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$358,000
3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 3 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated 3-bedroom, 2-bath home in the Villas of Casselberry. Inside, you’ll find a bright and functional floor plan with comfortable living spaces, a convenient 1-car garage, and extra outside storage. Thoughtful updates throughout make this home move-in ready from day one. New roof 6/2025, new driveway, fenced in back yard, new kitchen with quartz countertops, vinyl flooring throughout. Step outside to enjoy the fully fenced backyard and private rear patio—ideal for gatherings, pets, or simply relaxing outdoors. With low HOA fees, this home is a fantastic opportunity for first-time buyers, downsizers, or investors. Perfectly located near top-rated Seminole County schools, UCF, Full Sail University, OIA, and the shops and dining of Winter Park’s Park Avenue, you’ll love the balance of convenience and comfort this home provides.

1827 Blaine Terrace, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ Fernbrook Trails Ph 3 SubDv. ⋅ 32792 Zip Code
Completely Renovated 2 bedroom and 2 bath Townhome in Winter Park! Welcome to 7777 Fernbrook Way, a beautifully updated 2 bedroom, 2 bath home in the desirable Fernbrook Trails community. This move-in ready property has been fully renovated with high-end finishes, modern conveniences, and thoughtful upgrades throughout. Step inside to find tile flooring throughout (2023), freshly retextured ceilings, and energy-efficient LED lighting. The open kitchen features new cabinets with quartz waterfall countertops (2023), LG stainless steel appliances (2021), and updated LED spotlights. Bathrooms were refreshed with new vanities and toilets (2021), and all matching ceiling fans were installed in 2021. Major systems are updated for peace of mind, including a new AC (2021), new windows and sliding glass door (2024), and French drain with sump pump system (2025). Additional improvements include upgraded baseboards, matching blinds, new exterior LED lights, an added shed, and fresh sod in the backyard. The home also comes with a transferrable active termite bond. Roof 2021 Outside, enjoy a private backyard with mature landscaping and low-maintenance living in a well-kept community close to schools, shopping, and major roadways. This is truly a turnkey Winter Park home—every big-ticket upgrade has already been done for you. Don’t miss the opportunity to make it yours!

7777 Fernbrook Way, Winter Park
$935,000
5 Beds ⋅ 3 Baths ⋅ Lake Waunatta Village SubDv. ⋅ 32792 Zip Code
Stunning Lakefront Retreat in Winter Park! Welcome to your dream home on beautiful Lake Waunatta! This spacious and upgraded 5-bedroom/1-office/3-bathroom lakefront property offers over 3,850 sq. ft. of living space (5,113 sq. ft. total) on a nearly half-acre lot with ~100 feet of private shoreline. Enjoy breathtaking lake views from multiple rooms and the balcony. Open floorplan offers flexible living arrangements. Enjoy morning coffee/tea from the Florida Room to take in the glorious sunrise over the lake! Perfect for entertaining or relaxing, this home features a large, updated kitchen with an eat-in area, formal dining room, expansive living/family room, and a bright Florida Room with a stunning view. The large master suite is a luxurious retreat with a marble shower and a jacuzzi tub. Step outside to a huge dock with a covered boat house with powered lift, two jet ski lifts, and plenty of space to watch beautiful sunrises, rocket launches, and fireworks. The backyard is shady, spacious, and serene — perfect for morning sunrises or afternoon relaxation. Lake Waunatta is a ~72-acre private, spring-fed lake with no public access. It’s ideal for powerboating, jet skiing, windsailing, paddleboarding, and fishing. The property sits on an elevated lot that provides stunning lake views and minimizes flooding concerns. The home was extensively renovated and expanded in 2003, including updated plumbing, electrical, and structural additions. Recent upgrades include a new roof, new windows, sunshades, and new AC unit. Located on a quiet, limited-access street, you’re just minutes to Publix, Target, parks, restaurants, and top-rated schools. Easy access to Full Sail, UCF, Downtown Orlando, and airports. Don’t miss this rare opportunity to own a private slice of lakefront paradise, and to enjoy the best Florida offers, right from your backyard! This home offers the best value on a natural private ski lake in Winter Park!

7706 Waunatta Court, Winter Park
$285,000
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 1 SubDv. ⋅ 32792 Zip Code
Welcome to 2462 Harbour Way, a beautifully maintained single-story townhome nestled in the highly sought-after Windward Square community of Winter Park. This move-in ready 3-bedroom, 2-bathroom home offers comfort, style, and convenience—all in one of Central Florida’s most desirable areas. Step inside to discover a sunlit dinette that flows seamlessly into a spacious kitchen, featuring gleaming granite countertops and stainless steel appliances—perfect for everyday meals or entertaining guests. The inviting living room is accented by a unique atrium that fills the space with natural light, creating a bright and airy ambiance throughout. The private primary suite includes a walk-in closet and en-suite bathroom, providing a peaceful retreat at the end of the day. Two additional bedrooms offer flexibility for family, guests, or a home office. Enjoy Florida living year-round on your covered back porch and fully fenced patio—ideal for relaxing, grilling, or gathering with friends and family. Tile flooring throughout and NEW ROOF in December 2021. Windward Square offers low HOA fees and fantastic amenities, including a community pool, clubhouse, tennis court, shuffleboard, and playground. Plus, this prime location puts you close to top-rated schools, major universities, shopping centers, dining destinations, and easy access to major highways, Downtown Orlando, and Orlando International Airport—all within a 30-minute drive! Don't miss this opportunity to own a beautiful home in this desirable community in Winter Park. Schedule your private showing today!

2462 Harbour Way, Winter Park
$660,000
4 Beds ⋅ 3 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
**VA Assumable**A HIDDEN GEM nestled on Lake Deeks in Howell Estates! You have lake access from your back yard! As you enter your new home you will be captivated by the abundant natural light and the spacious open floor plan. The beautiful vintage front door signals this home is full of wonderful and unique touches. Pictures include a floor plan to show you the amazing layout with so much privacy with separate bedroom areas and how great the home is for entertaining. The primary bedroom has access to a private lanai with a sink and wood burning fireplace and leads to the pool and back yard. The guest suite on the opposite side of the house also has outdoor access to another larger lanai and the pool. The primary bathroom has a jet tub, large shower with double shower heads. The shower area is solid concrete reinforced for extra safety during weather events. The bathroom also has two walk in closets. The other two bedrooms are secluded with a full bath with a jet tub and a skylight. The kitchen is a culinary delight, featuring granite countertops, ample prep and cooking space, walk-in pantry, built in desk and a long breakfast bar. The oversized family room has a wood burning fireplace, vaulted ceiling with beams and four large window overlooking the pool with remote controlled shades. As you make your way to the back yard oasis you will find many surprises! Several paths will walk you through to see 20 banana trees, Meyer Lemon tree, Fig tree and much more. Enjoy the deck on the water for sunrises/sunsets and watching shuttle launches. There is a path that leads to the lake for launching your kayak, canoe and paddle board. More features include oversized paver driveway, pavers on the pool deck, garage with lots of built-in storage, floored attic area, large separate laundry room, solar panels (fully paid), water softener system, custom plantation shutters, transferable home warranty and termite bond. Your home is in a lovely quiet area but close to all shopping, transportation and renowned Seminole County schools. This great home is a must see and the perfect forever home for the sought after Florida lifestyle. Buyer to confirm room measurements.

1023 Princess Gate Boulevard, Winter Park
$350,000
3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Welcome to this quaint 3 bedroom, 2 bath property in the heart of Winter Park. Bring your imagination and design for a home you'll love, because this block home is the perfect blank slate. The large, open living/dining combination is perfect for entertaining or multi-functional living spaces. Additionally, an oversized, screened back porch provides indoor-outdoor living opportunity to enjoy the large, serene backyard. This lot backs up to the Interlachen Country Club, which is landscaped for privacy so the new owners will enjoy their space without any rear neighbors. Each of the two secondary bedrooms are outfitted with custom built-ins, perfect for office space(s), but could also be transformed into functional bedrooms. There is original terrazzo in the home as well as recently updated (2021) luxury vinyl flooring in the kitchen and living spaces. New owners will appreciate additional updates such as a 2022 roof and 2023 HVAC. The kitchen was renovated with quartz countertops and new cabinetry in 2021. This home is zoned for Seminole County Public Schools, which is consistently rated as the top school district in all of Florida. Only 1 mile from the nearest Publix, 0.5 miles from the Winter Park YMCA, and 30 minutes from Orlando International Airport, this home is conveniently located to the best of Orange and Seminole County's shopping and dining.

5128 Lake Howell Road, Winter Park
$739,000
4 Beds ⋅ 3 Baths ⋅ Preserve At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage Homes in the gated community of Hawk's Crest in Winter Park, includes numerous upgrades. This is the Pomelo model, equipped with an upgraded kitchen package that includes built-in double ovens and a stainless steel range hood. Beautiful quartz countertops feature an oversized kitchen island with excellent space for family gatherings. Other features include a walk-in pantry and fantastic lighting. The luxurious kitchen integrates with the dining and living areas. The dining area is enhanced by a screened-in deck overlooking a pond. The backyard features a new, large, extended patio for entertaining. The master bedroom has an ensuite bathroom with a double vanity, a small closet, and a large walk-in closet that can be customized for a future owner. The home also comes with new gutters. Other amenities in the Hawk's Crest community include a resort-style pool with a clubhouse, a splash pad, a fitness center, barbecue grills, playgrounds, a dog park, and a community fishing pier with views and access to beautiful Lake Howell. Nearby, you'll find shops, restaurants, and specialty physicians such as Kelly's Ice Cream, Foxtail Coffee, Sobol, Winter Park Pediatric Dentistry, and the Park Maitland Preschool Campus, along with excellent schools in the area. Enjoy a short drive to Downtown Winter Park, with its extensive dining and shopping options. Hawk's Crest is also very close to Rollins College and UCF. Schedule your private tour today!

2222 Marsh Sedge Lane, Winter Park
$360,000
3 Beds ⋅ 2 Baths ⋅ Autumn Glen SubDv. ⋅ 32792 Zip Code
Welcome to your new Winter Park home! Located in the highly sought-after community of Autumn Glen, this beautifully maintained property offers peace of mind and modern comfort with a new roof, newer A/C system, updated plumbing, and a remodeled kitchen featuring granite countertops, stainless steel appliances, and a spacious pantry. The L-shaped living and dining area boasts vaulted ceilings, perfect for both relaxing and entertaining. The primary suite includes a walk-in closet and sliding doors that lead to the covered and screened patio. Enjoy a split-bedroom layout with generously sized guest rooms, ceiling fans throughout, and a 2-car garage. The fenced yard provides privacy and room to enjoy the outdoors. The community is located just around the corner from Red Bug Elementary, Tuskawilla Middle and Lake Howell High School.. Other community features include tennis/pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for bringing your fishing pole. If you're looking for the right house in the right location, this is the one.

1767 Meadowgold Lane, Winter Park
$255,000
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
**This property qualifies for a closing cost credit up to $3,900 through the Seller’s preferred lender.** Charming Winter Park Townhome with Vaulted Ceilings and Sun-Filled Spaces. Welcome to 2398 Dominica Way, a beautifully maintained 2-bedroom, 2-bathroom townhome nestled in the heart of Winter Park. From the moment you arrive, you'll be drawn in by the inviting front patio, complete with a pergola and clear roofing—perfect for soaking up the sunshine while staying protected from Florida’s afternoon showers. Step inside and you’re greeted by a warm and functional layout. The kitchen, located just off the entry, boasts rich, warm cabinetry, sleek black and stainless steel appliances, and a serving window that opens into the spacious dining and living room combo, doubling as a breakfast bar for casual meals or entertaining guests. Continue into the main living area, where soaring vaulted ceilings and a wall of glass sliders flood the space with natural light and provide a beautiful view into the Florida room. Off to the left, a private hallway leads to the home’s bedrooms. The guest bedroom overlooks the front patio and features a ceiling fan and easy access to the second full bathroom, which includes a tub/shower combo. Across the hall, the primary suite offers a peaceful retreat with a walk-in closet, an ensuite bathroom with a walk-in shower, and private access to the rear porch through sliding glass doors. The spacious Florida room at the back of the home offers flexible indoor-outdoor living, with direct access to a shared grassy area—perfect for pets, gardening, or simply enjoying the fresh air. Whether you're a first-time homebuyer, downsizing, or looking for a low-maintenance lifestyle in a prime location, this gem in Winter Park is ready to welcome you home.

2398 Dominica Run, Winter Park
$1,065,000
4 Beds ⋅ 3 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to 1024 Wading Waters Circle—a rare offering in the gated, amenity-rich enclave of Hawk's Crest in Winter Park. This modern, single-story Palermo II model has been elevated far beyond builder-grade materials with over $300,000 in custom upgrades, blending refined design with seamless indoor-outdoor living and spectacular waterfront views. From the moment you arrive, this residence impresses with its expanded paver driveway, beautiful stone façade, and artfully curated landscaping with low-voltage and Phillips Hue lighting that transforms the home’s exterior by night. The stylish entry courtyard sets the tone for what awaits inside. Enter into a gallery-style foyer that opens to a bright, open-concept layout with wide-plank flooring, custom wood accent walls, designer lighting, built-in speakers throughout the home, and a crisp, modern aesthetic. The chef’s kitchen is a showpiece—outfitted with flat-panel two-tone cabinetry, quartz countertops, built-in JennAir appliances, and a waterfall-edge island. Matte black fixtures, a pot filler and a sleek integrated hood complete the space. The living and dining areas flow effortlessly to the expansive screened lanai, where the outdoor experience has been completely reimagined. Entertain in style with a custom-built summer kitchen featuring premium Hestan appliances, a gas grill, beverage fridge, sink, and stainless storage. A beautifully designed aluminum pergola, built for year-round enjoyment, provides a separate outdoor destination. The fenced backyard opens to serene water and fountain views, lush landscaping, and a charming cocktail citrus tree—offering an ideal setting for quiet mornings and sunset gatherings. The private primary suite is a peaceful retreat with large windows framing the water and includes a spa-like bath with double vanities, glass-enclosed shower and a custom walk-in closet. Three additional bedrooms and a dedicated office with glass French doors provide space for guests, work, and play. Additional highlights include a whole-home water filtration system, cloud-based security camera system, Wi-Fi dimmer switches controllable by phone, black aluminum fencing with three gates, and a spacious three-car garage equipped with a mini-split HVAC system and a Tesla 11.2-kilowatt solar system with a Tesla charger for added convenience. Residents of Hawks Crest indulge in a thoughtfully planned community featuring a resort-style swimming pool, virtual guard gate, clubhouse, fitness center, splash pad, playgrounds, dog park and access to Lake Howell. Park Maitland Preschool, Kelly's Ice Cream and Foxtail Coffee shop are at front of the neighborhood for added convenience. An exclusive respite, this home exemplifies a refined lifestyle for those who appreciate peaceful and convenient living. This is not just a home, it’s a lifestyle.

1024 Wading Waters Circle, Winter Park
$474,998
3 Beds ⋅ 3 Baths ⋅ Arrowhead Cove Unit 02 SubDv. ⋅ 32792 Zip Code
Nestled in desirable Arrowhead Cove, this meticulously maintained 3-bedroom, 2.5-bath home represents the pinnacle of Winter Park living. With 1,906 square feet of thoughtfully designed space, this move-in-ready residence blends character, comfort, and convenience in Central Florida's most coveted school district. BONUS FEATURE: PRIVATE WELL IRRIGATION SYSTEM – Enjoy beautifully maintained landscaping year-round while keeping utility costs exceptionally low! This home features a dedicated well pump irrigation system that’s completely independent from city water, providing significant monthly savings and eco-friendly watering for the stunning renovated yard and lush landscaping. EXCEPTIONAL RECENT UPDATES NEW ROOF & SKYLIGHT (2024) – Complete peace of mind ENERGY-EFFICIENT WINDOWS (2017) – Maximum comfort and utility savings HVAC SYSTEM REPLACEMENT (2018) – New AC unit and air handler SMART HOME FEATURES – Nest thermostat and Protect alarms NEW GARAGE DOOR & SMART OPENER (2024) – Modern convenience POWER GENERATOR CONNECTION (2020) – Florida weather ready FRESH EXTERIOR PAINT (2021) – Pristine curb appeal RESORT-STYLE BACKYARD TRANSFORMATION (2023) The completely renovated backyard is a masterpiece that must be experienced in person: Brand new decorative pavers for elegant entertaining New privacy fencing for complete seclusion Custom playground perfect for active lifestyles Low-maintenance professional landscaping Expansive screened patio for year-round Florida living Fully fenced yard providing security and privacy STYLISH INTERIOR Open, airy layout maximizes natural light through oversized windows. Seamless flow from living and family rooms into large formal dining area makes entertaining effortless. Thoughtfully designed bedroom placement ensures privacy, while the spacious primary suite features walk-in closet, dressing area, full bath with walk-in shower, and additional half bath. UNPARALLELED WINTER PARK LIFESTYLE Step outside to the scenic Cady Way Trail for morning jogs, evening bike rides, or weekend nature walks. Enjoy Park Avenue's boutique shopping, world-class dining, and cultural events just minutes away. Publix, Target, Walmart, Costco, Aldi provide convenient daily shopping. Outdoor enthusiasts love proximity to Winter Pines Golf Club, Lake Baldwin, and Central Florida's extensive trail system. Coffee lovers appreciate nearby cafes, while foodies discover diverse restaurants from casual to fine dining. WORLD-CLASS SCHOOLS Lakemont Elementary – Top 50% Florida ranking, 61% math/ 59% reading proficiency Maitland Middle – Highly-rated Winter Park feeder school Winter Park High – Ranked #153 of 807 Florida high schools, 98% graduation rate Near Full Sail, UCF, and Rollins College COMMUNITY EXCELLENCE Arrowhead Cove offers low $100 annual HOA and optional Lake Nan access for peaceful waterfront recreation. Weekend farmers markets, community events, and seasonal festivals create vibrant neighborhood connections. The backyard transformation and thoughtful upgrades must be experienced in person. Schedule your private showing today and embrace the Winter Park lifestyle!

7602 Lodge Pole Trail, Winter Park
$298,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Subd Unit No 16 SubDv. ⋅ 32792 Zip Code
This Winter Park BLOCK home offers 4 bedrooms, 2 full bathrooms and all with no HOA. This home features a SPLIT FLOOR PLAN and NEW ROOF (2022). The oversized enclosed porch is perfect for entertaining or relaxing after a long day of work. Front screened in patio to enjoy as well. Storage will not be an issue, as there is a 2 CAR GARAGE You're also located in a very established community that's highly desirable while being close to all major highways and 10 minutes from excellent shopping, hospitals, dining, theme parks and so much more. Schedule a showing!

2206 Bonanza Avenue, Winter Park
$1,160,000
6 Beds ⋅ 4 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
Exceptional Living Awaits in the Heart of Winter Park Nestled in the sought-after community of Waters Edge at Hawks Crest, this stunning 4268 square-foot energy-efficient home offers an exquisite blend of classic elegance and modern comfort. This Kerville II model, built by Meritage Homes in 2020, has been thoughtfully designed to be both welcoming and refined. From the moment you step through the front door, you’ll be captivated by the quality craftsmanship, thoughtful upgrades, and inviting spaces that make this home truly special. At the heart of the home is a chef-inspired kitchen, beautifully appointed with custom cabinetry, granite countertops, and a large center island that doubles as a breakfast bar. Stainless steel appliances make meal preparation effortless and enjoyable. Ample storage space, a butler’s pantry along with a sunlit breakfast area complete this culinary haven. The spacious family room flows seamlessly from the kitchen, featuring large sliding glass doors that open onto the private backyard oasis with the screened lanai and heated pool. The main floor also features a private en-suite bedroom with its own bathroom that offers direct access to the pool. Upstairs you will find four generous sized bedrooms and three full bathrooms. The luxurious master suite is a true retreat. Here, you’ll find an oversized dressing room/ walk-in closet, a newer spa-inspired en-suite bathroom complete with built ins, dual vanities, and a frameless glass shower. The additional bedrooms are spacious and bright, all with walk-in closets. Also featured on this level is the 6 th bedroom transformed into a dedicated home office which offers a quiet workspace and the versatile bonus room which can be tailored to fit your lifestyle—whether as a playroom, media center, or fitness studio. Waters Edge at Hawks Crest is a gated community featuring a resort style clubhouse with pool, fitness center, playgrounds, dog park, fishing dock and access to Lake Howell Don’t miss your chance to make this your forever home!

2080 Wood Thrush Ln, Winter Park
$272,500
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 1 SubDv. ⋅ 32792 Zip Code
Welcoming townhome on cul-de-sac with no rear neighbors. Step out onto your roomy 16 x 12 screened porch and take in the peaceful views of the tennis courts and green space—it’s the perfect spot to relax with your morning coffee or unwind after a long day. Inside, you’ll love the bright, open feel thanks to clerestory windows in the living room, freshly painted walls, and brand-new electrical panels for peace of mind. Easy-care 18” x 18” tile floors run throughout the home, and sliding glass doors from both the dining area and second bedroom open right out to the porch. The kitchen has a handy pass-through to the dining room and a bar where friends or family can pull up a barstool. Both bathrooms have tub-shower combos, and the primary bedroom features a walk-in closet and a big fixed window that lets in tons of natural light. The Windward Square community has something for everyone—multiple pools, tennis courts, a play area, and even a putting green. You’ll also have space for two possibly 3 cars to park right out front. Best of all, you’re close to great shopping and dining, with downtown Winter Park just a short drive away. Getting around is easy too, with quick access to 417 and only about 20 minutes to Orlando International Airport via Semoran Blvd.

2517 Windward Way, Winter Park
$510,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Multiple offers received - please submit HIGHEST & BEST by THURSDAY, JULY 17th at 5:00 PM. Welcome to the most gorgeous waterfront property in Winter Park for UNDER $500,000! This charming 4 bedroom, 3 bath home is situated on a third of an acre with a stunning pool and water features overlooking a serene water view. The backyard truly must be seen to be believed! Guests will be just as captivated by the interior of this home. Discover flexibility and comfort in this beautifully designed home featuring dual primary suites — one upstairs and one down — each with its own private ensuite bath. Whether you're accommodating multi-generational living, hosting guests, or simply seeking extra privacy, this layout offers the ultimate in versatility. Thoughtfully designed living spaces and stylish finishes continue in the living spaces as well. Wood floors flow throughout the downstairs. The great room is bright and sunny from four (4) oversized windows as well as French Doors leading to the covered patio. Cooking is a delight with a newer gas stove and a kitchen overlooking the dining and living room. Storage abounds thanks to an indoor laundry room, an oversized two-car garage, and ample closet space in each bedroom. Enjoy home efficiency thanks to HVAC updates in 2023 and a tankless water heater installed in 2024. Winter Park is celebrated for its renowned shopping, dining, parks, and schools - and you could be close to it all in this home! Zoned Winter Park High School and its sports facilities are minutes away. Come discover the Winter Park lifestyle you have dreamed of. It is now obtainable in this incredible estate!

2739 Amsden Road, Winter Park
$255,000
3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 1 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Freshly updated and ready for easy living, this concrete-block villa delivers three bedrooms, including a versatile flex room, plus two full baths across a smart 1,080-square-foot, single-story layout. The curb appeal pops thanks to 2023 exterior paint, a brand-new roof (2023), and a privacy fence (2023) that frames the fully fenced backyard. Step inside to an open living-dining core that flows to a screened back porch, perfect for morning coffee or evening grilling, while an attached storage shed keeps tools and toys neatly tucked away. Key systems inspire confidence: the electrical panel has been upgraded, a new water heater arrived in 2024, the HVAC dates to 2015, and the bathrooms feature recently installed raised toilets. Add in the community pool, low $39/month HOA, and Seminole County school zoning, and you’ve found a turn-key Winter Park address that keeps both maintenance and monthly costs pleasantly low.

3005 Casselwood Street, Winter Park
$513,000
4 Beds ⋅ 3 Baths ⋅ Autumn Glen Ph 2 SubDv. ⋅ 32792 Zip Code
Welcome to your own private retreat, perfectly situated at the end of a quiet CUL-DE-SAC on one of the most SCENIC LOTS in the neighborhood. This beautiful home sits on a gorgeous, oversized 1/4-ACRE LOT with UNOBSTRUCTED WATER VIEWS and is framed by mature trees, creating a natural canopy that offers both beauty and privacy. Whether you're sipping your morning coffee or winding down in the evening, the serene water views and peaceful setting make every moment feel like a getaway. Step inside to discover a thoughtfully updated interior filled with NATURAL LIGHT AND WATER VIEWS from every window in the family and dining rooms. The spacious family room features soaring VAULTED CEILINGS and a stunning brick WOOD-BURNING FIREPLACE, creating a cozy yet open space that’s perfect for gatherings year-round. The custom kitchen is as functional as it is beautiful, featuring MODERN GRAY SHAKER SOFT-CLOSE CABINETS, GRANITE COUNTERTOPS, a copper sink and faucet, and top-of-the-line STAINLESS STEEL LG APPLIANCES, including a French door refrigerator and double oven—perfect for everyday living and elevated entertaining. MAJOR SYSTEMS UPGRADES have already been taken care of, including a NEW ROOF (2022), BRAND NEW A/C (2025), FULL REPIPE, EXTERIOR PAINTED (2023), and DOUBLE PANE INSULATED WINDOWS throughout. Upstairs, you'll find NEWER LUXURY VINYL PLANK FLOORING, offering both durability and a fresh, contemporary feel. The primary bedroom includes a WALK-IN CLOSET, and the INSIDE LAUNDRY ROOM is complete with built-in cabinetry for added storage and convenience. Don’t miss the under-stairs storage area—perfect for seasonal items or organizing household extras. Outside the charm continues with an extended paver driveway welcomes guests, while the EPOXY-FINISHED GARAGE FLOOR adds both style and practicality. Out back, a FULLY FENCED BACKYARD—featuring a charming vinyl picket fence—includes a spacious COVERED PAVER PATIO and low-maintenance turf, ideal for play, pets, or relaxing with family and friends. This home is truly MOVE-IN READY, combining CHARMING CURB APPEAL, SMART UPGRADES, and a RARE, PICTURESQUE SETTING. All located within an amenity-rich community featuring two newly resurfaced tennis/pickleball courts and a refreshed playground—perfect for your next season of outdoor fun. Zoned for EXCELLENT SEMINOLE COUNTY SCHOOLS, this home offers the best of Florida living where comfort meets nature—and every detail has been carefully considered.

1819 Shadyhill Terrace, Winter Park
$605,000
4 Beds ⋅ 3 Baths ⋅ Lost Creek SubDv. ⋅ 32792 Zip Code
Buyer’s financing feel though the night before closing. The home has been inspected and it is in fine condition per inspectors’ reports! Tucked away on the tree-lined streets of the Lost Creek community, this contemporary two-story residence offers a rare blend of serenity and sophistication. Ideally located in sought-after Winter Park, this exceptional property offers exclusive creek-to-lake access leading to the sparkling waters of Lake Howell—just minutes away from vibrant city life and top-tier amenities. From the moment you arrive, the home makes a striking first impression with its stately architecture and bold navy double doors, creating a grand sense of arrival. Inside, a warm, welcoming foyer introduces an elegant layout, with a private office to one side and a formal dining room on the other—both adorned in rich wood flooring. The soaring ceilings of the great room bring in an abundance of natural light and airiness, while modern pendant lighting adds a contemporary flair. At the heart of the home lies a gourmet kitchen, beautifully appointed with crisp white Shaker cabinetry, Dovetail quartz countertops, and a sleek subway tile backsplash. The kitchen opens seamlessly to the sunny breakfast nook, with views of the lush, wooded preserve just beyond. The inviting family room centers around a cozy wood-burning fireplace, framed by built-ins and a custom art niche—perfect for showcasing treasured pieces. Step through French doors onto the lanai, where a wood-planked ceiling, ceiling fan, and wet bar create an effortless space for entertaining or quiet evenings under the stars. The primary suite, offers a tranquil escape with wood floors, crown molding, and soft blue hues that evoke a spa-like ambiance. The ensuite bath is equally luxurious, featuring an oversized vanity with framed mirror, a garden soaking tub, and a walk-in shower accented by coastal-inspired blue tile. Upstairs, a spacious open loft provides flexible living space ideal for a media room, home gym, or guest lounge. Two additional bedrooms complete the second floor, each generously sized and bathed in natural light. Step outside to your private backyard oasis, where a deck and firepit area offer peaceful moments overlooking the scenic landscape. A pathway leads to Howell Creek, where you can launch your own watercraft and enjoy a picturesque 15-minute cruise to 400-acre Lake Howell—a rare amenity in such a well-connected location. Additional highlights include: • New Roof (2021) • New Water Heater (2025) • Whole-Home Repipe (2017) • New A/C (2025) Ideally situated near premier dining, shopping, medical centers, and recreation—just minutes from Oviedo on the Park, Park Avenue, and Waterford Lakes Town Center. Top employers like Siemens, Lockheed Martin, and UCF are all within easy reach, along with quick access to the 417, making weekend getaways to the beaches or theme parks effortless. Zoned for top-rated Seminole County schools: Red Bug Elementary, Tuskawilla Middle, and Lake Howell High.

3102 Heartleaf Place, Winter Park
$331,985
2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Patio Homes SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. BACK ON THE MARKET AFTER EXTENSIVE RENOVATIONS!!! BRAND NEW KITCHEN, BATHS, BRAND NEW GORGEOUS LUXURY VINYL PLANK FLOORING THROUGHOUT! BRAND NEW ROOF AS WELL! Some Photos are Virtually Staged for decorating options. Welcome to this beautiful 2-Bedroom, 2-Bathroom patio home located in desirable Winter Park. This duplex offers a range of amenities that will surely enhance your living experience. This beauty has BRAND NEW Luxury Vinyl flooring that looks like hardwood that is seamless throughout the ENTIRE home. The Kitchen is all BRAND NEW with Shaker Cabinets, tile backsplash and Quartz Counters, as well as one year old stainless steel appliances. There is an eat-in area space with wonderful natural light from the window looking to the backyard, perfect for enjoying your morning coffee. There is also a pantry as well as a separate closet with washer/dryer hookups. With a split floor plan, you'll have added privacy, and the vaulted ceilings add an airy and spacious ambiance. There is a huge Great Room to ensure no wasted space. Sliding Glass doors open to an open patio and fenced backyard, providing a private space for outdoor activities or simply relaxing in the fresh air. With the sliding glass door open, this is true indoor/outdoor FL living! The Primary Bedroom has a large walk-in closet, and the ensuite Bathroom is completely BRAND NEW with a double Vanity, and a separate area with a Walk in Shower and toilet that can be closed off. On the other side of the home is Bedroom 2 and the BRAND NEW Full Hall Bathroom with a tub/shower combination, and is accessed from the common hallway. The interior is painted a beautiful neutral decorator paint color throughout, creating a blank canvas for you to personalize and make it your own. Some other features are ceiling fans in Great Room and the Primary Bedroom, updated fixtures, brand new baseboards, and all handles and door knobs are updated as well. The one-car garage offers convenience and additional storage space. ROOF is BRAND NEW MAY 2025. Situated in the Winter Park School District, this home is perfect for those seeking quality education. Additionally, you'll enjoy the convenience of being close to shopping and dining options, making errands and nights out a breeze. Conveniently situated just minutes from Advent Health Winter Park, Rollins College, Full Sail University, and UCF. This location is also right around the corner from multiple parks, Cady Way Pool and the Winter Park Pines Golf Course. Don't miss the opportunity to make this recently renovated duplex yours and experience the comfort and convenience this gorgeous Winter Park gem has! This newly renovated, move in ready home will not last long!

638 Warrenton Road, Winter Park
$585,000
4 Beds ⋅ 3 Baths ⋅ Lost Creek SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Huge price reduction! This stunning 4-bedroom, 3-bathroom residence is situated on a desirable corner lot, offering ample space and privacy. This home was recently updated with a brand new HVAC system installed (May 2025), and a roof that’s only 4 years old (2021), complete plumbing repipe done in (2020). This home boasts both efficiency and peace of mind. Step inside to discover a modern open floor plan that promotes seamless living and entertaining. Enjoy the elegant ambiance created by high vaulted ceilings and tasteful finishes throughout. The (3) beautifully remodeled bathrooms, completed in 2024, provide a spa-like retreat, while the kitchen shines with granite countertops and stainless steel appliances, perfect for culinary enthusiasts. For added safety and convenience, the home is equipped with hurricane storm shutters and comes with a generator. Don’t miss this fantastic opportunity to own a beautifully updated home in a charming neighborhood, close to local amenities, world class restaurants and fine boutique shopping on Park Ave and one of the best school districts in Florida! Schedule your showing today!

3115 Heartleaf Place, Winter Park
$430,000
4 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
Winter Park delight. Discover the potential of this wonderful, spacious Seminole County residence nestled in a well-established neighborhood. Amazing split floor plan with tons of potential. Picture creating your ideal kitchen, updating the bathrooms to your taste and opening up the living spaces to create a more contemporary flow. Gorgeous backyard oasis pool with pavers and waterfall. Fresh exterior paint and tons of new flooring. This house is sparkling clean and is move-in ready for a growing family. Enjoy ample room for entertaining and everyday living. Sliding doors across the Florida room bring in the sunsets over the pool. Well-maintained pavers in front and back, new water heater and garage door. Updated, mature landscaping. Easy access to the 417 and Semoran Boulevard. Don’t miss out on this great value.

1006 Bradford Drive, Winter Park
$279,000
2 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Phase 2 SubDv. ⋅ 32792 Zip Code
Move-In Ready and AFFORDABLE one-story townhouse with FENCED YARD, 1-Car Garage and LOW HOA!!!!Situated on a corner lot with a screened patio and no rear neighbors, it offers just the right mix of privacy and convenience. Inside, you’ll find ceramic tile and luxury vinyl flooring throughout...so no carpet in sight! A spacious kitchen, living and dining spaces, large bedrooms and 2 tastefully UPDATED Full Bathrooms... all topped off with a BRAND NEW ROOF! The layout is functional, the maintenance is easy, and it's move-in ready. All appliances stay- even the Washer & Dryer! Excellent investment for rental, perfect starter home and ideal for anyone looking for a turn-key, low maintenance property located in an established Seminole County neighborhood of Winter Park with community pool and low HOA!! Don't sleep on this one... it's a great deal!

3153 Greenwood St Unit Winter Spr, Winter Park
$260,000
3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 1 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath villa nestled in the highly sought-after community of Winter Park! This spacious home boasts an open floor plan, a convenient inside laundry room, and easy-to-maintain flooring—no carpet anywhere, and Solar panels! Step outside to a generously sized screened-in patio, perfect for relaxing or entertaining. Enjoy warm Florida days at the sparkling community pool just steps away. With a low HOA and a prime location close to top-rated shopping, dining, and entertainment, this home offers both comfort and convenience. Don’t miss your chance to own a piece of Winter Park!

3015 Casselwood Street, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 15 SubDv. ⋅ 32792 Zip Code
This POOL home is amazing in every way and is truly a must see! Original Owner with pride of ownership. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location just minutes to everything. This residence boasts an array of desirable features. Three bedrooms and two full baths with oversized primary bedroom. As you enter through the new, striking front door and stunning foyer with coat closet, you are mesmerized by the beauty and flow of home. Separate formal dining room and expansive formal living area creating a stylish, classic feel. Split Floorplan, each with full bathroom, offering privacy and convenience. Stunning, oversized primary bedroom overlooking the sparkling pool. Substantial walk-in closet offering more than ample storage. Large kitchen-family combo. Kitchen centered between airy family room and spacious formal dining room. Striking stainless steel appliances. Pocket door in kitchen for chef's privacy. Gorgeous wood flooring throughout combining durability and elegance. Beautiful French Doors leading out to lanai and open swimming pool. Close to a quarter acre of land completely fenced for your fury family. Very large, screened in lanai with fabulous swimming pool. Oversized 2 car garage with an abundant of storage options both inside and out. Comes with washer and dryer. This is the ideal entertainment home. What more could you ask for…I-4 and 417 minutes away for Disney or a day at the Beach. Offering supermarket, restaurants, shopping and so much more. Close to Historical Downtown Winter Park and desired Park Avenue with weekly Farmer’s Market. Then you have the convenient SunRail taking you around Central Florida. Excellent A-Rated Seminole County Schools. Location, Location, Location. Welcome Home!!!

2151 Conifer Avenue, Winter Park
$779,000
4 Beds ⋅ 3 Baths ⋅ Preserve At Hawks Crest SubDv. ⋅ 32792 Zip Code
This stunning and stylish one-story home built by Meritage in the gated community of Hawk's Crest in Winter Park includes many new upgrades. This is the Pomelo model built with the upgraded kitchen package featuring built-in double ovens and stainless steel range hood. Beautiful quartz countertops on an oversized kitchen island with room for four seats. Other features include a walk-in pantry, under cabinet lighting, and stone backsplash. The luxurious kitchen opens into your dining and living areas. In the large living room is a new custom built-in electric fireplace with decorative trim moulding. The dining room is enhanced by custom board and batten and a view of the back covered lanai with motorized screens. The backyard features a new large extended patio for entertaining. The yard is fenced in with a view of conservation trees. A total of four bedrooms and three bathrooms. The front bedroom includes custom built-in shelves and storage, which is used as an office, but can also still be used as a bedroom. The primary bedroom has a private bathroom with a double vanity, linen closet and a large walk-in closet that could be customized for a future homeowner. The home also comes with new gutters. Other amenities in the Hawk's Crest community include a resort-style pool with clubhouse, splash pad, fitness center, BBQ grills, playgrounds, dog park, and a community fishing dock overlooking beautiful Lake Howell. At the front of the neighborhood shops and dining includes Kelly's Ice Cream, Foxtail Coffee, Sobol, Winter Park Pediatric Dentistry and Park Maitland's Preschool Campus.

2247 Marsh Sedge Lane, Winter Park
$465,000
3 Beds ⋅ 2 Baths ⋅ Lost Creek SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,906 square feet of comfortable living space in the heart of Winter Park. Built in 1995, this home features a desirable split-bedroom floor plan, high ceilings, and tile flooring throughout the main living areas—perfect for everyday living and entertaining. The spacious layout includes both a formal living room and a separate family room, as well as an open-concept living and dining area that flows seamlessly into an eat-in kitchen with abundant natural light. The kitchen is equipped with stone or Corian countertops, a separate closet pantry, and French doors that lead directly to the screened-in patio. The primary suite is a peaceful retreat, complete with a walk-in closet, private access to the patio, and an ensuite bathroom featuring dual sinks, a walk-in shower, a soaking tub, and a private water closet. Two additional bedrooms offer generous closet space and share a well-appointed guest bathroom with a tub/shower combo. Enjoy outdoor living in the fully fenced backyard, accessible through sliding glass doors from the formal living room or the French doors off the kitchen and living room. A Dual Well System provides excellent utility savings—while the original well was installed approximately 10 years ago, a second well was added in 2021 to boost water output during dry seasons. Both wells operate on the same pump and contribute to reduced water bills. The home also includes an indoor laundry room, an attached 2-car garage, no popcorn ceilings, blinds throughout, and plenty of windows that allow for an abundance of natural light. Additional updates and features include a paver driveway and walkway, a covered front porch with charming curb appeal, a roof from 2017, A/C replaced in 2009, and a water heater replaced in 2015. All of this comes with a low HOA. Located in the highly desirable Lost Creek neighborhood within the top-rated Seminole County school district, this home offers both comfort and convenience in a fantastic Winter Park location near shopping, dining, and major roadways. Don’t miss the opportunity to make this your next home!

1173 Valley Creek Run, Winter Park
$540,000
4 Beds ⋅ 3 Baths ⋅ Arrowhead Cove SubDv. ⋅ 32792 Zip Code
Set in a quiet Winter Park cul-de-sac community, this renovated four-bedroom pool home offers an opportunity to live the Florida lifestyle you’ve been craving. Stepping inside, you’ll be struck by the versatility of its inviting, open floor plan. Flanking the foyer on either side are the living room, dining room, and a flex space, all connected by stylish luxury vinyl plank flooring. Just beyond, a large seamless quartz counter island, complete with additional under counter storage, draws your attention into the beautiful, bright kitchen that will surely become a favorite gathering place for all who walk through your door. The home’s split floor plan allows for a private primary bedroom location. You’ll appreciate the room’s ample size, en suite bathroom, and walk-in closet with dressing area. An additional bedroom can be found down the hall, around the corner and is perfect for use as either a bedroom or an office. Another tastefully updated hall bathroom serves two bedrooms on the opposite side of the house. A lifestyle house should have a lanai, and this one does not disappoint. Its massive area adds valuable room for extending your living space and serves as the perfect transition area to the home’s screened-in pool. Surrounding the pool is a deck that’s large enough for multiple seating areas; outside the screen, you’ll have plenty of fully-fenced yard space to enjoy gardening beds, outdoor grilling, and more. A paver walkway running the length of the house blends charm and practicality, allowing easy movement from the front yard to the back. Finally, an oversized garage that’s been beautifully enhanced with epoxy floor coating completes this amazing property and makes everyday life so easy. Located between Lake Nan and Lake Waunatta, the Arrowhead Cove community is zoned for highly-rated Winter Park High School, and is mere minutes from Trinity Prep, Full Sail, Rollins, and UCF. And whether you prefer outdoor recreational activities or the pleasures of shopping and dining, you’ll appreciate living near the Cady Way Trail, Winter Pines Golf Club, and all the shops, restaurants, and museums of Winter Park’s trendy Park Avenue mecca. Don’t miss your chance to own this irresistible gem, set in the serene neighborhood you’ve been looking for. Schedule your private showing today!

7852 Broken Arrow Trail, Winter Park
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code
Virtually Staged. Incredible Value!!! Major price reduction! Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront residence offers a serene retreat within an intimate gated enclave of just 28 homes. A setting that feels private and peaceful that is increasingly hard to find. Designed for both everyday comfort and effortless entertaining, the thoughtfully planned 4-bedroom, 3.5-bath layout includes a dedicated office, formal dining room and a desirable three-way split floor plan that provides flexibility and privacy for today’s lifestyle. At the heart of the home, the gourmet kitchen blends beauty and function with quartz countertops, a substantial center island, natural gas cooktop, 42" solid wood cabinetry, walk-in pantry, and a generous butler’s pantry—perfect for hosting or simply enjoying the flow of daily living. Rich wood flooring carries throughout the home connecting the kitchen seamlessly to the light-filled family room and casual dinette area. The primary suite is a true lakefront sanctuary featuring peaceful water views, two walk-in closets and a spa-inspired bath with dual sinks and an oversized shower with dual shower heads. Many upgrades are to be found through out this home such as an extra oversized storage closet, crown molding, custom mud room off of the laundry room, high ceilings, tray accents and abundant natural light to enhance the home’s relaxed, refined feel. Outdoors, the property transforms into a private lakefront escape. Enjoy sweeping water views, a sparkling pool and spa, custom rock waterfall, screened-in lanai and a fully fenced yard framed by tall privacy hedges and mature trees—ideal for quiet evenings or weekend gatherings. Direct lake frontage and access to a nearby community dock complete the lifestyle experience. A three-car garage with a separate AC wall unit offers added versatility—perfect for a workshop, home gym, or additional storage. Thoughtfully positioned, this home represents a rare opportunity to own a lakefront retreat that delivers serenity, lifestyle and value—all within close proximity to shopping, dining and top-rated schools in a prime location!

2922 Reef Knot Place, Winter Park
$910,000
4 Beds ⋅ 4 Baths ⋅ Eden Point SubDv. ⋅ 32792 Zip Code
FULLY FURNISHED HOME THAT IS MOVE-IN READY! ALL FURNITURE INCLUDED IN THE SALES PRICE! Amazing home located in a quiet gated subdivision in Winter Park near Trinity Prep. The home provides a wonderful layout with high ceilings and an open concept – perfect for entertaining. Updated kitchen with clean white cabinets, spacious chef’s island, and GE stainless steel appliances to cook a delicious meal that can be served in your extended dining room area! Beautiful light fixtures throughout the house and plush carpet on the 2nd floor as well. The owner’s suite on the first floor has it all – extra sitting room, dual vanities, walk-in shower with extra large rain head attachment, jacuzzi tub, and walk-in closet with built-in shelving. The second floor includes TWO loft spaces – perfect for a media room AND a separate play area/sitting room. Kids bedrooms include separate walk-in closets and jack & jill bathroom. The fenced in backyard area provides a calming pond view and large patio area to relax and enjoy the outdoors. Also included are solar panels which drastically reduce electricity costs. This home has it all!

1319 Heavenly Cove, Winter Park
$290,000
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 2 SubDv. ⋅ 32792 Zip Code
Discover One of Winter Park’s Best-Kept Secrets — Windward Square! Welcome to your beautifully renovated 2-bedroom, 2-bath townhome in the highly sought-after Windward Square community. This move-in ready home boasts a bright, open floor plan, with a modern kitchen that flows effortlessly into the spacious living area. The fully updated kitchen features brand-new stainless steel appliances, including a refrigerator with ice maker, plus 42" upper cabinets — ideal for everyday living and entertaining. The primary suite offers a generous walk-in closet, and both bedrooms are filled with natural light. Step outside to your private, screened-in patio and fenced backyard — perfect for morning coffee or evening relaxation. Additional highlights: Three dedicated parking spaces Beautiful green space throughout the community Resort-style amenities at Windward Square include: Three swimming pools, including a dedicated kids' pool Tennis courts Playground Putting Green Welcoming clubhouse Located just minutes from Full Sail University, UCF, shopping, dining, and all that Winter Park has to offer. Zoned for top-rated schools, this townhome provides the perfect blend of comfort, convenience, and community living. Don’t miss your opportunity to own a home in one of Winter Park’s most charming and well-maintained neighborhoods!

2541 Leeward Way, Winter Park