Winter Park Homes For Sale & Real Estate - 342 homes

Remarks: Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and a wet bar, ideal for relaxing or entertaining. The galley kitchen features granite countertops, a natural gas range, and a convenient laundry closet with a stackable washer and dryer. The primary bedroom boasts a walk-in closet with ample storage, additional closet in the rear alcove, and a primary bath with dual sinks and a walk-in shower. The secondary bedroom includes an adjoining office alcove, while the secondary bath offers a walk-in shower. Neutral tones flow throughout the condo, and the dinette provides beautiful views of Lake Osceola. Completely rebuilt in 2011 with new plumbing, electrical wiring, air conditioning, and ductwork, this home offers modern efficiency and peace of mind. A covered boat slip (#15) with lift, two covered parking spaces in the gated underground garage accessible with a key access in the elevator, approximately 90 sq ft of private utility storage, and a community pool complete this exceptional offering. Just steps from Park Avenue, enjoy walkable access to premier shopping, dining, museums, and seasonal events, making this a rare opportunity for true lakefront living in one of Winter Park’s most desirable locations.

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

Listing Agent: Megan Cross (407-353-9997)

Remarks: Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has a beautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 square feet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that create an open, airy feel throughout. The kitchen showcases elegant granite counters and modern stainless steel appliances. Hard flooring flows through the main living areas, offering both style and easy maintenance. Solar panels on the home save you hundreds each month on electricity. SELLER WILL PAY OFF SOLAR PANELS AT CLOSING! Step outside to your private backyard oasis with a screened-in pool and jacuzzi spa, ideal for year-round Florida living. The fully vinyl fenced yard provides privacy and security for families and pets. This move-in ready property means you can start enjoying your new home immediately. The location offers incredible convenience with easy access to Winter Park shopping, restaurants, and world-famous theme parks. Major roads are nearby, making commuting simple whether you work locally or need to travel throughout Central Florida. The gated community adds security and peace of mind. Winter Park is known for its charming downtown area, excellent schools, and beautiful parks. This neighborhood combines suburban tranquility with urban accessibility, giving you the best of both worlds. Schedule your showing today!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Kathy Williams (407-230-7305)

Remarks: Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home’s inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and effortlessly refined. Inside, light pours through expansive picture windows, illuminating marble floors that flow seamlessly through the living room, dining area and kitchen. Every space has been thoughtfully curated by New York City–based interior designer Paulette Pascarella, where classic architecture is elevated by contemporary finishes and a restrained, sophisticated palette. The new kitchen serves as a centerpiece and a gathering space, featuring custom cabinetry, quartz countertops with a full-height backsplash and a high-end appliance suite anchored by a Bertazzoni refrigerator, equally suited for everyday living or intimate entertaining. Just beyond, the family room or den introduces warmth and texture with beautiful wood floors and custom built-ins designed for function and form. Motorized shades by The Shade Store, lighting by Visual Comfort and Currey, and hardware details by Buster + Punch are layered throughout the home, complemented by exquisite textile selections from Brunschwig, Schumacher, Thibaut, and Cowtan & Tout, each detail quietly reinforcing the level of thought and design intention behind the renovation. The second floor is a serene retreat and allows for elevated view of Lake Sylvan. The primary suite with soaring ceilings offers a generous window framing treetop views. The spa-inspired bath features a large glass-enclosed shower and a custom built-in dressing area, creating a private sanctuary that feels removed from the everyday. Two additional bedrooms, one with an en-suite bath, complete the upper level, offering flexibility for guests, work-from-home needs or extended stays. Outdoors, the grounds have been thoughtfully reimagined to evoke a cottage garden feel, providing a peaceful backdrop for morning coffee or evening strolls along the brick-lined street. The location is equally compelling, in a neighborhood known for its winding roads and timeless charm, just minutes from shopping, dining and cultural offerings of Park Avenue. Offering a lock-and-leave lifestyle, this home lives beautifully as a primary residence or as a second or third home and presents a compelling alternative to condominium or townhome living, where privacy, design and a desired Winter Park setting come together in one exceptional offering. There is potential for a third bedroom suite by converting the den/family room on the first floor as it is adjacent to a full bath.

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

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

Remarks: Welcome to 151 Oakwood Way, a beautifully executed residence by LunDev Custom Homes, set on a quiet, tree-lined street in the heart of Winter Park. Blending timeless architecture with a clean transitional aesthetic, this newer pool home offers sophisticated design, comfortable livability, and the kind of indoor-outdoor flow today’s buyers are looking for. Inside, the home is filled with natural light and thoughtfully designed for both everyday living and entertaining. Wide-plank engineered hardwood flooring, quartz surfaces, premium Thermador appliances, and well-selected finishes create a refined, elevated feel throughout. The open-concept layout lives effortlessly, with inviting spaces that feel both polished and welcoming. The outdoor setting is a true highlight. A covered lanai with a summer kitchen and automatic screens opens to a beautiful saltwater pool and separate spa, creating a private, resort-style backdrop for relaxing or hosting year-round. A spacious flex room adds valuable versatility and can easily function as an office, game room, media space, or potential future guest suite, with plumbing already in place for added flexibility. Thoughtfully designed and exceptionally well located, 151 Oakwood Way presents a rare opportunity to own a newer luxury home in one of Winter Park’s most desirable settings.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Matthew Burks (407-257-5347)

Remarks: Timeless Olde Winter Park charm meets relaxed Florida living at 823 Granville Drive, a true Park Grove gem on an expansive 100' x 135' lot. Nestled among tree-lined streets in this coveted, well-established neighborhood, this single-story residence offers 4 bedrooms, 3.5 baths, and effortless indoor-outdoor living. Thoughtfully designed for entertaining, the home features two fireplaces that anchor inviting living and family spaces, creating a warm, elegant backdrop for gatherings large and small. The open, flowing layout keeps daily living convenient on one level while offering plenty of separation for guests or multi-generational living. Step outside to your own private retreat: a screened, enclosed pool area that feels like an outdoor living room, perfect for morning laps, weekend barbecues, or evening cocktails. The generous lot provides room to play, garden, or simply enjoy the lush surroundings and privacy Park Grove is known for. Practical features include a two-car garage, ample storage, and the rare opportunity to own a pool home in one of Winter Park’s most sought-after neighborhoods, just minutes to Park Avenue shopping, dining, lakes, and cultural venues. This is the Park Grove lifestyle—single-story, pool, charm, and location—all in one compelling property.

Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)

Listing Agent: Anthony Consalvo (407-599-7070)

Remarks: Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living spaces that all blend into a covered porch to backyard retreat. The kitchen is the center of the home with custom double-stacked cabinetry to ceiling, upgraded appliances, large pantry with barn door, center island with bar seating, and full granite slab backsplash and counters add to the artistry of the kitchen. Ceilings are upgraded throughout with floating box details with ambient lighting that gently wash the ceilings and colors can be changed as you wish. Dining and living spaces are generous, and lined with transom windows for privacy and natural light that creates a beautiful backdrop to gather and entertain in. Invisible back doors fully open to the lanai and slide into the wall, staying hidden, an elegant upgrade. Covered porch with tongue and groove ceiling overlooks saltwater pool with hot tub and spillway. Professionally landscaped includes a turfed putting green for the golf enthusiast. Additional main floor flex space can be additional living or home office. Secondary bedrooms are upstairs with generous bonus space and laundry. First-floor primary suite is light and bright, with coffered ceilings and a large walk-in closet. Primary bath is neutrally appointed with dual floating vanities with vessel sinks, a soaking tub, and walk-in shower with seamless glass. A transom window provides privacy and a glow of sunshine and warmth. Lots of seller upgrades. This property is turnkey. Orwin Manor is a special neighborhood blending historic homes with new builds and great neighborhood park to go to. It is also a strategic location, minutes to Park Avenue in Winter Park, known for its upscale dining, elevated cafés and luxury local shopping, also a short distance to Orange Avenue corridor in WP featuring Foxtail Coffee & Buttermilk Bakery and more, and minutes to the Mills district, Advent Health on Rollins as well as major roadways. Great schools, zoned for Edgewater High, known for its magnet program and close to Lake Highland and many other private school options.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: Low HOA!!! Spacious 2-bedroom unit offering 1,008 sq ft plus a 16x8 enclosed Florida room and a one-car garage, presenting a great opportunity for an investor or buyer ready to add value. The unit has been professionally cleaned, and following a water heater failure, ServPro inspected and addressed the area—no severe damage reported. As a result, baseboards have been removed throughout, and carpet has been removed from both bedrooms, leaving bare concrete and a blank slate for new flooring. The home features vaulted ceilings in the living and dining areas, a large welcoming foyer, and a functional kitchen with pantry and dual lazy Susan cabinets. Major components include a 2023 roof, 2025 water heater,2010 A/C, poly piping, and a Gould-brand electrical panel. HOA covers roof, exterior maintenance, termite bond, and pest control; buyer approval is required. Recent comparable sales support strong potential—bring your vision and make this one your own.

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

Listing Agent: Jacob Zampella (321-945-2273)

Remarks: One of the best views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water heater, freshly painted interior, new screened porch, and new toilet — giving you move-in-ready comfort and peace of mind. The kitchen comes fully equipped with range, dishwasher, refrigerator, and microwave. A stackable washer and dryer are conveniently located in the bedroom, and an additional community laundry room with two washers and dryers is available free of charge. Stratford residents enjoy an amenity-rich lifestyle including: • Two sparkling pools • Tennis courts • 24/7 fitness center • Clubhouse available for private gatherings • Pet station *Planned social events for residents. The HOA adds tremendous value by covering water, trash removal, internet, pest control, exterior maintenance, grounds care, and common areas — simplifying ownership and monthly budgeting. Located in a prime Winter Park area with easy access to 408, Semoran Blvd., 417, I-4, and State Road 50. Just minutes from shopping, dining, grocery stores, and within 20 minutes of UCF, Full Sail University, Rollins College, and Park Avenue. With its thoughtful updates, first-floor convenience, and exceptional community amenities, this condo offers more than just a home — it delivers an above-average lifestyle in one of Central Florida’s most desirable locations.

Listing is courtesy of: WATSON REALTY CORP (407-332-6000)

Listing Agent: Barbara Coy (407-497-1777)

Remarks: Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 location offering a fenced backyard, low HOA, and a flexible bonus space ideal for a home office, study, or hobby area. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly to the main living area plus upgraded appliances. The primary suite includes a private bath and generous closet space, while the secondary bedroom and full bath provide flexibility for guests, office use, or additional living needs. Enjoy outdoor living in the fully fenced yard—ideal for relaxing, gardening, or pets. Additional highlights include driveway parking, interior laundry, and low-maintenance living. -- NEW ROOF IN PROCESS -- Prime location with convenient access to major corridors and top destinations: ˜ 3 mi to Full Sail University, ˜ 5 mi to UCF, ˜ 4 mi to AdventHealth Winter Park, and ˜ 6 mi to Park Avenue and Downtown Winter Park. Nearby shopping, dining, and grocery options are within minutes, with quick connectivity to SR-436, University Blvd, and SR-417 for commuting throughout Central Florida. An excellent opportunity to own in Winter Park with space, privacy, and strong location value.

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: One or more photo(s) has been virtually staged. NESTLED IN THE HEART OF HISTORIC WINTER PARK, THIS CHARMING RESIDENCE AT 518 SHOREVIEW AVE OFFERS TIMELESS CHARCTER. JUST STEPS FROM BEAUTIFUL LAKE KILARNEY. INSIDE, YOU WILL FIND STUNNING HARDWOOD FLOORS THAT ADD WARMTH AND ELEGANCE THROUGHOUT, ALONG WITH AN UPDATED PRIMARY BATHROOM FEATURING A RELAXING GARDEN TUB.THE INVITING FLORIDA ROOM PROVIDES THE PERFECT SPACE TO UNWIND OR ENTERTAIN WHILE ENJOYING THE NATURAL SURROUNDINGS. THE KITCHEN FEATURES A REVERSE OSMOSIS SYSTEM TO FILTER THE DRINKING WATER. THIS PROPERTY IS A RARE OPPORTUNITY TO OWN A PIECE OF WINTER PARK HISTORY IN AN UNBEATABLE LOCATION NEXT TO FABULOUS SHOPPING AND DINING EXPERIENCES. ** SELLER HAS PLANS FOR ATTIC EXPANSION AVAILABLE.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Kendra Wallace (407-457-7069)

Remarks: Winter Park “Sweet Spot”, Priced to Sell: Rare 3/2 Opportunity in Eastbrook Discover the perfect blend of value, location, and versatility in Winter Park’s highly sought-after Eastbrook neighborhood. This 3-bedroom, 2-bathroom home is ideal for homebuyers looking to make new memories or savvy investors seeking a turn-key property. Move-in Ready: From the moment you step inside this roomy, open floor plan, it’s ready to enjoy. The heart of the home—kitchen, dining and living room—is tastefully renewed and has plenty of space. The ample primary bedroom has a full ensuite bathroom and large windows. Two additional bedrooms share a full guest bathroom. Recent functional improvements provide peace of mind: new water heater, window blinds and exterior paint, and a 12-year-old insurable roof. Outdoor enthusiasts will love the massive, fully fenced backyard, including firepit for chilly (yes, chilly!) Florida nights and “grass-covered” patio. This private oasis is ready for pets, play, or future expansions. BONUS exterior features include carport and multicar driveway, large separate laundry room, lots of elevated carport storage, and an additional cross-fenced and gated side yard. Under Market Value for Quick Sale: Motivated sellers + a price well below area comparables = a win-win. Investor Advantage: This property currently serves as a high-performing, low-maintenance rental with risk-free reliable tenants. In May, renew the lease for continued cash flow or transition the home to a primary residence when the lease expires. • Location: Quiet, safe, and walkable Eastbrook, with shopping less than a mile away. • Condition: Well-maintained with modern updates. • Inclusions: Everything in the home conveys with the sale (excluding tenant furnishings). • Value: Instant ROI for investors and equity potential—priced to move fast! Don’t miss your chance to own a piece of Winter Park at an unbeatable price. Schedule your showing today!

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)

Remarks: ***PRICE REDUCTION*** **Seller offering closing credit** Nestled on a quiet cul-de-sac in desirable Winter Park, this well-maintained home offers a thoughtful layout with bright, open living spaces designed for both comfort and everyday living. The kitchen flows seamlessly into the main living and dining areas, making it ideal for gathering and entertaining. Generously sized bedrooms provide flexibility for guests, a home office, or a growing household. Enjoy a private backyard perfect for relaxing or hosting, all while being conveniently located near shopping, dining, parks, and major roadways. A wonderful opportunity to enjoy the lifestyle Winter Park is known for.

Listing is courtesy of: OAK HOLLOW PROPERTIES (407-949-8809)

Listing Agent: Jakki Kim (407-949-8809)

Remarks: Excellent opportunity to build your dream home in Winter Park. 10,278 SqFt corner lot. Value is in the Land, home being sold AS-IS. Zoned for Lakemont, Maitland Middle, Winter Park High. Centrally located near restaurants, shopping, Winter Park Hospital & a short drive to Park Avenue, Rollins College & many local parks. This sale is strictly for the value of the land & location.

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

Listing Agent: Catherine D'Amico (407-252-3210)

Remarks: Under Construction. Spectacular new LUIH Luxury Home in the heart of Winter Park! Clean architectural lines, a bold façade, and curated exterior detailing set the tone for what unfolds inside. Beyond the entry, the home opens into a dramatic, light-filled living space featuring a sleek electric fireplace, framed by custom built-ins with ambient LED underlighting, while a glass-enclosed wine display serves as a stunning architectural detail. The kitchen is a true centerpiece, designed to impress at every level. Outfitted with a full suite of premium Thermador appliances, striking Calacatta quartz countertops, custom cabinetry, and a spacious walk-in pantry. Privately positioned, the primary suite is a sanctuary of calm and sophistication. The spa-inspired bath evokes a boutique hotel experience, featuring floating mirrors, a freestanding soaking tub, an expansive glass-enclosed walk-in shower, and refined finishes that create a sense of understated luxury. The custom walk-in closet is equally impressive, offering both scale and thoughtful organization. A rare and highly sought-after feature in Winter Park, the home offers two bedrooms on the first floor, ideal for guests. Upstairs, a spacious loft creates an additional living area perfect for relaxing or entertaining, complemented by a dedicated office and three generously sized bedrooms. The outdoor living experience is nothing short of amazing. As you step through the expansive sliders, the interior flows seamlessly to a covered lanai designed for true indoor-outdoor living. A fully equipped summer kitchen anchors the space, ideal for hosting, while the expansive backyard is transformed into a private retreat with a sparkling pool and spa, offering both tranquility and the perfect backdrop for entertaining. Perfectly positioned for the Winter Park lifestyle, you’re a short golf cart ride from the shops and dining of Park Avenue, with Cady Way Park, the YMCA, and Winter Park Village also just moments away. In a market where true quality is rare, this residence stands apart, an exceptional blend of design, craftsmanship, and livability that defines what luxury should feel like in Winter Park.

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

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

Remarks: Enjoy the Winter Park Lifestyle with this Beautiful 4 Bedroom Poolside Home. Fully Updated/ Move-in Ready! Open Floorplan with Entryway into the Living and Dining area that overlooks your Screen-Enclosed Pool/ outdoor Living Space with a Fenced Yard. Entertain in style with a Large Eat-In Kitchen, Stainless Steel Appliances, Soft-Close Cabinetry and Quartz Countertops. Versatile Flex Space perfect for a Home-Office, Entertainment Room, or cozy Family Retreat. Three Bedrooms on one side of the house with a Tranquil Master Suite on the other side. Indulge in the Oversized Walk-In Steam Shower, Custom Double Sinks with Backlit Mirrors and Double Closets in the Dressing Area. Master Suite has a Real Fireplace and Pool access through Sliding Glass Doors. Luxury Vinyl Plank Flooring and Fresh Paint throughout. Elegant Designer Wall and Floor Tiles in the Bathrooms with New Sinks, hardware, and faucets. Newer Roof (2021). Light and bright. This home is a gem. The floorplan must be seen to be appreciated. This home is nestled on a Quiet tree-lined street, near top-tier restaurants, businesses, shopping, parks, recreation, top rated schools, and Park Avenue only 4 miles away. Two Workshop/Sheds for storage and creative projects in the back yard. Schedule your private tour today!

Listing is courtesy of: A +ROI PROPERTY (407-718-7994)

Listing Agent: Rene Fossey (407-718-7994)

Remarks: This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have been remodeled and have tile flooring. The remodeled Primary Bedroom has Luxury Vinyl Flooring. The house has had all the windows and front door replaced. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently being used for storage. The Roof was replaced in 2022 and the yard has a sprinkler system. Make an appointment to see today!!

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

Listing Agent: Diane Gerry Pa (407-405-5550)

Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Noelle Leblanc (407-491-2744)

Remarks: Under contract-accepting backup offers. Welcome to 639 Friar Road, ideally situated on a quiet street in the highly desirable Winter Park Pines neighborhood. This extensively updated residence offers the character of a classic 1960s home with the quality and feel of a 2026 renovation. Major improvements include a new roof, new HVAC system with new ductwork, new panel box, and thoughtfully curated high-end kitchen, bath, and lighting design elements. Original terrazzo flooring has been meticulously restored and polished throughout, preserving the home’s timeless appeal. Featuring four bedrooms, three full baths, the home offers a functional open-concept layout with a desirable split floor plan. Two primary suites, each with private en-suite baths, provide flexibility for multi-generational living or guest accommodations. The property showcases strong curb appeal and continues to impress outdoors with a spacious backyard and an oversized lanai designed for entertaining. Zoned for highly rated Winter Park schools, this home delivers an exceptional blend of style, comfort, and indoor-outdoor living in one of Winter Park’s most established neighborhoods.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Dianne Moore (407-494-7575)

Remarks: Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

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

Listing Agent: Mary Colton (407-222-7388)

Remarks: Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and entertaining alike. All bedrooms are ensuite, offering comfort and privacy throughout, while hardwood floors run seamlessly across the entire home. Thoughtful architectural details, including custom ceiling treatments and built-ins, add depth and character throughout. The first-floor primary suite serves as a true retreat, complete with dual shower heads and a rain shower for a spa-like experience. In addition to the primary, the secondary bedrooms and office are all conveniently located on the first floor—providing a layout that lives comfortably day-to-day. Upstairs, you’ll find three spacious bedrooms, each with its own full bath, along with a generous bonus room and a large laundry room—offering flexibility for guests, family, or additional living space. Perfectly positioned within steps to Brookshire Elementary, the home is also just moments from the Cady Way Trail, Little League fields, parks with covered pavilions, and nearby medical facilities. Shopping, dining, and everyday essentials are just minutes away, with Park Avenue’s renowned restaurants and boutiques a short drive from your doorstep. A seamless blend of location, thoughtful design, and livability, this home offers an exceptional opportunity in one of Winter Park’s most established neighborhoods.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)