FRESH STYLE….FRESH PRICE! Behind the gates of The Oaks – Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style – 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for refined entertaining and everyday comfort, you’ll enjoy 4 bedrooms and 4 full baths – all on one level – within a bright, open floor plan with custom architectural details throughout. The impressive chef’s kitchen is both stylish and functional, featuring Silestone countertops, premium Sub-Zero and Wolf appliances, an expansive island with seating and a striking bar—perfect for hosting gatherings or enjoying relaxed mornings at home. Separate dining and living spaces allow room for dedicated entertaining – making any occasion a treat! The private primary suite is “magazine worthy” – a sublime but peaceful retreat complete with a tremendous walk-in closet, custom built-ins and a beautifully appointed bath showcasing dual vanities, quartz countertops and a seamless walk-in glass shower. The home is truly a split plan – offering privacy with three additional suites – perfect for guests, a study or exercise/hobby room. The home takes every advantage of space and storage – and you’ll be the envy of the neighborhood with the “thought of everything” laundry room and spacious garage. Step outside to exceptional outdoor living – designed for year-round Florida enjoyment. The expansive screened lanai features a heated pool and spa, elegant travertine pool deck, turfed yard with putting-green surface (only home in the Oaks) and new remote-controlled hurricane screens. Surrounded by mature, lush landscaping and a privacy wall, you’ll feel the design intent for ultimate seclusion and relaxation. The home not only looks beautiful – it’s been maintained to provide peace of mind with a newer roof (2021); impact-rated windows & doors (2021); 2 new HVAC units with UV purification (2021); motorized exterior hurricane shutters (2025); air conditioned garage and hurricane doors; 500 gallon propane tank (2022); electrical service panel (2021); rear yard golf turf (2025) and fresh interior & exterior paint. The Oaks – Bayside is a gated neighborhood with a private day dock on Little Sarasota Bay – perfect for launching kayaks or simply enjoying the sunset. The Oaks is one of the region’s most prestigious 24-hour guard-gated country club communities, residents enjoy an extraordinary lifestyle that includes: two championship 18-hole golf courses; three dining options and ballroom; tennis with 12 Har-Tru Hydro-Grid tennis courts; four pickleball courts; croquet lawns; fitness center and Junior Olympic heated pool; bocce, basketball, playground and extensive social opportunities. Perfectly located west of the trail in Osprey, you’re just minutes from Sarasota’s outstanding dining and cultural offerings, gorgeous beaches, Legacy Trail and Pine View School for the Gifted. A wonderful opportunity to enjoy Florida’s ideal county club lifestyle! (Club membership is required with no waitlist at the current time.)
Property Details
Price:
$1,749,990
MLS #:
A4684805
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKS
Neighborhood:
34229osprey
Listed Date:
Mar 10, 2026
Finished Sq Ft:
3,286
Total Sq Ft:
4,668
Lot Size:
14,674 sqft / 0.34 acres (approx)
Year Built:
1989
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Laurel Nokomis Middle
High School:
Venice Senior High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Microwave, Range Hood, Washer
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Luxury Vinyl, Tile
Heating
Central
Laundry Features
Laundry Room
Exterior
Association Amenities
Clubhouse, Fitness Center, Gated, Golf Course, Pickleball Court(s), Pool, Recreation Facilities, Security, Tennis Court(s)
Community Features
Clubhouse, Deed Restrictions, Gated Community – Guard, Golf Carts OK, Irrigation-Reclaimed Water, Park, Playground, Pool, Restaurant, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco
Exterior Features
Dog Run, French Doors, Hurricane Shutters, Irrigation System, Lighting
Roof
Tile
Financial
HOA Fee
$2,900
HOA Frequency
Semi-Annually
HOA Includes
Private Road, Security
HOA Name
Access Management/ Hope Root
Tax Year
2025
Taxes
$12,040
Map
Community
- Address140 SUGAR MILL DRIVE OSPREY FL
- SubdivisionOAKS
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BAYPOINTE VISTA 2
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN HARBOR WATERFRONT VILLAS PHASE 2
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- MERIDIAN AT THE OAKS
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-A
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OGBURNS T B ADD
- OSPREY EXECUTIVE PARK
- OSPREY HARBOR VILLAGE
- OSPREY PARK 2
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 1 OF BAY STREET
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL THE WOODLANDS
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WILLOWBEND PH 1
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WILLOWBEND PHASE 3
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of Mar 14, 2026
116
Single Family Listed
121
Avg DOM
458
Avg $ / SqFt
$1,410,027
Avg List Price
Property Summary
- Located in the OAKS subdivision, 140 SUGAR MILL DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $1,749,990 and features 4 beds, 4 baths, and has approximately 3,286 square feet of living space, and was originally constructed in 1989. The current price per square foot is $533. The average price per square foot for Single Family listings in OSPREY is $458. The average listing price for Single Family in OSPREY is $1,410,027. To schedule a showing of MLS#a4684805 at 140 SUGAR MILL DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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Courtesy of COLDWELL BANKER REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 140 SUGAR MILL DRIVE
OSPREY, FL









































































