
160 W ROCKWOOD WAY, WINTER PARK, FL, 32789
Active10 days on marketListed Sep 10, 2026MLS #O6437722
About this home
160 W ROCKWOOD WAY
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.
Facts & features
The home at a glance
5
Bedrooms
5.5
Bathrooms
4,015
Sqft
0.26 ac
Lot size
2
Garage
2017
Year built
Two
Levels
$846
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$21,327 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$21,327/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+40.3%
$/sqft vs FOREST HILLS
$846 vs $216
Days on market
10 vs 43 typical
Where $846/sqft sits among the 17 homes for sale in FOREST HILLS
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Forrest Hills
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Forrest Hills — neighborhood snapshot
Population
387
Median age
42
Median income
$239,372
Median home value
$1,214,819
Avg household
3
Households w/ children
61%
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
10 of 17
FOREST HILLS have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 317% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 160 W ROCKWOOD WAY
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$3,020,000
1820 ENGLEWOOD ROAD · same community
5 bd · 5.5 ba · 4,263 sqft · $708/sqft · 70 DOM
Sold · Dec ’25$1,350,000
130 W KINGS WAY · same community
5 bd · 3 ba · 3,145 sqft · $429/sqft · 54 DOM
Sold · Jul ’26$816,102
3208 W HAWTHORNE ROAD · same community
3 bd · 3.5 ba · 2,331 sqft · $350/sqft · 94 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Your agent
Frederick Paige
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 160 W ROCKWOOD WAY — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 160 W ROCKWOOD WAY — before you fall in love.
See it in person
Schedule a tour
Live availability from Frederick's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
160 W ROCKWOOD WAY FAQs
What would the monthly payment be for 160 W ROCKWOOD WAY?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $21,327/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 160 W ROCKWOOD WAY?+
The most recent tax bill on record (2025) was $18,901. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Park?+
At $3,395,000, this home is listed about 490% above the Winter Park median of $575,000. The market section on this page shows how the area is trending.
Which schools are assigned to 160 W ROCKWOOD WAY?+
Audubon Park School (elementary), Winter Park High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$3,395,000 runs 317% above the WINTER PARK 32789 median — but at 4,015 sqft it's also nearly twice the size of the typical Winter Park listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Strong assigned schools
Audubon Park School, Winter Park High — Audubon Park School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY · Alison Mosley. MLS #O6437722.
IDX information is provided exclusively 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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