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160 W ROCKWOOD WAY, WINTER PARK, FL - photo 1

$3,395,000

160 W ROCKWOOD WAY

WINTER PARK, FL 32789

Estimated payment $17,742/month

no HOA · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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5Beds
6Baths
4,015Sq Ft
$846Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

No HOA
Private Pool
Garage
Built in 2017
11,159 sqft Lot

About This Home

Under contract-accepting backup offers. 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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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:5
  • •Bathrooms:6 (5 full, 1 half)
  • •Full bathrooms:5
  • •Half bathrooms:1

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:4,015 sqft
  • •Total interior livable area:4,015 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:11,159 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:2017

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Price history

DateEventPrice
2026-09-10T00:00:00.000ZListed for sale$3,395,000$846/sqft

Listing Agent

Alison Mosley

PREMIER SOTHEBY'S INTL. REALTY

Brokerage Phone: 407-644-3295

Source: Stellar MLS · MLS #O6437722

Data Powered by Home Junction, Inc.

Nearby

Schools

AUDUBON PARK SCHOOL

Elementary · 0.7 mi

GLENRIDGE MIDDLE

High · 0.8 mi

ADVENTHEALTH UNIVERSITY

1.1 mi

Supermarkets

East End Market

0.6 mi

Winter Park Biscuit Company

0.6 mi

Mellow Market

0.6 mi

Dining

Stardust

0.4 mi

Jimbos Grill

0.5 mi

Stardust Video & Coffee

0.6 mi

Parks

Beeman Park

0.2 mi

Bonnie Burn Mini Park

0.7 mi

Mead Botanical Garden

0.8 mi

Beaches

Lake Baldwin Park Beach

1.4 mi

Conrad Beach

15.8 mi

East Beach

15.9 mi

Nearby amenity locations include data © OpenStreetMap contributors.