Location: Winter Park
Keyword(s): Glenridge Middle
Keyword(s) Middle School: Glenridge Middle
Do Not Show Listings
2652 ABBEY RD, WINTER PARK, FL 32792
$625,0007 Days on yellowkey MLS ID: O6419026
0 Days Off yellowkey (back on 6/29/2026)
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1938 Built: 1967 Tax: $7,337 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,337
Elementary School: Aloma Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Welcome to 2652 Abbey Road, a beautifully renovated home tucked away on a quiet cul-de-sac in the highly desirable Winter Park Estates community. Situated on a spacious corner lot, this stunning 4-bedroom, 2-bath residence with a dedicated office offers the perfect blend of modern design, functionality, and location. From the moment you step inside, you'll appreciate the open-concept floor plan designed for today's lifestyle. New flooring flows seamlessly throughout the home, complemented by updated interior doors, abundant natural light, and thoughtfully selected finishes. The private office, featuring elegant double glass doors, provides the perfect space for working from home, a playroom, or a flex space to fit your needs. The heart of the home is the completely redesigned kitchen, showcasing beautiful natural-tone soft-close cabinetry, sleek black hardware, premium stainless steel appliances, and luxurious Level 6 countertops that create both style and functionality. The spacious living and dining areas flow effortlessly together, making entertaining family and friends a breeze. The primary suite serves as a private retreat, featuring a large walk-in closet, dual vanity, and a beautifully appointed walk-in shower with designer finishes. Three additional bedrooms provide ample space for family and guests, while both bathrooms have been tastefully updated with modern touches throughout. Beyond the cosmetic updates, this home offers peace of mind with major improvements including a newer roof (2021), double-pane windows and sliding glass door (2021), updated HVAC system, new AC ductwork, new sprinkler system, and fresh sod. Every detail has been thoughtfully addressed to provide a truly move-in-ready experience. Outside, the oversized corner lot offers plenty of room to relax, entertain, or enjoy the mature surroundings of this established Winter Park neighborhood. The location is hard to beat, with easy access to Sprouts, Publix, Costco, Baldwin Park, Park Avenue, top-rated dining, boutique shopping, and major roadways connecting you to everything Central Florida has to offer. Combining quality renovations, flexible living spaces, and one of Winter Park's most convenient locations, 2652 Abbey Road presents a rare opportunity to enjoy modern living in an established neighborhood without sacrificing character or charm.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Mario Zendeli (407-325-3893)
744 CORNWALL RD, WINTER PARK, FL 32792
$675,000332 Days on yellowkey MLS ID: O6332168
REDUCED by $20,000 (2.9%) on 06/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1968 Built: 1968 Tax: $5,359 (2024)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$5,359
Elementary School: Brookshire Elem
Tax Year: 2024
Remarks: Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today! Also listed for rent
Listing is courtesy of: VERSALIS REALTY POWERED BY SELLSTATE (407-608-9593)
Listing Agent: Tammy Cuddy (407-608-9593)
2015 SUMMERFIELD RD, WINTER PARK, FL 32792
$1,275,00011 Days on yellowkey MLS ID: O6418198
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3024 Built: 1957 Tax: $7,243 (2025)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,243
Remarks: Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated schools. From the moment you arrive, the circular driveway, modern architecture, and professional landscaping create a memorable first impression. Inside, soaring natural light and oversized porcelain tile floors lead you through an open-concept floor plan designed for both everyday living and entertaining. The heart of the home is an extraordinary chef's kitchen featuring premium Bosch appliances, an oversized quartz island, custom cabinetry, a walk-in pantry, and a stylish wet bar. Whether hosting holiday gatherings or enjoying a quiet morning coffee, this space was designed to bring family together. The private owner's retreat feels like a luxury resort, offering direct pool access, a spa-inspired bathroom, soaking tub, oversized walk-in shower, custom closet, and a private beverage station for added convenience. Step outside and discover what truly sets this property apart. The backyard was designed for Florida living at its finest, featuring a sparkling pool, expansive covered lanai, outdoor dining area, and a fully equipped summer kitchen complete with grill, refrigeration, storage, and sink. It's the perfect setting for family gatherings, weekend entertaining, or relaxing after a long day. A dedicated office, versatile flex room, pool bath, and guest suite provide the flexibility today's buyers demand for work, fitness, hobbies, multigenerational living, or media space. Beyond the home itself, you'll enjoy a lifestyle few locations can match. Walk or bike to nearby parks and trails, spend evenings dining on Park Avenue, explore Baldwin Park's restaurants and shops, and enjoy quick access to Downtown Orlando and Orlando International Airport. With luxury finishes, smart-home upgrades, resort-style outdoor living, and a premier Winter Park address, this is more than a home—it's a lifestyle opportunity rarely available in Kenilworth Shores. Schedule your private showing today and experience the difference for yourself.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Courtney Lindsay (206-486-5015)
2774 BANCHORY RD, WINTER PARK, FL 32792
$645,0004 Days on yellowkey MLS ID: O6418821
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 1965 Tax: $7,220 (2025)Community: Winter Park PinesSingle Family
Taxes:$7,220
Remarks: Some homes are updated. Others are completely reimagined. At 2774 Banchory Road, the transformation started with a bold decision: remove the walls and rethink how the home lives. The result is a light-filled great room where the kitchen, dining, and living spaces flow together effortlessly—creating the kind of open, connected lifestyle today's buyers are searching for. The kitchen was designed to be the heart of the home, featuring a dramatic waterfall island, farmhouse sink, quartz countertops, and all-new stainless appliances. Wide-plank flooring runs throughout, while thoughtfully selected RH-inspired lighting adds warmth and character at every turn. Beautifully renovated baths, designer finishes, and thoughtful updates make this home feel both timeless and fresh. Beyond the beautiful finishes, nearly every major component has been improved—from new windows and doors to a new paver driveway, irrigation system, and a recently replaced roof—giving buyers the rare combination of style and peace of mind. Located in Winter Park Pines, one of Winter Park's most beloved neighborhoods, this home offers more than just a beautiful renovation. Residents enjoy zoning for highly regarded Aloma Elementary, Glenridge Middle School, and Winter Park High School, along with a location that's just minutes from Park Avenue, Rollins College, and downtown Winter Park. With easy access to downtown Orlando, you can enjoy the best of both worlds: a charming neighborhood setting with the city's dining, culture, and employment centers just a short drive away. This is what happens when a renovation focuses not just on how a home looks, but on how it lives. Reimagined. Refined. Ready for what's next.
Listing Agent: Shelley Dawson (407-492-1900)
1421 CHAPMAN CIR, WINTER PARK, FL 32789
$1,550,00017 Days on yellowkey MLS ID: O6415941
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3578 Built: 2005Monthly Fee: $268 Tax: $10,592 (2025)Community: Windsong Elizabeths Walk 43/81Single Family
Taxes:$10,592
Remarks: Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
240 N PHELPS AVE, WINTER PARK, FL 32789
$2,250,00018 Days on yellowkey MLS ID: O6415360
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2889 Built: 2026 Tax: $6,605 (2025)Community: Sylvan HeightsSingle Family
Taxes:$6,605
Remarks: A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
1741 MIZELL AVE, WINTER PARK, FL 32789
$1,050,00038 Days on yellowkey MLS ID: O6410059
REDUCED by $45,000 (4.1%) on 06/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2015 Built: 1982 Tax: $11,682 (2025)Community: Lake Monte SubSingle Family
Taxes:$11,682
Remarks: Culture, Convenience, Community! Discover refined living in the heart of Winter Park, where timeless luxury meets an unmatched lifestyle. This beautifully designed single-story residence offers three spacious bedrooms, a private office, two elegantly appointed baths and over 2,000 square feet of living space complete with a two-car garage and no HOA. Thoughtfully curated with sleek tile flooring throughout and no carpeting, the home exudes both style and comfort. The well-equipped kitchen features granite countertops, a pantry, and a charming breakfast area, flowing effortlessly into the expansive family and dining rooms. French doors open to a generous screened lanai and a private fenced backyard, creating the perfect setting for seamless indoor-outdoor entertaining. Designed with a desirable split floor plan, the luxurious primary suite offers private backyard access, dual walk-in closets plus an additional storage closet and a private bath with a spacious walk-in shower. Two additional guest bedrooms share a beautifully appointed bath with shower/tub, while one bedroom enjoys direct access to a dedicated office space, ideal for guests or working from home. Winter Park is celebrated for its distinctive blend of arts and culture, charming sidewalk cafés, acclaimed museums, upscale accessible neighborhoods, scenic lakes, outdoor recreation and year-round festivals. Surrounded by top-rated schools and picturesque tree-lined streets, this exceptional location offers premier conveniences. Near AdventHealth, Cady Way Trail and recreational parks, YMCA of Central Florida, public golf courses, Rollins College, Full Sail University and UCF. Whether you're seeking outdoor adventure, cultural enrichment, or everyday convenience, this location delivers it all. Schedule your private showing today and discover the best of Winter Park living. Roof - 2018, AC - 2015.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Farah Novin (407-234-0501)
2344 WOODCREST DR, WINTER PARK, FL 32792
$729,9008 Days on yellowkey MLS ID: O6418782
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1764 Built: 1960 Tax: $6,366 (2025)Community: Kenilworth Estates 1St AddSpa: NoSingle Family
Taxes:$6,366
Remarks: Resort Style Pool Home in KENILWORTH ESTATES! Conveniently located in Winter Park with a walking distance to Baldwin Park, Advent Health, Cody trail park! A short drive to Rollin College, Park Ave, Full Sail University, downtown Orlando, theme parks, and UCF! Close to restaurants, shopping centers, bars, Publix, CVS and gas stations. Welcome Home! through the main door, you will be amazed by its modern and spacious floor plan! A lovely living room with a fireplace, an extra room for home gym or office, on the right, a sparkling pool in front of your eyesight through a modern glass sliding door, sitting under porch, enjoying family gathering in this resort style garden! There are plenty closet spaces for storage! Spacious kitchen cabinets for cooking supplies. Be ready to live in a luxury and breath-taking Winter Park Pool home, while enjoying all Florida sunshine and outdoor biking, jogging and golfing at Winter Park Pine. House was repiped in 2021, Brand-new roof in 2023, Newer AC, like-new hot water heater! Entire home was renovated, new paints, new pool filter, new cabinets and appliances. Are you ready living in your dream home! Move in KENILWORTH ESTATES home today!
Listing is courtesy of: EXPLORE FLORIDA REALTY SERVICES LLC (407-982-9709)
Listing Agent: Shannon Lee (407-982-9709)
1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789
$1,650,00033 Days on yellowkey MLS ID: O6407841
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 1964 Tax: $4,844 (2025)Community: South Lakemont ShoresSpa: NoSingle Family
Taxes:$4,844
Elementary School: Baldwin Park Elementary
Remarks: Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home was completely renovated and expanded in 2013 creating a perfect blend of timeless architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Nicole Seybold (407-808-9374)
1864 GRINNELL TER, WINTER PARK, FL 32789
$1,599,00059 Days on yellowkey MLS ID: O6403822
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3028 Built: 2006 Tax: $16,615 (2025)Community: FremarSpa: YesSingle Family
Taxes:$16,615
Remarks: Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the home, the chef’s kitchen blends elegance and function with gleaming stainless steel appliances, crisp white cabinetry, granite countertops, and a well-appointed Butler’s pantry with a dedicated bar, creating a sophisticated setting for effortless entertaining. Integrated smart features further elevate daily living, including an intercom system for seamless communication, electronic blackout curtains for instant privacy and ambiance, and thoughtful, layered lighting throughout. The magazine-worthy primary bath—featured in Florida Home—feels like a private spa retreat, with floor-to-ceiling back-lit mirrors, a self-cleaning smart toilet with bidet, a custom Barclay soaking tub with black matte exterior, and Calcutta gold marble countertops and backsplash. These luxe finishes are anchored by an oversized chevron pattern tile by Crossville in Ice White, a throwback diamond-pattern shower floor, and a sculptural Kuzco LED chandelier that completes the space with dramatic flair. Expansive living areas open to resort-inspired outdoor spaces where a heated saltwater pool and spa, private mini-golf green, and a summer kitchen with tongue-and-groove wood ceiling create a true indoor-outdoor sanctuary. Velux solar-powered skylights with acoustic rain sensors that automatically close at the first sign of rain, a Mosquito NIX misting system, comprehensive surveillance, and electronic private gated access provide both comfort and peace of mind. Natural gas service and a dedicated hook-up for a whole-house generator underscore the home’s emphasis on performance and preparedness. Crafted for those who expect uncompromising quality, this Winter Park residence is more than a home—it is a refined sanctuary where architectural presence, rich materiality, and thoughtful technology converge in one coveted address.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Robyn Brehne-Glass (407-474-4038)
3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792
$179,9004 Days on yellowkey MLS ID: O6419959
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1984 Tax: $197 (2025)Community: Hidden. OaksSpa: NoCondo
Taxes:$197
Remarks: Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
426 WORTHINGTON DR, WINTER PARK, FL 32789
$2,499,0005 Days on yellowkey MLS ID: O6418049
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3520 Built: 2026 Tax: $9,459 (2025)Community: Kenilworth Shores Sec 01Spa: YesSingle Family
Taxes:$9,459
Remarks: Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
275 N RANGER BLVD, WINTER PARK, FL 32792
$775,00019 Days on yellowkey MLS ID: O6415904
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1950 Built: 1965 Tax: $6,817 (2025)Community: Winter Park Pines Merrie OaksSpa: NoSingle Family
Taxes:$6,817
Remarks: Completely reimagined and professionally renovated, this stunning Winter Park POOL home offers approximately 1,950 square feet of thoughtfully designed living space with a rare 4-bedroom, 3-full bathroom floor plan, a 2-car garage, and an exceptional blend of style, function, and quality craftsmanship. At the heart of the home is a show-stopping open-concept kitchen featuring custom shaker cabinetry, quartz countertops, a dramatic oversized center island, designer lighting, a custom range hood, and a striking tile feature wall that creates a true focal point for the home. Warm wood accents, curated finishes, and seamless flow into the living and dining spaces make this home ideal for both everyday living and entertaining. The split-bedroom floor plan provides privacy and flexibility, with the primary suite situated on one side of the home and the secondary bedrooms located on the opposite side. All three bathrooms have been completely gutted and beautifully remodeled with high-end finishes and timeless design selections. Luxury vinyl plank flooring extends throughout the home, creating a cohesive and modern aesthetic. Major improvements include a NEW roof (2026), NEW AC system, NEW windows, NEW electrical, NEW water heater, RESURFACED POOL, updated lighting throughout, inside laundry room, and extensive interior renovations that allow buyers to enjoy the benefits of a truly move-in-ready home. Situated in the highly desirable Winter Park Pines area, residents enjoy convenient access to Park Avenue, Downtown Winter Park, Cady Way Trail, Rollins College, Full Sail University, UCF, shopping, dining, major roadways, and Orlando International Airport. Combining designer finishes, an open modern layout, a private pool, and an unbeatable location, this is a rare opportunity to own a fully renovated home in one of Central Florida's most sought-after communities. Schedule your private showing today.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Belinda Gonzales (321-277-8994)
528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792
$535,00019 Days on yellowkey MLS ID: O6414677
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1656 Built: 1964 Tax: $6,000 (2025)Community: Winter Park PinesSingle Family
Taxes:$6,000
Remarks: Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home with fresh interior paint combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.
Listing Agent: Jonathan Cole (407-928-9516)
1507 GOLFSIDE DR, WINTER PARK, FL 32792
$899,00088 Days on yellowkey MLS ID: O6395355
REDUCED by $26,000 (2.8%) on 05/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 1981 Tax: $2,783 (2025)Community: Greenview At Winter PinesSingle Family
Taxes:$2,783
Remarks: Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!
Listing Agent: Catherine D'Amico (407-252-3210)
1813 HARLAND PARK DR, WINTER PARK, FL 32789
$1,875,00059 Days on yellowkey MLS ID: O6403483
REDUCED by $120,000 (6.0%) on 05/28/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3551 Built: 2013Monthly Fee: $268 Tax: $23,539 (2025)Community: Windsong - Knowles PlaceSpa: YesSingle Family
Taxes:$23,539
Remarks: Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.
Listing Agent: Marystuart Day (407-620-8683)
2715 PRINCE JOHN RD, WINTER PARK, FL 32792
$498,90021 Days on yellowkey MLS ID: O6415084
REDUCED by $6,000 (1.2%) on 06/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1565 Built: 1963 Tax: $7,101 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$7,101
Remarks: GREAT HOME & GREAT VALUE — home needs some TLC and if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All rooms dimensions must be independently verified by the buyer.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792
$157,50069 Days on yellowkey MLS ID: O6401114
REDUCED by $400 (0.3%) on 06/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 840 Built: 1990Monthly Fee: $370 Tax: $2,461 (2025)Community: Lancelot/Winter ParkCondo
Taxes:$2,461
Remarks: 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/month. The interior of condo was just completely repainted, and all closet doors were fixed!
Listing Agent: Christina Munkberg Bianca (407-340-1308)
333 CORNWALL RD, WINTER PARK, FL 32792
$579,00038 Days on yellowkey MLS ID: O6409379
2 Days Off yellowkey (back on 6/26/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1660 Built: 1963Monthly Fee: $5 Tax: $2,654 (2025)Community: Winter Park PinesSingle Family
Taxes:$2,654
Remarks: Under contract-accepting backup offers. Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, making this location a consistent choice for buyers prioritizing long-term value. In addition to the location, the home benefits from key updates already completed, including a 2022 roof, 2021 HVAC system, updated windows installed in 2017, along with an updated kitchen and bathrooms, offering peace of mind and modern functionality for the next owner. Ideally positioned to enjoy the Winter Park lifestyle. Close proximity to Park Avenue’s boutique shopping and exceptional dining, while the University of Central Florida, Rollins College, and Full Sail University are all within easy reach. AdventHealth Winter Park and Orlando International Airport are also close by, making both daily routines and travel simple. This is a home that delivers on every level, location, lifestyle, and lasting quality.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Melissa Johnson (407-681-4393)
2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792
$184,999494 Days on yellowkey MLS ID: OM695642
0 Days Off yellowkey (back on 6/26/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1984Monthly Fee: $442 Tax: $2,702 (2024)Community: Parkview VillageCondo
Taxes:$2,702
Remarks: PRICE REDUCED, Seller motivated. Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square feet with a thoughtfully designed floor plan. Updated Interiors: Recently remodeled with modern finishes, including appliances (convection oven, refrigerator, dishwasher), and washer/dryer in the interior laundry room. Outdoor Living: Relax on your private screened patio, perfect for morning coffee or evening unwinding. Community Features: Resort-Style Amenities: Enjoy a sparkling pool, a soothing hot tub, and meticulously maintained grounds. Pet-Friendly & Welcoming: Dog-friendly and community-oriented, providing a quiet and peaceful atmosphere. Prime Location: Zoned for A-rated Winter Park schools and just 2 miles away, this condo offers unmatched convenience: Walkable access to dining, shopping, and entertainment. Minutes from Park Avenue, Baldwin Park, Winter Park Hospital, and Downtown Orlando. Close to top educational institutions: Valencia College, Rollins College, Full Sail University, and UCF. With an HOA that provides excellent management and care, this is an incredible opportunity to own in a desirable and high-quality location.
Listing is courtesy of: GLOBALWIDE REALTY LLC (352-456-9788)
Listing Agent: Michell Carrasquero (305-850-2241)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.