160 W ROCKWOOD WAY, Winter Park, Orange, Residential

160 W ROCKWOOD WAY

MLS# O643772226 days on marketUpdated September 11, 2026 3:46 am

$ 846 / sqft

$ 3,395,000

Overview

UpdatedSeptember 11, 2026 3:46 am
MLS #O6437722
Bedrooms5
Bathrooms5.5
Size4,015 ft²
Year Built2017
Garage2

Description

Perfectly positioned in the heart of Old Winter Park, the quaint Forrest Hills neighborhood is lined with charming cobblestone streets that wind around Lake Sue. This custom home, designed and built by the celebrated Z-Properties, pairs timeless New England character with modern sensibilities. Every detail is intentional in this iconic design—nothing has been sacrificed.

Situated on a 0.25-acre lot, a private courtyard welcomes you through a solid wood arched gate and along a slate pathway to the front door. Cedar shake detailing, a block wall surrounding the property, and classic architectural elements add to the style and charm of this Hamptons-inspired home. The residence features five bedrooms and five-and-a-half baths, including a first-floor primary suite and a dedicated guest house. Spanning 4,018 square feet, the home offers a thoughtfully designed floor plan with the primary suite on the first floor, while additional bedrooms and flexible living space are located upstairs. The guest house includes two ensuite bedrooms and a living room with vaulted ceilings and exposed wood beam details.

Inside, a generous foyer welcomes you, where neutral-hued pine floors anchor the home and set a warm, inviting tone. Volume ceilings enhance the open floor plan, while an architectural skylight with transom windows floods the living room with natural light. A wall of custom built-in storage ensures everything has its place. The transition to the dining room is framed by backlit glass built-ins, while the centerpiece is a custom buffet accented by designer wall coverings and elegant lighting, creating a truly stunning entertaining space.
Glass doors open to a covered lanai with tongue and groove ceiling a summer kitchen with pellet grill and bar seating, all overlooking the sparkling pool. A turf grass surround minimizes maintenance while providing year-round beauty. The lanai connects to separate guest house featuring 2 ensuite bedrooms and living space. The center courtyard is intimate, offering incredible privacy for this special place.

The kitchen is beautifully appointed with paneled appliances, a Thermador chef's range with pot filler, and a stunning marble center island with counter seating. A butcher block work surface provides additional prep space, while a floor-to-ceiling wall of paneled cabinetry maximizes storage and organization. A breezeway drop zone with a built-in desk creates a functional everyday workspace, complemented by a separate laundry room.

This home doesn't miss a beat. With an exceptional location, thoughtfully considered design, and award-winning builder, it offers the very best of Winter Park living. Zoned for Audubon K–8 and Winter Park High School, nationally recognized for its International Baccalaureate program, the home is just minutes from Rollins College, downtown Orlando, Park Avenue, and the area's beautiful parks. This exceptional property perfectly captures the timeless lifestyle that makes Winter Park so special.

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Interior

  • AppliancesDishwasher, Disposal, Dryer, Range, Refrigerator
  • Bathrooms Full5
  • Bathrooms Half1
  • Bathrooms Total Integer6
  • Bedrooms Total5
  • CoolingCentral Air
  • CoolingYes
  • FlooringHardwood
  • FurnishedUnfurnished
  • HeatingCentral
  • HeatingYes
  • Interior FeaturesHigh Ceilings, Living Room/Dining Room Combo
  • Laundry FeaturesInside
  • LevelsTwo
  • Living Area4,015
  • Living Area SourcePublic Records
  • Living Area UnitsSquare Feet
  • Rooms Total8

Exterior

  • Attached GarageYes
  • Covered Spaces2
  • Direction FacesNorth
  • Exterior FeaturesCourtyard, Lighting, Outdoor Grill
  • FencingMasonry, Other
  • Garage Spaces2
  • GarageYes
  • Lot Size Acres0
  • Lot Size Area11,159
  • Lot Size Square Feet11,159
  • Lot Size UnitsSquare Feet
  • Patio And Porch FeaturesCovered, Rear Porch
  • Pool FeaturesIn Ground, Salt Water
  • Road Surface TypeBrick
  • RoofShingle

Structure

  • Building Area Total4,959
  • Construction MaterialsBlock, HardiPlank Type
  • Foundation DetailsSlab
  • Year Built2017

Utilities

  • SewerPublic Sewer
  • UtilitiesCable Available, Sewer Connected
  • Water SourcePublic

Financial

  • Parcel Number182230284401100
  • Tax Annual Amount18,901
  • Tax BlockA
  • Tax Book NumberK-90
  • Tax Legal DescriptionFORREST HILLS K/90 LOT 10 BLK A
  • Tax Lot10
  • Tax Year2025
  • ZoningR-1AA

Schools

  • Elementary SchoolAudubon Park K8
  • High SchoolWinter Park High
  • Middle Or Junior SchoolAudubon Park K-8

Location

  • CountryUnited States
  • County Or ParishOrange
  • DirectionsSouth Pennsylvania turns into Lake Sue right on Glencoe right on Chelton Circle Right on Rockwood.
  • Latitude29
  • Longitude-81
  • MLS Area Major32789 - Winter Park
  • Postal Code32789
  • Postal Code Plus46059
  • Street Direction PrefixW
  • Street NameROCKWOOD
  • Street Number160
  • Street Number Numeric160
  • Street SuffixWAY
  • Subdivision NameFOREST HILLS
  • Unparsed Address160 W ROCKWOOD WAY

Listing Info

  • Co-List Agent Full NameFrank Mosley
  • MCP RULES X261072535
  • Co-List Office MLS ID261014339
  • Co-List Office NamePREMIER SOTHEBY'S INTL. REALTY
  • List Price3,395,000
  • Contract Status Change DateSeptember 10, 2026
  • Cumulative Days On Market26
  • Days On Market26
  • Lease ConsideredYes
  • List Agent AOROrlando Regional
  • List Agent Emailalison@themosleyteam.com
  • List Agent Full NameAlison Mosley
  • List Agent Key9dcfbe0351299d482e84ba12bed0760c
  • List Agent MLS ID261087894
  • List Agent Preferred Phone407-304-6458
  • List Office MLS ID261014339
  • List Office NamePREMIER SOTHEBY'S INTL. REALTY
  • List Office Phone407-644-3295
  • Listing Contract DateAugust 31, 2026
  • Listing IDO6437722
  • Listing Key1866229ee468aed1d583f1a045a5de82
  • MLS StatusActive
  • Modification TimestampSeptember 11, 2026
  • On Market DateSeptember 10, 2026
  • Original Entry TimestampAugust 31, 2026
  • Original List Price3,395,000
  • Originating System Keystellar
  • Originating System NameStellar MLS
  • OwnershipFee Simple
  • Photos Change TimestampAugust 31, 2026
  • Photos Count72
  • Source System Key804188516
  • Special Listing ConditionsNone
  • Status Change TimestampSeptember 10, 2026

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Meet your agent

AM

Alison Mosley

Listing Agent · PREMIER SOTHEBY'S INTL. REALTY

BrokeragePREMIER SOTHEBY'S INTL. REALTY
Agent MLS ID261087894
Office MLS ID261014339

Get in touch

Office · 407-644-3295

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Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS# O6437722 · Listing agent Alison Mosley · Phone 407-304-6458 · Data last updated September 11, 2026 3:46 am

AMAlison Mosley

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