# 1240 HILLVIEW Drive, Sarasota, FL 34239 > **TL;DR:** 4bd/4ba single family, $14,950,000 ($3081/sqft), built 1992, 4,852 sqft. > Pool, Spa, Fireplace, Waterfront. Est. $79,955/mo. Listed 8 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $14,950,000 | | Price/sqft | $3081 | | Bedrooms | 4 | | Bathrooms | 3 full, 1 half | | Square Feet | 4,852 | | Year Built | 1992 | | Lot Size | 31,799 sqft (0.73 acres) | | Stories | 3 | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 8 | ## Why This Home Stands Out - **Pool** - Porch, Patio, Deck - **Waterfront** - Waterfront location listed - **Views** - Water, Harbor ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $75,595 | | Estimated Insurance | $4,360 | | **Total** | **$79,955** | ## Nearby Schools - **Elementary:** Southside Elementary - **Middle:** Sarasota Middle - **High:** Sarasota High ## Key Amenities - Pool - Spa - Fireplace - Waterfront - View - A/C ## Property Highlights - Built in 1992 - 0.73 acre lot - 3 stories - Private pool - Fireplace - Waterfront ## Description ### Agent Description Introducing "Gatsby Manor," set along Hillview Drive, one of Sarasota's most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood's most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood paneled library, formal dining with 12-foot ceilings, and a wet bar-perfectly blending elegant entertaining with comfortable daily living. The chef's kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner's suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home's ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence's living experience-ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25' * 60' heated saltwater pool with integrated sun shelf and spa. A brand-new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property's boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village's restaurants and boutiques, minutes from downtown Sarasota's celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota's most prestigious waterfront neighborhoods. ## Location - **Address:** 1240 HILLVIEW Drive, Sarasota, FL 34239 - **County:** Sarasota - **Neighborhood:** HARBOR ACRES - **Coordinates:** 27.316651, -82.543906 - **Google Maps:** https://www.google.com/maps?q=27.316651,-82.543906 ## Virtual Tour & Media - **Video Tour:** https://pix360.com/video/42130/ ## Listing Agent - **Name:** Ryan Ackerman, PA - **Brokerage:** Coldwell Banker - **Broker Phone:** (813) 754-3586 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1240-Hillview-Dr_Sarasota_FL_34239_M60828-10054?f=listhub&s=MFRMLSFL&m=A4710661&c=propsimple) ## Photos ![1240 HILLVIEW Drive - Photo 1](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f309593326r.jpg) ![1240 HILLVIEW Drive - Photo 2](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f3932321437r.jpg) ![1240 HILLVIEW Drive - Photo 3](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1773605175r.jpg) ![1240 HILLVIEW Drive - Photo 4](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f4188722532r.jpg) ![1240 HILLVIEW Drive - Photo 5](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2438000268r.jpg) ![1240 HILLVIEW Drive - Photo 6](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f692612792r.jpg) ![1240 HILLVIEW Drive - Photo 7](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1639906690r.jpg) ![1240 HILLVIEW Drive - Photo 8](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1436884006r.jpg) ![1240 HILLVIEW Drive - Photo 9](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f3722711295r.jpg) ![1240 HILLVIEW Drive - Photo 10](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1303720324r.jpg) ![1240 HILLVIEW Drive - Photo 11](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f3523010598r.jpg) ![1240 HILLVIEW Drive - Photo 12](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2960104676r.jpg) ![1240 HILLVIEW Drive - 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Photo 33](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2247445989r.jpg) ![1240 HILLVIEW Drive - Photo 34](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2375148291r.jpg) ![1240 HILLVIEW Drive - Photo 35](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2011650396r.jpg) ![1240 HILLVIEW Drive - Photo 36](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2601911788r.jpg) ![1240 HILLVIEW Drive - Photo 37](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1702772833r.jpg) ![1240 HILLVIEW Drive - Photo 38](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f319041884r.jpg) ![1240 HILLVIEW Drive - Photo 39](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f364835947r.jpg) ![1240 HILLVIEW Drive - Photo 40](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2087431112r.jpg) ![1240 HILLVIEW Drive - Photo 41](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2947428284r.jpg) ![1240 HILLVIEW Drive - Photo 42](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f3136869422r.jpg) ![1240 HILLVIEW Drive - Photo 43](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f508210258r.jpg) ![1240 HILLVIEW Drive - Photo 44](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f326678275r.jpg) ![1240 HILLVIEW Drive - Photo 45](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f4247428421r.jpg) ![1240 HILLVIEW Drive - Photo 46](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f946943276r.jpg) ![1240 HILLVIEW Drive - Photo 47](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f85881666r.jpg) ![1240 HILLVIEW Drive - Photo 48](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f235999097r.jpg) ![1240 HILLVIEW Drive - Photo 49](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1571855154r.jpg) ![1240 HILLVIEW Drive - Photo 50](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1676667691r.jpg) ![1240 HILLVIEW Drive - Photo 51](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1252186133r.jpg) ![1240 HILLVIEW Drive - Photo 52](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f45377913r.jpg) ![1240 HILLVIEW Drive - Photo 53](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f1732874814r.jpg) ![1240 HILLVIEW Drive - Photo 54](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f3730719374r.jpg) ![1240 HILLVIEW Drive - Photo 55](http://lh.rdcpix.com/4c3d6893128abaeb94b8fcd4558abb97l-f2490189718r.jpg) --- **MLS#:** A4710661 | **Updated:** 2026-10-29 **Source:** listhub *Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/1240-hillview-drive-sarasota-fl-34239-ed8ac8f3d0924517bbeebc5b8f3a0f3c) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/1240-hillview-drive-sarasota-fl-34239-ed8ac8f3d0924517bbeebc5b8f3a0f3c#listing", "url": "https://www.propertysimple.ai/listing/1240-hillview-drive-sarasota-fl-34239-ed8ac8f3d0924517bbeebc5b8f3a0f3c", "name": "1240 HILLVIEW Drive, Sarasota, FL 34239", "description": "Introducing \"Gatsby Manor,\" set along Hillview Drive, one of Sarasota's most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood's most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood paneled library, formal dining with 12-foot ceilings, and a wet bar-perfectly blending elegant entertaining with comfortable daily living. The chef's kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner's suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home's ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence's living experience-ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25' * 60' heated saltwater pool with integrated sun shelf and spa. A brand-new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property's boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village's restaurants and boutiques, minutes from downtown Sarasota's celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. 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