Winter Park Single Family Homes For Sale - 314 homes

Remarks: (HUGE PRICE REDUCTION & NEWLY ENHANCED REAR LANDSCAPING ADDED FOR EXCEPTIONAL PRIVACY AND MORE SECLUDED OUTDOOR LIVING EXPERIENCE) Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped in upgraded pavers, offering both elegance and functionality. A very rare 4-car garage in Winter Park with two in the rear and two in the front of the home. Starting with entering through massive 10 ft. double iron doors flowing into the foyer with 11ft high ceiling beginning with the flex/office room and formal dining to your left and right. Followed by entering the gallery that leads to the great room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" wood cabinetry, a custom walk-in pantry, and top-of-the-line Thermador professional series. That Includes a 48' refrigerator, 48" gas cooktop, custom hood, dishwasher, built-in microwave, double convection ovens and built in coffee station. On your way to the formal dining, you pass by the show-stopping, Tempered glass wine room. Its crystal-clear glass enclosure offers a striking view of your curated collection, while the built-in wine chiller ensures each bottle is perfectly preserved. This elegant transition creates a seamless blend of function and sophistication, setting the tone for unforgettable dining experiences just steps away. The primary suite offers tranquility peace of mind, and the primary bath has a spa-like oasis with a spacious shower stand-alone tub. Followed by a custom closet thoughtfully design with plenty of room and storage. The guest retreat area has a huge bedroom, access to a full bath including private access to the Lania and pool. Tucked away with its own private entrance attached to the rear garage, the in-law suite above the garage offers the perfect blend of comfort and independence. This thoughtfully designed space includes a full bath, a cozy living area, and a convenient space with a kitchenette—ideal for extended stays or multi-generational living. Make your way to the second floor that has 11ft ceilings as well. As you reach the top the space opens into a massive game room with a wet bar, perfect for entertainment retreat with a balcony. All second-floor bedrooms have a thoughtfully design with a full bath for privacy. As you make your way back downstairs to outside, step through the oversized sliding glass doors and into your private outdoor oasis. Effortlessly extending your living space into the open air. Just beyond, the sparkling gas heated/saltwater pool and spa framed by lush landscaping and designed for both relaxation and recreation. Also, the fully equipped summer kitchen features gas grille, beverage refrigerator and ample counter space—perfect for alfresco dining and effortless entertaining. This masterpiece is equipped with a full irrigation system around the home, exterior lighting, exterior cameras for security. Smart home system ready for lighting, music and security controlled by Control 4 system for your convenience. Interlachen Golf community less than 5 min, Phelps Park walking distance, Park Ave 10 min and restaurant and retail minutes away.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Prentice Williams (321-438-8955)

Remarks: Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Liz Jones (407-619-6345)

Remarks: One or more photo(s) has been virtually staged. Welcome to 241 W. Lake Sue Avenue, a rare offering in Virginia Heights, one of Winter Park’s most coveted and established neighborhoods. Set along a charming oak-canopied brick street and surrounded by multimillion-dollar estates, this beautifully updated pool home sits on an oversized 12,000-square-foot lot and offers a lifestyle that is increasingly difficult to find in Olde Winter Park. Designed for effortless indoor-outdoor living, the residence showcases sun-drenched interiors, soaring ceilings, architectural wood beam accents, travertine flooring, and inviting gathering spaces that overlook a private backyard retreat. The chef’s kitchen serves as the heart of the home, seamlessly connecting the living and dining areas while offering picturesque views of the pool, spa, and lush outdoor living spaces. The spacious primary suite provides a tranquil escape, featuring vaulted ceilings, a spa-inspired bath, and generous walk-in closet. Recent improvements, including a newer roof, updated HVAC system and ductwork, and a complete replumb, offer peace of mind and modern efficiency. What truly distinguishes this property is its location within Virginia Heights, where residents enjoy deeded access to a private Lake Virginia waterfront park. Just a short stroll away, homeowners have access to a private dock, canoe and kayak storage, open green space, and breathtaking lakefront views across from Rollins College, an amenity few Winter Park neighborhoods can offer. Located moments from the boutiques and fine dining of Park Avenue, as well as nearby parks, cultural attractions, and top-rated schools, this exceptional property combines timeless charm, modern comfort, and an unparalleled Winter Park lifestyle. Opportunities to own in Virginia Heights are limited. Opportunities with private lake access, an oversized lot, and a resort-style backyard are even rarer.

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

Listing Agent: Ken Dalton (407-928-8587)

Remarks: Under contract-accepting backup offers. Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one-story residence ideally situated just moments from the vibrant shops and dining of Park Avenue and all that downtown Winter Park has to offer. With charming curb appeal, pristine landscaping and timeless architectural appeal, this home makes a stunning first impression. Inside, a thoughtfully designed floor plan offers seamless flow, perfectly suited for both everyday living and effortless entertaining. Beautiful wood flooring spans the main living areas, while the Florida room showcases distinctive Mexican tile, adding warmth and character. Designer lighting, curated tile selections and stylish wallpaper accents create a bright, inviting aesthetic throughout. The formal sitting room, complete with custom built-ins and an elegant dining room provide refined gathering spaces. At the heart of the home, a light-filled kitchen opens to the spacious family room, where a cozy wood-burning fireplace serves as a focal point. The adjacent Florida room is lined with windows, offering serene views of the sparkling pool and lush, private backyard. The generously sized primary suite is thoughtfully positioned for privacy, featuring its own wood-burning fireplace, a large walk-in closet and a beautifully appointed ensuite bath with dual vanities and an oversized walk-in shower. Four additional bedrooms are located on the opposite side of the home, two of which include ensuite baths, ideal for guests or multi-generational living. Outdoor living is equally impressive, with a beautifully paved lanai overlooking the pool and ample space for alfresco dining, entertaining and relaxing poolside. Tucked away in one of Winter Park’s sought-after neighborhoods, this home offers tranquility and convenience, with easy access to downtown Orlando, major hospitals, top-rated public and private schools and key roadways. A rare blend of style, comfort and location; this is Florida living at its finest.

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

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

Remarks: Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2022. A detailed list of all renovations is available upon request.

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

Listing Agent: Jan Walker (407-718-9644)

Remarks: One or more photo(s) has been virtually staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.

Listing is courtesy of: MID-STATE PROPERTIES PSL LLC (561-843-9537)

Listing Agent: Stacy Morano (561-843-9537)

Remarks: BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty and 1% concession at close! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchored by a 4-panel grand pocket slider that fully retracts, opening the entire living space to the covered patio for true indoor-outdoor living. The chef’s kitchen overlooks the main living area and flows seamlessly outside to a fully equipped outdoor kitchen with grill, sink, and fridge, complemented by a spacious seating area and pool—ideal for hosting year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

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

Listing Agent: Eric Trumble Ii (407-592-8624)

Remarks: Under contract-accepting backup offers. In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

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

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

Remarks: *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

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

Listing Agent: Ryan Leitter (321-684-9699)

Remarks: Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)

Listing Agent: Sidney Galloway (407-421-9990)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. PRICE REDUCTION...priced to move! Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect for modern living. Enjoy the freedom of no HOA, along with a layout ideal for families or entertaining. Midcentury modern-inspired design meets an open-concept layout with a spacious kitchen offering a large island, stainless steel appliances, pantry, granite countertops, full-height granite backsplash, and extensive cabinetry. The primary bath includes dual sinks and a frameless glass shower. Enjoy a large indoor laundry room and a private, oversized fully fenced backyard with a new paver deck and no rear neighbors. Ideal for outdoor living and entertaining. Additional highlights include a newly painted block shed with tin roof (2025) Zoysia grass installed in backyard, pavers installed in back, vinyl fence installed in backyard, GE refrigerator, washer and dryer, (2021) French doors in dining room and primary bath showerhead, (2020) Bosch dishwasher and (2018) Mitsubishi split air conditioner installed in primary bedroom and Mitsubishi split air conditioner installed in second bedroom. Just a short distance to the Winter Park YMCA, and minutes from vibrant Park Avenue, where you’ll find boutique shopping, the popular Winter Park Farmers' Market and a variety of top-rated dining options. In a sought-after school district, Lakemont Elementary, Maitland Middle and Winter Park High. This home combines location, lifestyle and convenience, making it a rare opportunity in one of Central Florida’s desirable communities.

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

Listing Agent: Maryanne Branner (321-377-3909)

Remarks: Rare opportunity to own on one of the most desirable streets in Audubon Park with a coveted Winter Park address. Just a few blocks from East End Market and surrounded by many of Orlando’s Michelin-recognized restaurants, this location offers an unbeatable combination of walkability, lifestyle, and top-rated schools. Zoned for Audubon Park K-8 and Winter Park High School, you’ll enjoy the best of both worlds: the character and community of Audubon Park with the prestige and convenience of Winter Park. This thoughtfully updated home features a 2024 roof, tankless water heater, new carpet, fresh interior and exterior paint, newer insulation, solid-core interior doors, Rain Bird irrigation with well, Vivint security system with cameras, and an Ecobee smart thermostat. The sunken living room creates a unique space for entertaining (it can provide stadium seating or be a conversation pit), while the detached mother-in-law suite adds flexibility for guests, multigenerational living, or rental income. Tucked away from the noise of Corrine Drive yet only blocks from East End Market, neighborhood parks, coffee shops, and dining, this is a rare chance to own in one of Orlando’s most sought-after neighborhoods. Front door does not convey and will be replaced with a similar refinished wood door prior to closing.

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

Listing Agent: Patrick Arenson (305-951-6054)

Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!

Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)

Listing Agent: Yuleisy Marquez (407-937-8450)

Remarks: Tucked away along the tree-lined streets of the desirable Lost Creek community, this beautifully updated two-story residence is truly move-in ready. Major updates include a new roof in 2022 and a new water heater in 2026, offering peace of mind for years to come. Ideally situated in sought-after Winter Park, this exceptional home also includes exclusive creek-to-lake access leading to the sparkling waters of Lake Howell—perfect for enjoying Florida’s outdoor lifestyle while remaining close to premier amenities and entertainment. Step inside to soaring ceilings and an abundance of natural light that fill the spacious great room, creating an open and airy atmosphere. The gourmet kitchen flows seamlessly into a sunny breakfast nook and overlooks the inviting family room, complete with a cozy wood-burning fireplace—ideal for both everyday living and entertaining. The primary suite serves as a peaceful retreat with relaxing views of the sparkling pool. The ensuite bathroom features an oversized vanity with framed mirror, a garden soaking tub, and a beautifully tiled walk-in shower. Upstairs, an expansive open loft offers versatile living space perfect for a media room, home gym, office, or guest lounge. Two additional generously sized bedrooms and a full bathroom complete the second floor. Step outside to your own private backyard oasis featuring a screened-in pool and ample green space beyond—perfect for holiday cookouts, family gatherings, or simply relaxing outdoors. Conveniently located near premier dining, shopping, medical centers, and recreation, this home is just minutes from Oviedo on the Park, Park Avenue, and Waterford Lakes Town Center. Major employers including Siemens, Lockheed Martin, and UCF are all within easy reach, along with quick access to SR-417 for effortless trips to Orlando’s attractions, beaches, and beyond. Zoned for highly rated Seminole County schools: Red Bug Elementary, Tuscawilla Middle, and Lake Howell High School.

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

Listing Agent: Shirley Jones (407-719-9180)

Remarks: This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. The water heater was replaced in 2025, the AC was replaced in late 2021, and the roof in 2017. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.

Listing is courtesy of: MNT INTERNATIONAL (844-668-7589)

Listing Agent: Mostafa Boulhanna (407-536-1484)

Remarks: Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer finishes, and contemporary ambiance that immediately sets the tone for the home. Beyond the entry, the main living spaces unfold into an open-concept kitchen, dining, and living area designed for both everyday comfort and elevated entertaining. The chef’s kitchen is beautifully appointed with custom cabinetry, a Wolf stove, Bosch dishwasher, a premium side-by-side True Residential refrigerator and wine column combination, and a separate under-island beverage refrigerator designed for effortless entertaining. Expansive PGT sliding doors connect the interior spaces seamlessly to the lanai and outdoor retreat, while the Klipsch 5.1 surround sound system, electric fireplace, Anderson windows, ceiling fans, and integrated Elon smart-home system enhance the experience throughout the home. The outdoor living area was designed as a private modern zen-inspired escape, featuring a fully air-conditioned and heated lanai with cedar-lined ceilings, rolled screens, and direct access to the serene backyard retreat complete with a four-person sauna. Thoughtfully integrated technology and upgrades include Jellyfish lighting, Nest cameras, power-over-Ethernet shades, leak protection system, water filtration systems including Aqua Sauna Water Filter and Kohler Connect Water Minder, as well as two separate AC units serving each floor independently. The first floor also offers a private guest suite, ideal for visitors or multigenerational living. Upstairs, the second level features a spacious laundry room, two additional en-suite bedrooms, and an impressive primary suite designed as a true retreat. The luxurious primary bathroom showcases a standing shower with digital water controls, dual sinks with custom storage cabinetry, and an expansive custom walk-in closet. Additional highlights throughout the home include engineered wood flooring, electric blinds, and refined designer details at every turn. Crowning the residence is a spacious third-floor bonus area offering endless flexibility for a media room, fitness studio, office, or additional lounge space, all fully air-conditioned for year-round comfort. Combining exceptional craftsmanship, advanced smart-home functionality, and an unbeatable Winter Park location with exceptional proximity to both Park Avenue and Winter Park Village, this extraordinary residence places premier dining, boutique shopping, cafés, entertainment, and everyday conveniences just moments from home while delivering a truly elevated lifestyle experience.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Nick Mckee (407-913-0171)

Remarks: Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in the highly sought after Penn Place neighborhood. One of the few homes fronting the park with beautiful views from upper and lower porches, balconies and windows. This home provides the perfect balance of quiet privacy and convenient access to everything. The heart of the home features white kitchen cabinets, New stainless steel appliances and gas cooktop, overlooking eat-in breakfast nook and family room with gas fireplace & three sets of French doors opening to a bird and butterfly paradise with a huge covered, porch. There is also a dedicated office with built-in's and wet bar. The upstairs can be reached by both Elevator or elegant staircase and houses the owner’s suite with private balcony. It includes a large bathroom with dual sinks + makeup vanity, tub & separate shower, and oversized custom closet. Two additional bedrooms split from the master, as well as upstairs laundry room. Custom built by Maroon Fine Homes and beautifully updated and maintained, the high quality details and finishes can be felt throughout - features include high ceilings, crown molding, plantation shutters, and hardwood floors throughout. New Roof, New interior/exterior paint, acp tankless gas water heater and three covered patios. Fenced/Gated yard with four zone sprinkler system, paver driveway and attached 2 car garage with back alley entry. With its unparalleled location and custom details, 622 Penn Place is a rare opportunity to own in walking distance to downtown. Don’t miss your chance to make this exceptional property your next home!

Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)

Listing Agent: Douglas Addeo (561-251-3408)

Remarks: Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit, and more. Natural sunlight flows throughout the home reflecting off the refinished wood floors creating an inviting and cozy environment. The open kitchen features quartz countertops, glass crafted tile backsplash, custom cabinets, breakfast bar and stainless steel appliances. Feel refreshed and relaxed as you step into the primary suite with barn doors leading into the spa-inspired bathroom, complete with dual vanities and a large walk-in tiled shower. The backyard is fully fenced and the outdoor patio is screened-in and covered. Extra storage space can be used in the outdoor shed or the one car attached garage. No HOA and not in a flood zone. The property’s exceptional location offers close proximity to I-4 East and West, upscale award-winning Winter Park restaurants and boutiques, Winter Park Village, WP9 Golf Course, Park Ave, and the upcoming state-of-the-art Lifetime Fitness center which features over 85,000 SqFt and 5 acres of the best that wellness amenities have to offer. Nearby EV charging stations located within 2 miles away make sustainable living effortless. Rare opportunity to settle into or invest in a peaceful updated retreat located in the highly desirable and vibrant community of Winter Park.

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

Listing Agent: Michael Domi (407-212-8841)

Remarks: Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)

Listing Agent: Elizabeth Nordquist (407-694-0996)

Remarks: Location. Design. Lifestyle. Newly built in 2025 by Nautilus Homes and lightly lived in, this exceptional custom residence offers the perfect blend of modern construction, elevated design, and an unbeatable Winter Park location. Ideally positioned between Orlando Avenue and Orange Avenue, just moments from Park Avenue, Mead Botanical Garden, acclaimed dining, boutique shopping, and cultural attractions, this is a rare opportunity to enjoy the very best of Winter Park living. Framed by mature landscaping and featuring dual front porch seating areas, the home encompasses over 3,000 square feet of thoughtfully designed living space and more than 4,000 square feet under roof, with four bedrooms, four full baths, and a dedicated first-floor office. More than $100,000 in post-construction enhancements further elevate the home's style, functionality, and everyday comfort. Inside, wide-plank Crème Brûlée hardwood flooring flows throughout, creating a warm and sophisticated backdrop. Custom closet systems in every bedroom, plantation shutters, and designer Arhaus lighting add a refined touch throughout the home. The spacious great room is anchored by a custom-built entertainment wall featuring a sleek vapor fireplace and integrated LED accent lighting, creating a striking focal point for both relaxing and entertaining. The chef’s kitchen seamlessly combines beauty and function with ceiling-height custom cabinetry, a handcrafted wood range hood, premium finishes, and an elegant butler’s pantry accented by designer Kit Kat tile. A built-in wine and coffee bar enhances the home's entertaining appeal while providing everyday convenience. Designed for flexibility and privacy, the floor plan offers a first-floor guest suite and office, while three additional en-suite bedrooms are located upstairs. The luxurious primary suite serves as a private retreat, featuring a spa-inspired bath with a soaking tub, oversized nine-foot walk-in shower, dual shower systems, frameless glass enclosure, and linear drain detailing. Outdoor spaces have been thoughtfully curated for effortless living. Professional landscaping, mature trees, full gutter systems, artificial turf, and decorative rock accents create a private, low-maintenance backyard sanctuary. The oversized 24' x 22' garage is equally impressive, featuring custom cabinetry, a dedicated tool wall, overhead storage systems, and Shark Coating epoxy flooring. Zoned for highly regarded Audubon Park K-8 and Winter Park High School, and located just minutes from Park Avenue and Winter Park’s vibrant dining and entertainment district, this move-in-ready residence delivers luxury, convenience, and timeless design in one of Central Florida’s most sought-after neighborhoods. This property may be under audio/visual surveillance.

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Frank Benevento (407-492-5153)