Location: Winter Park
Do Not Show Listings
2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792
$267,000105 Days on yellowkey MLS ID: O6398500
INCREASED by $4,000 (1.5%) on 07/30/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1987 Tax: $1,107 (2025)Community: Cedarwood Village 1Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,107
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant, durable flooring throughout the home ensures easy maintenance. Enjoy the walk-in shower and bathtub with upgraded plumbing and tile. A convenient coffee nook sits just off the kitchen. The spacious patio is ideal for entertaining guests and enjoying outdoor time. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Robert Arnold, Jr (407-389-7318)
3220 NETHERWOOD DR, WINTER PARK, FL 32792
$269,000196 Days on yellowkey MLS ID: O6374172
REDUCED by $10,990 (3.9%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1982 Tax: $1,222 (2025)Community: Coronation AddHalf Duplex
Taxes:$1,222
Remarks: BACK ON MARKET!! Buyer financing fell through! Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future expansion. Ideal for a first-time homebuyer or anyone seeking stress-free living. Best of all, NO HOA! Conveniently located near major highways, great schools, shopping, and dining in the highly desirable Winter Park area. Don’t wait—make this home yours today!
Listing is courtesy of: THE FIRM RE (407-227-3345)
Listing Agent: Nimrah Ashraf (786-356-6611)
2336 SUN VALLEY CIR #BLDG 20, WINTER PARK, FL 32792
$285,000302 Days on yellowkey MLS ID: O6342993
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1669 Built: 1986Monthly Fee: $511 Tax: $3,477 (2024)Community: Cedarwood VillageSpa: NoCondo
Taxes:$3,477
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: This is one of the largest floor plans in the community. Two bedrooms, two bathrooms, and a loft that you can use as a third bedroom, home office, or gym. Welcome to the established and well-maintained community of Cedarwood Village, located in highly desirable Winter Park! TREE-LINED STREETS lead you to this two-story, 2-bedroom, 2-bath BLOCK-CONSTRUCTED condominium offering 1,669 square feet of interior living space, this includes an enclosed lanai (under air), for extra living space. The open living and dining area features VAULTED CEILINGS, two skylights, creating a bright and inviting space. From here, enjoy serene views of the enclosed lanai and lush green space beyond. A WET BAR adds a perfect touch for entertaining. Upstairs the loft has a skylight, ceiling fan and is carpeted. The kitchen is thoughtfully designed with a space for a charming eat-in nook that overlooks your PRIVATE COURTYARD and is accessible through sliding glass doors—perfect for morning coffee or outdoor dining. For added convenience, the laundry closet with a WASHER AND DRYER is tucked right into the kitchen. The primary suite is a peaceful retreat, with a beautifully en-suite bathroom with a brand-new vanity with granite, featuring both a WALK-IN closet, and a shower enclosure and the lanai under air, is accessible through sliding glass doors. The spacious second bedroom also features a walk-in closet and attached access to the second bathroom, offering privacy while still serving guests comfortably. Additionally, this home is located across from green space, has two designated parking spaces, and a private mailbox. Re-roofed and new skylights were installed in 2020; entire complex was recently painted. Upgrades include newer AC and just painted in July 2026. A beautiful master bathroom cabinet and sink —providing comfort and style. With low HOA dues, residents enjoy access to a sparkling community pool, clubhouse, tennis and basketball courts, pickleball, a FENCED DOG RUN, and a pet walk with waste stations. Monthly fees also cover roof and exterior building maintenance, pest control, and landscaping. This ideal Winter Park location is just minutes to Park Avenue, UCF, Rollins College, Full Sail University, shopping, restaurants, entertainment, and medical facilities.
Listing is courtesy of: PR REAL ESTATE SERVICES (407-447-9500)
Listing Agent: Lizzie Beaudoin (321-287-4001)
1113 VIA DEL MAR, WINTER PARK, FL 32789
$1,595,000177 Days on yellowkey MLS ID: O6379697
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2012 Built: 1957 Tax: $13,924 (2024)Community: Tuscany TerraceSpa: NoSingle Family
Taxes:$13,924
Elementary School: Dommerich Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.
Listing is courtesy of: BAY HILL REALTY LLC (407-790-9810)
Listing Agent: David Barany (407-790-9810)
4353 STEED TER, WINTER PARK, FL 32792
$609,90036 Days on yellowkey MLS ID: TB8517548
REDUCED by $5,090 (0.8%) on 07/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2275 Built: 1989Monthly Fee: $29 Tax: $7,031 (2024)Community: Kings CoveSingle Family
Taxes:$7,031
Elementary School: Red Bug Elementary
Remarks: MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the moment you arrive, you'll appreciate the spacious layout and impressive updates throughout. The heart of the home features a beautifully appointed kitchen with quartz countertops, ample cabinetry, and a seamless flow into the family room, making it perfect for everyday living and entertaining. Vaulted ceilings and a cozy wood-burning fireplace create a warm and inviting atmosphere. Step outside to your own private outdoor oasis. The screened-in pool area is designed for year-round enjoyment and features a spacious patio, covered lanai, and a fully equipped outdoor kitchen complete with refrigerator, sink, and cabinetry—ideal for hosting family and friends. The primary suite offers a relaxing retreat with dual sinks and plenty of space to unwind. Additional highlights include a fenced backyard, new windows (2021), new roof (2019), and a new AC system (2024), providing peace of mind for years to come. Conveniently located with easy access to SR 417, shopping, dining, and everyday conveniences, this exceptional home combines comfort, style, and location. Don't miss this opportunity—schedule your private showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Barbara Robinson (706-540-4593)
5444 PEACO PL, WINTER PARK, FL 32792
$250,0003 Days on yellowkey MLS ID: O6428383
0 Days Off yellowkey (back on 7/29/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 924 Built: 1984 Tax: $2,640 (2025)Community: Grand PinesHalf Duplex
Taxes:$2,640
Remarks: WELCOME HOME!!! This CHARMING refreshed WINTER PARK GEM 2/2 is ready for YOU! Roof is 2024!!! FRESHLY PAINTED inside and out! As you drive up to the home you see the freshly mulched front of the home. Make you way into the front door and you see the open floor plan. The first thing you notice is the consistent floor throughout the living space in the home. the kitchen offers plenty of cabinet space to work with & NEW COUNTERTOPS! As you walk this home you notice it is in MOVE IN CONDITION and all you need to do is bring your furniture! The LARGE backyard is fenced in and offers options for pets and little ones to run free and play. There are 2 cement pads in the back ready to put patio furniture to sit and relax after a hard day at work. This home is conveniently located close to shopping, restaurants , the highway and more! WELCOME HOME!!!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Dean Gonzalez (407-325-7804)
7026 HAMMOCK WAY, WINTER PARK, FL 32792
$362,0009 Days on yellowkey MLS ID: O6427437
1 Days Off yellowkey (back on 7/29/2026)
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)
330 ELKHORN CT, WINTER PARK, FL 32792
$544,900187 Days on yellowkey MLS ID: O6376757
REDUCED by $5,000 (0.9%) on 06/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1570 Built: 1965 Tax: $2,086 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,086
Remarks: 330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods. Owner says to bring all offers!
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Neil Chetram (407-752-1597)
4965 ORANGE AVE, WINTER PARK, FL 32792
$379,90022 Days on yellowkey MLS ID: O6423739
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1444 Built: 1959 Tax: $2,909 (2025)Community: Suburban Homes First AddSingle Family
Taxes:$2,909
Elementary School: Lakemont Elem
Remarks: Updated 4-Bedroom Home for Sale | No HOA | Top-Rated Winter Park School Zone ... Welcome to low-maintenance Winter Park living at 4965 Orange Ave in 32792 with no HOA constraints or fees. Nestled on a quiet lot zoned for top-rated Orange County Public Schools Lakemont Elementary, Maitland Middle, and Winter Park High School, this move-in ready four-bedroom single-family home offers major high-ticket capital improvements already completed. Upgrades include a NEW Roof, two NEW A/C systems for dual-zone energy efficiency, NEW dual-pane insulated windows, fresh interior and exterior paint, and modern fixtures throughout. The carpet-free interior boasts easy-to-clean polished terrazzo and modern ceramic tile flooring, an updated galley kitchen with stainless steel appliances and solid wood cabinets, and two thoughtfully remodeled bathrooms. Designed with incredible layout versatility, the split four-bedroom floor plan includes direct exterior access through sliding glass doors, making it exceptionally well-suited for a multi-generational setup, in-law suite, private guest retreat, or dedicated home office. Outside, the expansive fully fenced backyard provides ample room for pets, outdoor entertaining, or a future pool, while the attached carport offers covered parking and a dedicated laundry utility storage room. Enjoy an unbeatable Central Florida location just minutes from Park Avenue dining, boutique shopping, local parks, and major Orlando commute routes.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Allison Day (407-617-2881)
1750 CAROLLEE LANE, WINTER PARK, FL 32789
$1,780,000133 Days on yellowkey MLS ID: O6391179
REDUCED by $40,000 (2.2%) on 07/16/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3249 Built: 2012 Tax: $24,658 (2025)Community: Green Terrace V/140 Lot 3 Blk BSingle Family
Taxes:$24,658
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Michelle Hochfelder (407-221-5073)
1347 CHAPMAN CIR, WINTER PARK, FL 32789
$1,395,00077 Days on yellowkey MLS ID: O6408189
0 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2922 Built: 2013Monthly Fee: $268 Tax: $16,875 (2025)Community: Windsong Elizabeths WalkSpa: NoSingle Family
Taxes:$16,875
Remarks: Under contract-accepting backup offers. Beautiful Windsong custom home completely reimagined with a sophisticated interior design overhaul that now presents as a true Winter Park boutique luxury residence. This stunning 4 bedroom, 3.5 bath home blends timeless elegance, thoughtful craftsmanship, and warm entertaining spaces in one of the area’s most sought-after neighborhoods. Every room feels intentional and refined, showcasing elegant finishes, designer touches, and a fresh, elevated aesthetic throughout. Recently fully repainted and enhanced with gorgeous new quartz countertops and a crisp white pearl subway tile backsplash, the home now feels both current and timeless while maintaining the charm and character buyers love about Winter Park living. At the heart of the home is a spectacular chef’s kitchen featuring top-of-the-line Viking and Bosch stainless steel appliances, including a Viking gas range with griddle, a large center island with counter seating, stunning cabinetry, and a dramatic 10-foot coffered ceiling. The kitchen flows seamlessly into the inviting family room with gas fireplace and custom window seating, creating the perfect setting for both everyday living and upscale entertaining. Triple French doors open to a generous covered lanai complete with a summer kitchen, built-in grilling station, and beautifully designed outdoor spaces beaming with old-world charm rarely found in newer construction homes. The turf backyard offers easy maintenance while creating a warm and private atmosphere for gatherings year-round. The formal dining room is equally impressive with crown molding, wainscoting, abundant natural light from the oversized bay window, and direct access to a convenient butler’s pantry and dry bar, making hosting effortless. Upstairs, the magnificent owner’s retreat offers oversized walk-in closets and a luxurious spa-inspired bathroom adorned with glorious marble tile work and elegant designer finishes. Two additional generously sized bedrooms share a marble bath and the 4th bedroom is currently shown as an office, with adjacent hall full bath. A downstairs powder room outfitted in new england blue theme is great for guests. Additional luxury features include hardwood flooring, plantation shutters, surround sound, tankless gas water heaters, an electric vehicle charger, oversized two-car garage with high ceilings and level 5 drywall finish, and countless thoughtful upgrades throughout. Located within the highly desirable Windsong community, residents enjoy access to incredible amenities including two resort-style pools, lakefront clubhouse, water park, playground, fishing pier, kayaks, paddleboards, and even a residents-only pontoon boat to explore the Winter Park Chain of Lakes. Just minutes from Park Avenue, Baldwin Park, and top-rated Winter Park schools, this is your opportunity to step directly into the Winter Park home of your dreams—fully upgraded, impeccably styled, and ready now.
Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)
Listing Agent: Justin Pekarek (407-808-3695)
1150 VIA SALERNO, WINTER PARK, FL 32789
$3,975,000398 Days on yellowkey MLS ID: O6321143
REDUCED by $220,000 (5.2%) on 07/29/2026
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3850 Built: 2025 Tax: $10,158 (2024)Community: Cloister Grove SubSpa: NoSingle Family
Taxes:$10,158
Remarks: In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,850-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Padgett Mccormick (407-645-4321)
2430 CHANTILLY AVE, WINTER PARK, FL 32789
$1,599,00078 Days on yellowkey MLS ID: O6401352
REDUCED by $66,000 (4.0%) on 07/07/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2916 Built: 2026 Tax: $4,730 (2025)Community: Winter Park VillageSpa: NoSingle Family
Taxes:$4,730
Remarks: Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking facade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
2217 SUSSEX RD, WINTER PARK, FL 32792
$499,000252 Days on yellowkey MLS ID: O6362648
REDUCED by $20,999 (4.0%) on 07/07/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2092 Built: 1968 Tax: $4,939 (2024)Community: Winter Woods Unit 01Spa: NoSingle Family
Taxes:$4,939
Remarks: PRICE REDUCED!!! ROOF 4 yrs. old, newer A/C, In-ground Pool. Enclosed Patio — a beautifully maintained turnkey home nestled in the heart of Winter Park, one of Central Florida’s most sought-after communities. Surrounded by renowned golf courses, top-rated Seminole County schools, lush parks, and family-friendly neighborhoods, this exceptional residence offers the perfect blend of comfort, convenience, and the elevated Winter Park lifestyle buyers are searching for. This spacious 4-bedroom + office home is completely move-in ready and vacant — just bring your furniture and clothes and start living! From the moment you walk through the front door, you’ll love the bright open-concept layout filled with natural light, updated finishes, granite countertops, modern appliances, and an inviting wood-burning fireplace that creates the perfect family gathering space. Designed for entertaining and Florida living, the oversized Florida room/lanai overlooks a stunning private pool and beautifully landscaped fenced backyard, creating the ultimate indoor-outdoor experience. Whether hosting weekend BBQs, pool parties, holiday gatherings, or simply relaxing after work, this home was built for making memories. Additional highlights include: • 2,092 square feet of living space • 4 bedrooms plus dedicated office/bonus room • Large open kitchen with granite countertops and abundant cabinet space • Spacious primary suite with pool views • Huge covered Florida room perfect for entertaining • Private in-ground pool • Full irrigation system and landscaped yard • Wood-burning fireplace • NO HOA • Attached 2-car garage plus additional parking • Fully fenced backyard for privacy and pets • Move-in ready condition Located in the highly desirable Winter Woods/Lake Howell area, this home is centrally positioned near major highways including SR-417, I-4, Howell Branch Road, and SR-436, making commuting to Downtown Orlando, Winter Park Village, UCF, Orlando International Airport, beaches, shopping, dining, and all Central Florida attractions incredibly convenient. Winter Park is known for its charm, tree-lined streets, upscale dining, boutique shopping, beautiful golf communities, and strong sense of community. Families love the area for its excellent schools, nearby parks, recreational amenities, and safe neighborhood atmosphere. This is more than just a home — it’s a lifestyle opportunity in one of Florida’s premier communities.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Thess Hubilla (407-309-1141)
721 PANSY AVE, WINTER PARK, FL 32789
$1,850,000283 Days on yellowkey MLS ID: O6352857
3 Days Off yellowkey (back on 7/29/2026)
REDUCED by $75,000 (3.9%) on 06/10/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2653 Built: 2018 Tax: $15,480 (2025)Community: Villa View ParkSingle Family
Taxes:$15,480
Remarks: Under contract-accepting backup offers. Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From the moment you enter, the home makes an impression. French clay tile flooring anchors the defined foyer, opening into an expansive great room where Bolivian rosewood built-ins frame a gas fireplace and oversized windows draw the eye toward the pool and lanai beyond. The living, dining and kitchen spaces connect seamlessly, designed for everyday ease and effortless entertaining. The kitchen is equipped for the serious home cook, anchored by a full Thermador appliance package and thoughtfully appointed beyond the expected. The large island integrates a sink, microwave drawer, ice maker and refrigeration drawers alongside generous seating, while a walk-in pantry, concealed outlets and a warming drawer round out a workspace as purposeful as it is refined. Outdoor living is equally deliberate. A covered lanai with fireplace and space for a mounted television flows to an open-air terrace and dedicated grilling area, all overlooking a linear pool with water feature and professionally designed landscaping with evening lighting. Upstairs, the primary suite is positioned at rear of the home for added privacy, with abundant natural light, a generous walk-in closet and an en-suite bath. Two additional bedrooms each offer their en-suite baths and built-in closets. A well-appointed laundry room, along with a linen closet and dedicated storage closet in the hall, complete the second floor. On the main level, a fourth bedroom is finished as a library with custom white oak built-ins and French doors opening to the exterior of the home, offering flexible living or professional workspace. Throughout, Panaget engineered hardwood flooring, decorative crown molding, Sierra Pacific windows and doors, cast stone accents, and integrated stair lighting reflect the home's elevated attention to detail. Additional highlights include a detached two-car garage, extensive storage throughout and an infrastructure designed for future elevator conversion. A rare opportunity to own a newer custom home in one of Winter Park's accessible and beloved neighborhoods.
Listing Agent: Drew Henner (407-406-0662)
2525 LAFAYETTE AVE, WINTER PARK, FL 32789
$1,749,0003 Days on yellowkey MLS ID: O6428823
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2715 Built: 2026 Tax: $4,700 (2025)Community: Winter Park VillageSingle Family
Taxes:$4,700
Remarks: Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brings contemporary design and elevated living to one of Winter Park's most desirable neighborhoods. Offering 4 bedrooms, 3.5 bathrooms, and 2,715 square feet of thoughtfully designed living space, the home blends clean architectural lines with warm, inviting interiors designed for both everyday living and effortless entertaining. The open-concept floor plan is filled with natural light and seamlessly connects the main living areas, creating a spacious and functional layout. Designer finishes, sophisticated details, and carefully selected materials elevate every space, while the chef-inspired kitchen serves as the heart of the home. Step outside to your private backyard retreat featuring a resort-style pool and spa, providing the perfect setting for relaxing or entertaining year-round. Ideally located just minutes from Park Avenue, residents will enjoy easy access to award-winning dining, boutique shopping, parks, golf courses, and Winter Park's vibrant cultural scene.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matt Tomaszewski (407-719-5956)
5117 CYPRESS CT, WINTER PARK, FL 32792
$449,99078 Days on yellowkey MLS ID: O6407713
1 Days Off yellowkey (back on 6/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1534 Built: 1972 Tax: $3,877 (2025)Community: Wrenwood HeightsSpa: NoSingle Family
Taxes:$3,877
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully renovated home tucked away on a quiet cul-de-sac in Winter Park. Thoughtfully redesigned with a modern open-concept layout, this home offers an expansive single-story layout with over 1,500 square feet of inviting living space designed for both everyday living and effortless entertaining. From the moment you enter, you’re greeted by a welcoming foyer with new flooring running throughout the home, complemented by fresh interior and exterior paint and updated lighting that creates a bright, contemporary feel. The spacious living room flows effortlessly into a new kitchen, featuring updated cabinetry, sleek countertops, and a large breakfast bar, creating an ideal space for gathering with family and friends. The private primary suite serves as a relaxing retreat, featuring generous proportions, abundant natural light, and a well-appointed en-suite bath. Two additional bedrooms are thoughtfully positioned, each offering spacious closets and flexibility for family, guests, or a home office setup. With two full bathrooms, comfort and convenience are built into every corner. A large enclosed patio extends the living space outdoors, creating the perfect spot for morning coffee and year-round entertaining while overlooking the backyard, ready to create your own outdoor retreat. A large detached workshop is perfect for additional storage or to convert into a dedicated workshop for your creative projects. Major upgrades include the replacement of aluminum wiring with copper, providing long-term reliability and added buyer confidence. Additional highlights include updated finishes throughout, recessed lighting, new flooring throughout, fresh neutral interiors, and ample storage. Located in an established neighborhood just minutes from shopping, dining, and major roadways, this move-in-ready home is a rare opportunity to own a fully updated property in Winter Park without the wait or hassle of renovations. Schedule your showing today, homes like this don’t last. Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details!
Listing is courtesy of: EXP REALTY LLC (407-305-4300)
Listing Agent: Kristin Mcintosh, Pa (407-492-5666)
7509 GLENMOOR LN, WINTER PARK, FL 32792
$499,50029 Days on yellowkey MLS ID: O6421887
0 Days Off yellowkey (back on 7/5/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2067 Built: 1986 Tax: $2,931 (2025)Community: GlenmoorSingle Family
Taxes:$2,931
Remarks: Welcome to this charming home nestled at the end of a quiet cul-de-sac in the desirable Glenmoor community. Featuring 2,067 sq ft of inviting living space, this property offers a perfect blend of comfort and convenience. The open floor plan includes an eat-in kitchen and a spacious family room, ideal for entertaining. Relax in the living room with a cozy wood-burning fireplace. Enjoy outdoor living with a sparkling pool, raised gardens galore, and a fenced yard backing to a tranquil retention pond — no rear neighbors! The home boasts a large driveway, a 2-car garage, and a dedicated RV power hookup. Recent updates include all new vinyl windows to be installed in the enclosed lanai and remodeled bathrooms. This home is situated in a prime location with top-rated schools, close to dining, shopping, and entertainment options, including Winter Park, Baldwin Park, and easy access to highways 408 and I-4. Commuting is a breeze — just 25 minutes to Orlando International Airport, 20 minutes to Downtown Orlando, and within an hour of Cocoa Beach, Disney World, and Universal Studios. Schedule your private tour today and make this fantastic Orlando area home yours!
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Matt Erickson (407-432-8498)
1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789
$1,025,00035 Days on yellowkey MLS ID: O6420090
REDUCED by $25,000 (2.4%) on 07/22/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2434 Built: 2005Monthly Fee: $500 Tax: $10,213 (2025)Community: Virginia Heights RepTownhouse
Taxes:$10,213
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: George Stringer (407-222-7047)
1849 VIBURNUM LN, WINTER PARK, FL 32792
$399,900358 Days on yellowkey MLS ID: O6333863
REDUCED by $8,100 (2.0%) on 07/02/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1627 Built: 1961 Tax: $3,645 (2024)Community: Eastbrook Sub Unit 05Single Family
Taxes:$3,645
Remarks: This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lesly Hijar (321-347-7383)
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