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Welcome to 2423 Via Sienna, gracefully positioned on a quiet cul-de-sac in the heart of Winter Park. This charming, established enclave is just moments from the Winter Park Racquet Club, Phelps Park, the YMCA, and the renowned boutiques and dining of Park Avenue. This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with timeless finishes and thoughtful design throughout. Upon entry, soaring ceilings and expansive windows create a light-filled, open interior ideal for both everyday living and elegant entertaining. The living and dining spaces are accented by tongue-and-groove ceilings, a gas fireplace, and bespoke built-ins, flowing seamlessly into a sun-drenched sunroom destined to become a favorite retreat. Chicago brick flooring, fixed glass windows, and accordion doors frame serene views of the private backyard oasis. The gourmet kitchen is both stunning and functional, featuring custom soft-close cabinetry, quartz countertops, floating shelving, exquisite millwork, and a full suite of Thermador appliances. A generous 4.9-by-10-foot island with storage on both sides anchors the space, complemented by a cozy breakfast nook and built-in bar. French doors provide effortless indoor-outdoor connection. Just beyond, a thoughtfully designed mudroom and pool bath with Chicago brick flooring offers convenient access to the pool area. A spacious first-floor bedroom"”ideal as a guest suite, office, or den"”along with a full bath completes the main level. Upstairs, the luxurious primary suite offers a private sanctuary with dual walk-in closets and a spa-inspired bath featuring separate vanities, soaking tub, steam shower, and private water closet. Two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas for comfort and privacy. The expansive laundry room adds charm and practicality with a retro sink, built-in ironing board, and abundant storage. The tranquil backyard is designed for quintessential Florida living, showcasing a beautifully resurfaced pool surrounded by lush landscaping"”perfect for entertaining or quiet relaxation. Additional highlights include engineered hardwood flooring throughout, designer lighting, a wrought-iron staircase, new baseboards and crown molding, fresh interior and exterior paint, newer roof (2023), two HVAC systems (2022 & 2023), and an oversized two-car garage with dedicated workshop space. Located within highly regarded A-rated schools.
| DAYS ON MARKET | 1 | LAST UPDATED | 3/6/2026 |
|---|---|---|---|
| TRACT | CINNAMON SHORES | YEAR BUILT | 1990 |
| COMMUNITY | 32789 - Winter Park | GARAGE SPACES | 2.0 |
| COUNTY | Orange | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | Dommerich Elem |
|---|---|
| Jr. High School | Maitland Middle |
| High School | Winter Park High |
| ADDITIONAL DETAILS | |
| AIR | Central Air, Zoned |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Bar Fridge, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Range, Refrigerator, Washer |
| AREA | 32789 - Winter Park |
| CONSTRUCTION | Brick, HardiPlank Type |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central, Propane, Zoned |
| INTERIOR | Built-in Features, Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s) |
| LOT | 0.3 acre(s) |
| LOT DESCRIPTION | Cul-de-sac, Landscaped, Paved |
| PARKING | Driveway, Garage Door Opener, Oversized, Attached |
| POOL | Yes |
| POOL DESCRIPTION | Gunite, In Ground, Private |
| SEWER | Public Sewer |
| STORIES | 2 |
| SUBDIVISION | CINNAMON SHORES |
| TAXES | 18918 |
| UTILITIES | Cable Available, Electricity Connected, Propane, Sewer Connected, Water Connected |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Wendy Williams Crumit, FANNIE HILLMAN & ASSOCIATES, 407-644-1234
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 3/6/26 6:01 PM PST.
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