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$1,050,000
4 Beds ⋅ 4 Baths ⋅ Shadow Oaks SubDv. ⋅ 34240 Zip Code
Your private oasis close to everything awaits! Welcome home to this beautiful extensively upgraded 4 bed, 4 bath, 4452 square foot home on over an acre complementing contemporary expectations with timeless country charm. Within you’ll discover a truly flexible living space for modern families & everyone’s hobbies with a master suite option on both floors, spacious living areas, dedicated office & an extra flex room, game room, playroom, gym or guest suite. Or the south wing could simply be a generous multi-generational retreat…. The 2020 renovations enlightened & streamlined the interior with a huge chef’s kitchen & dining room combo, all new bathrooms, updated bedrooms with walk-in closets & flooring too–all while maintaining the home’s warm & inviting character. Two wood-burning fireplaces add a cozy ambiance to both living rooms, upstairs & down. Outside, enjoy true Florida living with a screened-in heated saltwater pool, outdoor kitchen with built-in grill & large covered patio–perfect for entertaining or quiet relaxation. Warblers, sandhill cranes & a little family of deer will bring joy to your days as will stunning sunsets by the pool at night. With 200 feet along peaceful Philippi Creek, this private lot features outdoor lighting, irrigation, mature oaks, bamboo, banana trees, rows of foxtail palms & ample room for all the big & little kid toys you’ve been wishing for! The oversized two-car garage features EV charging, rear garage door, additional storage & extra room. Additional energy & cost-savings bonuses include a 3-zoned HVAC system & other mechanical updates throughout. No HOA or CDD fees. Flood zone X for extra savings & peace of mind. Perfect for nature lovers & exercise enthusiasts, the world-famous Celery Fields bird & nature refuge is 0.4 miles away for you to hike, bike, paddle, fish & birdwatch as a daily routine. When you must run errands, this generous retreat is also only minutes from many shopping/dining choices at Bee Ridge, Fruitville, UTC, Lakewood Ranch & Costco along nearby Interstate exits & is within thirty minutes of the airport, St Armands Circle, Lido & Siesta Key beaches & downtown Sarasota too. Then come home again & disappear into the rare rustic charm of this tropical sanctuary estate.

2308 Shadow Oaks Road, Sarasota
$713,000
3 Beds ⋅ 3 Baths ⋅ Shadow Oaks SubDv. ⋅ 34240 Zip Code
Discover this tranquil lifestyle; Imagine coming home at the end of the day to a peaceful retreat with over an acre of land and a private pond. This one-owner two-story pool home is perfectly situated at the end of a quiet cul-de-sac in the heart of Sarasota. This residence offers privacy and charm with tranquil pond views from the backyard and direct water access for kayaking or relaxing by nature. Inside, you'll find three spacious bedrooms and two-and-a-half bathrooms with luxury vinyl plank flooring throughout the main living areas. The inviting family room features a cozy fireplace, while the living and dining room combination creates the ideal setting for entertaining or every day living. The eat-in kitchen provides plenty of space for casual meals with a view of the pool and yard. Recent updates include a NEW AIR CONDITIONING SYSTEM (2025) and IMPACT WINDOWS for peace of mind. The two-car garage includes the laundry area and plumbing already in place for a future half bath that connects conveniently to the pool area; perfect for outdoor gatherings. Step outside to your private screened pool and patio, surrounded by mature trees and lush landscaping, creating a serene outdoor retreat. No CDD or HOA fees, so bring your boat or RV! Only a short drive to Siesta Key, Lakewood Ranch, Downtown Sarasota and located in a top school district; this home blends solid construction, modern comfort, and a quiet cul-de-sac setting for the perfect Florida Lifestyle.

2115 Shadow Oaks Road, Sarasota
$570,000
3 Beds ⋅ 2 Baths ⋅ Shadow Oaks SubDv. ⋅ 34233 Zip Code
Live, Work, and Play — All at Home! Discover the perfect property for a home-based business or contractor right in the heart of Sarasota! Situated on just under an acre, this fully fenced .86-acre estate offers incredible flexibility and income potential. Main Home: 3 bedrooms, 2 baths, featuring a spacious primary suite, bright enclosed patio, and a sparkling pool with waterfall. Recent updates include a new AC, 5-year-old septic system (with warranty), and a 200-ft deep freshwater well with a submersible pump system. Warehouse: Approx. 1,500 sq. ft. with an air-conditioned office—ideal for storage, business operations, or creative workspace. Additional Dwellings includes a separate Mother-In-Law cottage —perfect for multigenerational living. Bonus Features: Ample parking for work trucks, RVs, and all your toys, plus a camper electric hookup. No deed restrictions! All this, just minutes from top-rated schools, world-class dining, shopping, golf, and Sarasota’s famous Gulf Coast beaches.

4429 Hicks Street, Sarasota
$549,000
3 Beds ⋅ 3 Baths ⋅ Shadow Oaks SubDv. ⋅ 34240 Zip Code
Handyman Special! Sold to settle estate. A great opportunity for someone looking for a project that offers a gorgeous private acre lot in a very desirable central Sarasota location! Non deed restricted with gorgeous mature Oaks and a pond at the rear. Although recently occupied, the house does have a lot of wood rot and deteriorated siding and deferred maintenance throughout. The property is most likely not financeable. Bring your contractor to assess or buy it for the lot and build your dream home! Priced accordingly.

6841 Porter Road, Sarasota
$542,000
3 Beds ⋅ 3 Baths ⋅ Shadow Oaks SubDv. ⋅ 34744 Zip Code
Charming Ranch on 1 Acre + Private Saltwater Pool – NO HOA! Beautifully renovated 3BR home with open-concept living, bonus room, private office space, and newly updated kitchen & baths featuring stainless steel appliances, quartz waterfall countertops, and 32”x32” porcelain tile. Enjoy your private saltwater pool with new pump, a well on property, and peaceful surroundings—just minutes from town. Space, privacy, and convenience all in one! Realtor related to seller.

949 Shadow Oaks Road, Kissimmee
$475,000
4 Beds ⋅ 3 Baths ⋅ Shadow Oaks SubDv. ⋅ 34690 Zip Code
Designed with entertaining in mind, this oversized 4 bedroom, 2.5 bath pool home PLUS BONUS ROOM AND GAME ROOM is tucked away on a peaceful cul-de-sac and features a highly sought-after triple split floor plan with expansive gathering spaces throughout. The open concept layout centers around an updated kitchen with black stainless steel appliances, custom epoxy flooring, and easy flow into the main living areas, making it ideal for hosting everything from casual get-togethers to large celebrations. Just off the kitchen, a very large bonus room offers endless flexibility and can be used as a home office, movie theater, or private in-law suite. The dedicated game room and bar area create the ultimate entertainment hub and convey fully furnished, including the pool table, allowing you to host instantly with no setup needed. Additional Information: Roof Replaced 2023, Pool Resurfaced 2024 Outdoors, the screened pool and spacious, fully fenced backyard provide a private setting for pool parties, weekend gatherings, and outdoor dining, with ample room for additional seating or recreation. The backyard is also suitable for a chicken coop if desired. Fresh interior paint and a new front door add to the move-in-ready appeal. No HOA to contend with adds flexibility and freedom, while generous room sizes, multiple entertaining zones, and a layout designed for hosting make this home ideal for bringing people together with ease.

5801 Lenmar Court, Holiday
$349,000
4 Beds ⋅ 2 Baths ⋅ Shadow Oaks SubDv. ⋅ 34690 Zip Code
Four bedroom house in nicer, quiet community. Modern, 2000 construction. Plenty of space in two car garage. Didn't come close to flooding. Your backyard neighbors are ducks in a creek. Permitted, professionally remediated subsidence has warranty that can be transferred to new owner. Qualifies for some FHA and most Conventional mortgages. Roof 2023, AC 2016, Water Heater 2021.

3123 Shadow Oaks Drive, Holiday