4742 OLD FARM ROAD
SARASOTA, FL 34233
About this home
First Time Ever Offered by the Original Owners! Welcome to one of Sarasota's hidden gems—Oakleaf, a private enclave of custom homes tucked beneath mature oak trees just off Proctor Road. Lovingly maintained by the original owners since it was built, this exceptional custom Pruett-built residence showcases timeless craftsmanship, quality construction, and the pride of ownership that only comes from meticulous care over the years. This true 4-bedroom, 3-bathroom, 3-car garage pool home offers the spacious floor plan today's families are searching for. Unlike many homes that count an office or den as a fourth bedroom, this home features four genuine bedrooms along with generous living spaces designed for everyday comfort and effortless entertaining. Step outside to your own private Florida retreat where an oversized resort-style swimming pool and spa have been beautifully resurfaced and are surrounded by an elegant travertine pool deck, creating the perfect setting for relaxing weekends, family gatherings, and year-round outdoor living. The mature preserve behind the home provides exceptional privacy while lush tropical landscaping creates outstanding curb appeal from the moment you arrive. Major improvements have already been completed, allowing the next owner to simply move in and enjoy. Recent updates include a **new barrel tile roof (2022), resurfaced pool and spa with travertine pool deck (2022), fresh interior and exterior paint, new HVAC system (2025), and water heater (2021). This home truly reflects decades of careful maintenance and thoughtful investment. Oakleaf remains one of Sarasota's most desirable established communities, offering larger homesites, mature tree-lined streets, sidewalks, low HOA fees, and a peaceful neighborhood atmosphere that's increasingly difficult to find in newer developments. The location is second to none—just minutes to Siesta Key Beach, Lido Key, Downtown Sarasota, St. Armands Circle, UTC Mall, Interstate 75, Legacy Trail, Nathan Benderson Park, championship golf courses, waterfront dining, shopping, fitness centers, and countless restaurants. Healthcare is equally convenient with both Sarasota Memorial Hospital and Doctors Hospital of Sarasota just a short drive away, making this an outstanding location. Families will appreciate the home's proximity to Ashton Elementary School, Sarasota Middle School, and Sarasota High School (buyer to verify current school assignments), as well as several highly regarded private schools nearby including The Out-of-Door Academy, NewGate School, Sarasota Christian School, Classical Academy, and Sarasota Military Academy, offering exceptional educational opportunities from preschool through high school. If you've been searching for a move-in ready Sarasota pool home, 4-bedroom home in Sarasota, custom home near Siesta Key, family home with a private preserve view, or a centrally located Sarasota home close to beaches, shopping, dining, hospitals, and top schools, this is the opportunity you've been waiting for. Homes of this caliber, in this location, and with this level of care rarely become available. Already generating significant pre-market interest, this exceptional Oakleaf residence is not expected to remain on the market for long. Schedule your private showing today and discover why so many buyers have been waiting for a home exactly like this.
Facts & features
Interior
- Bedrooms
- 4
- Bathrooms
- 3
- Living area
- 2,347 sqft
- Heating
- Heat Pump
- Cooling
- Central Air
- Flooring
- Hardwood, Laminate, Tile, Travertine
- Stories
- 1
- Features
- Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo…
- Appliances
- Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater…
Exterior & lot
- Lot size
- 10,000 sqft (0.23 ac)
- Pool
- Yes
- Roof
- Tile
- Construction
- Block
- Exterior
- Rain Gutters, Sliding Doors
Parking
- Garage
- 3 spaces
Financial
- HOA dues
- $55 / monthly
- Annual tax
- $4,659 (2025)
- Price / sqft
- $292/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- Cable Connected, Electricity Connected, Fire Hydrant, Sewer Connected
Property
- Property type
- Single Family
- Year built
- 1996
- Subdivision
- OAKLEAF
- County
- Sarasota
Assigned schools
- Elementary
- Ashton Elementary
- Middle
- Sarasota Middle
- High
- Sarasota High
Listing
- Status
- Active
- Days on market
- 1 day
- MLS #
- MFR800086061
- Source
- Stellar MLS
Listed by Ervina Fink · PLATINUM REAL ESTATE
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Sample estimate — not an appraisal
Based on 20 comparable sales within 3 miles of SARASOTA, FL, this home is priced over RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $3,646/mo
- Property tax
- $400/mo
- Home insurance
- $200/mo
- HOA dues
- $55/mo
Tax, insurance and HOA are editable estimates with Florida-typical defaults — Florida homeowners insurance in particular varies widely by location and elevation. Confirm exact figures with a lender and insurer.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Aug 7, 2026 | Listed | $685,000 | — |
NeighbourhoodSample data
Reference scores for SARASOTA, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.
Location
Frequently asked questions
What would 4742 OLD FARM ROAD, SARASOTA cost per month?
About $4,249 a month: $3,464 principal and interest, $388 property tax, $343 insurance, $55 HOA. That assumes 20% down at 6.5% over 30 years.
Is 4742 OLD FARM ROAD, SARASOTA priced fairly?
Comparable sales nearby put it between $579,510 and $666,748, with $623,129 in the middle. That is from 8 properties of the same type and size within three miles, at a median of $266 a square foot.
How does 4742 OLD FARM ROAD, SARASOTA compare to nearby homes?
8 comparable properties within three miles. The nearest: 4407 DIAMOND CIRCLE, SARASOTA, FL at $525,000, 1,857 sq ft, 0.2 miles away; 4576 BLISS ROAD, SARASOTA, FL at $385,000, 1,475 sq ft, 0.21 miles away; 4696 LONG LAKE DRIVE, SARASOTA, FL at $499,900, 2,447 sq ft, 0.23 miles away.
How long has 4742 OLD FARM ROAD, SARASOTA been on the market?
1 day on the market.
Has the price of 4742 OLD FARM ROAD, SARASOTA changed?
The price has not moved since it was listed.
How big is 4742 OLD FARM ROAD, SARASOTA?
4 bed, 3 bath, 2,347 square feet. That is $292 a square foot.
What year was 4742 OLD FARM ROAD, SARASOTA built?
Built in 1996.
What is the HOA fee at 4742 OLD FARM ROAD, SARASOTA?
The association fee works out to $55 a month.
What are the property taxes at 4742 OLD FARM ROAD, SARASOTA?
Property tax works out to about $388 a month, $4,659 a year.
Is 4742 OLD FARM ROAD, SARASOTA still available?
It is still on the market.
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