Casselberrry/Winter Springs / Tuscawilla Homes with Trees/Woods View

Casselberrry/Winter Springs / Tuscawilla Homes with Trees/Woods View

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, a hidden gem nestled in the heart of Seminole County, Florida. This picturesque area boasts a perfect blend of suburban tranquility and vibrant community life, making it an ideal place for families, young professionals, and retirees alike.

As you explore the neighborhoods, you'll discover an array of charming homes surrounded by lush greenery and majestic trees. Many properties here offer stunning views of the woods, creating a serene backdrop that invites relaxation and outdoor enjoyment. Imagine sipping your morning coffee on your patio, with the gentle rustle of leaves and the sweet chirping of birds as your soundtrack.

Winter Springs is known for its excellent schools, beautiful parks, and a strong sense of community. The nearby Tuscawilla area features a variety of recreational opportunities, including golf courses, nature trails, and scenic lakes perfect for kayaking or fishing. The region is also conveniently located near major highways, providing easy access to the bustling city of Orlando, where you can indulge in shopping, dining, and entertainment.

Whether you're seeking a cozy single-family home or a spacious property with room to grow, the Casselberry/Winter Springs/Tuscawilla area offers an impressive selection to suit your lifestyle. Embrace the beauty of nature while enjoying the comforts of suburban living. Discover your dream home in this charming region, where every day feels like a retreat into the woods. Your slice of Florida paradise awaits!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Trees/Woods View

$650,000
4 Beds ⋅ 3 Baths ⋅ Tuskabay Ph 1 SubDv. ⋅ 32708 Zip Code
UPDATED WINTER SPRINGS POOL HOME IN THE HIGHLY DESIRABLE TUSKAWILLA AREA! Welcome to 4951 Courtland Loop, where timeless character, extensive upgrades and the Florida lifestyle come together. This impressive .38-acre homesite is surrounded by beautiful mature oaks. TUSKABAY is located in the heart of TUSCAWILLA, one of ORLANDO's Best COMMUNITIES. Offering 4 bedrooms, 3 full baths and 2,562 square feet, this is the MOVE-IN READY Winter Springs home you've been waiting for. Top features include a desirable FIRST-FLOOR PRIMARY & Sec.Bedrooms, Gourmet KITCHEN, SIDE-ENTRY GARAGE, spacious living areas and impressive indoor-outdoor layout designed for entertaining. Main entry offers view of large living area with cozy, BRICK WOOD BURNING FIREPLACE with POOL & YARD VIEWS. OPEN CONCEPT DINING- LIVING ROOM COMBO flanking the kitchen, primary and secondary downstairs' bedrooms flows.The PRIMARY BEDROOM boasts CATHEDRAL CEILINGS, DOUBLE CLOSETS, TRANSOM/FULL LENGTH WINDOWS, immersing the room in natural light. Warm, wood style flooring contrasts the lighter finishes exquisitely and leads to the ENSUITE, LUXURY BATHROOM. The remodeled primary bath adds another touch of luxury with QUARTZ COUNTERTOPS, GOLD FINISHES, FARMHOUSE-STYLE SINK and GLASS ENCLOSED SHOWER with SUBWAY TILE. At the heart of the home is a beautifully RENOVATED KITCHEN offering a timeless look,appealing to discriminating buyers. Crisp, LIGHT CABINETRY with clean lines offers abundant storage, complemented by EXPANSIVE QUARTZ COUNTERTOPS and a classic backsplash. The butcher-block island compliments the STAINLESS STEEL APPLIANCES package including the JennAir range, low maintenance KitchenAid appliances with double oven, dishwasher, wine and beverage cooler. This kitchen was created for everyday living and entertaining, blending style and practicality. Upstairs you'll find two large, private bedrooms with a bathroom and loft view of the downstairs. Through the FRENCH DOORS to the outside you'll discover your own backyard retreat. Enjoy the swaying oak trees from your private lanai, in-ground POOL, expansive PAVER PATIO, extended walkways, over .38 ACRE FENCED YARD and mature landscaping provide an incredible setting for weekend gatherings, quiet mornings and year-round outdoor living. Enjoy the parklike feel from the comfort of home. Even more impressive is the investment already made in the home's major systems available to a buyer without having to assume the payment or finance a new roof or solar system. Buy HASSLE FREE, no insurance issues here with a 2021 installed roof, seller-owned 11.745 kW solar system, TESLA POWERWALL BATTERY, DOUBLE PANE WINDOWS, high-efficiency heat-pump water heater, WHOLE-HOME WATER FILTRATION AND SOFTENER, Nest thermostats and EV CHARGING combine modern technology with energy-conscious living. The sellers' transfer offers an incredible opportunity for a savvy buyer to buy an outstanding home at an even better VALUE. Too many improvements like upgraded irrigation, newer gutters and additional improvements to mention that make this home truly stand apart. If you've been searching for a WINTER SPRINGS POOL HOME, Tuskawilla home, updated 4-bedroom home, energy-efficient home or move-in-ready home in Seminole County, 4951 Courtland Loop deserves to be at the top of your list. Space. Pool. Upgrades. Energy efficiency. Exceptional Winter Springs LIFESTYLE. This is the home buyers have been waiting for—schedule your private showing today.

4951 Courtland Loop, Winter Springs
$399,900
3 Beds ⋅ 2 Baths ⋅ Highlands Sec 1 SubDv. ⋅ 32708 Zip Code
Welcome to your private retreat in the heart of Winter Springs. Set beneath mature trees in the established Highlands community, this inviting single-story pool home offers three bedrooms, two full baths and a thoughtfully updated interior designed for comfortable Florida living. Vaulted ceilings enhance the open main living space, while a wood-burning fireplace creates a warm and memorable focal point. The updated kitchen features crisp white cabinetry, granite countertops, stainless-steel appliances and an easy connection to the dining and gathering areas. The same wood-look ceramic tile flooring flows throughout the entire home, creating a cohesive appearance with no carpet to maintain. Both bathrooms have been remodeled, including the primary bath in 2020 and the secondary bath in 2023. Step outside to a screened, heated pool made for morning swims, relaxed afternoons and year-round entertaining. The pool heater and roof were replaced in 2022, while the fully fenced backyard provides additional outdoor space and privacy. An oversized two-car garage offers plenty of room for vehicles plus additional storage, recreational equipment or weekend toys. Highlands residents enjoy a clubhouse, community pool, playground, tennis and pickleball courts, and neighborhood trails—all with convenient access to shopping, dining and major roadways. This is the Florida pool-home lifestyle buyers have been waiting for.

872 Falkirk Drive, Winter Springs
$489,900
2 Beds ⋅ 3 Baths ⋅ Greens At Tuscawilla SubDv. ⋅ 32708 Zip Code
Welcome to the exclusive gated enclave know as The Greens of Tuscawilla. This luxury townhome delivers a rare combination of superior construction, premium finishes, prime location, and a maintenance-free lifestyle. Nestled amongst the trees in the heart of Tuscawilla is The Portofino II Model with Golf, Water and Conservation Views. Level One offers Open Concept Living with the ability for a future Elevator. (Elevator closets are located on both floors and are currently used as walk in storage closets). Level Two allows for privacy with all bedrooms located on this floor. Throughout the unit you will find soaring volume ceilings, crown molding, tall doors, recessed lighting, wood or tiled floors, fresh paint, granite countertops, 42 inch cabinets, designer lighting, fans, fire safety sprinkler system and much more. Start and end each day on your private screened porch where the views are unparralleled. The Greens consists of 15 buildings and 60 units. Residents enjoy lush landscaping, manicured lawns and a private dog park. Partake in the Country Club lifestyle with the private Golf Cart path that leads to Tuscawilla Country Club. Membership provides access to championship golf, Har-Tru clay tennis courts, pickleball court, Jr. Olympic-sized pool, fitness center, private restaurant/bar, and social calendar. The Tuscawilla Community has parks, sports courts and fields, playgrounds, hiking trails and splash pads. Walk, run, or ride while taking in the many natural areas throughout the 3500 acre community.

1541 Corkery Court Unit 1541, Winter Springs
$665,000
4 Beds ⋅ 3 Baths ⋅ Chestnut Estates Ph 2 SubDv. ⋅ 32708 Zip Code
MOTIVATED SELLER! Elegant conservation retreat in prestigious Chestnut Estates-Tuscawilla. On a quiet cul-de-sac, this impeccably maintained four-bedroom, three-bath residence offers a rare combination of privacy, timeless comfort and everyday luxury. Backing to a serene conservation area with no rear neighbors, the home is surrounded by mature landscaping and picturesque natural views, creating a peaceful retreat, and rear patio has new pavers. Thoughtfully designed with a desirable split-bedroom floor plan, the spacious interior offers functionality and elegance. Generous closet space, large pantry and built-in workspace provide everyday convenience, while the open concept kitchen flows seamlessly into the family room and casual dining area, creating a warm and welcoming atmosphere that's ideal for gathering with family and friends. An oversized bonus room/enclosed Florida room with rich wood flooring expands the living space and offers endless possibilities, including a game room, music room and fitness studio. Enhanced with a mini-split system installed in 2025, this versatile space provides year-round comfort and is the ideal setting for entertaining or enjoying quiet evenings while overlooking the tranquil conservation backdrop. Roof (2023) with secondary barrier, HVAC (2025) with AC purification system included, plumbing updates and newer water heater. Schedule your private showing today!

223 Blue Creek Drive, Winter Springs
$689,900
4 Beds ⋅ 3 Baths ⋅ Howell Creek Reserve Ph 3 SubDv. ⋅ 32708 Zip Code
THERE ARE HOMES YOU SEE...and HOMES YOU FEEL! Privacy, space, and a peaceful conservation setting come together in this 4-bedroom, 3-bath pool home in the gated community of Howell Creek Reserve. Backing to conservation with no rear neighbors, the backyard feels like your own private retreat—perfect for relaxing by the pool or entertaining family and friends. Inside, the thoughtfully designed triple-split floor plan offers exceptional privacy, while soaring ceilings, crown molding, and updated lighting create an inviting, open atmosphere. The spacious primary suite features a tray ceiling, sitting area, walk-in closet, and an additional closet for extra storage. The kitchen offers granite countertops, a newer refrigerator and dishwasher, and opens seamlessly to the living spaces. Two bathrooms were renovated in 2020, and major updates include newer roof (2019), new HVAC (2026), newer water heater (2024), and a newer pool pump. Located just minutes from the Cross Seminole Trail, parks, shopping, dining, and top-rated Seminole County schools, this home offers the perfect balance of comfort, convenience, and Florida outdoor living. CALL TODAY to schedule your private Showing.

197 Nandina Terrace, Winter Springs
$544,900
3 Beds ⋅ 2 Baths ⋅ Country Club Village Unit 3 SubDv. ⋅ 32708 Zip Code
Renovated, remodeled, and reimagined in the highly sought-after Country Club Village at Tuskawilla. This beautifully renovated residence has been thoughtfully transformed with an extraordinary level of quality and attention to detail, delivering a truly turnkey opportunity for today’s discerning buyer - NO EXPENSE SPARED! Extensive recent improvements include a NEW TILE ROOF (July 2025), new gutters, all-new plumbing throughout (2026), fresh interior and exterior paint, and newly textured ceilings throughout, creating a clean, modern aesthetic from top to bottom. Inside, elegance meets functionality with stunning European white oak wood flooring throughout the main living areas, complemented by new carpet in the secondary bedrooms for added comfort. The heart of the home is the beautifully reimagined kitchen, featuring new 42-inch cabinetry, quartz countertops, all-new appliances, and a designer backsplash that adds both sophistication and visual appeal. Entertain effortlessly with a stylish wet bar complete with a beverage refrigerator and matching designer backsplash. Every bathroom has been completely remodeled, showcasing luxurious finishes and quartz surfaces throughout. Additional upgrades include new lighting fixtures inside and out, new door handles and hinges, new plugs and switches, custom roller shades throughout, and a custom closet system in the primary suite. Outside, refreshed landscaping enhances curb appeal and completes this impressive renovation, making this home a rare blend of timeless design, modern luxury, and move-in-ready convenience. The HOA-maintained lawn allows for low-maintenance living, while the location places you just moments from the private Tuscawilla Country Club. Zoned for some of the highest-rated public schools in the state and offers exceptional convenience—just 25 minutes from downtown Orlando, 30 minutes to Orlando International Airport, and less than an hour from Florida’s beautiful beaches and world-renowned theme parks. This property may be under audio/visual surveillance.

1329 Augusta National Boulevard, Winter Springs
$3,199,000
7 Beds ⋅ 7 Baths ⋅ Dunmar Estates SubDv. ⋅ 32708 Zip Code
Rare opportunity to own a private estate in the heart of Central Florida. Situated on nearly 6 acres in Dunmar Estates community of Winter Springs, this exceptional property is fully fenced BY METAL FENCE AND SOLID WALL FENCE FROM 6ft to 10 ft and gated, offering outstanding privacy, security, and a true retreat-like setting. The main residence features over 12,000 square feet of living space, including 7 bedrooms, multiple living and entertaining areas, and a unique indoor heated pool that can be enjoyed year-round regardless of weather. Expansive grounds and mature landscaping create a peaceful and secluded environment rarely found in today’s market. A standout feature of the property is its two separate Mother-in-Law Suites, ideal for multigenerational living, extended family, long-term guests, caregivers, private offices, or flexible living arrangements. Additional amenities include a tennis court, circular driveway, 6-car garage, and abundant outdoor space, offering endless opportunities for customization, renovation, and creating a truly one-of-a-kind family compound. Conveniently located just minutes from top-rated schools, shopping, dining, and major highways, this estate combines the tranquility of private country-style living with the convenience of city access. A rare offering with exceptional space, privacy, and unlimited potential.

593 Dunmar Circle, Winter Springs
$1,085,000
5 Beds ⋅ 5 Baths ⋅ Reserve At Tuscawilla Ph 1 The SubDv. ⋅ 32708 Zip Code
NEW PRICE! Luxury living awaits in this custom pool home located within Tuscawilla Reserve, an exclusive gated community in Winter Springs, Florida. Offering more than 4,000 square feet of living space, this impressive estate features five bedrooms, five full bathrooms, a private office or bonus room, a three-car side-entry garage, and a flexible floor plan designed for modern living. The heart of the home is the spectacular two-story kitchen and family room, where soaring ceilings and expansive windows fill the space with natural light and frame views of the pool and backyard. Sleek wood flooring flows throughout the main living areas, creating a warm, open setting for everyday living and entertaining. The chef’s kitchen features JennAir appliances, double ovens, a convection oven and microwave combination, an oversized granite island, a built-in buffet with an integrated wine refrigerator, and a large walk-in pantry. With abundant counter space, storage, and seating, the kitchen serves as both a functional workspace and a striking centerpiece of the home. The thoughtfully designed floor plan offers excellent flexibility for families, guests, remote work, and multigenerational living. The upstairs retreat includes an additional bedroom, full bathroom, and expansive flex space that can be used as a media room, playroom, second office, fitness area, or private guest suite. Outside, enjoy a private backyard oasis with a sparkling pool and spa, new pool heater, mature landscaping, and a fully fenced yard. The spacious outdoor setting offers privacy while providing plenty of room for relaxing, entertaining, and enjoying the Florida lifestyle. Additional features include a whole-house water softener, generous storage, expansive living areas, and a three-car side-entry garage. Tuscawilla Reserve is conveniently located near the Seminole Trail and Tuscawilla Country Club, offering nearby access to golf, tennis, swimming, dining, and social activities. Golf carts are a popular way to travel throughout the Tuscawilla community, adding to the neighborhood’s charm and convenience. The property is also zoned for highly regarded Seminole County schools and is convenient to shopping, dining, parks, and major Central Florida destinations. For buyers searching for a luxury home in Winter Springs, a gated community home with a pool, or a custom estate near Tuscawilla Country Club, this exceptional property offers space, privacy, natural light, and elevated indoor-outdoor living. Schedule your private showing and experience Tuscawilla Reserve living at its finest.

149 Cherry Creek Circle, Winter Springs
$649,900
4 Beds ⋅ 3 Baths ⋅ Winding Hollow Unit 2 SubDv. ⋅ 32708 Zip Code
MAJOR PRICE IMPROVEMENT!! Pride of ownership is evident throughout this beautifully updated, MOVE-IN PERFECT, one-owner home located in the highly sought-after WINDING HOLLOW community of Winter Springs. This ideal two-story floor plan offers 4 BEDROOMS, 3 FULL BATHS, BONUS ROOM, 3-CAR GARAGE, and a LARGE SCREENED LANAI, showcasing timeless style, thoughtful updates, and versatility with TILE FLOORING throughout the first floor and LAMINATE WOOD FLOORING upstairs. The bright, OPEN-CONCEPT floor plan offers exceptional flow and is perfect for entertaining, featuring spacious formal living and dining rooms with soaring ceilings that create an inviting sense of space. The heart of the home is the beautifully designed ISLAND KITCHEN, perfectly positioned between the breakfast nook and impressive family room with 18-FOOT CEILINGS and dramatic upper windows that flood the home with natural light. The kitchen features GRANITE COUNTERTOPS, ABUNDANT WOOD CABINETRY with PULL-OUT DRAWERS, STAINLESS STEEL APPLIANCES, PANTRY, and convenient access to the garage and laundry room with additional storage. The spacious FIRST-FLOOR PRIMARY SUITE offers a sitting area, TWO WALK-IN CLOSETS, and an updated spa-inspired bath featuring a SOAKING TUB, GLASS SHOWER, and DUAL QUARTZ VANITIES, creating the perfect private retreat. A SPLIT FIRST-FLOOR GUEST SUITE with a full bath provides ideal accommodations for visitors or MULTI-GENERATIONAL LIVING. Upstairs you’ll find BEDROOMS 3 & 4, a full hallway bath, and a versatile BONUS ROOM/FLEX SPACE with a walk-in closet overlooking the family room below. Easily used as a 5TH BEDROOM, MEDIA ROOM, PLAYROOM, HOME OFFICE, or HOME GYM, this flexible space adapts to your family’s needs. Enjoy Florida living year-round from the expansive TILED SCREENED LANAI, accessible from the formal living room, family room, and primary suite while overlooking the PRIVATE, LUSHLY TREED BACKYARD. Additional highlights include PLANTATION SHUTTERS THROUGHOUT, a spacious 3-CAR GARAGE with overhead storage, an EXPANDED BRICK-PAVER DRIVEWAY, 2018 ROOF, TWO ZONED A/C SYSTEMS (2022 & 2019), 2019 WATER HEATER, and COMPLETE PLUMBING REPIPE (2025). Ideally located WITHIN WALKING DISTANCE TO THE CROSS SEMINOLE TRAIL & CENTRAL WINDS PARK, and just minutes from TOP-RATED WINTER SPRINGS SCHOOLS, shopping, dining, SR 417, and US 17-92, this exceptional home truly offers the perfect combination of LOCATION, LIFESTYLE, AND VALUE. WELCOME HOME!

525 Saddlewood Lane, Winter Springs
$480,000
3 Beds ⋅ 2 Baths ⋅ Amherst SubDv. ⋅ 32708 Zip Code
Virtually Staged. Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. Property has fiber optics, 50 amp car charger in garage, and nest thermostat for A/C. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.

1055 Chesterfield Circle, Winter Springs
$674,900
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 14b SubDv. ⋅ 32708 Zip Code
Rare opportunity to own a spacious pool home on a private 2.1-acre conservation homesite in the highly desirable Chelsea Woods section of Tuscawilla. Offering 4 bedrooms, 3 bathrooms and over 3,100 square feet of living space, this home features a dedicated office with custom built-ins, formal living and dining areas, a wood-burning fireplace, and a large upstairs loft that provides flexible space for a media room, game room, home gym, or additional living area. The kitchen overlooks the main living spaces and pool area, while French doors open to an expansive covered lanai and screened pool enclosure designed for year-round Florida living. Step outside and enjoy your own backyard retreat featuring a large pool and spa with waterfall features, outdoor grilling area, generous deck space, mature landscaping, and peaceful conservation views with no rear neighbors. Major improvements include a roof replaced approximately 3 years ago and HVAC systems replaced approximately 3 years ago, providing peace of mind for years to come. Conveniently located near top-rated Seminole County schools, parks, golf, shopping, dining, and major commuter routes. Optional HOA membership available. Homes offering this combination of acreage, privacy, pool, location, and living space rarely become available.

1838 Seneca Blvd, Winter Springs
$329,900
3 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code
Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

335 Kirkcaldy Drive, Winter Springs
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