14343 TILDEN ROAD, Winter Garden, FL, 34787 | $998,800

Under contract-accepting backup offers. This is a truly rare find—a sprawling, MULTIGENERATIONAL COMPOUND on nearly an acre with no rear neighbors. Offering two homes for the price of one, this well-maintained property features a massive screened-in pool and spa, creating the ultimate private retreat.

The main residence boasts FIVE bedrooms and 2. 5 bathrooms, with a spacious formal living and dining area, plus a large family room complete with a wood-burning fireplace. Connected by a covered breezeway, the entirely separate one-bedroom, one-bathroom home offers its own full kitchen, great room, and private one-car garage. This unique setup is perfect for aging parents, onsite caretakers, or adult children needing their own space with a private entrance. It also presents an excellent rental opportunity to help offset living expenses.

The expansive circular driveway and oversized parking area provide ample room for RVs, boats, or work vehicles—all with no HOA restrictions. 3 car side entry garage and additional 1 car garage for lawn equipment and storage, you never will need anything offsite again ! The meticulously manicured grounds feature mature landscaping, a huge covered lanai, an oversized screened-in pool & spa, and a party deck with a dedicated cabana bath, ensuring an incredible outdoor living experience. Relax by the waterfall and stream at rear of property and enjoy a Florida evening anytime you desire.

Adding even more value, the seller will pay off the whole-home solar system at closing, significantly reducing electric costs, while the well water system eliminates monthly water bills. This prime location is just minutes from extensive shopping, dining options, plus highly sought-after K-12 school district. Several private school campuses short distance from your front door. With Disney less than 15 minutes away and easy access to the 429 Expressway, Florida’s Turnpike, and the 408 Expressway, commuting is effortless. Zoned A-1, this property offers endless possibilities at an unbeatable price. Act fast—this exceptional home won’t last long!

ROOF IS 2022, AC UNITS 2017, NEWER WATER HEATERS and everything has been meticulously maintained. ZONED A-1 so chickens are allowed !!!

Features

  • Rooms: 15
  • Bedrooms: 5
  • Baths: 3 full / 1 half
  • Laundry: Inside
  • Year Built: 1984
  • Garage: 4-car Circular Driveway, Garage Faces Side, Parking Pad, RV Parking, Split Garage, Workshop in Garage
  • Heating: Central, Electric
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 4,464
  • Acreage: 0.88
  • Est. Taxes: $6,475
  • Lot Desc: Conservation Area, Landscaped, Oversized Lot
  • View: Trees/Woods
  • Elem. School: Lake Whitney Elem
  • Middle School: SunRidge Middle
  • High School: West Orange High
  • Pool: Gunite, In Ground, Screen Enclosure
  • Pet Policy: Yes
  • Appliances: Dishwasher, Microwave, Range, Refrigerator, Washer
  • MLS#: O6295258
  • Days on Market: 9 days
  • Website: https://www.raveis.com
    /prop/O6295258/14343tildenroad_wintergarden_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 5/5/2025 12:02:09 PM)

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NMLS Mortgage Loan Originator ID 6314

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14343 TILDEN ROAD, Winter Garden, FL, 34787

$998,800

Christine Turano

Licensed Salesperson

William Raveis Real Estate

Phone: 781.589.4918

Christine.Turano@raveis.com

Bob Flynn

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 508.944.8218

Bob.Flynn@raveis.com

NMLS Mortgage Loan Originator ID 6314

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $799,040 $799,040 $799,040
Term 360 months 360 months 180 months
Initial Interest Rate** 6.125% 6.500% 6.375%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.848% 6.613% 6.560%
Monthly Tax Payment $540 $540 $540
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $4,855 $5,050 $6,906
Total Monthly Payment $5,487 $5,682 $7,538

* 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.