CENTURY 21 Edge
$3,395,0005 bd5.5 ba4,015 sqft$846 /sqft$21,327 /mo all-in ↓

160 W ROCKWOOD WAY, WINTER PARK, FL, 32789

Active10 days on marketListed Sep 10, 2026MLS #O6437722

Private poolSingle Family ResidenceFOREST HILLS

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

Private pool

Inside

FlooringHardwood
AppliancesDishwasher · Disposal · Dryer · Range · Refrigerator
InteriorHigh Ceilings · Living Room/Dining Room Combo
LaundryInside
CoolingCentral Air
HeatingCentral

Outside & construction

RoofShingle
ConstructionBlock · HardiPlank Type
FoundationSlab
FacesNorth
ExteriorCourtyard · Lighting · Outdoor Grill

Community & fees

Taxes (2025)$18,901/yr

Utilities & systems

UtilitiesCable Available · Sewer Connected
WaterPublic

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%

Principal & interest$18,319
PMI (est., until 20% equity)$1,273
Property tax — 2025 actual bill$1,575
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $339,500Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

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

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $339,500
Interest rate6.00%
Loan term

Estimated payment

$21,327/mo

Principal & interest$18,319
PMI (est., until 20% equity)$1,273
Property taxes (actual bill)$1,575
Est. insurance$160

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.

List $3.4M
$2.3MedgeAI estimate $2,420,289 · range $2.4M$2.5M$3.5M

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

13
2
0
0
0
2 · this home
$133–260$260–386$386–512$512–639$639–765$765+

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

Downtown Orlando11 min
Universal Orlando24 min
Orlando Int’l Airport (MCO)27 min
Walt Disney World36 min

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

ElementaryAudubon Park School★★★★★
HighWinter Park High★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Winter Park market

Seller’s marketLeans seller3.8 months of inventoryBuyer’s 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

Sep 10, 2026Listed at $3,395,000 · 10 days on market since
2017Built · FOREST HILLS

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.

1820 ENGLEWOOD ROADSold · Oct ’25

$3,020,000

1820 ENGLEWOOD ROAD · same community

5 bd · 5.5 ba · 4,263 sqft · $708/sqft · 70 DOM

130 W KINGS WAYSold · Dec ’25

$1,350,000

130 W KINGS WAY · same community

5 bd · 3 ba · 3,145 sqft · $429/sqft · 54 DOM

3208 W HAWTHORNE ROADSold · 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.

Frederick Paige

Your agent

Frederick Paige

REALTOR® · CENTURY 21 Edge

Tours, negotiation, and every question about 160 W ROCKWOOD WAY — start here.

Andrew Acosta

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.

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.

Never miss a listing

New Winter Park homes, in your inbox

Like 160 W ROCKWOOD WAY but not quite? A daily digest of every new listing in Winter Park — straight from the MLS, hours after it goes live. Unsubscribe anytime.

Just watching this one home? Ask Frederick to ping you on any price or status change →

CENTURY 21 Edge
© 2026 CENTURY 21® and the CENTURY 21 Logo are registered service marks owned by Century 21 Real Estate LLC. Sunseria Real Estate Group LLC d/b/a CENTURY 21 Edge fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with, or related to Century 21 Real Estate LLC nor any of its affiliated companies.

MLS® Disclaimers

Stellar MLS / MFRMLSCopyright © MFRMLS.com. 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 September 20, 2026 at 10:39 PM UTC. The listing information on this page last changed on September 20, 2026 at 10:39 PM UTC. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of MFR MLS. Updated on September 20, 2026 at 10:39 PM UTC.

StellarMLS DMCA Notice: The Digital Millennium Copyright Act of 1998, 17 U.S.C. §512, the DMCA, provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owners behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Southeast Florida MLSCopyright Southeast Florida Multiple Listing Service © 2026. Accuracy of listing information is not guaranteed. Listing information is provided for personal consumer, non-commercial use, solely to identify potential properties for potential purchase. All other use is strictly prohibited, is a violation of the terms of use, and may violate federal and state law. Data Last Updated: September 20, 2026 at 10:39 PM UTC.

Space Coast AORThese listings are provided by the IDX Program of Brevard County, Florida. Real Estate listings held by brokerage firms other than CENTURY 21 Edge Central Florida are marked with the IDX Logo and detailed information about them includes the name of the listing brokers. 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. Information deemed reliable but not guaranteed.

Beaches MLSAll 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 consumer''s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.