
2068 ROBERTS POINT DRIVE, WINDERMERE, FL, 34786
Active99 days on marketListed Apr 16, 2026MLS #O6397543
About this home
2068 ROBERTS POINT DRIVE
Virtually Staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace. The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family. Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality. Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide. Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities. Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools. For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity. **Private tours available by appointment**
Facts & features
The home at a glance
5
Bedrooms
4
Bathrooms
4,876
Sqft
1.04 ac
Lot size
4
Garage
1999
Year built
Two
Levels
$461
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.
$14,499 /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
$14,499/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
+42.1%
$/sqft vs Windermere actives
$461 vs $348
Days on market
99 vs 32 typical
Where $461/sqft sits among the 239 Windermere 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 Waterford Pointe
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Windermere. See the full Windermere guide →
Waterford Pointe — neighborhood snapshot
Population
699
Median age
43
Median income
$224,336
Median home value
$771,900
Avg household
3
Households w/ children
81%
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Windermere market
$839K → $1.0M
Windermere median sold, yr/yr
96.4%
Sale-to-list ratio (12 mo)
114 of 239
Windermere actives have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 178% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 2068 ROBERTS POINT DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$2,500,000
12923 WATER POINT BOULEVARD
5 bd · 4.5 ba · 5,005 sqft · $500/sqft · 135 DOM
Sold · Aug ’25$2,400,000
3412 LILAS COURT
4 bd · 5 ba · 4,712 sqft · $509/sqft · 96 DOM
Sold · Jun ’26$1,975,000
3413 LILAS COURT
4 bd · 4.5 ba · 5,084 sqft · $388/sqft · 0 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 2068 ROBERTS POINT DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2068 ROBERTS POINT DRIVE — 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
2068 ROBERTS POINT DRIVE FAQs
What would the monthly payment be for 2068 ROBERTS POINT DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $14,499/mo — principal and interest, the actual property-tax bill, the $325/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 2068 ROBERTS POINT DRIVE?+
The association fee works out to $325 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2068 ROBERTS POINT DRIVE?+
The most recent tax bill on record (2025) was $12,356. 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 2068 ROBERTS POINT DRIVE?+
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 Windermere?+
At $2,250,000, this home is listed about 105% above the Windermere median of $1,099,500. The market section on this page shows how the area is trending.
Which schools are assigned to 2068 ROBERTS POINT DRIVE?+
Lake Whitney Elementary (elementary), West Orange High (high), Sunridge Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$2,250,000 runs 178% above the WINDERMERE 34786 median — but at 4,876 sqft it's also 52% larger than the typical Windermere listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Time on market is leverage
99 days on market against a Windermere median of 32 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Lake Whitney Elementary, West Orange High, Sunridge Middle — Lake Whitney Elementary rates 5 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $2,350,000, now $2,250,000 — a $100K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of CENTURY 21 CARIOTI · David Dorman. MLS #O6397543.
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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