Casselberrry/Winter Springs / Tuscawilla Homes with Rain Gutters Exterior Features

Casselberrry/Winter Springs / Tuscawilla Homes with Rain Gutters Exterior Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area offers a unique blend of suburban charm and natural beauty, making it a sought-after destination for families, retirees, and everyone in between. With its lush landscapes, picturesque parks, and top-rated schools, Winter Springs is celebrated for its strong sense of community and excellent quality of life.

As you explore the neighborhoods of Tuscawilla, you’ll discover stunning homes that perfectly complement the serene surroundings. Many properties in this area feature desirable exterior attributes, including practical and stylish rain gutters. These essential additions not only enhance the aesthetic appeal of your home but also provide critical protection against Florida's seasonal rains. With well-designed rain gutters, homeowners can effectively manage water runoff, safeguarding their landscaping and foundation from potential water damage.

The homes in this region boast a variety of architectural styles, from charming single-family residences to modern townhomes, each equipped with features that cater to today’s lifestyle. With easy access to local amenities, shopping centers, and recreational areas, residents enjoy a perfect balance of convenience and tranquility.

If you’re considering a move to this picturesque corner of Florida, you’ll find that Casselberry, Winter Springs, and Tuscawilla offer not just a place to live, but a community to call home. Experience the warmth and charm of this exceptional area, where every day feels like a vacation. Your dream home awaits!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Rain Gutters Exterior Features

$475,000
3 Beds ⋅ 2 Baths ⋅ Deer Run Unit 23a SubDv. ⋅ 32708 Zip Code
Tucked beneath a canopy of majestic oaks in the established Tuscawilla Forest community, this charming 3-bedroom, 2-bath, 2-car garage home offers approximately 1,700 square feet of living space on a spacious .26-acre lot—along with something you simply can't recreate overnight: character, mature landscaping and the welcoming feel of an established neighborhood. Cherished by the same homeowner since 2004, this has been a much-loved home for more than two decades. The owners have especially treasured their wonderful neighbors and convenient location, and now it's time for a new owner to begin their own chapter here. Step inside and you'll immediately appreciate the desirable split-bedroom floor plan, vaulted ceilings and skylights that bring natural light into the main living areas. At the heart of the home, the inviting living space features a double-sided fireplace, warm wood accents and built-in shelving. The kitchen offers real wood cabinetry, generous counter space, breakfast bar, stainless-steel appliances and stylish tile backsplash, opening naturally to the main living area. The primary suite offers a private retreat with a beautifully remodeled bath featuring dual vanities, soaking tub and separate glass-enclosed walk-in shower with striking tile and pebble-stone accents. The secondary bath has also been beautifully remodeled. MAJOR IMPROVEMENTS HAVE ALREADY BEEN MADE, including a NEW ROOF IN 2021 with new gutters and gutter guards, A/C SYSTEM IN 2020 with parts-and-labor warranty noted through 2030, REMODELED BATHROOMS IN 2024, PEX PLUMBING, TWO-TONE VINYL PRIVACY FENCE IN 2023 and NEW ST. AUGUSTINE GRASS IN 2023. Additional improvements include the updated kitchen, lighting and ceiling fans, flooring and sprinkler system. And then there's the OUTDOOR LIVING! Sliding glass doors lead to an expansive screened and covered lanai, perfect for morning coffee, weekend gatherings or simply enjoying Florida living. Beyond the lanai, the large, private fenced backyard is shaded by beautiful mature trees with plenty of room for gardening, pets, play, entertaining—or perhaps that future pool you've been dreaming about. Whether hosting friends, enjoying a quiet evening under the trees or simply unwinding after a long day, this backyard offers the space and privacy to enjoy being home. LOCATION, LOCATION, LOCATION! Enjoy the charm of an established Winter Springs neighborhood with access to Seminole County Public Schools while staying close to everything. Nearby Trotwood Park, Central Winds Park, Bear Creek Nature Trail and the Cross Seminole Trail provide walking, biking, sports, playgrounds and outdoor recreation. Shopping, dining and everyday conveniences are nearby, with easy access to Oviedo, UCF, Winter Park, SR 417 and the greater Orlando area. With its mature surroundings, nearby parks and trails, convenient location and the kind of neighbors the current owners will truly miss, it's easy to understand why they called this home for more than 20 years. Some homes simply have a story—and this one has been loved for more than two decades. Filled with memories and thoughtfully cared for through the years, 288 Ringwood Drive is ready for its next chapter...and its next owner to call it HOME.

288 Ringwood Drive, Winter Springs
$549,000
3 Beds ⋅ 4 Baths ⋅ Seminole Crossing Townhomes SubDv. ⋅ 32708 Zip Code
Welcome to 1166 Spotted Sandpiper Loop in Winter Springs, a spacious three-story, 3-bedroom, 3.5-bath townhome in Seminole Crossing. With a floor plan that offers plenty of room to spread out, this home is one of only two townhomes in the community featuring this unique layout. Its multi-level design gives the home more character and separation than the typical boxy townhome, with gathering spaces and private retreats thoughtfully placed across three floors. The first floor features a private bedroom and full bathroom, making it ideal for guests, extended family, or a home office, along with an oversized rear-facing garage and covered front porch. Upstairs, the main living level brings the gourmet kitchen, dining area, and family room together in an open, light-filled space. Designed with both everyday living and entertaining in mind, the gourmet kitchen features a walk-in pantry, generous prep and storage space, and double ovens. French doors open to an expansive balcony, creating an inviting spot to enjoy some fresh air or unwind at the end of the day. The third floor is home to the primary suite, a second bedroom, and a flexible loft. The primary suite offers a large walk-in closet and spacious bathroom with dual sinks, soaking tub, and separate shower. The second bedroom also has a walk-in closet, with a full bathroom conveniently located just outside the bedroom, while the loft can easily become a lounge, media area, study, or home office. The laundry room is conveniently located nearby. One of the biggest perks of townhome living here is the maintenance-free exterior. The HOA takes care of the outdoor upkeep, including mowing, weeding, flower beds, tree trimming, and more. When the time comes, the HOA is also responsible for exterior painting and roof replacement, giving you even less to worry about. And the location makes everyday errands surprisingly easy. The Cross Seminole County Trail is just a short distance from the home located right outside the neighborhood, while nearby grocery stores and restaurants are also just a walk away. Starbucks is even closer, with Chick-fil-A, Wawa, and Ace Hardware coming soon. Residents also enjoy access to a community pool, sidewalks, and additional recreational spaces, with convenient access to SR 434, Winter Springs Town Center, Oviedo, and surrounding Seminole County. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

1166 Spotted Sandpiper Loop, Winter Springs
$210,000
2 Beds ⋅ 2 Baths ⋅ Moss Cove SubDv. ⋅ 32708 Zip Code
Virtually Staged. Charming Winter Springs Townhouse – Perfect for Buyers or Investors! Welcome to 113 Kristi Ann Court, a beautifully maintained 2BR/1.5BA townhouse in the highly sought-after Winter Springs area. Offering 898 sq ft of thoughtfully designed living space, this home features a bright, open living area and a well-appointed kitchen optimized for everyday comfort. Step outside to your private, screened-in patio—the perfect spot to relax and enjoy the Florida lifestyle. Superb location provides seamless access to premier shopping, local dining, parks, top-rated schools, and major roadways for an easy commute. An exceptional opportunity for first-time homebuyers, downsizers, or savvy investors looking for excellent rental potential. Immediate income producing opportunity for investors. No detail overlooked, functional layout, and unbeatable location. Schedule your private tour today!

113 Kristi Ann Court, Winter Springs
$497,000
4 Beds ⋅ 3 Baths ⋅ Fox Glen At Chelsea Parc Tuscawilla SubDv. ⋅ 32708 Zip Code
Welcome to this beautiful 4-bedroom home in the heart of Tuscawilla! This well-appointed home offers a comfortable and versatile floor plan with a primary bedroom conveniently located on the main floor. Upstairs, you'll find three additional bedrooms and a spacious loft-perfect for a reading area, sitting room, home office or additional living space. Relax and enjoy the peaceful private garden views from the enclosed patio, creating a wonderful space for morning coffee, entertaining or simply unwinding at the end of the day. Property amenities include a large community pool, jacuzzi, fitness room and clubhouse. Enjoy an exceptional Tuscawilla location near Tuscawilla Country Club, Bear Creek Nature Trail, Sam Smith Park, Trotwood Park and just minutes from the Oviedo Mall and Oviedo on the Park offering a variety of dining, shopping and entertainment options. The home is located within the highly regarded Seminole County Public Schools, an A-rated school district and minutes from University of Central Florida. Conveniently located in Central Florida, approximately an hour from Walt Disney World, Universal Studios and many of Florida's beautiful beaches making this an ideal location for enjoying everything the area provides. Come see why this Tuscawilla home is the perfect combination of comfort, location and convenience!

1610 Fox Glen Court, Winter Springs
$525,000
4 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 6 SubDv. ⋅ 32708 Zip Code
Welcome home to this spacious 4-bedroom, 2-bath pool home located in the highly desirable Winter Springs community! Designed with a functional split-bedroom floor plan, this home offers the perfect balance of privacy, space, and comfortable everyday living. Step inside to soaring vaulted ceilings, abundant natural light, and separate formal living and dining rooms that provide plenty of flexibility for entertaining, working from home, or gathering with family. The heart of the home opens to a large screened lanai and sparkling pool, creating the perfect setting for Florida living year-round. Whether you’re enjoying a quiet morning outside, hosting friends for a weekend barbecue, or cooling off on a summer afternoon, the expansive outdoor living space is sure to become a favorite part of the home. The generously sized lot offers plenty of room to enjoy the outdoors and also features a storage shed with electricity—ideal for a workshop, hobby space, or additional storage. Major improvements offer added peace of mind, including a NEW ROOF, NEW PLUMBING, and NEW WATER HEATER. Best of all, the home is ideally situated in sought-after Winter Springs within walking distance of the area’s schools, making everyday routines incredibly convenient. With its spacious floor plan, beautiful natural light, private pool, large lot, and valuable recent updates, this home offers an incredible opportunity to enjoy everything Winter Springs has to offer!

699 N Endeavour Drive, Winter Springs
$629,999
4 Beds ⋅ 2 Baths ⋅ Avery Park SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully upgraded 4-bedroom, 2-bathroom home in Avery Park, where modern finishes, impressive architectural details, and incredible indoor-outdoor living come together. A generous front porch overlooks the community’s large pond, creating a peaceful setting to enjoy your morning coffee or unwind at the end of the day. Inside, the formal entry hall immediately makes an impression with Venetian plaster niches, soaring 10-foot ceilings, crown molding, and artist-painted raised tray ceilings. The thoughtful details continue throughout the home, including a private office with crown molding and recessed lighting, along with formal living and dining rooms featuring beautiful tray ceilings. The kitchen is designed for both everyday living and entertaining, featuring a large island with seating, stainless steel appliances, a walk-in pantry, and a beautiful backsplash. A spacious interior laundry room provides additional storage and convenience. The primary suite offers its own retreat with beautiful tray ceilings, his-and-hers closets, and an updated ensuite bath featuring a spacious walk-in shower with frameless glass, floor-to-ceiling tile, and built-in niches. French doors open directly to the wood-ceilinged rear porch and private garden beyond. Another bedroom also features its own ensuite bathroom, offering added privacy and convenience for guests or family. Upstairs, a large private bonus room offers endless possibilities as an additional bedroom, art studio, hobby space, media room, home gym, or whatever best fits your lifestyle. Step outside to a lush backyard oasis surrounded by mature vegetation, complete with your own private pond and spa/hot tub. Whether entertaining, relaxing on the porch, or simply enjoying the peaceful surroundings, this outdoor space feels tucked away from it all. A rear-entry three-car garage adds even more functionality while maintaining the home’s inviting curb appeal. Located within Avery Park, a premier gated community offering resort-style amenities including a neighborhood pool, playground, basketball court, and stocked fishing pond. The home is also zoned for highly rated Seminole County schools and conveniently located near Winter Springs Town Center, the Cross Seminole Trail, Central Winds Park, SR 417, shopping, dining, and more. With upgraded interiors, flexible living spaces, a three-car garage, and a private backyard retreat, this home offers something special both inside and out.

116 Avery Lake Drive, Winter Springs
$425,000
3 Beds ⋅ 2 Baths ⋅ Country Club Village Unit 2 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath POOL home nestled on a quiet, tree-lined street in the highly sought-after Country Club Village of Tuscawilla. This inviting home offers a versatile floor plan ideal for both everyday living and entertaining, with volume ceilings, abundant natural light, and attractive, low-maintenance tile and luxury vinyl plank flooring throughout. The spacious living and dining areas provide wonderful flexibility and can easily be arranged to complement your lifestyle. At the heart of the home, the kitchen overlooks the dinette and family room and features stainless steel appliances, ample prep and storage space, pull-out drawers, a built-in pantry and built-in wine rack. Its thoughtful location also offers possibilities to open or expand the kitchen toward the rear of the home, creating an even greater connection to the outdoor living and pool area. A charming greenhouse window in the dinette is perfect for growing fresh herbs or displaying your favorite plants. The spacious owner's suite provides a relaxing retreat with direct access to the back porch, a beautifully updated shower and vanity with granite countertop, an oversized window overlooking the atrium, and generous closet space. Two sizable secondary bedrooms are located toward the front of the home, with one offering direct access to the charming atrium. Step outside and enjoy your morning coffee or unwind at the end of the day on the private back patio overlooking the sparkling pool and hot tub, all tucked behind a privacy wall to create your own peaceful outdoor retreat. The pool screen was replaced in 2022 for added peace of mind. The OVERSIZED two-car garage is another standout feature, offering an extended workshop area with ample room for a golf cart, along with built-in shelving, attic stair access and a convenient rear-exit door. Hot water heater replaced Sept 2026. Country Club Village offers the perfect combination of a peaceful neighborhood setting and exceptional convenience. Located adjacent to Tuscawilla Country Club, optional memberships provide access to golf, tennis, fitness facilities, social activities, clubhouse amenities and more. Enjoy nearby parks and nature trails, highly rated Seminole County schools, shopping and dining, along with convenient access to UCF, Seminole State College, Orlando Sanford International Airport, Orlando International Airport and major roadways 417, 408, 528 and I-4. Don't miss the opportunity to make this exceptional Tuscawilla pool home your own—schedule your private showing today!

1162 E Winged Foot Circle, Winter Springs
$179,900
2 Beds ⋅ 2 Baths ⋅ Bay Tree Sec 09 SubDv. ⋅ 32708 Zip Code
Virtually Staged. If you’ve been dreaming of a MOVE-IN READY home where you can enjoy scenic parks, peaceful walking trails, and beautiful green spaces, welcome to Baytree 9, one of the charming communities within the Highlands of Winter Springs. This WELL-MAINTAINED two-story, 2-bedroom, 1½-bath condo offers the perfect blend of comfort, convenience, and carefree Florida living. Ideally located near highly rated schools, top medical facilities, shopping, dining, and major roadways, you’ll enjoy easy access to everything you need while coming home to a peaceful, nature-filled setting. Inside, the thoughtfully designed open floor plan creates an inviting space for everyday living. The kitchen flows into the dining and living areas, while oversized sliding glass doors fill the home with natural light and lead to your private patio – an ideal spot to sip your morning coffee, unwind after a long day, or simply enjoy the tranquil surroundings. The updated kitchen features granite countertops, a breakfast bar, pantry, neutral tile flooring, and all appliances convey. Upstairs, you’ll find a spacious primary suite, a comfortable second bedroom, a shared bath with direct access from the primary suite, and a conveniently located laundry closet designed for everyday ease. Enjoy peace of mind with numerous recent updates, including a NEW A/C in 2023 and, in 2024, a NEW ROOF, WATER HEATER, stainless steel kitchen APPLIANCES, full-size WASHER and DRYER, carpet, blinds, and chair-height toilets. One of the greatest benefits of this home is its low-maintenance lifestyle. The HOA covers exterior and grounds maintenance, giving you more time to enjoy the community’s OUTSTANDING AMENITIES. Spend sunny afternoons at the clubhouse and pool, gather with friends at the picnic areas with grills, explore the scenic nature trails, or enjoy the playgrounds, volleyball, basketball, and tennis courts. Conveniently located just off SR 434 with easy access to SR 436, Highway 17-92, SR 417, and I-4, you can enjoy Cranes Roost Park, Altamonte Mall, Winter Park Village, and the boutiques and restaurants along charming Park Avenue. Whether you’re looking for your first home, an investment, downsizing, or searching for a low-maintenance lifestyle surrounded by nature, this exceptional condo is ready to welcome you home. Schedule your private showing today and discover why so many love calling the Highlands of Winter Springs home! This home may be under audio or video surveillance.

70 Moree Loop Unit 61, Winter Springs
$339,900
3 Beds ⋅ 3 Baths ⋅ Barclay Reserve Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to the beautiful, tree-lined, gated community of Barclay Reserve. This 3 bedroom, 2.5 bathroom, end unit townhome is offered fully furnished and move in ready. Brand new A/C July 2025, new refrigerator April 2025 and new washer & dryer May of 2023. Enjoy a waterfront view with the soothing fountain sound from the living space and two bedrooms. Both the original owner and current owner used the property as a second home which means less wear and tear. The property is less than 10 minutes away from Ovideo on the Park and 15 minutes away from UCF, making the home a perfect purchase for parents needing student housing. It’s only 2 minutes from SR-417 for easy access to the airport, 408 and I-4. 33 guest parking spaces are distributed around the circle so you don’t have to worry about dodging street parking. Peace, security and a prime location seeking its next owner.

617 Pinebranch Circle, 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
$520,000
4 Beds ⋅ 2 Baths ⋅ Deer Run Unit 21a SubDv. ⋅ 32708 Zip Code
Don’t miss your chance to own this luxury 4-bedroom, 2-bath pool home retreat in the highly sought-after Tuscawilla Forest, featuring a BRAND NEW ROOF upon signed contract. Beautifully designed for everyday living and comfortable formality, this home offers an open layout with multiple living spaces. Walk in to a formal conversation area followed by a chef's kitchen with all granite countertops, and backsplashes. A spacious primary bedroom with an en suite spa like bathroom featuring large his and hers walk-in closets, a custom carrara quartz double vanity, and tied together with modern organic finishes. Have peace of mind with updated plumbing throughout. Step outside to your private fully fenced backyard oasis, featuring a sparkling pool and expansive outdoor area perfect for relaxing evenings, weekend gatherings, and enjoying the Florida nature. Ideally located near shopping, dining, parks, top-rated schools, and major roadways, this home provides the perfect combination of convenience, comfort, and modern luxury.

324 Ringwood Circle, Winter Springs
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