Winter Park Real Estate for Sale by Neighborhood

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ALOMA real estate for sale ALOMA TRAILS real estate for sale
BROOKSHIRE HEIGHTS real estate for sale BROOKSHIRE HEIGHTS 1ST ADD real estate for sale
CAPENS ADD real estate for sale CASA ALOMA real estate for sale
CEDARWOOD VILLAGE 1 real estate for sale CHARMONT real estate for sale
CHATEAUX DU LAC real estate for sale CLOISTER GROVE SUB real estate for sale
CLOISTERS CONDO real estate for sale COLONIES real estate for sale
COMSTOCK PARK real estate for sale CORONATION ADD real estate for sale
DIXIE TERRACE real estate for sale DUBSDREAD HEIGHTS real estate for sale
EASTBROOK SUB UNIT 05 real estate for sale EASTBROOK SUB UNIT 13 real estate for sale
EASTBROOK SUB UNIT 14 real estate for sale EASTGATE SUB real estate for sale
ELLNO WILLO real estate for sale ENCLAVE AT HAWKS CREST real estate for sale
FONTAINEBLEAU real estate for sale FOREST HILLS real estate for sale
FOUR SEASONS CONDO real estate for sale GEORGETOWN ESTATES real estate for sale
GLENCOE SUB real estate for sale GOLDENROD VILLAS CONDO real estate for sale
GOLFSIDE SEC 03 real estate for sale GOLFSIDE VILLAS CONDO real estate for sale
GOLFVIEW HEIGHTS real estate for sale GRAYSON SQUARE real estate for sale
GREEN OAKS REP real estate for sale GREEN OAKS REP 02 real estate for sale
HAWKS CREST real estate for sale J KRONENBERGER SUB real estate for sale
KAROLINA ON KILLARNEY real estate for sale KENILWORTH SHORES SEC 04 real estate for sale
KENILWORTH SHORES SEC 06 real estate for sale KENILWORTH SHORES SEC 07 real estate for sale
KILLARNEY CIRCLE real estate for sale KILLARNEY ESTATES real estate for sale
LAKE FLORENCE PRESERVE real estate for sale LAKE FOREST PARK real estate for sale
LAKE KNOWLES TERRACE real estate for sale LAKESIDE ESTATES real estate for sale
LAKESIDE MANOR APTS CONDO real estate for sale LAKEVIEW TERRACE real estate for sale
LANCELOT/WINTER PARK real estate for sale LANDINGS AT HAWKS CREST real estate for sale
LAWNDALE real estate for sale LAZY OAKS CONDO real estate for sale
LORDS SUB real estate for sale LOST CREEK real estate for sale
MAITLAND SHORES real estate for sale MAITLAND SHORES FIRST ADD real estate for sale
MEADOWS AT HAWKS CREST real estate for sale MONDRIAN/WINDER PARK TWNHMS real estate for sale
ORANGE TERRACE real estate for sale ORWIN MANOR WESTMINSTER SEC real estate for sale
PARKLANDO real estate for sale PARKVIEW VILLAGE real estate for sale
PHILLIPS CIRCLE REP real estate for sale ROBERT DHU MACDONALD PARK real estate for sale
STRATFORD A WINTER PARK CONDO real estate for sale SYLVAN HEIGHTS real estate for sale
SYLVAN LAKE SHORES real estate for sale TANGLEWOOD SEC 3 REP real estate for sale
TEMPLE TERRACE real estate for sale THE ENCLAVE WINTER PARK real estate for sale
WATERFALL COVE real estate for sale WHISPERWOOD CONDO real estate for sale
WINTER PARK PINES real estate for sale WINTER PARK VILLAGE real estate for sale
WRENWOOD CONDO real estate for sale

Newest Real Estate in Winter Park by Neighborhood

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  • 688 BRECHIN DR, WINTER PARK, FL - MLS# O6403080

    KENILWORTH SHORES SEC 04 - O6403080 - 688 BRECHIN DR, WINTER PARK, FL 32792
    Just Added on 04/30/2026 2:51PM

    $724,900 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Discover one of the most sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally located within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin Park, and chef-driven local restaurants in Audubon Park. Kenilworth Shores isn't just a location, it's a community, and this 4-bedroom, 2-bath Florida Ranch is your family's invitation to join. At nearly 1,600 square feet, this home provides charm, function, and thoughtful design with upgraded LVP flooring flowing throughout the easy layout. Old-world brick detailing gives the exterior genuine curb appeal, while a thoughtfully renovated interior delivers a ready to move-in home. A gorgeous brick fireplace anchors an open kitchen, family & dining room combination, with loads of natural light and function to entertain in style. The kitchen is outfitted with white shaker custom cabinetry, granite counters, a soft glass tile backsplash, stainless steel appliances, and glass pendant lighting over bar seating. A desirable split-bedroom plan provides privacy for guests, while the primary suite opens to the backyard and includes a completely renovated master bathroom. The flexible fourth bedroom is outfitted with a custom-designed built-in Murphy bed system with flanking closets and storage. Sitting off the primary living area, this bedroom provides options to fit flexible needs: home office, guest room, playroom, or secondary family space. Step into the back yard and experience your personal Florida oasis with a screened covered porch and grand Florida pool to cool off in the heat of summer. The surrounding, spacious yard is adorned with artificial turf (beautiful, durable, and effortlessly low-maintenance) complete with a putting green that will make this yard the destination for every playdate, summer BBQ, or birthday party. Completed Upgrades Include: New Roof (2021), Resurfaced pool (2021), New Irrigation & Well (2022), New Wood Fence (2023), New Dishwasher and Built-in Microwave (2023), HVAC (late 2023), New Washer & Dryer (2024), New Pool Pump Motor (2025). The best part of this special neighborhood is the connected community. Zoned for Brookshire Elementary, Glenridge Middle & WP High, some of the best Orange County Schools. Cady Way Park is steps away with a community pool, baseball fields, a playground, pickleball courts, and miles of walking and bike trails. This location checks all the boxes, schedule your private showing today.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 1550 NORFOLK AVE, WINTER PARK, FL - MLS# O6402927

    ORWIN MANOR STRATFORD SEC - O6402927 - 1550 NORFOLK AVE, WINTER PARK, FL 32789
    Just Added on 04/30/2026 10:52AM

    $725,000 | Single Family Home | 3 beds | 2.0 baths | 3 gar

    Welcome to this exceptional residence at 1550 Norfolk Ave, perfectly positioned in the highly sought-after Orwin Manor neighborhood of Winter Park. Set on a spacious corner lot, this beautifully maintained home offers 3 bedrooms and a rare 3-car garage, combining comfort, functionality, and timeless appeal. Inside, you’ll find rich hardwood floors, plantation shutters, and an extra-large family room ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry with convenient pull-out drawers, balancing style and efficiency. This home also embraces modern sustainability solar panels power the entire property, providing clean energy year-round and the capability to continue powering the home for approximately 24 hours in the event of a power outage. Peace of mind comes from thoughtful updates, including new windows (2022), new garage doors (2023), a roof replaced in (2014), and new insulation installed in (2025) to enhance energy efficiency. Step outside to your private retreat a fully fenced backyard with a sparkling pool and spa, where the spa is heated using natural gas, offering comfort and relaxation at any time of year. An outstanding opportunity to own a well-appointed, energy-efficient home in one of Winter Park’s most desirable neighborhoods.

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 1611 CHESTNUT AVE, WINTER PARK, FL - MLS# O6402502

    LAKE KNOWLES TERRACE - O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789
    Just Added on 04/30/2026 12:10AM

    $1,100,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar

    Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood with the bones of new construction. Gutted to the studs and rebuilt with intention, every system is new — electrical, AC, roof, ductwork, drywall — and every finish is elevated, from the designer tile and quartz countertops to the gleaming floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings.

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 1077 MINNESOTA AVE, WINTER PARK, FL - MLS# O6403223

    NA - O6403223 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789
    1 Day on yellowkey

    $1,625,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar

    Built in 2025 by Nautilus Homes and lightly lived in, this custom Winter Park residence offers a rare blend of new construction quality, thoughtful owner upgrades, and a highly desirable location between Orlando Avenue and Orange Avenue, just minutes from Park Avenue shopping, dining, and cultural attractions. Set behind mature landscaping and two inviting front porch seating areas, the home delivers over 3,000 square feet of living space, more than 4,000 square feet under roof, 4 bedrooms, 4 full baths, and a dedicated main-level office with a custom door package. More than $100,000 in post-build owner upgrades further enhance the home’s design, function, and everyday livability. Inside, Crème Brûlée wide-plank wood flooring runs throughout the home. Every bedroom features custom-built closets, while Arhaus lighting fixtures and plantation shutters add a refined finish across the interior. The main living area centers around a custom built-in entertainment wall with a vapor fireplace and integrated LED shelf lighting. The chef’s kitchen features ceiling-height custom cabinetry, a handcrafted wood range hood, and an adjoining butler’s pantry finished with Kit-Kat tile between the kitchen and formal dining room. A built-in wine and coffee bar sits just off the main living space, creating an easy flow for entertaining. The layout is both flexible and practical, with one en-suite bedroom and the dedicated office on the main level, plus three additional en-suite bedrooms upstairs. The primary suite includes a spa-inspired bath with soaking tub, oversized 9-foot walk-in shower, dual sprayers, frameless glass enclosure, and linear drainage. Outdoor spaces were designed for easy living, with professional front-yard landscaping, mature tree work, full gutters, and a private low-maintenance backyard retreat featuring artificial turf and decorative rock. The oversized 24x22 two-car garage has been fully built out with custom cabinetry, a full tool wall, overhead storage, and Shark Coating epoxy flooring. Zoned for Audubon Park K-8 and Winter Park High School, and located near Park Avenue, Mead Botanical Garden, and the Winter Park dining corridor. Showings by appointment. Buyer to verify school zoning, room dimensions, square footage and all property details.

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    Listing is courtesy of: SHAHRAM SONDI + CO.

  • 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL - MLS# O6402984

    MORSELAND SUB - O6402984 - 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789
    1 Day on yellowkey

    $1,185,999 | Apartment | 6 beds

    Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.

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    Listing is courtesy of: COMPASS FLORIDA LLC

  • 5450 PEACO PL, WINTER PARK, FL - MLS# O6403088

    GRAND PINES - O6403088 - 5450 PEACO PL, WINTER PARK, FL 32792
    1 Day on yellowkey

    $280,000 | Half Duplex | 3 beds | 2.0 baths | 2 gar

    Welcome Home! Winter Park property for under $300k! As you step up to this property you notice the fresh paint and the fresh mulch. Step into the home and you see consistent floor tile throughout the home as well as freshly painted walls. Take a step to the left and you see the large kitchen space to be able to freely move around as you cook. The primary bedroom is located in the rear and has access to the back yard. Bedroom sizes are a fair size. New garage door opener just installed This home is great for investors and also a GREAT WINTER PARK starter home. This property is close to highways, shopping and more! Welcome Home!

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    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY

  • 2707 TIERRA CIR, WINTER PARK, FL - MLS# O6398979

    CASA ALOMA - O6398979 - 2707 TIERRA CIR, WINTER PARK, FL 32792
    1 Day on yellowkey

    $495,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Tucked into one of Winter Park's most convenient pockets, this thoughtfully updated residence offers a seamless blend of comfort, style, and convenience. With three bedrooms and two bathrooms, the layout provides flexibility for a variety of living arrangements while maintaining a warm, welcoming feel throughout. The updated kitchen is both functional and inviting, featuring a gas stove and a dedicated coffee bar that adds a touch of everyday luxury. Living spaces flow effortlessly to the outdoors, where a large screened-in porch invites year-round enjoyment, complemented by a paved patio with a firepit that's ideal for relaxed evenings. The yard is perfectly sized for easy maintenance and enjoyment, complete with built-in swings that add a unique and playful detail. Positioned in a highly desirable location, this home is just moments from Interlachen Country Club, Full Sail University, and AdventHealth Winter Park, with everyday essentials like Costco nearby. Enjoy quick access to the shopping and dining of Park Avenue, just 15 minutes away. A rare opportunity to enjoy a move-in-ready home in one of Winter Park’s most convenient and connected areas. Recent updates include a 2021 roof, offering peace of mind and move-in ready convenience.

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    Listing is courtesy of: RE/MAX 200 REALTY

  • 3053 GEORGE MASON AVE #8A, WINTER PARK, FL - MLS# O6402957

    COLONIES - O6402957 - 3053 GEORGE MASON AVE #8A, WINTER PARK, FL 32792
    1 Day on yellowkey

    $75,000 | Condo | 1 beds | 1.0 baths

    One or more photo(s) has been virtually staged. Welcome to this charming 1 Bedroom/1 Bath condo located on the first floor featuring a spacious living room with a cozy dinette area and a functional galley kitchen. The kitchen features shaker cabinets, large stainless-steel sink and stackable washer/dryer, all appliances convey. Sliding glass doors open to a covered patio overlooking a peaceful courtyard-style backyard—perfect for relaxing or outdoor dining. The community offers a refreshing pool, clubhouse one assigned parking space, and ample guest parking. Sold As-Is, presenting a great opportunity for an investor or owner-occupant. Conveniently located just minutes from Full Sail University, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. Zoned for highly rated Winter Park schools. Within walking distance to shopping and dining.

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    Listing is courtesy of: COLDWELL BANKER REALTY

  • 420 OHIO ST, WINTER PARK, FL - MLS# O6399541

    KAROLINA ON KILLARNEY - O6399541 - 420 OHIO ST, WINTER PARK, FL 32789
    2 Days on yellowkey

    $1,360,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar

    Pre-Construction. To be built. On a prominent corner lot in the evolving Killarney neighborhood, this offering presents a rare chance to create a custom residence in the heart of the 32789 zip code. Set among a mix of established homes and new construction, the setting reflects the ongoing transformation of the area while remaining close to the amenities that define Winter Park living. The proposed plan features over 3,700 square feet of living space with a layout designed for both everyday comfort and entertaining. Current plans accommodate five bedrooms, five and a half baths, and a dedicated office, with flexibility to tailor the design or incorporate an accessory dwelling unit (ADU) depending on buyer preferences and final approvals. The building process is structured to allow selections to be made through a private showroom experience, offering an opportunity to personalize finishes and design elements throughout. Inside, the home is envisioned with clean architectural lines and a focus on natural light. The kitchen is designed as a central gathering space with quartz countertops, custom cabinetry, and an oversized. The primary suite is planned as a private retreat with a spacious bath, dual vanities, a glass-enclosed shower, and curated tile finishes. Flooring is specified as wide-plank luxury vinyl throughout the main areas, combining durability with a warm, cohesive aesthetic. The lot size and configuration provide the option to design an outdoor living environment, including space for a future pool, subject to final plans. The location offers convenient access to Park Avenue, the Winter Park Chain of Lakes, I-4, and nearby medical facilities, with dining options such as Hillstone within close proximity. Offered at a starting price of $1,360,000, this to-be-built opportunity combines location, flexibility, and a structured customization process for buyers seeking new construction in a well-located, established area. Buyers should verify all specifications, plans, pricing, and timelines with the builder.

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    Listing is courtesy of: COMPASS FLORIDA LLC

  • 7917 PLEASANT PINE CIR, WINTER PARK, FL - MLS# O6402666

    ENCLAVE AT ALOMA - O6402666 - 7917 PLEASANT PINE CIR, WINTER PARK, FL 32792
    2 Days on yellowkey

    $599,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Under contract-accepting backup offers. Professional photos coming! Come see this BEAUTIFULLY MAINTAINED, EMACULATE WINTER PARK HOME ON A QUIET STREET IN A SECLUDED GATED ENCLAVE OF HOMES! This is a one owner home and has been maintained in pristine, like new condition. Located in a small gated community moments from Trinity Preparatory School, Park Avenue Shoppes and Rollins College. When entering this home you are greeted by a beautiful entry way and foyer. This single story four bedroom home has a spectacular open floor plan with natural lighting galore and beautiful wood look tile throughout the entire home, stainless steel appliances, stunning granite countertops, a large island in the kitchen, custom extended cabinetry perfect for the cooking enthusiast and great for entertaining, master bedroom extended with sitting room, beautiful back lanai and a large backyard that is beautifully designed! When entering the back lanai you are greeted by a serene, private, landscaped Oasis. The landscaping and location of the home within the community creates an amazingly private, secluded and peaceful backyard with just the occasional sounds of birds chirping. This home is in an amazing location! You will be located about one mile to Trinity Preparatory School, Publix, Restaurants and more shopping as well as the 417, you are just a few miles from Rollins College, Park Avenue/Downtown Winter Park, Advent Health Winter Park, The Country Club at Deer Run, Interlachen Country Club, St. Luke’s School and Masters Academy just to name a few and more shopping & restaurants galore! This is a prime location for all conveniences and with a Winter Park Address! This home has some of the latest energy qualities such as double pane insulated windows and has been constantly covered under a termite bond. Come visit this Warm, Friendly Neighborhood because you are sure to want to stay forever! Updates in the last 1 to 2 years include: Painting of complete exterior and interior, All kitchen appliances replaced, flooring replaced, bathrooms updated, backsplash in kitchen added, tile on front porch and back lanai, soft close on all kitchen cabinets, extension of kitchen cabinets & countertops into dining room. HVAC system has been and is serviced constantly since home was built.

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    Listing is courtesy of: LORI GILMORE REAL ESTATE LLC

  • 1900 WINTER PARK RD, WINTER PARK, FL - MLS# O6402566

    CHARMONT - O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789
    3 Days on yellowkey

    $941,000 | Single Family Home | 4 beds | 2.0 baths | 1 gar

    Positioned in one of Central Florida’s most iconic and sought-after locations, this rare opportunity at 1900 Winter Park Road in Winter Park invites you to create something truly exceptional. Set on a spacious homesite, this property offers the flexibility to renovate, expand, or build your custom dream home from the ground up. Whether you envision a modern architectural masterpiece or a timeless estate, this is your canvas to bring that vision to life. What makes this opportunity even more compelling is the location. Just minutes from the charm and sophistication of Park Avenue, you’ll find yourself surrounded by brick-lined streets, boutique shopping, fine dining, and vibrant cultural experiences. Spend your mornings enjoying coffee at local cafés, your afternoons exploring art galleries, and your evenings dining under the lights of one of Central Florida’s most beloved destinations. Living in Winter Park is more than owning a home—it’s embracing a lifestyle. From the scenic beauty of the Winter Park Chain of Lakes, to the historic elegance of Rollins College, this area blends natural beauty, culture, and community in a way few places can. Residents enjoy: Boat tours and waterfront living along the chain of lakes Weekly farmers markets and local events A thriving arts scene including museums, galleries, and theaters Top-rated dining and boutique retail experiences A true sense of community with timeless charm This is more than just land. This is where vision meets opportunity. This is where your next chapter begins. Build the life you’ve been dreaming of—in the heart of Winter Park

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    Listing is courtesy of: RE/MAX ASSURED

  • 1725 CAROLLEE LN, WINTER PARK, FL - MLS# O6402656

    GREEN TERRACE - O6402656 - 1725 CAROLLEE LN, WINTER PARK, FL 32789
    3 Days on yellowkey

    $1,015,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias, gardenias, and more. Just minutes from Park Avenue’s beloved restaurants, cafés, and boutiques, as well as the scenic Winter Park Chain of Lakes, this home offers both character and convenience. With easy access to I-4, SR-417, Orlando International Airport, and top-rated schools, it is a wonderful opportunity to enjoy classic Winter Park charm in a beautifully cared-for home.

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 446 MELROSE AVE, WINTER PARK, FL - MLS# O6402113

    VIRGINIA HEIGHTS REP - O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789
    3 Days on yellowkey

    $1,695,000 | Single Family Home | 4 beds | 2.0 baths

    A distinctive offering where design, location, and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance, and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, perfect for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with both durability and efficiency in mind. Major improvements include a commercial- grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century inspired landscaping designed for both beauty and ease of maintenance. Palms, agave, and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances both ambiance and function. Just moments from the desirable Park Avenue, this architecturally significant modern residence is ideally positioned in one of Winter Park’s most sought-after neighborhoods, near Lake Virginia, Rollins College, and the Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north- facing orientation and beautiful natural light throughout the day.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 1660 WALNUT AVE, WINTER PARK, FL - MLS# O6395277

    LAKE KNOWLES TERRACE - O6395277 - 1660 WALNUT AVE, WINTER PARK, FL 32789
    3 Days on yellowkey

    $1,650,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar

    Introducing a standout new construction in Winter Park’s coveted Tree Streets! As you arrive the home’s modern façade is complemented by a charming front porch, creating a warm yet striking introduction that feels both inviting and intentional. Inside, the home unfolds with a highly functional floor plan designed to enhance everyday living while still accommodating entertaining with ease. Clean lines, curated finishes, and natural light define the main living spaces, where the kitchen, dining, and living areas flow seamlessly together. The kitchen serves as a true focal point, featuring Calacatta Gioia quartz countertops, custom cabinetry with ample storage, a paneled refrigerator, and a full suite of Thermador appliances. The space transitions naturally into the dining area and living room, where a built-in wet bar with a wine fridge adds an elevated layer of functionality and style. The living room is designed to feel both open and connected, anchored by expansive pocketing sliders that completely open to the outdoor living area. The primary suite is thoughtfully positioned on the main level, serving as a calming retreat, featuring a spa-inspired bathroom with dual vanities, a freestanding soaking tub, and a spacious walk-in shower. Upstairs, three additional bedrooms are generously sized and well laid out, providing flexibility for guests, family, or a secondary living setup. The outdoor living experience is equally impressive, centered around a large covered lanai that offers ample space for al fresco dining and lounging. The spacious pool area is designed to complement the home’s indoor-outdoor lifestyle, creating a private setting that feels both relaxed and elevated. Beyond the home itself, the location is what truly sets this home apart. Situated in the heart of the Tree Streets, you are just a short walk to Phelps Park and the YMCA, minutes from Interlachen Country Club, and only a quick golf cart ride to the shops, dining, and energy of Park Avenue. Homes of this caliber and location are few and far between, making this a standout opportunity in today’s market.

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    Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC

  • 7484 CANFORD CT #8, WINTER PARK, FL - MLS# O6402492

    WHISPERWOOD CONDO - O6402492 - 7484 CANFORD CT #8, WINTER PARK, FL 32792
    3 Days on yellowkey

    $250,000 | Condo | 3 beds | 2.5 baths | 2 car

    This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer stainless steel appliances, and a closet pantry. There is a separate dining room that opens onto a very private brick paver patio with a new privacy fence. This unique condo features a flexible layout, an inside utility, and includes the washer & dryer. Modern-design porcelain tile flooring. The home has a large screen porch, which is considered by many in Florida, to be extra living space. There is also a front courtyard that is perfect for a raised bed garden or ???. Highly desired Winter Park schools. A 2-car carport with an ample lockable storage closet. New roof in 2020 and an updated electric system. The complex has a private community pool

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    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO

  • 639 SAINT JOHNS CT #639, WINTER PARK, FL - MLS# O6402025

    WINTER PARK VILLAS - O6402025 - 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792
    4 Days on yellowkey

    $199,900 | Condo | 2 beds | 2.0 baths

    Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.

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    Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC

  • 2009 SHADYHILL TER, WINTER PARK, FL - MLS# O6402256

    AUTUMN GLEN PH 2 - O6402256 - 2009 SHADYHILL TER, WINTER PARK, FL 32792
    4 Days on yellowkey

    $535,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Beautifully updated 3 bedroom, 2 bath home with a sparkling in-ground pool, located in highly sought-after Winter Park. This move-in ready property features fully upgraded kitchen with features like quartz countertops and soft close cabinets, updated bathrooms, new stone composite plank flooring, and double pane windows that bring in abundant natural light. Major system updates include a new roof (2022) and full house re-pipe (2025). Freshly painted, this home offers both style and peace of mind. Escape to your own backyard Oasis with a beautiful pool surrounded by lush landscaping and a covered patio for entertaining friends and family. A true turnkey opportunity ready to impress the pickiest buyer.

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    Listing is courtesy of: HOUSE HUNTING IN FLORIDA LLC

  • 3440 ALLSTON LN, WINTER PARK, FL - MLS# O6401731

    VILLAS OF CASSELBERRY PH 4 - O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792
    4 Days on yellowkey

    $420,000 | Single Family Home | 3 beds | 2.5 baths | 1 gar

    Exceptional Single-Family Home in Winter Park, FL This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC system (2023), providing peace of mind for years to come. Enjoy Florida living at its finest on the private screened patio - perfect for relaxing or entertaining. Ideally situated 25 minutes from Downtown Orlando, 30 min from OIA, and 40 min from world-class attractions, this home is also just 6 minutes from Full Sail University, 12 minutes from the prominent Rollins College, and 19 minutes from UCF - making it an ideal choice for families and investors alike. A true must-see - schedule your showing today.

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    Listing is courtesy of: EXIT GLOBAL REALTY

  • 1832 E CHERYL DR, WINTER PARK, FL - MLS# O6402209

    CAROLYN ESTATES - O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792
    6 Days on yellowkey

    $439,995 Increased | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Welcome to Carolyn Estates in highly desirable Winter Park—a charming enclave of just 63 homes ideally located near Lake Howell High School. This beautifully renovated residence offers a truly unique floor plan—the only one of its kind in the community. Featuring 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, this home blends comfort with functionality. Enjoy cozy evenings by the wood-burning fireplace or unwind in the screened-in patio, perfect for relaxing or entertaining. Step inside to an inviting open-concept layout highlighted by soaring ceilings and abundant natural light. Renovated in April 2026, this home showcases numerous upgrades, including fresh interior and exterior paint, new sod and lush landscaping, a fully remodeled second bathroom, new convection range and microwave, updated interior door hardware, a complete electrical update, and new lighting and ceiling fans throughout. Additional major improvements include newer windows and hot water heater (2019) and full home replumbing (2022), providing added peace of mind. Seller will provide a $10,000 credit towards a new roof with Full Price Offer. This move-in-ready home combines modern updates with a prime location—schedule your private showing today!

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    Listing is courtesy of: SELECTIVE REALTY GROUP LLC

  • 1287 VERDANT GLADE PL, WINTER PARK, FL - MLS# O6400331

    MEADOWS AT HAWKS CREST - O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792
    6 Days on yellowkey

    $850,000 | Single Family Home | 5 beds | 3.5 baths | 2 gar

    **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 5 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both comfortable living and easy entertaining. Inside, the home feels bright, expansive, and well connected, with generous living areas that flow naturally from one space to the next. The open design creates an inviting setting for everyday routines, gatherings, and holiday hosting, while the separate office adds flexibility for working from home, studying, or creating a quiet retreat. With two primary bedroom suites, a large game room, and an additional loft, there is plenty of space to accommodate guests, a growing household, or changing lifestyle needs. The home also features thoughtful upgrades that elevate both style and function. A gourmet kitchen serves as the heart of the home, complete with quartz countertops, 42-inch cabinetry, and the kind of workspace and storage today’s buyers appreciate. Eight-foot interior doors add to the sense of scale throughout, while details such as a pocket door in the bathroom enhance convenience and flow. Large sliding glass doors open wide to create a seamless connection between the indoor living spaces and the outdoor entertaining area. Step outside to an oversized screened and covered patio that extends the living space and creates a relaxing place to enjoy morning coffee, outdoor dining, or quiet evenings at home. Beyond the patio, the private yard offers even more appeal, with no rear neighbors behind the home for added privacy and a more open feel. The rear eastern exposure welcomes beautiful morning sun, making the backyard setting especially enjoyable at the start of the day. Located in Winter Park, the home benefits from a highly desirable area known for its established residential feel, convenient access to shopping and dining, and close proximity to parks, schools, and major roadways. The neighborhood adds to the home’s appeal by offering a blend of comfort, accessibility, and the everyday convenience that makes Winter Park such a sought-after place to live. With its flexible two-story layout, dual primary suites, game room, loft, gourmet kitchen, oversized patio, and private backyard setting, 1287 Verdant Glade Place delivers the space, upgrades, and lifestyle features buyers are looking for.

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    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS

  • 1822 YORKSHIRE DR, WINTER PARK, FL - MLS# O6401364

    PARK MANOR - O6401364 - 1822 YORKSHIRE DR, WINTER PARK, FL 32792
    6 Days on yellowkey

    $624,000 | Single Family Home | 3 beds | 3.0 baths | 1 car

    One or more photo(s) has been virtually staged. 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.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 363 N PHELPS AVE, WINTER PARK, FL - MLS# O6401811

    SYLVAN PARK - O6401811 - 363 N PHELPS AVE, WINTER PARK, FL 32789
    7 Days on yellowkey

    $1,249,000 | Single Family Home | 4 beds | 3.0 baths

    This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate the interior space, but they are also impact-resistant, energy-efficient, noise-reducing, and offer UV protection. The interior renovation was designed with minimal barriers between living areas, creating open, fluid spaces that enhance day-to-day living. The bedroom and bathroom layout is ideal, offering maximum privacy: two large bedrooms share one full bathroom on one side of the house, another bedroom with an en-suite bathroom is at the center, and the primary bedroom and bathroom are on the other side. Wood or natural stone flooring, extensive millwork, vaulted ceilings, new paint, updated lighting fixtures, and new fans enhance the spaces throughout. The kitchen was renovated to include an oversized, under-mount farmhouse sink, commercial-grade faucet, new LED lighting, and quartz countertops with a waterfall edge. The primary suite was updated by a former owner but was renovated by the current owner to add a second walk-in closet with custom organization. All bathrooms received light renovations, ranging from hardware and paint to new fixtures or vanities and countertops. In addition to the visually appealing renovations, the roof was replaced in 2019 and the house was re-plumbed in 2020. The outdoor improvements may be the most valued, as they created endless opportunities for outdoor living and entertaining on the newly constructed deck and enhanced landscape. All of the outdoor living benefits Florida provides are available here. A natural gas line was brought to the house as part of the renovation, allowing for easy future modifications such as a tankless gas-fueled water heater or gas-fueled outdoor grill. Located just one and a half miles from the notable retail stores and restaurants of Park Avenue and within a well-graded public school zone, there is nothing you won’t love about this home or its location.

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    Listing is courtesy of: CREEGAN GROUP

  • 2111 MALLARD CIR, WINTER PARK, FL - MLS# O6401350

    QUAIL HOLLOW - O6401350 - 2111 MALLARD CIR, WINTER PARK, FL 32789
    7 Days on yellowkey

    $1,350,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Tucked away on a quiet circle in one of Winter Park's most sought-after neighborhoods, this distinctive pool home offers a rare opportunity. Set on an approximately .26-acre lot, the home features striking architectural lines, soaring wood ceilings with exposed beams, polished concrete flooring, and an abundance of natural light throughout. This is the only home currently for sale in Quail Hollow. Access to top rated schools. The exterior has been comprehensively updated: both the metal and flat roof sections (2022) and dual A/C units (2022) are already behind you, along with fresh interior and exterior paint, refinished ceilings, and new carpet. The backyard is a genuine retreat — the pool deck and fencing were both redone in 2026 — with a fully fenced yard and expansive deck ready for patio furniture, a barbecue, and effortless entertaining. Inside, a flexible and spacious layout offers room to put your own stamp on a truly special property. Practical upgrades round out the package: a Level 2 EV charger in the garage, a second Level 2 EV circuit wired to the driveway, fiber optic internet connectivity, and a recent refrigerator and dishwasher replacement. Conveniently located near Winter Park's best shopping, dining, parks, and major roadways, this home combines an unbeatable location with a strong foundation of recent improvements — and real upside for the buyer ready to make it their own.

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    Listing is courtesy of: BREC PROPERTIES INC

  • 7761 FOX KNOLL PL, WINTER PARK, FL - MLS# O6401159

    BRIDGEWATER - O6401159 - 7761 FOX KNOLL PL, WINTER PARK, FL 32792
    7 Days on yellowkey

    $425,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Fantastic, move-in ready 3 Bedroom, 2 Full-Bath home in Winter Park. Situated in the sought-after Bridgewater community, you'll enjoy tranquil surroundings while being close to practically everything. A newer roof (2022), beautifully updated bathrooms, modern fixtures, newer paver-patio with drainage system, an ideal floor plan, and a 2-car garage are just some of the reasons to love this home. Enter to a bright and welcoming foyer. Eye-catching wood floors anchor the open Living & Dining spaces. Kitchen features stainless appliances, pantry, and breakfast bar. Bonus space adjacent to kitchen provides extra room to entertain, watch TV, or set up an office area. Primary bedroom is split from guest bedrooms and offers ensuite bath with stunning walk-in shower (renovated March 2026) and dual sinks. Hall offers access to guest bath w/ tub and 2 guest bedrooms. Screened porch is perfect for relaxing and overlooks scenic backyard with gorgeous patio and landscaping. Entertain guests with a backyard cookout or just enjoy nature. Zoned for desirable Lake Howell HS within the Seminole County Public School district. Enjoy plenty of nearby shopping and dining, easy access to major roadways (including SR-417 & SR-436), major hospitals and Central Florida's world-class theme parks. Roughly a 10-minute drive Downtown Winter Park, Baldwin Park and Oviedo; about 20 mins to Orlando or Sanford, and usually under 30 minutes to Orlando Int'l Airport. 1-hour drive to Cocoa Beach, New Smyrna Beach & Daytona Beach. Bike trail with access to Baldwin Park and Oviedo less than 1 mile away. Don't miss out on this home. Be sure to take the 3-D walkthrough tour!

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    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY

  • 1250 S DENNING DR #117, WINTER PARK, FL - MLS# O6401802

    MEAD GARDEN - O6401802 - 1250 S DENNING DR #117, WINTER PARK, FL 32789
    7 Days on yellowkey

    $240,000 | Condo | 2 beds | 1.5 baths

    Remodeled two-bedroom, one-and-one-half-bath residence in the Mead Garden Condominium community. Spanning 908 square feet, this first-floor home features a move-in-ready interior with an open-concept layout, luxury vinyl plank flooring throughout, and in-unit washer and dryer hookups, a rare offering within the building, located in the half bath. The kitchen includes raised-panel cabinetry in a warm wood tone, a mosaic tile backsplash and black appliances, including a refrigerator, range and dishwasher. A curved island with additional storage provides space for casual dining and entertaining. The kitchen opens to the dining area and living room, highlighted by a chandelier and access to a sunroom with sliding glass doors overlooking the community pool and landscaped grounds. The primary bedroom offers natural light from a pool-facing window, a walk-in closet, and an en-suite bath with a walk-in shower featuring white subway tile and a black-and-white mosaic tile floor. The second bedroom provides flexible space for guests or a home office. A half bath includes a pedestal sink, decorative mirror and gold-tone fixtures. Additional features include crown molding, updated plumbing fixtures, new windows and a leaded-glass front entry door. Near Azalea Park, Seven Oaks Park, Mead Botanical Garden and the Orange Avenue district with dining and retail. Close to Rollins College and Park Avenue.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 7120 BROOKSIDE TRL, WINTER PARK, FL - MLS# O6398534

    REPLAT OF LTS 1 2 & 3 BROOKSIDE SUB - O6398534 - 7120 BROOKSIDE TRL, WINTER PARK, FL 32792
    7 Days on yellowkey

    $510,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Under contract-accepting backup offers. SWIM WHENEVER YOU LIKE! Discover a new dimension of living - Sparkling pool awaits you, so come and dip your toes here! Pool party ideas come naturally in this proud-to-show huge fenced-in backyard with lots of entertaining space. Oversized pool deck and large rock patio, plus huge screened in porch, make a great space for Florida living. This rock-solid ranch offers 4 bedrooms and 2 baths set in over 1700+ sf. Great curb appeal with cool rock trimming and freshly landscaped beds. Roomy formal living room greets you as you enter. The primary bedroom is split from the other 3 bedrooms and lies off the living room. This primary suite offers closet space galore. Plus, pretty double vanity, separated from the shower area. Terrific, updated kitchen with neat rustic tile, quartz counters, tile backsplash, stainless appliances, cool single bowl sink and faucet, shiplap wall and closet pantry round out this kitchen space. The family room is a great size, and the kitchen quartz counter/bar also serves as a gathering place flowing into the family room, which features a shiplap TV wall and blind-inside sliders to the screened in porch. The other 3 bedrooms and 2nd bath are off the family room. All are nice sized and the bath with nifty vintage tile, has an access door to outside/pool area. Pretty luxury vinyl plank flooring through living areas. All set in Winter Park on a .23 acre lot and Cul-De-Sac street. Conveniently close to schools, hospital, shopping, Costco and restaurants. Plus, easy access to highway 436 and straight shot to the Orlando International Airport. Don’t wait on this rock-solid ranch in desirable Winter Park...it’s ready for its new owners!

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    Listing is courtesy of: KELLY PRICE & COMPANY LLC

  • 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL - MLS# O6400425

    THE COLONIES - O6400425 - 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL 32792
    7 Days on yellowkey

    $133,000 | Condo | 2 beds | 2.0 baths

    Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the heart of Winter Park! Perfectly positioned for both convenience and lifestyle, this home offers quick access to the 408 Expressway and is just minutes from Downtown Orlando, making daily commutes effortless. Step inside to discover a bright and inviting interior featuring upgraded light fixtures, and an abundance of natural light that enhances the open feel of the space. The thoughtfully designed layout includes generously sized bedrooms and a spacious living area ideal for both relaxing and entertaining. The kitchen is highlighted by a breakfast bar with new granite countertops, creating a functional and stylish focal point. This unit can be sold fully furnished, offering a true turnkey opportunity for homeowners or investors alike. All appliances are included, making for a seamless move-in experience from day one. Location is everything—and this one delivers. Just minutes from Full Sail University, University of Central Florida, and Valencia College, this property is ideally situated for strong rental potential. Plus, enjoy being within easy reach of world-famous attractions like Walt Disney World and the beautiful shores of Cocoa Beach. Whether you’re searching for a primary residence, vacation getaway, or investment property, this Winter Park gem offers the perfect blend of comfort, location, and value.

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    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS

  • 266 W LYMAN AVE, WINTER PARK, FL - MLS# O6399048

    LYMAN AVE VILLAS 1 - O6399048 - 266 W LYMAN AVE, WINTER PARK, FL 32789
    8 Days on yellowkey

    $1,375,000 | Townhouse | 3 beds | 3.0 baths | 2 gar

    ONE BLOCK FROM PARK AVENUE! Welcome to this beautifully renovated townhouse in the heart of Winter Park, offering the perfect blend of luxury and convenience. Whether you're looking for a full-time residence or a lock-and-leave property, this home delivers on every level. Designed with entertaining in mind, the open-concept layout creates a seamless flow from the kitchen into the main living areas. The kitchen features high-end appliances, including a Wolf refrigerator and GE Monogram suite, along with dedicated wine and beverage refrigeration—perfect for hosting or everyday use. A new A/C unit has also been installed, providing added peace of mind. That same attention to entertaining continues outdoors, where a screened-in kitchen, hot tub, and professionally installed turf create a private, low-maintenance space ideal for hosting or relaxing. Inside, the home offers a very spacious primary suite complete with a walk-in closet. A full bathroom is conveniently located downstairs adjacent to the study, which can also function as a third bedroom, adding flexibility to the layout. The two car garage has been upgraded with a durable epoxy-coated floor for a clean, finished look. Located just minutes from Winter Park Village and only a short drive to major roadways including Interstate 4 and State Road 436, this home offers unmatched access to shopping, dining, and downtown. Enjoy the charm of tree-lined streets and historic surroundings, all just steps from the shops and restaurants of Park Avenue. This is a rare opportunity to own a turnkey property in one of Winter Park’s most desirable locations.

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    Listing is courtesy of: REAL BROKER, LLC

  • 2838 WRIGHT AVE, WINTER PARK, FL - MLS# O6399931

    LAKE FOREST PARK - O6399931 - 2838 WRIGHT AVE, WINTER PARK, FL 32789
    8 Days on yellowkey

    $2,399,000 | Single Family Home | 5 beds | 4.5 baths | 2 gar

    Under Construction. A refined expression of new construction by LUIH Homes, this exceptional two-story residence blends timeless architecture with thoughtfully curated modern living in one of Central Florida’s desirable locations. From moment of arrival, the home impresses with beautiful curb appeal, a welcoming presence and a design that balances elegance with everyday comfort. Inside, gorgeous oak floors extend throughout the main living areas, complementing an open-concept floor plan designed for entertaining and relaxed living. The spacious chef’s kitchen serves as the heart of the home, featuring premium quartz countertops, custom cabinetry, a stylish wine bar with beverage refrigerator, and a high-end Thermador appliance package including a gas range, built-in oven and microwave. Overlooking the inviting family room with fireplace, a wall of glass sliders seamlessly connects the interior to the expansive covered lanai, creating an effortless indoor-outdoor lifestyle. The outdoor living space is equally impressive, offering generous room for lounging and dining, along with a fully equipped summer kitchen complete with a 32-inch built-in grill and beverage cooler. Beyond, a sparkling pool and spa are set within a meticulously landscaped, fenced backyard, an ideal setting for entertaining and quiet enjoyment. The first-floor primary suite provides a private retreat, featuring a large walk-in closet with a custom organization system and a spa-inspired bath with dual vanities, a soaking tub and an oversized glass-enclosed shower. A secondary bedroom suite with a private bath is also on the main level, offering flexibility for guests or multi-generational living. A spacious laundry room with Samsung washer and dryer and a well-appointed powder bath complete the first floor. Upstairs, the home continues to impress with three additional bedrooms, including one with an en-suite bath and two connected by a Jack and Jill bath. A dedicated office and a generous gathering or bonus room provide additional space for work, recreation or relaxation. Additional highlights include a two-car garage with epoxy flooring and an electric vehicle charger. Ideally just minutes from boutiques and dining of Park Avenue, as well as the vibrant restaurant scenes of Baldwin Park and Audubon Park, the home also offers convenient access to major roadways, downtown Orlando, leading hospitals, and Orlando International and executive airports. In a highly regarded A-rated public school district (Audubon K-8 and Winter Park High), this residence presents an exceptional opportunity to enjoy luxury, location and lifestyle in harmony.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL - MLS# O6401114

    LANCELOT/WINTER PARK - O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792
    9 Days on yellowkey

    $159,000 | Condo | 2 beds | 2.0 baths

    One or more photo(s) has been virtually staged. Welcome to this inviting 2-bedroom, 2-bathroom condo located in the desirable Lancelot at Winter Park community, offering the perfect blend of comfort and convenience for investors, first-time buyers, or anyone seeking low-maintenance living. This well-appointed unit features an open and airy layout with abundant natural light, seamlessly connecting the living and dining areas to create an ideal space for both relaxing and entertaining. The modern kitchen provides a functional workspace designed for everyday ease. Residents will also enjoy access to a community pool, perfect for unwinding or hosting guests, along with professionally maintained common areas that enhance the overall appeal of the neighborhood. Ideally situated, this condo offers close proximity to UCF and Full Sail University, making it an excellent option for rental potential, as well as convenient access to major shopping centers, dining options, and key highways including I-4 for easy commuting. Whether you're searching for a primary residence, a second home, or a strong investment opportunity, this property delivers exceptional value in a prime location. The property was previously leased at $1,625 per month.

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    Listing is courtesy of: COLDWELL BANKER REALTY

  • 1307 FORMOSA AVE, WINTER PARK, FL - MLS# O6400711

    GOLFVIEW - O6400711 - 1307 FORMOSA AVE, WINTER PARK, FL 32789
    9 Days on yellowkey

    $375,000 | Single Family Home | 2 beds | 1.0 baths | 1 gar

    Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living areas, ceramic tile in the kitchen and dining spaces, and strong natural light from multiple window exposures. The kitchen has been updated with white cabinetry, granite countertops, and a mix of stainless steel and black appliances. The bathroom features updated finishes including a modern vanity and shower. Additional features include a covered front porch, one car attached garage with laundry area, central air conditioning with updated ductwork, and a fenced backyard with deck space suitable for outdoor use. The property is connected to public water and sewer and offers practical living with no HOA. Located near Dubsdread Golf Course and within close proximity to AdventHealth, College Park, and Downtown Orlando. Easy access to I-4 and surrounding roadways supports convenient travel to employment, dining, and retail centers. This property is suitable for a primary residence or investment opportunity in a well located Winter Park area.

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    Listing is courtesy of: LPT REALTY, LLC

  • 2889 ROUEN AVE, WINTER PARK, FL - MLS# L4961275

    WINTER PARK MANOR - L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789
    9 Days on yellowkey

    $399,500 | Single Family Home | 3 beds | 2.0 baths | 1 car

    Welcome to 2889 Rouen Avenue, Fresh exterior paint and move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand New water heater. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. see private remarks and showing time for direct seller’s contact.

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    Listing is courtesy of: HELLOSOLD LLC

  • 106 S INTERLACHEN AVE #518, WINTER PARK, FL - MLS# O6400228

    CLOISTERS CONDO - O6400228 - 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789
    9 Days on yellowkey

    $1,950,000 | Condo | 3 beds | 2.0 baths | 1 car

    Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 1319 BESSMOR RD, WINTER PARK, FL - MLS# O6400395

    WINTER PARK VILLAGE - O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789
    9 Days on yellowkey

    $595,000 | Single Family Home | 3 beds | 2.0 baths

    Under contract-accepting backup offers. 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.

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    Listing is courtesy of: GALLOWAY REAL ESTATE

  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL - MLS# O6399199

    COUNTRY LANE - O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792
    10 Days on yellowkey

    $480,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, wood burning fireplace, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living areas, hallways and one bedroom have engineered hardwood flooring, wet areas have tile flooring and there is carpet in the primary bedroom and bedroom 3. There is also a small nook that would be perfect for a craft area, office or library and it opens to the side courtyard which is fully fenced and a good size storage shed for your convenience. The Kitchen has all standard appliances including refrigerator, range, dishwasher and disposal. There is also a cozy eat in breakfast nook. The Primary Bedroom is located in the back of the home and has a nice walk-in closet with en-suite bath. There are sliding glass doors that open to the huge screened-in patio with optimal views of the lake! You will love to wake up to the gorgeous view! There are two additional Bedrooms and Full Hall Bathroom. Each bedroom has direct access to the screened in porch. This home has a finished two car garage with opener and washer/dryer hookups. Enjoy coffee in your hammock while watching the ski boats inside the screened patio that runs the full rear length of the home, providing the amazing view to the lake and is perfect for entertaining or enjoying an evening cocktail. Close to most major roadways, this home will not last long!

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER VANGUARD EDGE





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