
42 WINCHESTER ROAD, ORMOND BEACH, FL, 32174
Sold1608 days on marketListed Feb 24, 2022Sold Sep 19, 2022MLS #V4923171
About this home
42 WINCHESTER ROAD
Your dream home awaits YOU! 42 Winchester Road is in a gated and very private neighborhood. Eagle Rock subdivision is a special neighborhood and homes aren't available in here very often. It's just too hard to find something similar. This is an Equestrian community, so bring your horses if you have them or just enjoy the extra space if you don't! As you drive down the entrance road and go through the gate, you peer around at your neighbors and drive down the street. When you get to the end of the neighborhood, you start to realize just how little traffic there is and the amount of privacy you'll have. Not to mention, the average house in here is not for the first time home buyer. There have been several lottery winners who have called Eagle Rock home. Your home values are in good hands with other surrounding valuable homes. Nestled among the trees in this 5-acre (see the video), full waterfront lot, is a 5 bedroom 2.5 Bath with a 2-car attached garage. This ranch-style, brick, pool home has so much to offer! With a detached 2-story concrete block barn/workshop (EVERY MANS DREAM SET UP FOR HEAVY MACHINERY) you will have all the room for your new workshop one would need. It also has its own electric meter. Upstairs is ready to become an apartment or consider it to be the hang out spot! Plenty enough room for a pool table, ping-pong table, foosball table, and a large couch with a TV. 2 more detached air-conditioned workshops/studios allow for everyone to have their own space. If you have are a dog lover, one of these is already set up to be a kennel and has a fenced dog run behind it. The main home has a very lush front yard with scattered palms to bring more privacy. The beautiful brick fireplace sits right next to the oversized windows where you have a clear view of the pool. There is access to the half bath right off the pool deck! There are two very spacious living rooms, which are silently screaming to be combined into one giant living space. The oasis, a screened pool enclosure, with an automatic chlorinator and cleaner will surely be a place to spend most of your time if you aren't at the beach dozing off while the sweat drops off the drink in your hand. When the sand is only 20 minutes away, why wouldn't you? New 22 Kilowatt (Aug. 2020) whole house generator system, New whole house Kinetico water conditioner, 2 separate AC units - one for main house and the other one for the bedrooms, Reverse Osmosis for drinking/ice-making, Roof replaced in 2015. The Home Warranty is transferrable and valid through 1/15/2023. Flood insurance (not required but have anyway) paid through mid-2022. Termite bond is good for another year. The whole house has electronics protection as well. There are many items available for negotiation and purchase not mentioned. Please ask and we can talk about that.
Facts & features
The home at a glance
5
Bedrooms
2.5
Bathrooms
3,168
Sqft
5 ac
Lot size
2
Garage
1984
Year built
One
Levels
$296
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
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.
$/sqft vs Ormond Beach actives
$296 vs $237
Days on market
1608 vs 41 typical
Where $296/sqft sits among the 400 Ormond Beach actives
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 Ormond Beach
Get to know Ormond Beach. See the full Ormond Beach guide →
The numbers that matter
The Ormond Beach market
$390K → $415K
Ormond Beach median sold, yr/yr
96.3%
Sale-to-list ratio (12 mo)
198 of 400
Ormond Beach actives have cut their price
Median sold price, Ormond Beach, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 120% above the Ormond Beach median. See the full Ormond Beach market guide →
Paper trail
This home's history
Reality check
What actually sold near 42 WINCHESTER ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$1,090,000
1106 OXBRIDGE LANE
4 bd · 3.5 ba · 3,165 sqft · $344/sqft · 4 DOM
Sold · Feb ’26$700,000
15 WINCHESTER ROAD
5 bd · 2.5 ba · 3,110 sqft · $225/sqft · 298 DOM
Sold · Aug ’25$1,375,000
514 WINGSPAN DRIVE
4 bd · 3 ba · 3,243 sqft · $424/sqft · 60 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
Shawn Headley
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 42 WINCHESTER ROAD — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 42 WINCHESTER ROAD — before you fall in love.
Selling nearby?
What's your home worth today?
This sale is one data point — your home is another. Get a data-driven estimate built from real closed sales like this one, in about a minute.
The brief
Three things that matter here
01Positioned at the premium end
$937,000 runs 120% above the Ormond Beach median — but at 3,168 sqft it's also 63% larger than the typical Ormond Beach listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
1608 days on market against a Ormond Beach median of 41 — sellers in this position are usually ready to negotiate.
Keep looking
Similar homes nearby
Listing courtesy of EXP REALTY LLC · Maxwell Van Noppen. MLS #V4923171.
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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