1166 OAKS BOULEVARD, Winter Park, FL, 32789 | $1,590,000

Under contract-accepting backup offers. HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-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

Features

  • Rooms: 10
  • Bedrooms: 4
  • Baths: 3 full / 1 half
  • Laundry: Inside, Laundry Room
  • Style: Custom
  • Year Built: 2018
  • Garage: 2-car Driveway, Garage Faces Side
  • Heating: Central
  • Cooling: Central Air
  • Approx Sq. Feet: 2,860
  • Acreage: 0.18
  • Est. Taxes: $21,866
  • Lot Desc: Corner Lot, City Lot, Landscaped, Near Public Transit, Sidewalk
  • Elem. School: Lakemont Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High
  • Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener
  • MLS#: O6341707
  • Days on Market: 153 days
  • Website: https://www.raveis.com
    /eprop/O6341707/1166oaksboulevard_winterpark_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 3/1/2026 2:26:28 AM)

William Raveis Family of Services

Our family of companies partner in delivering quality services in a one-stop-shopping environment. Together, we integrate the most comprehensive real estate, mortgage and insurance services available to fulfill your specific real estate needs.

The One TeamSales Associates

OneandCompany@raveis.com

Our family of companies offer our clients a new level of full-service real estate. We shall:

  • Market your home to realize a quick sale at the best possible price
  • Place up to 20+ photos of your home on our website, raveis.com
  • Provide frequent communication and tracking reports showing the Internet views your home received on raveis.com
  • Showcase your home on raveis.com with a larger and more prominent format
  • Give you the full resources and strength of William Raveis Real Estate, Mortgage & Insurance and our cutting-edge technology

To learn more about our credentials, visit raveis.com today.

Kevin DeTullioVP, Mortgage Banker / Production Manager, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 1724767

203.305.5736

Kevin.DeTullio@Raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
  • Is in constant contact with a full processing, underwriting, and closing staff to ensure an efficient transaction

Brian SkellyVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 793093

203.415.2989

Brian.Skelly@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
  • Is in constant contact with a full processing, underwriting, and closing staff to ensure an efficient transaction

Diane PadelliInsurance Sales Director, William Raveis Insurance

203.444.0494

Diane.Padelli@raveis.com

Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
  • Partners with major insurance companies including Chubb, Kemper Unitrin, The Hartford, Progressive,
    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

1166 OAKS BOULEVARD, Winter Park, FL, 32789

$1,590,000

The One Team

Sales Associates

William Raveis Real Estate

Phone: 860.850.0500

OneandCompany@raveis.com

Kevin DeTullio

VP, Mortgage Banker / Production Manager

William Raveis Mortgage, LLC

Phone: 203.305.5736

Kevin.DeTullio@Raveis.com

NMLS Mortgage Loan Originator ID 1724767

Brian Skelly

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 203.415.2989

Brian.Skelly@raveis.com

NMLS Mortgage Loan Originator ID 793093

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $1,272,000 $1,272,000 $1,272,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.250% 5.750% 5.500%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.046% 5.846% 5.700%
Monthly Tax Payment $1,822 $1,822 $1,822
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $7,024 $7,423 $10,393
Total Monthly Payment $8,971 $9,370 $12,340

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.