Location: Winter Park
Do Not Show Listings
723 SYMONDS AVE, WINTER PARK, FL 32789
$1,800,00029 Days on yellowkey MLS ID: O6406823
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3065 Built: 2023 Tax: $15,884 (2025)Community: Horton AaronSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$15,884
Elementary School: Audubon Park K8
High School: Winter Park High
Tax Year: 2025
Middle School: Audubon Park K-8
Remarks: Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer finishes, and contemporary ambiance that immediately sets the tone for the home. Beyond the entry, the main living spaces unfold into an open-concept kitchen, dining, and living area designed for both everyday comfort and elevated entertaining. The chef’s kitchen is beautifully appointed with custom cabinetry, a Wolf stove, Bosch dishwasher, a premium side-by-side True Residential refrigerator and wine column combination, and a separate under-island beverage refrigerator designed for effortless entertaining. Expansive PGT sliding doors connect the interior spaces seamlessly to the lanai and outdoor retreat, while the Klipsch 5.1 surround sound system, electric fireplace, Anderson windows, ceiling fans, and integrated Elon smart-home system enhance the experience throughout the home. The outdoor living area was designed as a private modern zen-inspired escape, featuring a fully air-conditioned and heated lanai with cedar-lined ceilings, rolled screens, and direct access to the serene backyard retreat complete with a four-person sauna. Thoughtfully integrated technology and upgrades include Jellyfish lighting, Nest cameras, power-over-Ethernet shades, leak protection system, water filtration systems including Aqua Sauna Water Filter and Kohler Connect Water Minder, as well as two separate AC units serving each floor independently. The first floor also offers a private guest suite, ideal for visitors or multigenerational living. Upstairs, the second level features a spacious laundry room, two additional en-suite bedrooms, and an impressive primary suite designed as a true retreat. The luxurious primary bathroom showcases a standing shower with digital water controls, dual sinks with custom storage cabinetry, and an expansive custom walk-in closet. Additional highlights throughout the home include engineered wood flooring, electric blinds, and refined designer details at every turn. Crowning the residence is a spacious third-floor bonus area offering endless flexibility for a media room, fitness studio, office, or additional lounge space, all fully air-conditioned for year-round comfort. Combining exceptional craftsmanship, advanced smart-home functionality, and an unbeatable Winter Park location with exceptional proximity to both Park Avenue and Winter Park Village, this extraordinary residence places premier dining, boutique shopping, cafés, entertainment, and everyday conveniences just moments from home while delivering a truly elevated lifestyle experience.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
2702 PARKLAND DR, WINTER PARK, FL 32789
$1,139,75077 Days on yellowkey MLS ID: O6397997
REDUCED by $35,250 (3.0%) on 05/18/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2656 Built: 1949 Tax: $5,269 (2025)Community: ParklandoSingle Family
Taxes:$5,269
Remarks: Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.
Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)
Listing Agent: Elizabeth Nordquist (407-694-0996)
1870 WALKER AVE, WINTER PARK, FL 32789
$1,299,000105 Days on yellowkey MLS ID: O6390504
REDUCED by $100,000 (7.1%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2046 Built: 2026 Tax: $3,981 (2025)Community: Osceola HeightsSingle Family
Taxes:$3,981
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
950 ENCLAVE PL, WINTER PARK, FL 32792
$2,125,00029 Days on yellowkey MLS ID: O6410963
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3797 Built: 2027Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Taxes:$9,900
Tax Year: 2026
Remarks: Pre-Construction. To be built. Discover refined modern living in The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 custom residences by FG Schaub Custom Homes. Tucked beneath mature oak canopies and surrounded by lush natural beauty, this intimate neighborhood offers a rare blend of privacy, walkability, and timeless architectural design. Ideally located just moments from Phelps Park, the YMCA, exceptional dining, boutique shopping, and the cultural attractions of downtown Winter Park, The Enclave delivers an elevated lifestyle in one of Central Florida’s most sought-after locations. This striking custom residence showcases contemporary architecture with clean lines, dramatic windows, and exceptional curb appeal. Thoughtfully designed for both everyday living and upscale entertaining, the home features expansive open-concept spaces, soaring ceilings, and seamless indoor-outdoor flow. Every detail reflects superior craftsmanship and designer-selected finishes curated to create a timeless yet modern aesthetic. Luxury appointments include premium Wolf and Sub-Zero appliances, high-performance low-E double-pane windows, 8-foot solid-core interior doors, and tankless gas water heaters for comfort and efficiency. Spacious living areas are complemented by a resort-style outdoor experience featuring a sparkling pool and a fully equipped summer kitchen, ideal for year-round entertaining. Beautifully landscaped grounds and quality construction create a private retreat while remaining connected to the very best of Winter Park living. Buyers still have the opportunity to personalize select finishes and explore certain floor plan modifications. Optional upgrades may include a detached cabana and/or guest house, subject to lot compatibility, community guidelines, and additional pricing. A rare opportunity to build a truly custom luxury home within one of Winter Park’s most exclusive new communities.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Laura Earl (443-994-9441)
930 ENCLAVE PL, WINTER PARK, FL 32792
$2,050,00043 Days on yellowkey MLS ID: O6403032
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3813 Built: 2026Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing Agent: Matthew Burks (407-257-5347)
914 ENCLAVE PL, WINTER PARK, FL 32792
$1,895,00098 Days on yellowkey MLS ID: O6391825
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3617 Built: 2026Monthly Fee: $372 Tax: $10,000 (2025)Community: The Enclave Winter ParkSingle Family
Taxes:$10,000
Remarks: Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create a elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
1927 ELAND AVE, WINTER PARK, FL 32789
$820,000135 Days on yellowkey MLS ID: O6381009
REDUCED by $5,000 (0.6%) on 06/15/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2242 Built: 1957 Tax: $3,190 (2024)Community: Lake Bell TerraceSingle Family
Taxes:$3,190
Elementary School: Hungerford Elem
High School: Edgewater High
Tax Year: 2024
Middle School: College Park Middle
Remarks: *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ryan Leitter (321-684-9699)
1316 BLUE STEM LN, WINTER PARK, FL 32792
$725,00012 Days on yellowkey MLS ID: O6416828
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2196 Built: 2022Monthly Fee: $243 Tax: $6,788 (2025)Community: Landings At Hawks CrestSingle Family
Taxes:$6,788
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an exceptional blend of luxury, comfort, and modern convenience. Upon entry, you're greeted by a dramatic two-story foyer with soaring 20-foot ceilings and abundant natural light. The open-concept living spaces feature luxury vinyl plank flooring throughout, plantation shutters, and corner sliding glass doors that seamlessly connect indoor and outdoor living. Enjoy breathtaking west-facing water views, a picturesque fountain and bridge backdrop, and spectacular sunset views from your private backyard. One of the home's standout features is its generously sized, aluminum-fenced backyard, offering ample space for outdoor entertaining, play, pets, gardening, or even a future pool while still enjoying tranquil waterfront views. Thoughtful smart-home upgrades include electric curtains on the sliding doors, Eufy security cameras, smart door locks, and a MyQ-enabled garage door. The oversized two-car garage also features convenient touchpad access. Residents of Hawks Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, and scenic walking trails. Outdoor enthusiasts will appreciate direct access to Lake Howell for kayaking and canoeing. HOA dues include professional landscaping maintenance, allowing homeowners to enjoy a beautifully maintained property with less upkeep. This move-in-ready home offers the perfect combination of elegant design, premium upgrades, abundant outdoor space, low-maintenance living, and an unbeatable waterfront lifestyle.
Listing is courtesy of: AFFINITY REALTY LLC (407-706-6961)
Listing Agent: Matthew Fong (321-274-3287)
2831 MULFORD AVE, WINTER PARK, FL 32789
$735,00019 Days on yellowkey MLS ID: O6414319
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1647 Built: 1952 Tax: $3,192 (2025)Community: Orangewood ParkSpa: NoSingle Family
Taxes:$3,192
Elementary School: None
High School: None
Middle School: None
Remarks: Rare opportunity to own on one of the most desirable streets in Audubon Park with a coveted Winter Park address. Just a few blocks from East End Market and surrounded by many of Orlando’s Michelin-recognized restaurants, this location offers an unbeatable combination of walkability, lifestyle, and top-rated schools. Zoned for Audubon Park K-8 and Winter Park High School, you’ll enjoy the best of both worlds: the character and community of Audubon Park with the prestige and convenience of Winter Park. This thoughtfully updated home features a 2024 roof, tankless water heater, new carpet, fresh interior and exterior paint, newer insulation, solid-core interior doors, Rain Bird irrigation with well, Vivint security system with cameras, and an Ecobee smart thermostat. The sunken living room creates a unique space for entertaining (it can provide stadium seating or be a conversation pit), while the detached mother-in-law suite adds flexibility for guests, multigenerational living, or rental income. Tucked away from the noise of Corrine Drive yet only blocks from East End Market, neighborhood parks, coffee shops, and dining, this is a rare chance to own in one of Orlando’s most sought-after neighborhoods. Front door does not convey and will be replaced with a similar refinished wood door prior to closing.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Patrick Arenson (305-951-6054)
2914 REEF KNOT PL, WINTER PARK, FL 32792
$1,725,0008 Days on yellowkey MLS ID: O6418185
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4173 Built: 2019Monthly Fee: $186 Tax: $17,688 (2025)Community: Lake Florence PreserveSpa: NoSingle Family
Taxes:$17,688
Remarks: Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
1287 VERDANT GLADE PL, WINTER PARK, FL 32792
$825,00063 Days on yellowkey MLS ID: O6400331
REDUCED by $22,000 (2.6%) on 06/19/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3020 Built: 2020Monthly Fee: $413 Tax: $6,133 (2025)Community: Meadows At Hawks CrestSingle Family
Taxes:$6,133
Remarks: **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 4 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.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
1946 STRATHAVEN RD, WINTER PARK, FL 32792
$650,00030 Days on yellowkey MLS ID: O6411329
REDUCED by $25,000 (3.7%) on 06/19/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2102 Built: 1960 Tax: $8,540 (2025)Community: Kenilworth Shores Sec 07Single Family
Taxes:$8,540
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: ? FULLY REMODELED WINTER PARK POOL HOME NEAR BALDWIN PARK! ? Welcome to 1946 Strathaven Road — a beautifully updated 4-bedroom, 3-bath home with a dedicated office, ideally located near both Winter Park and the highly sought-after Baldwin Park community, known for its lakeside dining, walkability, parks, boutiques, and vibrant neighborhood atmosphere. ? This move-in ready home features an open and light-filled layout with designer finishes throughout, including updated flooring, custom cabinetry, modern lighting, and beautifully remodeled bathrooms and kitchen with premium appliances and upscale countertops. Major upgrades include a NEW roof (2023), windows (2023), water heater (2023), electrical panel (2023), plus updated plumbing and electrical throughout for true peace of mind. Enjoy spacious living areas, a luxurious primary suite, and a private backyard perfect for relaxing or entertaining. Conveniently located near top-rated schools, parks, shopping, dining, Park Avenue, and everything Winter Park living has to offer, this home combines modern updates with an unbeatable Central Florida location.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Youbel Montesino (954-608-4838)
1571 WOODLAND AVE, WINTER PARK, FL 32789
$6,000,00028 Days on yellowkey MLS ID: O6411706
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 7397 Built: 2007 Tax: $31,040 (2025)Community: Comstock ParkSpa: YesSingle Family
Taxes:$31,040
Remarks: Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.
Listing Agent: Vonda Fields (321-438-6906)
2715 PRINCE JOHN RD, WINTER PARK, FL 32792
$504,90018 Days on yellowkey MLS ID: O6415084
REDUCED by $15,000 (2.9%) on 06/19/2026
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. 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 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)
1110 ALABAMA DR, WINTER PARK, FL 32789
$1,699,00085 Days on yellowkey MLS ID: O6395692
0 Days Off yellowkey (back on 6/19/2026)
REDUCED by $51,000 (2.9%) on 05/19/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2488 Built: 1958 Tax: $12,858 (2025)Community: J Kronenberger SubSpa: NoSingle Family
Taxes:$12,858
Remarks: Under contract-accepting backup offers. Come home to this gorgeous 3 Bed/3 Bath Winter Park masterpiece on a premier corner lot at the intersection of the coveted Alabama Drive and Palmer Avenue. FULLY RENOVATED DOWN TO THE STUDS IN 2020. Located in one of Winter Park’s most highly sought-after areas, the property is beautifully framed by the iconic tree-lined brick streets of the Chain of Lakes district and surrounded by historic estate homes. The Lifestyle: Central Florida's Premier Luxury Destination Living at 1110 Alabama Drive means immersing yourself in the rich culture and timeless elegance of Winter Park. This historic city is celebrated for its deep canopy oak trees, world-class amenities, and a laid-back atmosphere. A Walker's & Boater's Paradise: You are just a short, scenic stroll from the exclusive boutiques, acclaimed sidewalk cafes, and Michelin-starred dining lining Park Avenue. Spend your weekends grabbing fresh produce at the famous local farmers' market or launching a boat onto the stunning interconnected freshwater Chain of Lakes. Surrounded by Beauty: This home places you moments from the breathtaking, massive cypress trees and vibrant blooms of Kraft Azalea Gardens, as well as the private, historic Winter Park Racquet Club. The Residence: Fully Renovated & Refined No detail has been spared in this total home transformation, seamlessly blending a classic, highly coveted location with cutting-edge modern amenities. Gourmet Kitchen: Discover a massive chef’s footprint appointed with premium granite countertops and high-end finishes, making it the focal point for both daily living and grand entertaining. Designer Upgrades: Rich hardwood flooring flows effortlessly throughout the home, beautifully complemented by high-efficiency upgraded Pella windows that provide enhanced aesthetics and excellent energy savings. Modern Infrastructure: Enjoy total peace of mind with meticulously updated systems, including a 5-year-old tankless water heater, a custom-designed garage door, and a well-maintained 12-year-old roof. The Ultimate Outdoor Oasis Designed intentionally for the true Florida lifestyle, the exterior of this property serves as a completely private sanctuary. Signature Screened Porch: Step out into an expansive outdoor living space anchored by a cozy gas fireplace—serving as the ultimate venue for year-round entertaining. The Grounds: Relax by the private, open-air pool surrounded by lush, tropical landscaping and a fully irrigated lot, capturing resort-style living in your own backyard. Whether you are searching for a turnkey luxury residence or looking to secure a rare, premier canvas in Central Florida’s most coveted zip code, this estate has it all.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Omar Albaba (813-951-7475)
1434 VIA SANGRO PL, WINTER PARK, FL 32792
$1,300,00013 Days on yellowkey MLS ID: O6416325
0 Days Off yellowkey (back on 6/13/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3063 Built: 2016Monthly Fee: $182 Tax: $9,764 (2025)Community: Lakeside EstatesSingle Family
Taxes:$9,764
Remarks: beautiful home
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Maha Matta, Pa (407-340-6911)
1177 KENWOOD AVE, WINTER PARK, FL 32789
$1,800,000105 Days on yellowkey MLS ID: O6390592
0 Days Off yellowkey (back on 5/21/2026)
REDUCED by $70,000 (3.7%) on 05/13/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4363 Built: 2007 Tax: $16,206 (2025)Community: Dixie TerraceSpa: NoSingle Family
Taxes:$16,206
Remarks: Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat, complete with a walk-in closet and an en-suite bathroom featuring dual sinks, and a separate soaking Jacuzzi. Step outside to enjoy the covered patio—perfect for entertaining or unwinding. The backyard a outdoor escape with a sparkling in-ground pool and a fenced area for added versatility. Inside, the home has been refreshed with new interior paint and partial flooring updates, giving it a clean, updated feel. Don’t miss the opportunity to make this beautiful property your next home. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
2614 PARKLAND DR, WINTER PARK, FL 32789
$1,890,000432 Days on yellowkey MLS ID: O6301489
REDUCED by $34,450 (1.8%) on 06/18/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3307 Built: 2007 Tax: $12,712 (2024)Community: Parklando 03Spa: YesSingle Family
Taxes:$12,712
Remarks: Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Completely remodeled in late 2022, this home radiates warmth and sophistication. Solid light oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape.The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge.
Listing is courtesy of: JW GASTON LLC (321-239-5540)
Listing Agent: Ryan Gaston (321-239-5540)
1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792
$475,00067 Days on yellowkey MLS ID: O6399199
0 Days Off yellowkey (back on 5/17/2026)
REDUCED by $5,000 (1.0%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 1984Monthly Fee: $49 Tax: $6,243 (2024)Community: Country LaneSingle Family
Taxes:$6,243
Remarks: Under contract-accepting backup offers. 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!
Listing is courtesy of: COLDWELL BANKER VANGUARD EDGE (800-948-0938)
Listing Agent: Jodie Ma (407-221-0775)
2054 EASTBROOK BLVD, WINTER PARK, FL 32792
$500,00024 Days on yellowkey MLS ID: V4949389
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 1966 Tax: $5,054 (2025)Community: Eastbrook Sub Unit 8Single Family
Taxes:$5,054
Remarks: Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.
Listing Agent: Melissa Stalzer (386-405-3457)
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