Winter Park Single Family Homes For Sale - 253 homes

Remarks: SELLER MOTIVATED! Get ready to fall in love with this stunning Winter Park home! Tucked away in a peaceful cul-de-sac, this fully renovated 3-bedroom, 2-bath beauty blends modern style with everyday comfort. Step into the family room and instantly feel the openness of the bright, airy layout. The open floor plan creates a seamless flow from the living area to the brand-new kitchen, making the entire space feel spacious and inviting. Luxury vinyl flooring runs throughout the home, while quartz countertops sit elegantly atop all-new cabinetry. The grand center island pairs perfectly with the custom-built dry bar, complete with open shelving and extra cabinet storage, an entertainer’s dream! All brand-new stainless steel appliances are included. Just off the kitchen sits the light-filled Florida room, wrapped in oversized windows and sliding glass doors that flood the home with natural sunshine year-round. Both bathrooms have been tastefully updated with new tile, flooring, gold finishes, and beautiful new vanities. With a 2022 roof, two-car garage, fresh interior and exterior paint, and thoughtful upgrades throughout, this home delivers the peace of mind and elevated living you’ve been looking for. Don’t miss out, your Winter Park retreat is waiting! Schedule your showing today!

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Linda Jokbengboon (336-404-8871)

Remarks: Miami Beach/Coral Gables meets Winter Park high-end luxury for today's upscale lifestyle. Phil Kean completely re-imagined this 3400 sq ft one story home from top to bottom leaving virtually nothing untouched! If you are looking for one level, indoor-outdoor living, all of the most up-to-date Bells and Whistles, in a #10 location,on a private oversized lot with circular driveway, minutes to Downtown Park Avenue, nestled among some of the most beautiful waterfront mansions in all of Winter Park, this will blow your socks off! Available to tour by appointment only. This is a show home for the International Builders Show, now completed and ready to show to the world. Understated elegance This one is not to be missed!

Listing is courtesy of: PHIL KEAN REAL ESTATE LLC (407-982-2265)

Listing Agent: Brad Grosberg (321-439-1494)

Remarks: Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity. The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space that feels both private and expansive. Inside, the home has been thoughtfully updated while still leaving room for your own design vision. The layout offers comfortable living spaces with plenty of natural light and flexibility for everyday living or entertaining. Convenience is a major highlight. Located near top-rated schools, including Lakemont Elementary School, Maitland Middle School, Winter Park High School, and just minutes from local favorites like Park Avenue, Rollins College, and the Cady Way Trail. Nearby access to the SunRail adds another layer of accessibility. This location delivers a strong mix of lifestyle and connectivity, with dining, shopping, parks, and daily essentials all close by. Offered with clear motivation due to relocation, this is a rare chance to secure a well-located pool home with long-term upside in one of Central Florida’s most established communities.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: David Plasencia, Llc (407-579-9369)

Remarks: This stunning custom residence built by respected Winter Park Builder Charles Clayton blends classic elegance with refined modern comfort, offering seamless indoor–outdoor living and impeccable craftsmanship throughout. From the manicured lawn and stately traditional exterior to the welcoming front porch with old Detroit brick, the home’s curb appeal sets a tone of understated luxury, all wrapped in an elegant exterior. A foyer with extensive custom molding immediately captures attention, with sightlines extending to the private backyard and pool which creates a natural flow between interior living spaces and the outdoor retreat. Flanking the foyer, a richly detailed private study features custom millwork and a built-in bookcase, while the formal dining room provides an elegant space for entertaining. Expansive family room/dining area offers extensive molding, a gas fireplace, surround sound, and a wall of French doors which open to a covered Detroit Brick porch, creating a natural flow between interior living spaces and the outdoor retreat including a porch and pool. The space easily accommodates a large casual dining area and opens seamlessly to the kitchen. The light-filled chef’s kitchen showcases extensive marble surfaces, a Sub-Zero refrigerator, large farmhouse sink, and an open layout ideal for gathering. The main-level primary suite is a private retreat with direct porch access, dual walk-in closets. The primary bath features marble finishes, a glass-enclosed shower, pedestal soaking tub, and dual vanities. A spacious mudroom, large laundry room, and pantry area sit just off the kitchen, complete with a half bath and convenient access to the garage and porch. The two-car garage includes additional storage, complemented by a brick driveway. Upstairs, a central stair hall opens to an upstairs Family/Kid’s Gathering/Game Area. Bedroom 2 functions as a second primary-style suite, while bedroom 3 is a private suite with its own sitting area. Bedrooms 4 and 5 share a Jack-and-Jill bath, providing flexible space for family or guests. There is an upstairs storage room. Outdoor open pool with living is equally impressive. This exceptional home offers the ideal balance of architectural character, luxury finishes, engineered wood floor and a floor plan designed for comfort, privacy, and unforgettable gatherings.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Brian Mitnik (407-421-2832)

Remarks: One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional bedrooms, a versatile loft, and a conveniently placed laundry room. A first-floor guest suite adds flexibility for visitors or a dedicated workspace. Outside, a spacious backyard and custom gazebo create an inviting place to unwind. Zoned for Princeton Elementary and positioned for quick, easy access to everything College Park and Winter Park have to offer, this home delivers rare quality and exceptional value for 32789. This home is available immediatly.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Kris Kennedy (813-947-3509)

Remarks: One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric fireplace and wine refrigerator. The sleek, updated kitchen offers a gas range, stylish finishes and a functional layout perfect for everyday living and entertaining.  Retreat to the spacious primary bedroom with a fabulous ensuite bath, complete with a soaking tub, dual vanities, a large separate shower, and a generous walk-in closet. A split-bedroom floor plan provides added privacy and comfort. The fully fenced backyard offers plenty of room for a pool and includes private parking for a boat on the side of the home. Whether you enjoy the home as it is or choose to build your dream residence, the possibilities are endless. New roof installed in 2022.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Cindy Kuykendall (407-718-3235)

Remarks: Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Canal Front Oasis on the Winter Park Chain of Lakes! (Seller Financing Available for Qualified Buyers) Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. *The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes.) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rustic charm with modern luxury. Step inside to discover an open floor plan anchored by a gas fireplace, open kitchen and dining room, warm custom woodwork, and thoughtful built-ins throughout. The renovation includes new electrical, plumbing, new kitchen and baths, engineered hardwood flooring throughout, amongst many more upgrades. The redesigned layout adds over 1,000 square feet, featuring a spacious first-floor laundry room and an all-new second story with a luxurious primary suite, a guest bedroom (currently used as an office), and a full bathroom. Outdoors, enjoy a new boathouse on a canal and an inviting outdoor living area — perfect for entertaining or unwinding along the peaceful canal that connects directly to Lake Maitland and the renowned Winter Park Chain of Lakes. The rear of the property backs up to a wooded conservation area that provides privacy and tranquility. The current owner received a variance for a future pool, and Orange County previously had no objections to pool installation (new owner would need to reapply). The property sits in one of Central Florida’s most sought-after school zones: Dommerich Elementary, Maitland Middle, and Winter Park High. Families here often bike or walk to school. Enjoy regular walks through scenic streets lined with mature cypress trees, palms, vibrant native vegetation and beautiful homes that line Lake Maitland. With no HOA, residents may optionally join the neighborhood association (approx. $120/year) for access to two lakefront parks and a private boat ramp. From the modern amenities and artful landscaping to the serene waterfront setting, this is truly a one-of-a-kind property that blends nature, comfort, and sophistication in the heart of Winter Park. *Canal boat tour video that showcases the trip from the canal to Lake Maitland is available via the virtual tour link in the listing.

Listing is courtesy of: PLAID PROPERTIES, LLC (407-702-0864)

Listing Agent: Andrew Birr (407-702-0864)

Remarks: Under contract-accepting backup offers. Investor Special – Fixer Upper Opportunity in Winter Park / College Park Area. Rare opportunity to acquire a true fixer-upper in the desirable Winter Park area of College Park. This 2 bedroom, 1 bathroom property needs a full renovation and is being sold as a shell—perfect for investors or builders looking for their next project. Situated on an oversized lot at the end of a quiet dead-end street, the location offers both privacy and strong potential. Conveniently located near I-4, Park Avenue, restaurants, shopping, and popular area attractions. With its prime location and generous lot size, this property presents an excellent opportunity to renovate, rebuild, or reimagine. Ideal for investors seeking value-add potential in a highly sought-after area.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Mike Rance (407-629-6330)

Remarks: Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite offers 3,851 square feet of living space, remarkable flexibility, and the kind of charm that simply cannot be replicated. Buyers will also appreciate the peace of mind that comes with major recent updates, including a metal roof installed in 2017, two HVAC units replaced in 2026, a third HVAC unit replaced in 2022, and two water heaters installed in 2025. The pool was resurfaced in 2025, the exterior and interior of the home was painted in 2025, & the house has also been completely re-plumbed! From the moment you arrive, the home makes a lasting impression with its large brick front porch, circular driveway, mature landscaping, detached oversized 2 car garage, and classic architectural presence. Large windows and thoughtfully designed living spaces fill the home with natural light, while hardwood floors, custom built-ins, plantation shutters, fireplaces, and refined traditional details create a warm and inviting feel throughout. This is the perfect blend of classic Winter Park charm and functional modern updates. The floor plan offers both elegance and versatility. In addition to five bedrooms, the home features an office space that can also serve as a formal living room, library, or flex space depending on your needs. The spacious family room is anchored by one of the home’s two wood burning fireplaces and opens beautifully to the outdoor living area, creating an easy flow for both everyday living and entertaining. The kitchen offers granite countertops, custom cabinetry, abundant counter space, a large island, and lots of natural light. It is open, functional, and well positioned at the heart of the home, allowing the next owner to enjoy it as is or make it their own. The primary suite is generously sized, featuring its own fireplace, an oversized bathroom with large walk-in shower, extensive vanity space, and a huge custom closet. One of the most special features of this home is the attached in-law suite, with its own separate entrance while still remaining accessible from the main home. Complete with a living room, bedroom, full bathroom, and kitchenette, this apartment style space offers exceptional flexibility for multigenerational living, live in family, guests, or even potential income producing use. Outside, the screened pool and spa area is a true highlight. Beautifully integrated into the architecture of the home, this private outdoor setting offers a covered lanai, lush tropical landscaping, and a peaceful courtyard style feel that makes it easy to relax, entertain, and enjoy Florida living year-round. The large paver driveway and detached garage create an impressive amount of parking and enhance the home’s unique layout and curb appeal. All of this is located less than 1.5 miles from Rollins College, Park Avenue, downtown Winter Park, public access to the Winter Park Chain of Lakes, and all the dining, shopping, boating, and everyday convenience that make this area so desirable. This is more than just a home. It is a rare chance to enjoy the Winter Park lifestyle in a custom home full of character, flexibility, and lasting value.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Under Construction. Introducing the newest showpiece from LUIH Luxury Homes, perfectly positioned in the heart of Winter Park. Set on an oversized homesite along a quiet, tree-lined street, this residence immediately captivates with its expansive front lawn and timeless architectural presence. Inside, the home unfolds with a thoughtfully designed and highly functional floor plan that balances refined living with effortless entertaining. The spacious family room serves as the heart of the home, anchored by a sleek electric fireplace and framed by open sightlines into the kitchen and main living spaces, creating a warm yet sophisticated gathering environment. At the center of it all is a chefs kitchen designed to impress, featuring striking Calacatta quartz countertops, a full suite of Thermador appliances, custom cabinetry, an oversized center island, and an expansive walk-in pantry. Just beyond, the dining area is intentionally set apart to create a more intimate atmosphere, enhanced by a beautifully appointed wet bar with a wine refrigerator and floating shelving illuminated by elegant LED underlighting. The first-floor primary suite offers a true private retreat, with sliding glass doors opening directly to the pool and outdoor living areas. The spa-inspired bathroom is finished in exquisite marble tile and features a freestanding soaking tub, an oversized walk-in shower, dual vanities, and a generous custom walk-in closet designed for seamless organization. A rare and highly desirable feature for Winter Park living, the main level also includes a private guest suite along with a dedicated office, providing flexibility for hosting guests or working from home in comfort and style. Upstairs, a spacious loft-style living area creates the perfect setting for a media room, lounge, or secondary gathering space. Three additional bedrooms offer generous accommodations, each thoughtfully designed to provide comfort and privacy. Outdoor living is equally impressive. A large covered lanai with a fully equipped summer kitchen sets the stage for year-round entertaining and elegant alfresco dining. The backyard feels both expansive and secluded, highlighted by a resort-style pool and spa and complemented by ample green space for relaxation and recreation. Ideally located just minutes from the iconic shops, restaurants, and cafes of Park Avenue, the home offers the perfect balance of tranquility and connectivity. Residents are also moments from Cady Way Park and Winter Park High School, placing some of the area's best amenities right at your doorstep.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Under contract-accepting backup offers. Welcome home to this immaculately maintained 3-bedroom, 3-bathroom brick home in Winter Park, ideally located in one of Central Florida’s most sought-after areas and offering the freedom of no HOA. Thoughtfully cared for and upgraded, this home blends timeless construction with modern comfort and exceptional functionality, making it perfect for everyday living and entertaining. The heart of the home is the stunning kitchen, featuring quartz countertops, an oversized farmhouse sink, stainless steel appliances, stylish cabinetry, and updated lighting, creating a bright and inviting space for cooking and gathering. Wood-look flooring flows through the main living areas, leading to a warm and welcoming living room highlighted by a charming painted brick fireplace. The spacious layout offers comfortable bedrooms and well-appointed bathrooms, providing flexibility for families, guests, or work-from-home needs. A large laundry room with a utility tub sink adds everyday convenience and functionality. Step outside to your private backyard retreat with a screened patio and sparkling pool, ideal for enjoying Florida living year-round. A storage shed in the backyard provides convenient space for tools, lawn equipment, and outdoor gear. The oversized two-car garage is a rare and valuable feature and includes a full bathroom with shower, making it perfect for a workshop, hobby area, home gym, or pool access. The garage refrigerator, workbench, and shelving convey, creating a move-in-ready space for projects and storage. Additional peace of mind comes with a roof replaced in 2021, adding long-term value and helping reduce insurance concerns. Located close to parks, shopping, dining, and everything Winter Park is known for, this home offers the perfect blend of style, flexibility, and lifestyle. This is a rare opportunity to own an immaculately maintained brick 3/3 home in Winter Park with no HOA, modern updates, and features that truly set it apart.

Listing is courtesy of: PHOENIX REALTY ADVISORS LLC (407-692-5939)

Listing Agent: Joseph Giardino (407-692-5939)

Remarks: Under contract-accepting backup offers. Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming “sleeping room,” now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property’s appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen—perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home’s curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park—a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers’ Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living—whether it’s sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation. One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare expansion (subject to licensing and approvals)—a unique value-add opportunity for growing operators. The property is already configured for childcare use with existing operations in place, making this an ideal turn-key opportunity for families looking to step into business ownership or operators seeking to expand their footprint. Sale includes real estate. Business goodwill, licensing, and operations may be included or negotiated separately. Convenient location with strong demand for childcare services. Please do not disturb staff or business operations. Showings by appointment only.

Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)

Listing Agent: Ronald Trotter (321-331-1585)

Remarks: Taylor Morrison, Anastasia Model, 4 bdrm 3.5 baths on premium lot overlooking pond in the Meadows at Hawk's Crest. Large, spacious open floor plan with 20'+ ceilings, plantation shutters and builtins. Gourmet kitchen with pantry opens to dining area overlooking the great room. Master suite downstairs, laundry room, and half bath. Upstairs 3 bedrooms and 2 baths including an additional primary suite and loft area. Exterior features paver drive, tile roof., screen patio overlooking pond with fountain Community features: Fitness Center, pool, playground, dock, beautiful clubhouse. Short drive to Park Maitland School, Kelly's and Foxtail at community entrance; close to Shopping and Restaurants, and a short drive to Park Avenue and easy access to major roads to airport, attractions and UCF.

Listing is courtesy of: BECK REALTY LLC (407-256-6369)

Listing Agent: Joann Beck (407-256-6369)

Remarks: Under contract-accepting backup offers. Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park Chain of Lakes. This well-maintained home features a layout with warm and inviting living spaces and abundant natural light. The original front door faces Palmer Avenue, while a later addition created the day-to-day entrance along Old England Avenue. Two separate living areas provide versatility for both relaxing and entertaining, and both the family room and the original living room, currently used as an office, feature wood-burning fireplaces. Just off the family room, a screened porch overlooks the lap pool and backyard, creating an easy connection between indoor and outdoor living. The dining room is lined with built-in bookcases, one of several thoughtful details found throughout the home. The kitchen enjoys views of the backyard and opens to a breakfast area with built-in cabinetry and French doors leading outside. A walk-in pantry adds practical storage. Off the original living room, an enclosed sunroom with original tile and additional built-ins offers a cozy space for reading, working, or unwinding. The primary bedroom opens to the backyard through French doors and includes built-in drawers in addition to closet storage. Its bath features a pedestal sink and clawfoot tub. A second bedroom is located across the home with access to a bathroom off the hallway, providing comfort and privacy for guests or family. Recent updates include a 2014 roof, gas water heater (2022), HVAC systems (2022 and 2023), and updated plumbing and electrical panels. A sprinkler system adds convenience for maintaining the grounds. This is a rare opportunity to build your dream home or enjoy this charming property as-is, ideally located just a couple of blocks from Park Avenue.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Wendy Williams Crumit (321-356-8590)

Remarks: In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Hal George (407-832-8751)

Remarks: PRICE ADJUSTMENT! Welcome to this beautifully maintained 3-bedroom, 2-bath home for sale in Winter Park located in the highly sought-after Garden Grove community. Situated on a generously sized lot, this property offers the perfect blend of comfort, functionality, and outdoor living, with plenty of room to add a pool and create your own private backyard retreat. Inside, you’ll love the spacious split-bedroom floor plan designed for both privacy and everyday convenience. Ceramic tile flooring throughout adds style and easy maintenance, while the open family and dining room combination creates a warm and inviting space for relaxing or entertaining. A charming wood-burning fireplace adds character and comfort, making this home feel cozy and welcoming. The updated kitchen is a standout feature, opening seamlessly to the dining area and offering granite countertops, new cabinetry, and a convenient breakfast bar that is perfect for casual dining or hosting guests. Sliding glass doors lead directly to the expansive fenced backyard, making indoor-outdoor living easy and enjoyable. The oversized backyard is one of this home’s biggest attractions. Whether you envision weekend barbecues, a play area for pets, lush gardening, or extra space for your RV, boat, or recreational vehicles, this property offers flexibility that is hard to find in Winter Park. With room for a pool, the possibilities are endless. Major improvements include a roof replaced in 2019, giving buyers added peace of mind. Conveniently located near shopping, dining, parks, and major roadways, this Winter Park home offers space, value, and versatility in one of the area’s most established and desirable neighborhoods. If you are searching for a home with a large fenced yard, updated kitchen, split floor plan, and room for all your toys, this Garden Grove gem is a must-see.

Listing is courtesy of: WATSON REALTY CORP (407-323-3200)

Listing Agent: Carla Robles (407-462-2347)

Remarks: One or more photo(s) has been 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!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ellen Bessette (407-496-0076)

Remarks: Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive, you’ll notice the peaceful ambiance—towering trees, lush greenery, and the soothing backdrop of untouched landscape. Inside, the home features a spacious and inviting layout with approximately 4 bedrooms and 3 bathrooms, designed for both comfortable living and effortless entertaining. Large windows frame picturesque views of the wooded backdrop, filling the home with natural light and bringing the outdoors in. The kitchen flows seamlessly into the main living areas, while the split floor plan offers privacy for the primary suite, complete with tranquil views of the conservation area. Step outside to your backyard oasis where you can unwind, host gatherings, or simply enjoy the sights and sounds of nature along Howell Creek. Opportunities like this are incredibly rare—nearly an acre of protected land, no rear neighbors, and a location just minutes from everything Winter Park has to offer. Experience the perfect balance of privacy, space, and convenience in this truly special home.

Listing is courtesy of: CHAMPION HOMES (863-420-0007)

Listing Agent: Nadia Kurakin (509-981-9819)