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Jamie Deihl
REALTOR®
(719) 468-9744

2299 Via Tuscany, Winter Park, FL 32789

$2,295,000

60 Total Photos [Click to View All]

Property Description

Welcome to 2299 Via Tuscany, a remarkable 4-bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40-acre private lot, offers a blend of luxury and comfort. The property has seen recent updates in the kitchen and bathrooms and features a new architectural shingle roof (2023), Pebble-tech style pool finish and a manicured landscape. Inside, enjoy the elegance of solid hardwood and modern tile flooring, high ceilings, and two wood burning fireplaces. The chef's kitchen is equipped with premium appliances, including SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor boasts a secluded primary suite, a guest bedroom suite, and a study/library with closet and built-ins. Upstairs, find two additional bedrooms and a full bath. Modern amenities include zoned A/C, a new EV charger and epoxy flooring in the 2-car garage. Conveniently located near parks and the Winter Park Racquet Club, this home offers easy access to downtown Winter Park's shops, dining, and cultural venues, making it ideal for families and active lifestyles. This property also offers deeded lake access to the Winter Park Chain of Lakes by becoming a member of the Maitland Shores Lakefront Preservation Association for an annual fee. The access is very convenient and offers a private ramp to store and launch kayaks, canoes, etc. This location offers effortless access to schools, green parks, fitness centers/trails, cultural venues-an ideal blend of amenities, charm and location for any homebuyer.

2299 Via Tuscany | MLS# O6355858

This single family home located at 2299 Via Tuscany, Winter Park, FL 32789 is currently listed for sale with an asking price of $2,295,000. This property was built in 1953 and has 4 bedrooms and 3 full and 1 partial baths with 3986 sq. ft. Via Tuscany is located in the MAITLAND SHORES subdivision. Search MAITLAND SHORES real estate on jamiedeihl.watsonrealtycorp.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air, Zoned
Fenced: Yes
Garage: 2 car attached
Heating: Central
Home Style: Mid-Century Modern, Traditional
Lot Size: 0.40 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $26,034
Year Built: 1953
Square Feet: 3,986

Amenities

High Ceilings
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Split Bedroom
Stone Counters
Vaulted Ceiling(s)
Window Treatments
Awning(s)
Garden
Private Mailbox
Sidewalk

Feature Descriptions

Appliances: Dishwasher, Disposal, Electric Water Heater, Range Hood
Community Features: Park, Playground, Sidewalks, Tennis Court(s)
Days on Site: 126
Directions: From Palmer take Mayfield to Via Tuscany to home on left. Or from Horatio to Via Tuscany to home on right.
Exterior: Block
Fencing: Other, Wood
Fireplace: Family Room, Living Room, Wood Burning
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Tile, Wood
Foundation: Crawlspace, Slab
Home Warranty Y/N: No
Lot: Landscaped, Oversized Lot, Private, Sidewalk, Street Brick
Lot Dimensions: 0.4
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Side, Golf Cart Parking, Guest
Parking Notes: Circular Driveway, Driveway, Electric Vehicle Chargi
Patio/Porch: Covered, Front Porch, Patio
Pets Allowed: Yes
Pets Restrictions: Please check with City of Winter Park and Orange County Ordinances.
Pool: In Ground, Lighting, Other
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Septic Tank
Showing Instructions: Appointment Only, Listing Agent Must Accompany, ShowingTime
Special Sale Provisions: None
Special View Info: Water
Swimming Pool: Yes
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, Natural Gas Connected, Public, Water Connected
Water: Public
Water Access: Lake - Chain of Lakes
Water Access Y/N: Yes
Waterfront Features: Boat Ramp - Private
Zoning: R-1AA

Room Sizes

Dining Room: 24x12
Great Room: 24x16
Kitchen: 22x14
Florida Room: 25x11
Primary Bedroom: 23x14
Bedroom 2: 17x12
Family Room: 22x18
Bedroom 3: 15x11
Bedroom 4: 15x11
Utility Room: 14x8
Balcony/Porch/Lanai: 40x14

Local Schools

High School: Winter Park High
Middle School: Maitland Middle
Elementary School: Dommerich Elem

Listed By / Shown By

Listed By

Agency Name: CORCORAN PREMIER REALTY
Agency Contact: 407-965-1155

Shown By

Agent Name: Jamie Deihl
Agent Phone: (719) 468-9744
Agency Title: Watson Realty Corp., REALTORS ®

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Estimated Payment

$ 13,905.71 per month $11,066.84 Principal & Interest $2,169.50 Property Tax $669.38 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 03/10/2026. The listing information on this page last changed on 03/10/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 03/10/2026 12:42:09 AM EST) or GAMLS (last updated Mon 03/09/2026 11:14:58 PM EST) or Stellar MLS (last updated Tue 03/10/2026 12:29:11 AM EST) or SPC MLS (last updated Mon 03/09/2026 11:20:30 PM EST) or Martin MLS (last updated Mon 03/09/2026 11:38:19 PM EST) or Indian River MLS (last updated Mon 03/09/2026 11:30:27 PM EST) or Daytona MLS (last updated Mon 03/09/2026 11:36:51 PM EST) or Northeast Florida MLS (last updated Tue 03/10/2026 12:18:46 AM EST) or Beaches MLS (last updated Tue 03/10/2026 12:35:40 AM EST) or BORMLS (last updated Mon 03/09/2026 11:15:20 PM EST) or Golden Isles MLS (last updated Mon 03/09/2026 11:26:41 PM EST) or Amelia/Nassau MLS (last updated Mon 03/09/2026 11:25:21 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 03/09/2026 11:42:28 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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