Location: Winter Park
Do Not Show Listings
2974 CHANTILLY AVE, WINTER PARK, FL 32789
$500,00053 Days on yellowkey MLS ID: O6412851
INCREASED by $1,000 (0.2%) on 07/24/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1433 Built: 1960 Tax: $1,178 (2025)Community: Winter Park ManorSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,178
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: One or more photo(s) has been virtually staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the oversized 76x133 lot, inviting front porch, and clean curb appeal set the tone. Inside, original terrazzo floors, vaulted ceilings, and a bright open great room create warmth, charm, and livability. French doors open to a screened porch overlooking the spacious backyard. The split-bedroom floor plan features two renovated bathrooms, while the redesigned kitchen offers brand-new appliances, cabinetry, and quartz countertops. A spacious 19x12 family room with tile flooring connects to a large inside laundry room with abundant storage and flexible workspace options. Beyond the visible updates, this home stands apart because so many of the expensive and often-overlooked improvements have already been done, including roof, plumbing re-pipe, electrical updates and full-house rewire, hurricane-impact windows, impact front and rear doors, new mini-split HVAC systems, cast iron drain replacement, interior and exterior paint, and more. A rare opportunity to own a thoughtfully improved home in one of Winter Park’s most desirable locations — with no HOA. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
616 BRECHIN DR, WINTER PARK, FL 32792
$999,00068 Days on yellowkey MLS ID: O6409911
REDUCED by $46,000 (4.4%) on 07/24/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2638 Built: 1961 Tax: $4,251 (2025)Community: Kenilworth Shores Sec 04Single Family
Taxes:$4,251
Elementary School: Brookshire Elem
Remarks: Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor living, the property features four bedrooms, 4.5 baths, including three complete en-suite setups that offer maximum privacy for family or guests, plus a dedicated 130-square-foot office. Key property features include elegant design. Step onto gorgeous, rich Brazilian cherry wood flooring that flows beautifully through the open living spaces. Work from home where a dedicated, quiet office space provides an environment for remote work, study or creative projects. Spacious kitchen allows you to enjoy an open-concept floor plan, an eating space in the kitchen, solid wood cabinetry, Silestone countertops and coordinating GE Profile appliances, including a convection oven microwave, giving the kitchen dual oven capacity. Indoor laundry room is a convenient, separate indoor laundry room that keeps household chores organized, quiet and out of sight. Private saltwater oasis allows you to relax in your fully fenced, private backyard featuring an in-ground saltwater pool with spa jets and solar heat. Turnkey infrastructure where peace of mind comes built-in with a new roof (2022), fresh exterior paint and trim (2022), and an updated 200-amp electrical panel. Smart home and systems, equipped with an app-controlled smart security system covering all doors and windows, an EcoBee thermostat and energy-efficient LED recessed lighting. Location and lifestyle benefits include top-tier education, zoned for premier Orange County schools, including Brookshire Elementary, Glenridge Middle School and Winter Park High School (home to a globally recognized International Baccalaureate program). Active recreation to Cady Way Park to enjoy the community pool, playground, sports fields and extensive bike trails. Unbeatable convenience just minutes away from Winter Park Pines Golf Course, two Publix grocery stores, and the upscale dining, boutique shopping, and museums of Park Avenue and Baldwin Park Town Center. This exceptional property blends classic Winter Park lifestyle with the modern infrastructure you demand.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1130 PARK NORTH PLACE, WINTER PARK, FL 32789
$2,200,000125 Days on yellowkey MLS ID: O6392394
0 Days Off yellowkey (back on 7/24/2026)
REDUCED by $295,000 (11.8%) on 06/29/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4011 Built: 1968 Tax: $9,744 (2025)Community: Park NorthSingle Family
Taxes:$9,744
Elementary School: Lakemont Elem
Remarks: Under contract-accepting backup offers. WALK TO PARK AVENUE from this RARE nearly HALF ACRE homesite with OVER 4,000 SQUARE FEET and 5 BEDROOMS in one of Winter Park's most desirable locations. Leave your car at home and enjoy Park Avenue's renowned restaurants, boutiques, cafés, parks, and the Winter Park Golf Course just moments from your front door. Tucked away on a quiet cul-de-sac, this timeless two story residence offers the perfect combination of space, warmth, and an exceptional floor plan designed for both everyday living and effortless entertaining. From the moment you step inside, the home feels welcoming with expansive living spaces, soaring ceilings, and abundant natural light. The main level is anchored by a spacious primary suite, while the family room features dramatic ceilings and opens seamlessly to the kitchen and casual dining area, creating the true heart of the home. French doors lead to a screened patio with a charming Southern feel that overlooks the expansive backyard, offering endless possibilities for a pool, outdoor entertaining, or future expansion. A separate formal living room provides additional flexibility, while the formal dining room connects to a butler's pantry, making hosting gatherings both functional and elegant. Upstairs, you'll find four generously sized bedrooms with beautiful original hardwood floors, providing ample space for family, guests, home offices, or a playroom. LOCATION. LOT SIZE. WALKABILITY. Opportunities to own a nearly half acre property this close to Park Avenue are exceptionally rare. Enjoy the very best of Winter Park with premier shopping, award winning dining, parks, golf, and everything that makes this one of Central Florida's most coveted addresses just a short stroll away.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Jennifer King (407-595-3272)
708 BALMORAL RD, WINTER PARK, FL 32789
$1,690,00020 Days on yellowkey MLS ID: O6423883
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2786 Built: 1960 Tax: $6,459 (2025)Community: Kenilworth Shores Sec 06Spa: NoSingle Family
Taxes:$6,459
Middle School: Glenridge Middle
Remarks: A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential. Coming soon. Reach out to the listing agent if you would like more information about the property.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Caitlin De Oliveira (407-267-7196)
2914 REEF KNOT PL, WINTER PARK, FL 32792
$1,725,00041 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
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
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)
216 BLOSSOM LN, WINTER PARK, FL 32789
$624,9009 Days on yellowkey MLS ID: O6426403
0 Days Off yellowkey (back on 7/23/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1933 Built: 1955 Tax: $5,912 (2025)Community: Shores Lake KillarneySpa: NoSingle Family
Taxes:$5,912
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. Completely updated and move-in ready, this stunning Winter Park home offers the perfect blend of timeless charm and modern comfort! Located in the desirable Shores of Lake Killarney, this 4-bedroom, 2-bath home features 1,933 square feet of thoughtfully updated living space, deeded access to Lake Killarney, and NO HOA! As you step inside, an open layout creates a seamless flow between the kitchen, dining, and living area. The updated kitchen features quartz countertops, stainless steel appliances, generous cabinetry, an island with breakfast bar, and dining area. Sliding doors off the living area open to a private, fully fenced backyard! Whether you're enjoying a quiet morning coffee or hosting outdoor gatherings, this large, inviting space provides the perfect extension of the home's living space! Enjoy peace of mind knowing the major updates have already been completed, including a new roof (2023), new A/C and hot water heater (2025), new windows (2024), complete re-pipe (2021), new electrical panel (2021), and many additional improvements throughout the home. Conveniently located near Winter Park Village, Park Avenue, Rollins College, top-rated dining, shopping, entertainment, and major roadways, this location puts the best of Winter Park and Greater Orlando within easy reach. This is the perfect opportunity to own a move-in-ready Winter Park home that offers the character of an established neighborhood with the peace of mind and convenience of modern updates. Call to set up a private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Katie Tedesco (321-247-8097)
2708 LION HEART RD, WINTER PARK, FL 32792
$614,500147 Days on yellowkey MLS ID: O6387685
REDUCED by $500 (0.1%) on 07/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1785 Built: 1963 Tax: $7,007 (2024)Community: Winter Park Pines RepSpa: NoSingle Family
Taxes:$7,007
Tax Year: 2024
Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
1037 N VIRGINIA AVE, WINTER PARK, FL 32789
$649,00034 Days on yellowkey MLS ID: O6419694
Bed: 3 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1101 Built: 1960 Tax: $7,186 (2024)Community: Tantum AddSpa: NoSingle Family
Taxes:$7,186
Remarks: Under contract-accepting backup offers. THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors, new kitchen with stainless appliances, renovated bath, 3 generous bedrooms, bonus Florida Room, PLUS single car garage. Open patio in backyard with separate firepit seating area overlooking the golf course. Great rental and/or build your dream home! Don’t miss this “one of a kind – live your best Winter Park life” opportunity!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Lisa Gould (407-721-7612)
2504 FORFARSHIRE DR, WINTER PARK, FL 32792
$630,00013 Days on yellowkey MLS ID: O6424656
0 Days Off yellowkey (back on 7/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1915 Built: 1962 Tax: $2,733 (2025)Community: Brookshire Heights 2Nd AddSingle Family
Taxes:$2,733
Remarks: RARE TWO-OWNER MID-CENTURY MODERN HOME IN WINTER PARK PROPER!! You will fall in love as the canopy of trees along Forfarshire Drive leads you to the door of this desirable Winter Park address. A fresh exterior re-envisioning brings a modern curb appeal, complete with a beautifully tiled covered front porch, glass entry door, Zen fountain and low architectural awnings provide an immediate sense of style and anticipation of what awaits inside the home. Upon entry, a large open living area with over-sized picture window and a stylish dining area, adorned with Brazilian hardwood flooring create a relaxed living experience. Updated kitchen includes white cabinetry (undermount counter lighting), Sile Stone countertops with undermount sink, stainless fridge & dishwasher and brush nickel hardware finishes. A large rear bonus room with storage closet space (designer built-ins) and oversized slider door leads to fenced and private backyard, the perfect retreat to relax and unwind. This wide-shoulder split floorplan offers a left-side primary bedroom with hardwood flooring and a large en suite office with access door to backyard, all wrapped windows with sophisticated Plantation shutters. The right side guest wing includes two large bedrooms flanking a remodeled full guest bathroom. KEY UPDATES INCLUDE: Architectural Shingle Roof (2016), Double Pane Windows (throughout), Knockdown Ceilings, Recessed LED Lighting & Touch Control Switches, PEX Plumbing, Interior Panel Box, Garage Opener. Walking distance from the finest amenities in the area: Cady Way Walking Trail, Ward Park, Winter Park Pines Golf Club and the area’s finest Winter Park School District (Brookshire Elementary, Glenridge Middle, Winter Park High). This home combines prestige and affordability in one irreplaceable address. See it before the opportunity has passed you by!!
Listing is courtesy of: RE/MAX CENTRAL REALTY (407-333-4400)
Listing Agent: Bill Miller (407-415-2263)
1271 PALMER AVE, WINTER PARK, FL 32789
$2,275,0009 Days on yellowkey MLS ID: O6426530
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2835 Built: 1948 Tax: $23,515 (2025)Community: J Kronenberger SubSpa: NoSingle Family
Taxes:$23,515
Remarks: This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Sheri Malin (407-603-5221)
1660 PALMER AVE, WINTER PARK, FL 32789
$4,950,000524 Days on yellowkey MLS ID: O6282425
3 Days Off yellowkey (back on 5/7/2026)
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 6406 Built: 2024 Tax: $6,144 (2024)Community: Comstock ParkSpa: YesSingle Family
Taxes:$6,144
Remarks: Under contract-accepting backup offers. New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator, that offers nearly 770 square feet of multi-use space. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...
Listing Agent: Mick Night (407-629-4446)
259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789
$459,90033 Days on yellowkey MLS ID: O6419225
REDUCED by $5,600 (1.2%) on 07/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1953 Tax: $5,488 (2025)Community: Orange TerraceSingle Family
Taxes:$5,488
Remarks: Beautifully renovated three-bedroom, two-bath home in desirable Winter Park 32789. Extensively updated throughout, this move-in-ready home offers the perfect blend of modern style, comfort and convenience. Filled with natural light, this home features a stunning renovated kitchen with an open pass-through breakfast bar and seating, ideal for entertaining and everyday living, a large stainless sink beneath a window and plenty of stunning quartz countertop space. Both baths have been tastefully remodeled, and nearly every aspect of the home has been thoughtfully updated to create a fresh, contemporary feel. Major improvements provide added peace of mind, including a new roof in October 2023, an HVAC system in 2023 and a water heater in 2024. Enjoy the convenience of a large covered carport with built-in storage, plus a huge backyard with endless possibilities for gardening, pets, play or future expansion. An additional storage shed, added in 2018, offers even more space for tools, hobbies and outdoor equipment. Ideally located with quick access to Interstate 4 and 17-92 and just minutes from Park Avenue, Winter Park Village, College Park and Downtown Orlando, you'll enjoy some of Central Florida's finest shopping, dining, entertainment and cultural attractions right at your fingertips. Best of all, no HOA. Combining extensive renovations, major system updates, an oversized backyard and an unbeatable location, this exceptional Winter Park home is truly move-in ready and waiting for its next owner. Call to schedule your appointment today!
Listing Agent: Jo Ann Lamar (321-231-0052)
1885 TEMPLE DR, WINTER PARK, FL 32789
$2,195,000259 Days on yellowkey MLS ID: O6359471
REDUCED by $30,000 (1.3%) on 07/23/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3691 Built: 1963 Tax: $6,073 (2025)Community: Lugano TerraceSpa: NoSingle Family
Taxes:$6,073
Remarks: Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Jennifer Sloan (407-810-8333)
4437 GLENMOOR CT, WINTER PARK, FL 32792
$525,00016 Days on yellowkey MLS ID: O6424511
REDUCED by $14,000 (2.6%) on 07/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2633 Built: 1986 Tax: $8,163 (2025)Community: GlenmoorSpa: NoSingle Family
Taxes:$8,163
Remarks: Beautiful meticulously maintained 3-bedroom, 2-bath split floor plan home situated on a desirable corner lot in the established Glenmoor community. Move-in ready, this home features vaulted ceilings with exposed wood beams, a floor-to-ceiling brick fireplace, carpet, and fresh interior paint. The kitchen offers contemporary cabinetry, Silestone countertops, a skylight, stainless steel range, microwave, and refrigerator, and opens to the spacious eating area. A formal dining room provides additional entertaining space. The private primary suite features a walk-in closet, en-suite bath with double vanities and a walk-in shower. The Flex room is currently being used as a 4th bedroom/office with high ceilings and lots of natural light. Leading out you will find a fully fenced backyard retreat with a brick paver patio, tropical landscaping and a gazebo—ideal for outdoor entertaining. Additional features include a two-car garage, inside laundry room with washer and dryer, 12' x 20' storage shed, and a secondary driveway with parking for up to four additional vehicles, boat, or RV. No HOA! Conveniently located near SR 417, Full Sail University, Rollins College, UCF, shopping, dining, parks, and top-rated Winter Park schools. New roof 2024, new gutters 2024, fresh exterior paint 2025, new exterior lighting 2025.
Listing is courtesy of: TAL BUSIDAN PA (407-227-3001)
Listing Agent: Rob Rallo (407-448-2427)
1492 VIA SANGRO PL, WINTER PARK, FL 32792
$920,00012 Days on yellowkey MLS ID: O6426006
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3063 Built: 2015Monthly Fee: $188 Tax: $7,066 (2025)Community: Lakeside EstatesSpa: NoSingle Family
Taxes:$7,066
Elementary School: None
High School: None
Middle School: None
Remarks: Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Maha Matta, Pa (407-340-6911)
3009 NICHOLSON DR, WINTER PARK, FL 32792
$449,90034 Days on yellowkey MLS ID: O6419862
3 Days Off yellowkey (back on 7/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1645 Built: 1980 Tax: $1,274 (2025)Community: Wrenwood Unit 3 3Rd AddSingle Family
Taxes:$1,274
Remarks: Welcome home to this beautifully remodeled **4-bedroom, 2-bath** residence in sought after Winter Park! BRAND NEW ROOF IN 2024! Thoughtfully renovated from top to bottom, this move-in-ready home offers the perfect combination of modern style, quality craftsmanship, and peace of mind with virtually every major system already updated. Step inside to discover beautiful new luxury vinyl flooring throughout, a stunning kitchen featuring brand-new cabinetry, elegant quartz countertops, and updated finishes designed for both everyday living and entertaining. Both bathrooms have been completely remodeled with stylish tile, new vanities, fixtures, and toilets, creating a fresh, contemporary feel throughout the home. The spacious primary suite has been completely reimagined and now features a beautifully remodeled bathroom along with a custom built-in closet organization system. New double patio doors provide abundant natural light while creating a seamless transition to the screened patio—perfect for enjoying Florida's beautiful weather. Beyond the cosmetic updates, this home offers the kind of improvements buyers truly appreciate, including a **new HVAC system with all-new ductwork, complete house replumb, new water heater, new electrical panel, new switches and outlets throughout, fresh interior and exterior paint, and a newly rescreened patio with a new screen door.** These significant upgrades provide years of worry-free ownership. Located within the highly sought-after Seminole County Public School District, this home is zoned for Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School. You'll also enjoy an incredibly convenient location just minutes from shopping, restaurants, parks, entertainment, major roadways, and everything Winter Park and the surrounding area have to offer. With its extensive renovations, desirable **4-bedroom** floor plan, exceptional location, and true move-in-ready condition, this is a rare opportunity you won't want to miss. Schedule your private showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Benjamin Simanton (407-790-2277)
7026 HAMMOCK WAY, WINTER PARK, FL 32792
$362,0007 Days on yellowkey MLS ID: O6427437
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1257 Built: 1978 Tax: $2,472 (2025)Community: Wrenwood Unit 3 2Nd AddSpa: NoSingle Family
Taxes:$2,472
Remarks: Virtually Staged. Imagine 7026 Hammock Way, recently enhanced with fresh interior paint throughout, establishing a bright and inviting atmosphere. The outdoor space includes a covered patio for outdoor enjoyment, extending to a fully fenced in backyard, providing defined outdoor boundaries. A perfect blend of fresh updates and functional outdoor living awaits.. 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)
2511 EASTBROOK BLVD, WINTER PARK, FL 32792
$365,0007 Days on yellowkey MLS ID: V4950333
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1520 Built: 1967 Tax: $2,865 (2025)Community: Eastbrook Sub Unit 8Single Family
Taxes:$2,865
Remarks: Don't miss this opportunity to own a beautifully updated home with a sought-after Winter Park address! Priced to sell, this move-in-ready 3-bedroom, 2-bath home offers the perfect combination of comfort, style, and location. Enjoy being just minutes from Park Avenue, Baldwin Park, Cady Way Park and Trail, Winter Pines Golf Club, shopping, restaurants, and major roadways, making it easy to enjoy everything Winter Park and the surrounding area have to offer. Inside, you'll love the open floor plan that's perfect for everyday living and entertaining. The updated kitchen features quartz countertops, stainless steel appliances, a large single-basin sink, beautiful cabinetry, and plenty of counter space. It opens to the spacious dining area and family room, creating a bright and welcoming space where everyone can gather. Tile flooring is featured in the foyer, kitchen, bathrooms, and the large open living area just off the kitchen, while warm wood flooring flows through the formal dining room, family room, hallway, and all three bedrooms for a clean, updated look. The primary suite offers a spacious closet and an oversized walk-in shower designed for comfort and convenience. Step outside to the oversized screened lanai overlooking a fully fenced backyard that's perfect for entertaining, pets, play, or simply relaxing after a long day. A large storage shed provides plenty of room for lawn equipment, tools, bikes, or seasonal storage. Recent updates include a 2021 roof and 2022 HVAC system, giving the next owner added peace of mind. Security bars on the windows provide an extra layer of protection and may qualify for insurance discounts. If you've been looking for an updated home in Winter Park that offers great value, this is one you won't want to miss!
Listing is courtesy of: PHOENIX REALTY ADVISORS LLC (407-692-5939)
Listing Agent: Joseph Giardino (407-692-5939)
405 LAKEWOOD DR, WINTER PARK, FL 32789
$6,700,0007 Days on yellowkey MLS ID: O6427244
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 4208 Built: 2008 Tax: $54,765 (2025)Community: Osceola Shores Sec 03Single Family
Taxes:$54,765
Remarks: Stunning Custom Estate on the Shores of Lake Osceola
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
2824 WOODSIDE AVE, WINTER PARK, FL 32789
$600,00021 Days on yellowkey MLS ID: O6423146
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 912 Built: 1952 Tax: $5,163 (2025)Community: Orangewood ParkSingle Family
Taxes:$5,163
Elementary School: Audubon Park K8
Remarks: Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom home! The yard is large. Large shed in the yard to store all of your yard essentials. You will love the area and the convenience to what makes this area special...steps from East End Market, lots of amazing restaurants, shopping, Leu Gardens, and so much more. Updates to the home include: Roof: 2020, HVAC 2019, Elecrical - new utility box, Plumbing: re-plumbed Kitchen and both bathrooms. Welcome Home.
Listing is courtesy of: PARKSIDE PROPERTIES, LLC (407-376-6635)
Listing Agent: Kristin Haughwout-Osorio (407-376-6635)
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