millwork and soaring ceilings that create an airy, welcoming atmosphere.

The chef-inspired kitchen is the heart of the home, featuring an abundance of custom solid-wood cabinets, gleaming quartz countertops, and a large island with seating for four. A generous walk-in pantry with custom shelving and top-of-the-line Thermador stainless steel appliances—including a 6-burner gas stove, double oven, and deep farm sink—make meal preparation and entertaining effortless. Adjacent to the kitchen, a charming dining area is perfect for memorable dinners, while the adjoining family room boasts a soaring cathedral ceiling, a natural gas fireplace with a custom stone mantel, and large windows that flood the space with natural light.

A cozy private den offers an ideal retreat for work or relaxation. On the opposite side of the first floor, you’ll find a guest suite with a private bath, two additional bedrooms with custom closets, a stylish full bath, and a laundry room with ample storage and a utility sink. The spacious mudroom, accessible from the two-car garage, provides practical storage with built-in cabinets and hooks.

Upstairs, the luxurious primary suite features a spa-inspired bathroom with double sinks, custom Restoration Hardware cabinetry, elegant lighting, and a large walk-in shower. A peaceful sitting area and a walk-in closet with custom shelving create a perfect private retreat. Additionally, an upstairs loft offers versatile space ideal for a home office, gym, or additional quiet area.

Outside, enjoy a private backyard oasis designed for relaxation and entertainment. Highlights include a “Michael Phelps Chilly Goat” hot/cold tub combo, outdoor TV, and speakers—creating your personal weekend paradise.

Additional amenities include a large two-car garage, solid-core doors, crown molding, wide base moldings, dual tankless water heaters, fully-owned solar panels (reducing energy costs), a water softener and purifier, new exterior paint (2023), professionally installed closet shelving (2023), and professionally landscaped gardens.

Flooded with natural light and warmth, this exceptional home offers a cozy yet elegant atmosphere. Zoned for top-tier schools—including Winter Park High School—and conveniently located near Lake Highland, Trinity Prep, the Winter Park YMCA, Racquet Club, and Interlachen Country Club, it’s ideal for a vibrant Florida lifestyle. Walkable to Winter Park’s renowned shopping and dining destination, don’t miss the opportunity to make this exquisite property your new home! AVAILABLE BY APPOINTMENT ONLY

Listing Id: O6341707
Price: $ 1,799,000
Property Size: 2,860 ft2
Property Lot Size: 0 ft2
Rooms: 10
Bedrooms: 4
Bathrooms: 3.5
Architectural Style: Custom
Bathrooms Full: 3
Bathrooms Half: 1
Modification Timestamp: September 15, 2025 at 01:55pm
Building Area Total: 3556
Construction Materials: Block, Stucco
Cooling: Central Air
CoveredSpaces: 2
CumulativeDaysOnMarket: 10
DaysOnMarket: 10
DirectionFaces: West
Directions: Park Ave North, then left onto Oaks Boulevard, property on corner lot.
Electric: Photovoltaics Seller Owned
ElementarySchool: Lakemont Elem
Fencing: Masonry
FireplaceFeatures: Family Room, Gas
Flooring: Porcelain Tile, Hardwood
FoundationDetails: Slab
Furnished: Unfurnished
GarageSpaces: 2
Heating: Central
HighSchool: Winter Park High
IDXParticipationYN: 1
InternetAddressDisplayYN: 1
InternetAutomatedValuationDisplayYN: 1
InternetConsumerCommentYN: 1
InternetEntireListingDisplayYN: 1
LaundryFeatures: Inside, Laundry Room
LeaseConsideredYN: 1
Levels: Two
List AOR: Orlando Regional
List Agent AOR: Orlando Regional
List Agent Email: kkelly32789@gmail.com
List Agent Full Name: Kevin Kelly
List Agent MlsId: 609023317
List OfficeKey: 3ba92dbd3ff195cd92f980477ff44e8b
ListOfficeMlsId: 51588
ListOfficeName: FANNIE HILLMAN & ASSOCIATES
ListOfficePhone: 407-644-1234
Listing Terms: Cash, Conventional
Living Area Source: Public Records
Living Area Units: Square Feet
Lot Features: Corner Lot, City Lot, Landscaped, Near Public Transit, Sidewalk
LotSizeArea: 7918
LotSizeSquareFeet: 7918
LotSizeUnits: Square Feet
MLSAreaMajor: 32789 - Winter Park
MiddleOrJuniorSchool: Maitland Middle
MlsStatus: Active
ModificationTimestamp: September 15, 2025 at 01:47pm
OnMarketDate: 2025-09-05
Originating System Name: Stellar MLS
Ownership: Fee Simple
Parcel Number: 062230210804010
Parking Features: Driveway, Garage Faces Side
Roof: Shingle
Security Features: Closed Circuit Camera(s), Fire Alarm, Security System, Smoke Detector(s)
Sewer: Public Sewer
Spa Features: Above Ground, Heated
State Or Province: FL
Status Change Timestamp: September 5, 2025 at 04:26pm
Street Name: OAKS
Street Number: 1166
Street Number Numeric: 1166
Street Suffix: BOULEVARD
Tax Annual Amount: 21866
Tax Block: D
Tax Book Number: L-133
Tax Year: 2025
Utilities: Electricity Connected, Natural Gas Connected, Propane, Sewer Connected, Street Lights
Water Source: Public
Window Features: Blinds, Drapes, Rods, Shutters
Year Built: 2018
Zoning: R-1A
FeedTypes: IDX
Source System Key: 769112787
Originating System Key: stellar
OriginalEntryTimestamp: September 5, 2025 at 04:26pm
OriginalListPrice: 1799000

Address: 1166 OAKS BOULEVARD
State/County:
Zip: 32789
Country: United States

Outdoor Details
Garage Attached
Other Features
Built-In Oven
Cathedral Ceiling(s)
Ceiling Fan(s)
Convection Oven
Cooktop
Crown Molding
Dishwasher
Disposal
Dryer
Has Cooling System
Has Fireplace
Has Garage
Has Heating System
High Ceilings
Irrigation System
Kitchen/Family Room Combo
Lighting
Open Parking
PrimaryBedroom Upstairs
Private Mailbox
Rain Gutters
Range Hood
Refrigerator
Sidewalk
Solid Surface Counters
Solid Wood Cabinets
Spa
Split Bedroom
Tankless Water Heater
Walk-In Closet(s)
Washer
Water Softener
Window Treatments

Education

Rollins College
(1.33 miles)Rollins College
F.I.R.S.T. Institute
(2.76 miles)F.I.R.S.T. Institute

Health & Medical

Whole Family Healthcare
(0.21 miles)Whole Family Healthcare
Orlando Health Women's Pavillion- Winter Park
(1.1 miles)Orlando Health Women's Pavillion- Winter Park

Shopping

Park Avenue Shopping Area
(1.06 miles)Park Avenue Shopping Area
Winter Park Village
(0.53 miles)Winter Park Village
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$ 9,223.83
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
$ 6,975.08

Fri 26 Sep
Sat 27 Sep
Sun 28 Sep
Mon 29 Sep
Tue 30 Sep
Wed 01 Oct
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DISCLAIMER TEXT: 1166 OAKS BOULEVARD | 519207 © 2023 All material presented here is for information purposes only.

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Janet Richmond