Casselberrry/Winter Springs / Tuscawilla Homes with Private Mailbox Exterior Features

Casselberrry/Winter Springs / Tuscawilla Homes with Private Mailbox Exterior Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is renowned for its charming neighborhoods, lush landscapes, and a welcoming community that truly feels like home. With its picturesque parks, scenic lakes, and family-friendly amenities, residents here enjoy a perfect blend of suburban tranquility and urban convenience.

Winter Springs is particularly celebrated for its top-rated schools, making it a prime location for families. The area boasts a variety of recreational opportunities, from the beautiful Central Winds Park to the serene trails of the Cross Seminole Trail, perfect for biking, walking, or enjoying a leisurely afternoon. The nearby Tuscawilla Golf Club offers a splendid golfing experience, while the local shopping and dining options cater to every taste.

One of the standout features of homes in this region is the charming private mailbox exterior. These distinctive mailboxes not only enhance curb appeal but also provide a touch of personalization to each residence. Imagine coming home to a beautifully landscaped yard with a mailbox that reflects your unique style—it's the little details that make a house feel like home.

In addition to the aesthetic appeal, having a private mailbox adds a sense of exclusivity and community. It fosters a connection with neighbors and enhances the overall living experience in this delightful area. Whether you're looking for a cozy family home or a spacious retreat, the Casselberry, Winter Springs, and Tuscawilla region has something to offer everyone. Come explore and discover your dream home in this captivating Florida locale!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Private Mailbox 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
$415,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2b SubDv. ⋅ 32708 Zip Code
Nestled in the desirable Oak Forest at Tuscawilla community, this 3 bedroom, 2 bathroom home is located near local parks, trails, shops, restaurants, and highly rated Seminole County schools. Inside, a spacious, open floor plan flows effortlessly between the living and dining areas, elevated throughout by custom crown molding and rich wood detailing that add a timeless, tailored feel rarely found at this price point. The lovely kitchen anchors the home with a center island and breakfast bar, perfect for casual meals or entertaining guests. The primary suite offers a peaceful retreat with a generous walk-in closet, while the additional bedrooms are equally impressive, each offering generous space and an abundance of natural light. Outside, a screened patio invites year-round outdoor living, and an attached 2 car garage completes this beautiful Winter Springs residence.

1067 Chokecherry Drive, Winter Springs
$439,900
3 Beds ⋅ 3 Baths ⋅ North Orlando Ranches Sec 08 SubDv. ⋅ 32708 Zip Code
Welcome home to this beautifully maintained 3 bedroom, 2.5 bathroom pool home tucked away on a quiet, well mainicured Winter Springs Street, where pride of ownership shines. Designed with entertaining in mind, the spacious great room features a wood burning fireplace and overlooks the backyard oasis, complete with a fully paved pool deck, bar area, and entertaining garden, an incredible space for relaxing or hosting family and friends. Inside, you'll find new luxury vinyl flooring (2026), updated bathrooms, and a cersatile third bedroom featuring a murphy bed and built-ins, perfect for guests, a home office or both. Major improvements include a NEW ROOF (2023), insulated impact windows, and new gutters. And there's NO HOA! Enjoy the freedom of home ownership along with a fantastic Winter Springs location convenient to restaurants, shopping, SR 417, and I-4, plus highly regarded Seminole County Schools.

625 Pearl Road, 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
$425,000
3 Beds ⋅ 2 Baths ⋅ Georgetowne Unit 1 SubDv. ⋅ 32708 Zip Code
Welcome to 744 Barrington Circle, a beautifully maintained home nestled in the heart of the sought-after Tuskawilla community of Winter Springs. Tucked away in the desirable Georgetown neighborhood, this 3-bedroom, 2-bath home offers a thoughtful split-bedroom floor plan, soaring vaulted ceilings, abundant natural light, and an inviting blend of indoor and outdoor living. A private courtyard welcomes you into the home, creating a charming space for gardening and enjoying the outdoors. Inside, the open living and dining areas feature beautiful wood floors and vaulted ceilings, creating an airy and spacious feel. The living room flows seamlessly into the Florida room, where three sets of updated sliding glass doors bring the surrounding greenery indoors and open to the tranquil backyard. With a beautiful greenbelt directly behind the property, there are no rear neighbors, offering exceptional privacy. The spacious eat-in kitchen features white cabinetry and stainless steel appliances, while the generously sized primary suite offers double-door entry, plenty of room for a king-size bed, a walk-in closet, built-in vanity, and an ensuite bath with a separate garden tub and shower. The split-bedroom layout provides privacy for everyone, with two additional bedrooms located separately from the primary suite and sharing a full bathroom. Another unique feature is the air-conditioned bonus room within the garage, providing endless possibilities as a home office, gym, workshop, playroom, hobby space, or additional hangout area. Additional updates include new windows and doors, a new garage door, epoxy garage flooring, and fresh exterior paint. Residents of Georgetown enjoy a community pool, while the HOA includes front-yard lawn maintenance, making it easy to enjoy the neighborhood without the added upkeep. The home is also located in a highly desirable school zone, especially Keeth Elementary, and just minutes from Tuskawilla Country Club (membership separate) and Trotwood Park, one of the area's favorite recreational destinations with a splash pad, playground, tennis and pickleball courts, baseball fields, fishing, open green space, pavilions, and picnic areas. Private, peaceful, and perfectly positioned in the heart of Tuskawilla, 744 Barrington Circle offers the space, flexibility, and lifestyle that make this one of Winter Springs' most desirable places to call home.

744 Barrington Circle, Winter Springs
$779,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 12a SubDv. ⋅ 32708 Zip Code
A rare opportunity awaits in the heart of Tuscawilla. Welcome to 992 Sleeping Rock Court, a distinctive 4 bedroom, 2.5 bath Parade of Homes model pool home offering approximately 2,701 square feet of beautifully updated living space on an oversized .38 acre cul de sac homesite with the exceptional freedom of NO HOA. Designed with character, warmth and impressive architectural detail, this custom Parade of Homes model home immediately stands apart. Striking vaulted tongue and groove cedar ceilings in both the family room and primary suite create a rich, inviting atmosphere, while the beautifully updated wood burning fireplace serves as a dramatic centerpiece to the main living area. The spacious split bedroom floor plan provides privacy and functionality for both everyday living and entertaining. The primary suite feels like a private retreat, showcasing vaulted tongue and groove cedar ceilings, smart LED lighting, a remote controlled smart ceiling fan, custom closet shelving and an ensuite bath overlooking a private atrium. Throughout the home, thoughtful improvements include updated flooring, crown molding, baseboards, interior doors, electrical outlets, faucets and new ceiling fans. The kitchen features 36 inch cabinetry and updated black stainless steel appliances, including a 2025 dishwasher, along with a generous walk in pantry offering excellent storage. A dedicated laundry room, updated hall and half baths, custom closet systems and numerous smart home upgrades add convenience throughout. Step outside and discover an exceptional setting designed for the Florida lifestyle. The expansive covered lanai creates an impressive outdoor living and entertaining space overlooking the private pool with a beautiful natural rock waterfall, mature landscaping and oversized yard. Whether hosting friends, enjoying a quiet evening or relaxing poolside to the sound of the waterfall, this backyard offers the space, privacy and atmosphere that are increasingly difficult to find. The exterior has also received extensive improvements, including new brick pavers, updated fencing, cedar fascia, updated gutters and soffits, refreshed pool equipment with a Pentair pool pump, updated irrigation with a smart WiFi controller and a new mailbox. Major improvements have already been completed, providing tremendous value for the next owner. Updates include a 2019 roof and skylights, 2020 A/C, electrical panel, ductwork repairs and partial replacement, 2023 windows and three sliding glass doors with a Home Depot lifetime warranty, a new front door and a 2024 water heater. Technology and security have also been thoughtfully incorporated throughout the home with fiber internet, CAT8 wiring, a Nest thermostat, Ring doorbell, Nest Yale keypad front entry, keypad garage entry and Ring spotlight video cameras positioned at the front of the property. This home offers the rare combination buyers are searching for: a substantial homesite, a private pool with natural rock waterfall, mature landscaping, architectural character, extensive updates, impressive outdoor living space, Parade of Homes distinction and NO HOA restrictions or monthly HOA dues. It is a distinctive, non cookie cutter property filled with character, thoughtful upgrades and exceptional indoor and outdoor living spaces. Homes offering this combination of size, privacy, improvements, architectural personality and freedom from an HOA are increasingly difficult to find.

992 Sleeping Rock Court, Winter Springs
$435,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 3 SubDv. ⋅ 32708 Zip Code
Welcome to 806 Big Buck Circle, a charming 3-bedroom, 2-bath home offering 1,887 square feet of living space in the established Oak Forest community of Winter Springs. This single-story home offers a comfortable, functional layout with plenty of opportunity to make it your own. Step outside to the screened-in back porch, a wonderful spot for morning coffee, outdoor dining, or relaxing while overlooking the spacious, grassy backyard. Enjoy all that Winter Springs has to offer with nearby parks, trails, shopping, dining, and recreation. Trotwood Park is just minutes away, with additional outdoor destinations including Central Winds Park and the Cross Seminole Trail. Winter Springs Town Center, Oviedo Mall, grocery stores, restaurants, and everyday conveniences are also within easy reach. Convenient access to SR-434 and SR-417 makes it easy to reach Oviedo, Winter Park, Lake Mary, UCF, and the greater Orlando area. With three bedrooms, a two-car garage, generous backyard space, and a screened outdoor living area, this well-loved home is ready for its next chapter. Come see the possibilities at 806 Big Buck Circle!

806 Big Buck Circle, Winter Springs
$510,000
3 Beds ⋅ 2 Baths ⋅ Eagles Watch Ph 1 SubDv. ⋅ 32708 Zip Code
Property is well maintained, had been owned by a former major league baseball prayer. Adjacent to a nice secluded pond. The pool and lanai area is wonderful for quiet sitting, meditation, reading and then jump into the pool for a refreshing dip. The subdivision is one minute from a convenience store and access to Rt 417 highway to all parts of Central Florida. Spacious master bedroom with very big walk-in closet. This is in move-in condition subject only to your color decorations. Part of the Tuscawilla Master Community !!

133 Redtail Place, Winter Springs
$434,900
3 Beds ⋅ 2 Baths ⋅ Sunrise Unit 2-B SubDv. ⋅ 32708 Zip Code
NEW ROOF COMING!! For this beautifully updated 3 bedroom, 2 bath home offering 2,116 square feet of comfortable living space on a spacious .28 acre corner lot, directly across from Sunrise Community Park. This move-in-ready home combines modern updates with a functional split-bedroom floor plan that's perfect for growing families, remote work, or entertaining. Step inside to discover fresh interior paint, beautifully remodeled master bathroom, and a renovated kitchen just five years ago. The improvements provide added peace of mind, including a complete repipe and fresh exterior paint, making this home as practical as it is attractive. Enjoy the fully fenced backyard offering plenty of room for the family, pets, gardening, or weekend barbecues, on a prime corner lot. If you're searching for your first home without sacrificing space, updates, or location, this one checks all the boxes. Move right in and start making memories in a home that's been thoughtfully updated and lovingly maintained.

1298 Madelena Avenue, 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
$605,000
5 Beds ⋅ 3 Baths ⋅ Winter Spgs Unit 4 SubDv. ⋅ 32708 Zip Code
Welcome home to this thoughtfully updated 5-bedroom, 3-bath residence nestled on an oversized lot beneath a canopy of mature trees in the highly sought-after Tuskawilla community of Winter Springs. Offering over 2,500 square feet of thoughtfully designed living space, this home features a desirable split floor plan with the primary suite tucked away in its own private wing, creating a peaceful retreat from the secondary bedrooms. At the heart of the home is the beautifully remodeled kitchen, featuring quartz countertops, updated cabinetry, modern fixtures, updated appliances, and plenty of space for gathering with family and friends. The spacious living and dining areas provide an inviting setting for everyday living and entertaining, while the fully enclosed Florida room serves as a true extension of the home, making it the perfect place to host movie nights, enjoy your morning coffee, or unwind while overlooking the spacious backyard shaded by mature trees. Recent improvements include luxury vinyl plank flooring and baseboards throughout, fresh interior and exterior paint, refreshed landscaping, an updated sprinkler system, a whole-house water softener and filtration system, and two beautifully renovated bathrooms featuring updated vanities, flooring, fixtures, toilets, and shower tile. Additional major updates include a roof replaced in 2018, HVAC replaced in 2020, updated plumbing, and an electrical panel replaced in 2023, providing added peace of mind for years to come. Located in one of Winter Springs' most established communities, residents enjoy a voluntary HOA, optional memberships to Tuskawilla Country Club with golf, swimming, fitness, tennis, and social amenities, nearby Trotwood Park, golf cart-friendly streets, and access to Seminole County's top-rated schools. Conveniently located near shopping, dining, and SR-417, this home offers the perfect combination of modern updates, timeless character, and an exceptional location.

1015 Antelope Trail, Winter Springs
$605,000
5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Enjoy waterfront views and your own private pool in this spacious 5-bedroom, 2-bath home located in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this home offers a desirable three-way split floor plan, open living spaces, and an ideal blend of comfort, functionality, and outdoor living. Inside, you’ll find luxury vinyl plank flooring throughout the main living areas, a beautifully updated kitchen featuring granite countertops, refinished cabinetry, and a stylish backsplash, along with tastefully remodeled bathrooms showcasing shaker-style vanities, updated fixtures, and wood-look tile flooring. Energy-efficient upgrades include Low-E double-hung windows, an updated roof (2021), Carrier HVAC system, LED lighting, a whole-house water filtration system, two mini-split air conditioning systems (2025), and an energy-efficient year-round. The backyard is also been fully fenced, creating a private space for pets, play, and outdoor enjoyment. Step outside to your own backyard retreat featuring a sparkling pool, relaxing spa, and picturesque water views. Whether you’re entertaining guests or enjoying a quiet evening watching the sunset over the pond, this outdoor space is sure to impress. Additional features include pool deck speaker pre-wiring and a 220-volt outlet ready for an electric vehicle charger. Parkstone residents enjoy an exceptional lifestyle with lawn maintenance included in the HOA, a community pool, fishing pier, tennis courts, playgrounds, walking trails, scenic ponds, and gated security. The community borders the Cross Seminole Trail and is just a short walk to Central Winds Park and the dog park. Located in Seminole County with highly rated A-rated schools and convenient access to shopping, dining, and major roadways, this home truly offers the best of Florida living. Don’t miss your opportunity to own this exceptional waterfront home in one of Winter Springs’ most desirable communities!

216 Tavestock Loop, Winter Springs
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