14001 RUGBY STREET, OAKLAND, FL, 34787
Active77 days on marketListed May 27, 2026MLS #G5112905
About this home
14001 RUGBY STREET
One or more photo(s) has been virtually staged. Price improved and ready for its next owner, this beautifully maintained pool home in the sought-after Verde Park community offers more than 4,240 square feet of thoughtfully designed living space on a beautiful 0.26-acre corner lot in one of Winter Garden’s most beloved communities. With 5 bedrooms and 4 bathrooms, the home delivers an exceptional combination of space, comfort, and Florida outdoor living with a flexible layout designed for everyday living and entertaining. Inside, elegant formal living and dining rooms, architectural archways, and generous gathering spaces create a warm and welcoming first impression. The expansive family room connects seamlessly to a gourmet kitchen complete with granite countertops, stainless steel appliances, a cooktop, built-in wall oven, and a sunny breakfast nook overlooking the outdoor living area - the kind of space where mornings feel easy and gatherings happen naturally. The versatile floor plan offers room for a variety of needs, including a downstairs Murphy bed office that is perfect for guests or working from home, plus an additional downstairs bonus room with exciting potential as a next-generation living space ideal for multigenerational families or extended stays. Upstairs, the primary suite wraps you in comfort with a large bedroom, spa-like bath, garden tub, dual vanity, separate walk-in shower, and a custom oversized walk-in closet with built-in storage. The second floor also features a large open loft with a convenient kitchenette and a dedicated media room, creating the perfect setup for movie nights or entertainment. Outdoors, enjoy a private screened pool and lanai, covered patio, and summer kitchen designed for year-round enjoyment. The home is also EV charging ready, adding modern convenience for today’s lifestyle. When you’re ready to explore, everything is right at your doorstep. Enjoy walkable access to the West Orange Trail, perfect for morning bike rides, jogging, or evening strolls. Major shopping, including Costco, popular retail, and everyday conveniences, is just minutes away, charming downtown Winter Garden, with its vibrant farmers market, local dining, and boutique shops, is a short drive from home. Add easy access to Montverde Academy and the Florida Turnpike, and this location truly checks every box. Some photos are virtually staged. Aerial property lines are approximate and should be verified by buyer. *Aerial photo property lines are an estimate and to be verified by buyer, some photos are virtually staged
Facts & features
The home at a glance
5
Bedrooms
4
Bathrooms
4,240
Sqft
0.26 ac
Lot size
2
Garage
2015
Year built
Two
Levels
$195
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 and the real association fee — not generic estimates.
$5,534 /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
$5,534/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
−54.8%
$/sqft vs Oakland actives
$195 vs $331
Days on market
77 vs 87 typical
Where $195/sqft sits among the 24 Oakland 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 Oakland
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Oakland. See the full Oakland guide →
The numbers that matter
The Oakland market
$605K → $743K
Oakland median sold, yr/yr
98.1%
Sale-to-list ratio (12 mo)
12 of 24
Oakland actives have cut their price
Median sold price, Oakland, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 3% below the Oakland median. See the full Oakland market guide →
Paper trail
This home's history
Reality check
What actually sold near 14001 RUGBY STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$509,000
17993 GOURD NECK LOOP · same community
4 bd · 3 ba · 2,736 sqft · $186/sqft · 175 DOM
Sold · Oct ’25$1,520,000
812 JOHNS POINT DRIVE
5 bd · 4 ba · 4,373 sqft · $348/sqft · 31 DOM
Sold · Jul ’26$1,749,000
902 JOHNS POINT DRIVE
4 bd · 4 ba · 4,085 sqft · $428/sqft · 10 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 14001 RUGBY STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 14001 RUGBY STREET — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
14001 RUGBY STREET FAQs
What would the monthly payment be for 14001 RUGBY STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,534/mo — principal and interest, the actual property-tax bill, the $121/mo association fee 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.
How much are the HOA fees at 14001 RUGBY STREET?+
The association fee works out to $121 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 14001 RUGBY STREET?+
The most recent tax bill on record (2025) was $5,903. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 14001 RUGBY STREET?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Oakland?+
At $825,000, this home is listed about 3% below the Oakland median of $850,000. The market section on this page shows how the area is trending.
The brief
Three things that matter here
01Under the Oakland market on paper
$825,000 is 3% below the Oakland median of $850,000, and at $195/sqft it sits under the Oakland average of $372.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03The price has already moved
Listed at $845,000, now $825,000 — a $20K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY · Ann Mertens. MLS #G5112905.
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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