Location: Sterling Park, Casselberry
Do Not Show Listings
295 QUAIL CT, CASSELBERRY, FL 32707
$425,0003 Days on yellowkey MLS ID: O6410280
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1541 Built: 1979Monthly Fee: $30 Tax: $2,807 (2025)Community: Sterling Park Unit 03Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,807
Elementary School: Sterling Park Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: South Seminole Middle
Remarks: Welcome to your private Florida retreat in the highly desirable Sterling Park community — where upgraded comfort, entertaining space, and everyday convenience all come together in this beautifully updated 3 Bedroom / 2 Bathroom home situated on a quiet cul-de-sac corner lot. Designed with comfort and functionality in mind, this desirable SPLIT FLOOR PLAN offers added privacy with a spacious owner’s suite separated from the guest bedrooms — creating the perfect layout for families, guests, remote work, or multigenerational living. From the moment you arrive, the mature landscaping, oversized driveway, ranch-style curb appeal, and newer vinyl fencing create a warm and inviting first impression. Step through the enclosed front porch into a bright OPEN-CONCEPT layout designed for both relaxing and entertaining. At the heart of the home, a stunning wood-burning fireplace anchors the main living area, while the formal dining space and oversized living room flow seamlessly together under recessed lighting and abundant natural light. French doors with built-in blinds open to your true OUTDOOR OASIS — an oversized covered lanai added in 2019 that creates the perfect indoor/outdoor Florida lifestyle experience. The kitchen was designed with both function and style in mind and will impress any home chef with its professional gas stove top, dramatic beautiful stone countertops, solid wood cabinetry, slow-close drawers, breakfast bar island, pantry storage, newer appliances, and open sightlines overlooking the living and dining spaces. Entertaining is effortless with the built-in wet bar and wine cooler ready for gatherings year-round. Privately positioned away from the secondary bedrooms, the spacious owner’s suite feels like a true retreat with room for a California King bed, a large walk-in closet with custom built-ins, and a beautifully remodeled spa-inspired bathroom featuring dual vanities, upgraded fixtures, oversized glass-enclosed tiled shower, dual shower heads, and a luxury rain shower feature. Additional upgrades and features include: Roof replaced in 2023 House generator connection Tankless water heater (2019) Water softener Luxury wood-look vinyl flooring Newer window treatments throughout Lawn irrigation system Attic fan Gas connection Washer & dryer included Newer appliances (within last 2 years) EV Charger in Garage The fully fenced backyard offers privacy and flexibility with plenty of room to create your dream outdoor lifestyle — whether you envision adding a future custom pool, creating an outdoor kitchen and entertaining area, or designing your own private vegetable and herb garden oasis. There is ample space to truly personalize the outdoor living experience while still enjoying room to relax, play, and entertain. Located in Sterling Park, residents enjoy access to community amenities including pool, tennis courts, playgrounds, sidewalks, golf nearby, and deed-restricted community living — all with convenient access to shopping, dining, parks, major roadways, and the greater Orlando area. This is the kind of home buyers walk into and immediately picture themselves living in. Schedule your private showing today.
Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)
Listing Agent: Rey Perez, Jr (407-443-6666)
141 SPRING WIND WAY, CASSELBERRY, FL 32707
$265,00017 Days on yellowkey MLS ID: O6407561
REDUCED by $5,000 (1.9%) on 05/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1136 Built: 1979Monthly Fee: $114 Tax: $1,123 (2024)Community: Sterling Park Unit 24Townhouse
Taxes:$1,123
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: One or more photo(s) has been virtually staged. **MOTIVATED SELLER**Welcome to the desirable Pinetree Village section of Deer Run, where comfort, convenience, and sunny Central Florida living all come together beautifully. This 2 bedroom, 2 bathroom townhome has the kind of feel buyers love the moment they walk in — bright, welcoming, and easy to imagine as home. Inside, the high ceilings help create an open and airy feel, while the natural light brings warmth into the main living space. The beautiful rock gas fireplace adds the perfect touch of character and creates a cozy focal point for relaxing evenings at home. The kitchen offers a great layout with a breakfast bar, making it perfect for casual meals, morning coffee, or chatting while dinner is being made. Step outside to your private patio — a sweet little spot to sip your coffee, unwind after a long day, add cozy seating, or enjoy a quiet evening under the Florida sky. You’ll also love the everyday conveniences this home offers, including inside laundry, a covered carport, and an attached one-car garage with extra storage space. Pinetree Village is a well-maintained community with amenities that make it easy to enjoy where you live, including a community pool, pickleball courts, basketball courts, and two miles of sidewalk trails right outside your door. You can even walk to Sterling Park Elementary School. The location is another big win — close to shopping, restaurants, Winter Park, and State Road 417, making commuting and weekend plans simple. Comfortable, inviting, and full of charm — this townhome is ready to welcome its next owner home.
Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)
Listing Agent: Frank Hopkins, Jr (305-775-8750)
309 REDWING WAY, CASSELBERRY, FL 32707
$375,00012 Days on yellowkey MLS ID: O6408660
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1400 Built: 1979Monthly Fee: $30 Tax: $3,811 (2024)Community: Sterling ParkSingle Family
Taxes:$3,811
High School: Lyman High
Remarks: WELCOME HOME to this charming single-family house in the desirable Sterling Park Community which is centrally located close to UCF, Full Sail, Rollins College and Winter Park. This home offers 3 bedrooms and 2 bathrooms. A large spacious eat-in kitchen, along with a sizable Great Room with vaulted ceilings! The Great Room includes a wood burning fireplace as a focal point, ranging the full height of the vaulted ceiling. Ceramic tile covers the living area, kitchen and bathrooms. There is new carpet in the bedrooms. The entire inside of the home has been freshly painted a nice neutral color for its new owners! Newer Roof was installed in 2018. New Garage Door motor 2025. There is a screened in porch to enjoy fresh air with your morning coffee! The large backyard is a clean slate! You have plenty of room! In fact, you have room to add a pool and will still have yard available for your family and/or pets to play! This home is a clean slate! You have the opportunity to put your own stamp on it, making it your own! It is located just minutes from shopping, dining and major highways! No matter what you need, it is close by!
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Tricia Ramsby (407-739-3986)
240 SPRING WIND WAY, CASSELBERRY, FL 32707
$279,00022 Days on yellowkey MLS ID: O6402835
5 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1451 Built: 1979Monthly Fee: $114 Tax: $1,054 (2025)Community: Sterling Park Unit 24Townhouse
Taxes:$1,054
Remarks: Under contract-accepting backup offers. There’s something special about a home that just feels right the moment you walk in. Located in the desirable Pinetree Village section of Deer Run, this 3 bedroom, 2 bathroom home offers comfortable living with soaring 18-foot ceilings and a warm, welcoming layout that makes the space feel open and inviting. Natural light fills the main living area, while thoughtful improvements throughout give the home a fresh, well-cared-for feel. Two private patios give you extra space to enjoy your morning coffee, unwind in the evenings, add container gardens, or create cozy outdoor seating areas for relaxing and entertaining. The kitchen features upgraded cabinets and countertops, along with recent interior paint, knockdown ceiling texture, and brand new tile in the bathrooms. You’ll appreciate the convenience of inside laundry, a covered carport, and an attached one-car garage with extra room for storage. Set in a lovely, well-maintained community with a pool, pickleball courts, and basketball courts, this neighborhood is made for enjoying the Florida lifestyle. Two miles of sidewalk trails are right outside your door, and you can even walk to Sterling Park Elementary School. The location couldn’t be more convenient — close to plenty of shopping and restaurants, just minutes from Winter Park, and with easy access to State Road 417 for an easy commute. Comfortable, inviting, and easy to love — this is the kind of home that simply fits your life.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Karen Ripperger (407-765-8105)
161 PINESONG DR, CASSELBERRY, FL 32707
$270,00023 Days on yellowkey MLS ID: O6405987
0 Days Off yellowkey (back on 5/15/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1136 Built: 1980Monthly Fee: $149 Tax: $2,317 (2024)Community: Sterling Park Unit 24Townhouse
Taxes:$2,317
Remarks: Welcome to this charming 2-bedroom, 2-bath home nestled in the sought-after Deer Run community of Casselberry. This well-maintained property features an open and inviting layout with vaulted ceilings, abundant natural light, and easy-flow living spaces perfect for both relaxing and entertaining. The kitchen offers ample cabinet and counter space with a convenient breakfast bar overlooking the main living area. The spacious primary suite includes a private bath and generous closet space, while the second bedroom is ideal for guests, a home office, or flex space. Step outside to enjoy your own private back porch, the perfect spot for morning coffee or quiet evenings overlooking a peaceful setting. Additional highlights include a private garage, indoor laundry area, and low-maintenance living. Located close to shopping, dining, parks, major roadways, and Seminole County schools, this home offers comfort, convenience, and privacy all in one.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Mikayla Mignacca (407-406-3331)
371 PINESONG DR, CASSELBERRY, FL 32707
$314,00073 Days on yellowkey MLS ID: O6391326
REDUCED by $15,000 (4.6%) on 05/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1344 Built: 1980Monthly Fee: $114 Tax: $2,191 (2025)Community: Sterling Park Unit 24Townhouse
Taxes:$2,191
Remarks: Welcome to this charming, move-in ready townhome in the highly desirable Pine Tree Village community of Deer Run. Filled with natural light, this bright and inviting home offers a warm, open living space perfect for both everyday living and entertaining. This townhome has no shared walls and lives like a single family home. The kitchen and bathrooms have been beautifully updated with granite countertops, modern cabinetry, and stainless steel appliances. All three bedrooms feature engineered hardwood flooring, and the interior has been freshly painted for a crisp, updated feel throughout. Newer Carrier AC and gutters with leaf guards. Residents enjoy low monthly dues and access to excellent community amenities, including a pool, clubhouse, and pickleball courts. Ideally located just minutes from Publix, Target, SR-436, and SR-417, this home combines comfort, style, and convenience in one exceptional package.
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: Brett Winters (352-267-8270)
732 LAUREL WAY, CASSELBERRY, FL 32707
$405,00030 Days on yellowkey MLS ID: O6403676
1 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 1972Monthly Fee: $30 Tax: $1,509 (2024)Community: Sterling Park Unit 01Single Family
Taxes:$1,509
Remarks: Under contract-accepting backup offers. Pond View + Updated + Walkable to Dew Drop Park in Casselberry Welcome to 732 Laurel Way! A beautifully updated 3 bedroom, 2 bathroom home on Dew Drop Pond in one of Casselberry’s established neighborhoods. Inside, you’ll find new flooring throughout, an updated kitchen, and a remodeled primary bathroom. A 2023 roof provides peace of mind, and the large garage, walk-in closets, and spacious bedrooms make this home as functional as it is inviting. Step onto the back porch and take in peaceful pond views. The kind that make morning coffee and evening sunsets feel special. Just a short walking path away, a brand new state-of-the-art park features basketball and pickleball courts, adding real lifestyle value for families and active buyers. Located in the Seminole County School District, known for highly rated public schools making it appealing for buyers looking to plant roots in a connected community. Move-in ready, thoughtfully updated, and priced at $405K...schedule your private showing and come see why this one stands out.
Listing is courtesy of: CENTRAL FLORIDA REALTY EXPERTS (407-542-4403)
Listing Agent: Kelly Althof (941-962-9933)
285 SANDPIPER DR, CASSELBERRY, FL 32707
$420,00048 Days on yellowkey MLS ID: O6398280
0 Days Off yellowkey (back on 5/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1454 Built: 1978Monthly Fee: $30 Tax: $2,029 (2025)Community: Sterling Park Unit 03Spa: NoSingle Family
Taxes:$2,029
Remarks: Under contract-accepting backup offers. MOVE-IN READY POOL HOME! In the Heart of one of Casselberry’s most sought-after neighborhoods Deer Run! 3 nice size bedrooms and a 4th Bonus Bedroom/Office - Enter your home with the beautiful accent tile foyer leading into the living room, and you will immediately feel the home open up with vaulted ceilings. All the big-ticket items have been taken care of for you: water heater 2018, roof/skylights 2020, and solar pool heater 2020. Master bathroom and guest bathroom beautifully updated from the studs, flooring, double vanities, exhaust fans with smart technology bluetooth Wi-Fi ambient bathroom lighting, with music 2021, HVAC 2021, Chimney professional cleaned and cap replaced 2024, and whole house re-plumbed 2026. This beautifully maintained 3-bedroom, 2-bath, office or 4th bedroom (with closet) pool home offers the perfect blend of comfort, style, and convenience. Not to mention an oversized garage with a work bench ready for your vehicles and toys. During the winter days and holidays enjoy an oversized fireplace floor to ceiling creating memories that will last a lifetime.Step inside to a bright, open floor plan featuring a spacious living room, beautiful open kitchen with newer stainless-steel appliances, and plenty of cabinet space. The Samsung Family Hub refrigerator is a high-tech kitchen centerpiece with a large touchscreen that manages smart home devices, streams music for your family gathering, cooking or watching tv. The Samsung smart gas stove has a built-in air fryer, with no preheat air frying, convection, 5 gas burners, including high-power options for fast boiling, and Wi-Fi technology for voice control for the family chef! The master suite includes a private bathroom featuring a spa-like rainfall shower, which brings a relaxing spa retreat and lighted Bluetooth speakers, and a generous walk-in closet, while the additional bedrooms are generously sized. Outside, enjoy a fully fenced backyard ideal for entertaining, gardening, or relaxing under the Florida sun. Backyard backs up to the neighborhood tree lined trail. Once you move in you will enjoy Deer Run’s charm, with tree-lined streets and a strong sense of community and wonderful neighbors. Take nice walks down tree lined paths to the neighborhood park that includes a pool and spa, tennis courts, basketball court, and a large park and playground area. It is conveniently located near shopping, dining, parks, and top-rated schools, with easy access to major highways for a quick commute to Orlando, Daytona, and surrounding areas. Make an appointment to see this home today and schedule your showing before it’s gone!
Listing is courtesy of: LOCAL CHOICE REALTY LLC (407-501-4936)
Listing Agent: Bryan Berns (407-801-9534)
328 SHADOW OAK DR, CASSELBERRY, FL 32707
$369,90053 Days on yellowkey MLS ID: O6396655
1 Days Off yellowkey (back on 5/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1499 Built: 1979Monthly Fee: $29 Tax: $2,622 (2025)Community: Sterling Park Unit 04Single Family
Taxes:$2,622
Remarks: Move-In Ready Home in Sterling Park / Deer Run community... Welcome to this beautifully updated 3 bedroom, 2 bathroom home in the highly desirable Sterling Park / Deer Run community in Seminole County. This move-in ready home features major upgrades including a new HVAC system (A/C), new water heater and all new interior paint, offering a fresh, modern feel and peace of mind for years to come. Step inside to a bright open floor plan with a large foyer leading into a spacious living room and dining room combo, perfect for entertaining. Sliding glass doors open to a huge backyard, providing ideal indoor-outdoor living and plenty of space for pets, play, or future outdoor additions. The home also includes a flex/bonus room—perfect for a home office, gym, or playroom. The kitchen features newer appliances, ample cabinet space, and a breakfast nook, all overlooking the main living area. The primary suite offers a walk-in closet, vanity, laminate flooring, and a walk-in shower. Additional bedrooms are generously sized with laminate flooring, making this home both functional and low maintenance. Enjoy the outdoors in your oversized backyard with mature oak trees, creating shade and privacy—perfect for relaxing or entertaining. Located in a top-rated Seminole County school zone, just minutes from Sterling Park Elementary, shopping, restaurants, and major highways. Close to the future Seminole County Park featuring walking trails, playgrounds, and recreational amenities.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kyle Clark (407-921-3287)
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