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32789 - O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 Just Added on 06/17/2026 5:18PM
$1,795,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by award-winning Catalyst Design, LLC, a 25-year firm and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one. Step through the custom pivot front door into a home that immediately announces its intentions. Soaring 10-ft ceilings throughout rise to a dramatic 22-ft volume in the great room, framed by sliding glass walls that dissolve the line between interior living and the private outdoor retreat beyond. Level 5 smooth drywall finish — the standard reserved for the finest custom builds — runs throughout, while wide-plank hardwood flooring flows across every living area. Italian porcelain tile anchors all bathrooms and the laundry room with precision and permanence. Every window and exterior door is imported from Germany — Unilux® precision-engineered for thermal performance, acoustic excellence, and longevity that no domestic product can match. Grohe® plumbing fixtures, also made in Germany, carry that same philosophy through every bathroom. Countertops are Cambria or Silestone® quartz with a thickened 3cm mitered edge throughout. Custom solid wood cabinetry is built to plan in the kitchen, laundry, and all bathrooms, finished with Emtek® hardware and 8-ft solid core architectural doors with 7" baseboard throughout. The Winter Park Chain of Lakes — 12 interconnected lakes spanning 2,781 acres of pristine Florida waterways — is moments away, offering boating, paddleboarding, and the beloved Winter Park Scenic Boat Tour. Over 70 parks, Kraft Azalea Gardens, Mead Botanical Garden, and more than a dozen walkable green spaces define the outdoor lifestyle. The Winter Park Farmers' Market, held every Saturday at the historic train station, is a community institution. Rollins College, one of the South's most respected liberal arts institutions, sits lakeside just minutes away, bringing cultural programming, the Bach Festival, and vibrant intellectual energy to the neighborhood year-round. Families are served by highly rated Orange County public schools, with Winter Park High School renowned for its academic rigor and championship programs, as well as exceptional private options, including Trinity Preparatory School and St. Margaret Mary. New construction in 32789 is genuinely rare — historic preservation standards and limited land availability make it so. For international buyers, Orlando International Airport is 30 minutes south. Disney, Universal, and the theme park corridor are under 30 minutes via I-4. Atlantic beaches are under an hour away. This is not a production home dressed up with upgrades. It is a ground-up, custom-built, German-engineered, the most coveted zip code in Central Florida. Schedule your private showing today.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)Listing Agent: Michael Elias (407-810-4303)
32792 - O6417858 - 7302 SWALLOW RUN #7302, WINTER PARK, FL 32792 Just Added on 06/17/2026 4:29PM
$1,495 | Condo | 2 beds | 2.0 baths
This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY (407-897-3366)Listing Agent: Matthew Kirsch (407-897-3366)
32789 - O6416927 - 101 S NEW YORK AVE #311, WINTER PARK, FL 32789 Just Added on 06/17/2026 4:23PM
$1,849,900 | Condo | 3 beds | 3.5 baths | 2 gar
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)Listing Agent: Tiffany Grindstaff (407-252-0927)
32792 - O6417872 - 2737 BRIGHT BIRD LN, WINTER PARK, FL 32792 Just Added on 06/17/2026 3:57PM
$2,600 | Townhouse | 3 beds | 3.0 baths | 1 gar
DO not miss out on this thoughtfully designed townhome! This gorgeous end unit Marigold two-story townhome has no direct rear neighbors, water view and features a Craftsman exterior. Townhome offers 3 bedrooms, 2 full bathrooms, a powder room, a two-car garage and a covered lanai. The kitchen is fully equipped with a pantry, modern gray cabinetry, a Suite Arabesque ceramic tile backsplash, Lagoon quartz countertops and beautiful Positano Blanco porcelain tile flooring. Upstairs the primary Suite features a spacious walk-in closet, and the primary bathroom offers a double sink quartz-topped vanity, a linen closet, private water closet and walk-in shower. Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off Howell Branch Road! This neighborhood has gated access, a resort-style pool with cabana and 1GB high-speed fiber optic internet, along with 75 streaming cable and music channels included in rent!!! Schedule your showing today!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)Listing Agent: Nicole Howell (321-217-7918)
32789 - O6414891 - 140 E MORSE BLVD #J, WINTER PARK, FL 32789 Just Added on 06/17/2026 3:13PM
$2,350,000 | Condo | 3 beds | 3.0 baths | 2 gar
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's most exclusive addresses. Situated directly along the coveted brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication, and walkable convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park, and the year-round events that have made Winter Park one of Central Florida's most sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for both comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower, and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private ensuite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security, and an unmatched Park Avenue lifestyle in the heart of Winter Park.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)Listing Agent: Mick Night (407-629-4446)
32792 - R4911483 - 4756 TANGERINE AVE #4756, WINTER PARK, FL 32792 Just Added on 06/17/2026 10:00AM
$195,000 | Condo | 2 beds | 2.0 baths
Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown ceilings, and a functional floor plan designed for comfortable everyday living. All kitchen appliances are included, making your transition even easier. The end-unit location provides additional privacy and natural light while offering pleasant views of the community pool. Built with solid concrete block construction, this condominium offers durability and low-maintenance ownership. An assigned parking space is included for added convenience. The bathrooms could benefit from updating, providing the perfect opportunity for the next owner to customize the home to their own taste and preferences. Whether you're a first-time homebuyer, downsizing, looking for a seasonal residence, or seeking an investment property, this home offers tremendous potential and value. Wrenwood Condominium allows up to two pets, with a maximum weight of 25 pounds each, making it a great option for pet lovers. Conveniently located near shopping, dining, entertainment, major highways, and everything Winter Park and the greater Orlando area have to offer. Don't miss this opportunity to own an affordable Winter Park condominium and create the home you've always envisioned.
Listing is courtesy of: HOME BUYER HELPER REAL ESTATE LLC (407-342-2664)Listing Agent: Ada Sanchez (407-342-2664)
32792 - O6417098 - 1605 PURITAN AVE, WINTER PARK, FL 32792 Just Added on 06/17/2026 8:57AM
$399,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)Listing Agent: Angelica Tomlinson Llc (407-222-8676)
32792 - O6416150 - 7628 ALOMA PINES CT, WINTER PARK, FL 32792 1 Day on yellowkey
$2,495 | Townhouse | 3 beds | 2.5 baths | 2 gar
This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and local shops, restaurants, and schools. Features include an open floor plan with tile flooring throughout the downstairs main living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, tiled back splash, an island, and walk-in pantry. Upstairs you will find the carpeted bedrooms and primary suite with dual sinks, walk-in shower, and 2 walk-in closets. Additional home features include a 2 car garage, patio with quiet backyard area, and laundry closet. Sorry, no students. Pets under 50 lbs. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
32792 - O6417268 - 3651 N GOLDENROD RD #B207, WINTER PARK, FL 32792 1 Day on yellowkey
$1,295 | Condo | 2 beds | 2.0 baths
Beautifully Updated 2-Bed/2-Bath Condo Near UCF & Full Sail! Step into this stylish and freshly updated second-floor condo, featuring two spacious bedrooms and two modern bathrooms. You'll love the new luxury vinyl plank flooring and fresh paint throughout, creating a clean, contemporary feel. Enjoy the light and airy open-concept living space, filled with natural sunlight and perfect for both relaxing and entertaining. The kitchen shines with updated white shaker cabinets and elegant marble-look countertops. Conveniently located just minutes from UCF and Full Sail University, this home is perfect for students, professionals, or anyone seeking easy access to everything East Orlando has to offer. Residents of Lancelot Condominiums enjoy access to a sparkling community pool.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)Listing Agent: Melissa Vance (407-489-5166)
32789 - O6416830 - 1105 MINNESOTA AVE #5, WINTER PARK, FL 32789 1 Day on yellowkey
$3,000 | Townhouse | 3 beds | 2.5 baths | 2 gar
Beautiful and very spacious 3BR/2.5BA with 2 car garage, large upstairs balcony, fenced patio, New wood flooring throughout the unit, all appliances including side by side refrigerator and full size washer and dryer. This property is centrally located in winter park FL,walking distance to shopping, restaurants, bars, coffee shops, Publix Supermarket, short driving distance to downtown Orlando and Advant Health Orlando hospital and close proximity to Park Ave Won't last long , please call to schedule your appointment today.
Listing is courtesy of: HPL REALTY INVESTMENTS (407-601-6057)Listing Agent: Moshe Sheffi (321-945-2367)
32789 - O6407606 - 313 SYLVAN DR, WINTER PARK, FL 32789 2 Days on yellowkey
$5,500,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar
Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.
32792 - O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 2 Days on yellowkey
$515,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Virtually Staged. Spacious and full of potential, this 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community includes an attached flex room. Perfect for a nursery, mother in law suite, office, or man cave! In the heart of Winter Park, designed for both everyday living and entertaining, this home gives your family room to spread out and enjoy. Inside, you'll find ceramic tile throughout most of the home, with warm wood laminate flooring in three of the bedrooms for added comfort and style. The kitchen has been updated and has ample kitchen and pantry cabinetry. The bathrooms have been updated, creating the perfect space full of modern touches. Major system updates provide peace of mind, including replumbing, a new electrical panel, and a newer roof. The side-entry 2-car garage adds curb appeal and functionality, while the oversized fenced backyard is a true highlight, shaded by two enormous oak trees that create a beautiful setting for relaxing, entertaining, or family gatherings. Conveniently located near shopping, dining, parks, and top-rated schools, this Cedar Ridge gem combines space, updates, and a fantastic location. Don’t miss your rare chance to own this spacious home with timeless charm and endless possibilities in a Winter Park neighborhood WITH NO HOA.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)Listing Agent: Nicholas Feinsod (407-607-7485)
32789 - O6414283 - 437 N CAPEN AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$849,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)Listing Agent: Brandon Geers (941-928-5152)
32792 - O6416828 - 1316 BLUE STEM LN, WINTER PARK, FL 32792 3 Days on yellowkey
$725,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
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)
32789 - O6416158 - 1836 WHITEHALL DR, WINTER PARK, FL 32789 3 Days on yellowkey
$3,500,000 | Single Family Home | 5 beds | 6.5 baths | 2 gar
Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath residence (and casita!) features a unique U-shaped floor plan ensuring natural light shines through every gathering space. Channeling the natural sands of a sunny retreat, the kitchen features white marble countertops and backsplash with blush pink undertones. A custom plaster hood, La Cornue gas range, a wall of cabinets with paneled GE Monogram appliances and a scullery with additional prep space create a kitchen ideal for entertaining. The marble island overlooks one of the main living rooms, where white oak trim highlights the precast stone surrounding the gas fireplace. A vaulted ceiling with natural wooden beams accentuates the bubble chandelier and level 5 drywall finish. Full-height sliding glass doors invite you to soak in the saltwater pool, summer kitchen, landscaped grounds and detached casita beyond. With accordion-style doors and a side entrance, the casita can serve as a pool house, personal home gym or additional bedroom with full bath. Sightlines from the main entrance lead you to the outdoors but also serve as observation points for the color-drenched first floor bedroom and primary suite with arched entry. A freestanding tub with smart glass window, zero-entry shower and extra thick Taj Mahal quartzite countertops elevate the primary bath to pure relaxation. Outside the primary suite, a concealed under-stairs laundry closet appears elegant, as impeccable millwork provides seamless transitions to the adjacent accent wall. Completing the first floor is a formal living room and dining room, a bold powder room, and a charming mudroom with custom cabinets. Follow the wrought-iron railing and engineered wood flooring to the expansive second floor. A flex room, three additional bedrooms and baths, a large laundry room, and built-in closets and benches keep everything organized and beautiful. This exceptional Winter Park home, crafted with intention and experience from award-winning local custom home builder, Urban Perch, elevates everyday living to approachable luxury.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)Listing Agent: Bianca Khoury (407-797-1121)
32792 - O6416635 - 8433 COMMANDER CV, WINTER PARK, FL 32792 4 Days on yellowkey
$465,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!
Listing is courtesy of: CEPEDA REAL ESTATE LLC (407-900-1792)Listing Agent: Brandi Cepeda (407-900-1565)
32792 - O6416143 - 200 SAINT ANDREWS BLVD #3206, WINTER PARK, FL 32792 4 Days on yellowkey
$230,000 | Condo | 2 beds | 1.5 baths | 1 car
**Welcome to Four Seasons — Where Winter Park Living Meets Modern Convenience**This sharp 2-bedroom, 1.5-bath townhome puts you right in the heart of one of Central Florida's most coveted zip codes. With 1,219 square feet of updated, move-in-ready living space, it's the perfect low-maintenance home base for a busy professional who wants style, comfort, and location all in one.The renovated kitchen features granite countertops, wood cabinetry, and all the essentials for weeknight cooking or weekend entertaining. A flexible dining area doubles effortlessly as a home office — because your lifestyle demands options. The living room opens to a private, shaded patio with pavers that offers a quiet escape after a long day.Both bedrooms are generously sized with ample closet space. Practical upgrades are already done for you: newer HVAC and water heater, and updated fixtures throughout.Four Seasons residents enjoy three pools, a fitness center, tennis courts, and tree-lined walkways — resort-style amenities without the resort price tag. Step outside the community and you're minutes from Park Avenue's best restaurants and boutiques, Aloma Avenue shopping, and major corridors including SR 436, 417, and 408.This is Winter Park without the compromise. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)Listing Agent: Ginny Adkins Llc (407-288-6497)
32789 - O6415591 - 1600 LEGION DR, WINTER PARK, FL 32789 4 Days on yellowkey
$3,995,000 | Single Family Home | 5 beds | 5.5 baths | 3 gar
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)Listing Agent: Brian Teach (407-923-9313)
32792 - O6416552 - 1023 WORTHING CT, WINTER PARK, FL 32792 5 Days on yellowkey
$450,000 Reduced | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to this beautifully maintained 3-bedroom, 2-bath home nestled on a quiet cul-de-sac! Featuring a desirable split-bedroom floor plan, this home offers both comfort and privacy. The kitchen includes a convenient breakfast bar, perfect for casual dining and entertaining. Step outside and enjoy true Florida living in the expansive screened lanai overlooking a large, fully fenced backyard filled with lovely flowers and plenty of room to relax or play. The sparkling 26x14 chlorine pool with a 7-foot-deep end is ideal for both entertaining and unwinding. The home also features a side-entry 2-car garage, adding to its curb appeal and functionality. Major updates include a new roof (Nov 2024) and new fence (Dec 2024). Ideally located close to shopping, dining, and with easy access to 417, this home offers the perfect combination of privacy, convenience, and lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)Listing Agent: Yolon Riveiro (321-228-4708)
32792 - S5151826 - 1000 S SEMORAN BLVD #103, WINTER PARK, FL 32792 5 Days on yellowkey
$1,750 | Condo | 3 beds | 2.0 baths
Virtually Staged. Stylish Winter Park Condo Living – Spacious 3-Bedroom Home in a Prime Location! Welcome to 1000 S. Semoran Blvd #103, a beautifully maintained 3-bedroom, 2-bath residence offering comfort, convenience, and an unbeatable Winter Park location. Featuring a bright and open floor plan, this home provides the perfect space for relaxing, entertaining, and enjoying everyday living. The well-designed layout includes spacious living and dining areas, generously sized bedrooms, and a private primary suite for added comfort. The kitchen offers ample cabinet and counter space, making meal preparation easy and enjoyable. Located in the heart of Winter Park, you'll enjoy convenient access to top-rated schools, shopping centers, restaurants, parks, entertainment, and major roadways. Whether you're commuting to work or exploring everything Central Florida has to offer, this location puts you close to it all. This inviting home combines spacious living with exceptional convenience, making it an outstanding rental opportunity. Don't miss your chance to call this Winter Park gem home—schedule your private tour today!
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)Listing Agent: Jacob Hara (407-933-5478)
32789 - O6415941 - 1421 CHAPMAN CIR, WINTER PARK, FL 32789 5 Days on yellowkey
$1,550,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)Listing Agent: Kelly Price (407-645-4321)
32789 - O6413910 - 121 E FAWSETT RD, WINTER PARK, FL 32789 5 Days on yellowkey
$3,490,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
Under Construction. New construction by LUIH Homes, ideally on a charming brick street in one of Winter Park’s desirable locations. Thoughtfully designed with over-the-top quality, exceptional functionality and timeless style, this five-bedroom, five-and-one-half-bath residence offers an outstanding floor plan for everyday living and entertaining. Elegant double entry doors open to a welcoming foyer and a light-filled interior featuring beautiful wood flooring throughout the main living areas and all bedrooms on both levels. The open-concept design seamlessly connects the spacious living room, dining area and chef’s kitchen, creating a warm and inviting atmosphere. Expansive windows and sliding glass doors flood the home with natural light while providing picturesque views of the covered lanai, pool and backyard. The kitchen is beautifully appointed with premium Thermador appliances, including a six-burner gas range with oven, built-in oven and microwave, and a Zephyr under-counter wine refrigerator. Custom cabinetry, generous workspace, and a large walk-in pantry make this kitchen as functional as it is stylish. The first floor also features a private guest suite complete with a walk-in closet and en-suite bath, as well as a dedicated office positioned toward the front of the home with views of the front entrance and driveway. Outdoor living is equally impressive. The expansive 40-by-14-foot covered lanai overlooks the approximately 40-by-15-foot pool and offers a fully equipped summer kitchen with abundant space for lounging, dining and entertaining year-round. Upstairs, the luxurious primary suite serves as a private retreat featuring a spa-inspired bath, oversized custom walk-in closet and access to a covered balcony. Three additional bedroom suites, each with a private bath, provide comfortable accommodations for family and guests. A spacious family/media room and secondary laundry room complete the second level. Enjoy an exceptional Winter Park lifestyle just minutes from the renowned shopping and dining destinations of Park Avenue, Hannibal Square and Winter Park Village. Zoned for sought-after Audubon K-8 and Winter Park High School, this outstanding location also offers convenient access to major hospitals, downtown Orlando, Orlando Executive Airport, Orlando International Airport and major roadways for easy commuting throughout Central Florida.
32792 - O6409708 - 3443 ALLSTON LN, WINTER PARK, FL 32792 5 Days on yellowkey
$299,999 | Townhouse | 3 beds | 2.0 baths | 1 gar
Under contract-accepting backup offers. 3-bedroom, 2-bath SINGLE-story block townhome with garage located in an excellent school district! Recent improvements include a BRAND-NEW ROOF (2025), BRAND-NEW HVAC SYSTEM (June 2026), and BRAND-NEW WATER HEATER (June 2026), all still under warranty! Plus fresh interior paint throughout (June 2026) and new flooring in the rear bedroom (no carpet in the home). With the big-ticket items already completed, this home offers exceptional peace of mind and truly worry-free ownership. The spacious floor plan features soaring living room ceilings, generously sized bedrooms, and a screened rear patio with ceiling fan and lighting, perfect for relaxing or entertaining—all on one level with no interior stairs. Two of the bedrooms feature sliding glass doors providing direct access to the backyard and abundant natural light. In addition to the screened patio, you’ll enjoy a large open patio area ready to become your own private outdoor retreat for grilling, gardening, or entertaining. Enjoy a super low HOA of just $65 per month, which includes access to a community pool just a short walk away, as well as a serene lake with a covered dock and gazebo perfect for relaxing, fishing, or socializing with neighbors. Ideally located near Downtown Winter Park, Park Avenue, Rollins College, Full Sail University, UCF, and Valencia College, with easy access to SR-436 and endless shopping, dining, and entertainment options just minutes away. This home is a true gem offering excellent schools, recent upgrades, a prime location, low HOA fees, and a warm, welcoming atmosphere. Whether you’re a first-time homebuyer, downsizing, or seeking a fantastic investment opportunity, this property checks all the boxes. Don’t miss your opportunity to make it yours!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)Listing Agent: Nikita Ager, Llc (310-800-3100)
32789 - O6415611 - 1220 WOODMERE DR, WINTER PARK, FL 32789 5 Days on yellowkey
$1,700,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Under contract-accepting backup offers. Welcome to 1220 Woodmere Drive, where timeless elegance and modern luxury come together in one of Winter Park’s most coveted neighborhoods. This exceptional 4-bedroom, 3.5-bath residence offers 2,815 square feet of thoughtfully designed living space, blending classic charm with today’s most desirable comforts. The spacious first-floor primary suite serves as a private retreat, complete with dual walk-in closets and a spa-inspired bath designed for relaxation. Rich solid hardwood floors flow throughout the main downstairs living areas, creating warmth and sophistication at every turn. Upstairs, a smart split-bedroom layout provides three additional bedrooms and two full baths, offering privacy and flexibility for family and guests alike. A detached two-car garage adds even more versatility, featuring an expansive bonus room above—perfect as a home office, fitness studio, creative space, or hobby room. Ideally positioned on one of Winter Park’s most sought-after streets, this home places you just moments from the Winter Park Racquet Club, the scenic Chain of Lakes, and the vibrant shops and dining of downtown Winter Park. With top-rated public schools nearby and an unbeatable location, this is a rare opportunity to enjoy the very best of Winter Park living. 1220 Woodmere Drive isn't just a home—it's a lifestyle.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)Listing Agent: John Mcdade (407-721-7275)
32792 - O6416235 - 2304 INAGUA WAY #2304, WINTER PARK, FL 32792 6 Days on yellowkey
$1,750 | Condo | 2 beds | 1.0 baths
Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the established community of Winward Square with access to a community pool and tennis courts, this home offers both convenience and comfort. Don't miss out on this opportunity to live in Seminole County in this lovely property. Sorry Pets are not permitted. *Washer and dryer are in as/is condition and for tenant convenience only *Tenant is required to carry Renters Insurance If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment. *RESIDENTS BENEFIT PACKAGE* Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application
Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)Listing Agent: Francisco Nieves-Taranto (321-248-4149)
32792 - O6415961 - 5894 SHALE CT, WINTER PARK, FL 32792 6 Days on yellowkey
$315,000 | Half Duplex | 2 beds | 2.0 baths | 1 gar
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Talk about location, location, location! Welcome to this beautifully updated and well-maintained 2-bedroom, 2-bathroom, 1-car garage home in Winter Park, perfectly situated in the charming Aloma Park community. Just about 1 mile from the 417 Greenway, this home offers easy access throughout Orlando, while also being walking distance to the Cross Seminole Trail and Cady Way Trailhead—perfect for biking, running, rollerblading, or simply enjoying an active lifestyle. Inside, this move-in-ready home feels bright, warm, and inviting with sandy-toned wood-look tile and laminate flooring that lighten the entire space. The kitchen has been beautifully updated with granite countertops, soft-close cabinets, stainless steel appliances, a new microwave, and ample storage. The popcorn ceilings in the main living areas have been removed and replaced with a clean knockdown finish, giving the home a fresh and updated feel. The bathroom updates are a major highlight: one bathroom has been fully renovated with a walk-in shower, while the second bathroom features a new countertop, new cabinetry, and soft-close cabinets. Additional updates include a 2021 roof, HVAC system from 2016, new water heater, washer and dryer, energy-efficient double-pane windows, energy-efficient French doors, LED fixtures, and solar tubes that fill the home with natural light. There is also attic space for convenient extra storage. The primary suite offers a bonus sunroom/flex space that is insulated and equipped with plexiglass sliders and a mini-split unit hook-up, making it perfect for a home office, greenhouse, playroom, sitting room, or creative space. French doors with built-in blinds lead out to the screened lanai, creating an easy indoor-outdoor flow. Outside, enjoy a beautifully landscaped, fully fenced backyard with a utility shed that has its own breaker—perfect for storage, hobbies, or the handy person in the house. The pavers in the front courtyard and back patio add even more charm and function to the exterior spaces. Aloma Park is a small, quaint Winter Park community with only two cul-de-sac streets, 42 duplex homes, and no through traffic. Residents enjoy access to a community pool, tennis courts, basketball courts, and a clubhouse available to rent for gatherings. Zoned for excellent A-rated Winter Park schools and conveniently located near UCF, Full Sail University, Rollins College, downtown Winter Park, Oviedo, shopping, dining, and major roadways, this home offers the perfect blend of comfort, convenience, and affordability. Hurry to see this Winter Park gem — there’s nothing to do here but bring your furniture!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)Listing Agent: Thomas Nickley, Jr (407-629-4420)
32792 - C7527235 - 1535 LAWNDALE CIR, WINTER PARK, FL 32792 6 Days on yellowkey
$450,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)Listing Agent: Raul Pino (305-662-1502)
32789 - O6415216 - 350 CAROLINA AVE #407, WINTER PARK, FL 32789 6 Days on yellowkey
$2,895 | Condo | 2 beds | 2.0 baths | 1 gar
Experience maintenance-free living in this spacious 2-bedroom, 2-bath condominium offering 1,529 square feet in the gated Park West community in the heart of Winter Park. Located on the top floor, this spacious residence features vaulted ceilings, hardwood flooring, quartz countertops, stainless steel appliances, walk-in closets, a soaking tub, a stacking washer and dryer, and charming Juliet balconies. Residents enjoy exceptional amenities, including a community pool, tennis courts, clubhouse, and an assigned garage parking space. Water service is included in the rent. Park West is across the street from the weekly Winter Park Farmers' Market, and one block from Park Avenue; you'll have easy access to boutique shopping, highly renowned restaurants, the SunRail station, and everything that downtown Winter Park offers. Cats will be considered on a case by case basis with a non-refundable pet fee and monthly pet rent. Prospective tenants are subject to the Park West Condominium Association approval process and associated application fee.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)Listing Agent: Anthony Consalvo (407-599-7070)
32792 - S5150999 - 3045 AARON BURR AVE #12D, WINTER PARK, FL 32792 6 Days on yellowkey
$1,650 | Condo | 2 beds | 2.0 baths
Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access to everything Orlando. Featuring new flooring and a clean, fresh interior, it is ideal for any lifestyle.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)Listing Agent: Angel Ramirez (407-967-5368)
32789 - O6415981 - 1265 ARLINGTON PL, WINTER PARK, FL 32789 6 Days on yellowkey
$879,000 | Townhouse | 3 beds | 3.5 baths | 1 gar
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)Listing Agent: Erika Beerbower (407-758-2727)
32789 - O6415985 - 1521 CAVENDISH RD, WINTER PARK, FL 32789 6 Days on yellowkey
$470,000 | Single Family Home | 2 beds | 1.0 baths | 1 car
Virtually Staged. Located in the heart of Orwin Manor, one of Winter Park’s most beloved historic neighborhoods, 1521 Cavendish Road is a beautifully renovated 2-bedroom, 1-bath home offering 1,042 square feet of thoughtfully updated living space. Positioned between Winter Park, College Park, and Downtown Orlando, residents enjoy convenient access to AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, Park Avenue, Ivanhoe Village, and some of the area's most celebrated dining, shopping, and cultural destinations. Surrounded by mature landscaping, manicured hedges, colorful garden beds, and stately palms, the home's curb appeal reflects the character and pride of ownership found throughout the neighborhood. French front doors open to a spacious foyer that leads into a bright family and dining room combination, where new pine laminate flooring, crown molding, plantation shutters, and updated lighting blend historic character with modern comfort. The renovated kitchen features shaker cabinetry, Silestone countertops, stainless steel appliances, abundant storage, and natural light. Both bedrooms have been thoughtfully updated with new flooring, LED recessed lighting, ceiling fans, and plantation shutters, while the recently renovated bathroom pairs basketweave tile flooring, subway tile, quartz countertops, and classic finishes that honor the home's original style. Outside, the large backyard has been transformed into a private retreat featuring a composite deck, new fencing, mature palms, raised garden beds, steel-edged landscaping, and a paver walkway. Thoughtfully updated while preserving its architectural charm, this home offers a rare opportunity to enjoy historic character in a neighborhood that continues to benefit from the growth, investment, and enduring appeal of Winter Park and Downtown Orlando. Schedule your private tour today.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)Listing Agent: John Goggin (321-332-3000)
32789 - O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 6 Days on yellowkey
$2,250,000 | Single Family Home | 5 beds | 4.5 baths | 2 gar
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)Listing Agent: Nick Mckee (407-913-0171)
32792 - O6415814 - 418 R GILBERT RD, WINTER PARK, FL 32792 6 Days on yellowkey
$4,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools.
Listing is courtesy of: SOTERA LIVING (407-725-9660)Listing Agent: Lianna Dangelo (321-446-3509)
32792 - O6415880 - 3949 COOL WATER CT, WINTER PARK, FL 32792 7 Days on yellowkey FORECLOSURE
$399,900 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Located on a quiet cul-de-sac in Winter Park, this home has the kind of layout and lot that are hard to find at this price point. Vaulted ceilings open up the main living area, and built-in display niches along the wall give the space character you won't find in newer construction. The kitchen has a breakfast bar peninsula and connects to a sunny dining space with a pendant light overhead. The primary suite is generously sized with two windows, a ceiling fan, walk-in closet, and a private bath with a double vanity and soaking tub. A second full bath features detailed tile work and a vanity with granite-look countertops. Additional bedrooms have ceiling fans and solid closet space. Out back is a large covered patio that opens to a fenced yard shaded by mature oak trees, the kind of backyard that actually works for people who want to spend time outside in Florida. There's room to run, entertain, or just let the week decompress. All of this in Winter Park, minutes from Park Avenue dining and shopping, Rollins College, Winter Park Village, and with quick access to I-4 and downtown Orlando.
Listing is courtesy of: ACME REAL ESTATE FLORIDA LLC (407-601-4958)Listing Agent: Regan Jackson (407-421-1420)
32789 - O6415537 - 685 OVERSPIN DR, WINTER PARK, FL 32789 7 Days on yellowkey
$629,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Super Location! Close to Urban Bike trail, Winter Park Village, Dubsdread Golf Course, Advent Health. This home was custom built with large white wood window casing, formal dining room with plenty of natural light, 10 foot ceilings, crown molding, 8 ft doors, upgraded tile, 3 sets of French Doors open to back and so much more. Gas fireplace in the family room with high-top bar seating in the kitchen also featuring upgraded granite countertops, stainless steel appliances including a gas range, and plenty of storage space with 42 cabinets. Oversized laundry room with extra storage space. Downstairs also features a spacious half bath with a new countertop.All 3 bedrooms are Upstairs. Bathrooms all have new Quartz counters from recent renovations. All bedrooms come with large closets. 2nd and 3rd bedrooms are connected with "Jack and Jill' bathroom with 2 separate sinks. Master Bathroom has large walk-in shower and separate Jetted Tub.Long driveway provides access to detached oversized garage in the back. Wrought iron fencing in backyard adds to a wonderfully landscaped yard.Nearby is Rollins College, the Charles Hosmer Morse Museum of American Art, Mead Botanical Garden, Albin Polasek Museum and Sculpture Gardens, the Enzian Theater, and so much more.Winter Park is also home to over 70 parks, all home to various events, festivals and celebrations throughout the year.A quick ride to almost anywhere in central Florida, minutes to Downtown Orlando, Winter Park Village, College Park, and Park Ave, 20 min to Disney World, and plenty of shopping and award-winning restaurants just minutes away! Pictures taken January 2024
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)Listing Agent: Corey Van Dyke (407-897-5400)
32789 - O6414890 - 231 CHELTON CIR, WINTER PARK, FL 32789 7 Days on yellowkey
$4,950,000 | Single Family Home | 4 beds | 6.0 baths | 3 gar
Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)Listing Agent: Joseph Doher (407-203-0007)
32789 - O6415735 - 151 N ORLANDO AVE #238, WINTER PARK, FL 32789 7 Days on yellowkey
$2,750 | Condo | 2 beds | 1.0 baths
Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.
Listing is courtesy of: COLONIALTOWN REALTY (407-896-7300)Listing Agent: Alexander Scures (407-925-5338)
32789 - TB8517242 - 2500 LEE RD #104, WINTER PARK, FL 32789 7 Days on yellowkey
$259,999 | Condo | 2 beds | 2.0 baths
Beautifully renovated and move-in ready 2-bedroom, 2-bath condominium offers thoughtful upgrades and a seamless open layout in one of Winter Park's most desirable lakefront communities. The heart of the home is the fully renovated kitchen (2025), featuring custom, soft close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, a white granite sink, and carefully selected high-end finishes, including antique brass hardware and faucet. Vinyl flooring creates a clean, cohesive look across the residence. Additional recent improvements include: Renovated primary shower featuring Italian porcelain tile and added storage shelving (2026) , Dining room chandelier and bedroom ceiling fans (2026), Fresh paint throughout (2026) Tankless water heater (2025) , New A/C system (2024), professionally serviced in June 2026, Renovated hallway bathroom and added storage shelving (2024). The floor plan offers a bright, open living space with two points of entry and an easy flow between the kitchen, dining, and living areas. Beyond the unit itself, residents enjoy an exceptional list of community amenities. The HOA includes water, trash, Spectrum high-speed internet, cable television with 150+ channels, and access to popular streaming services including Disney+, HBO Max, Peacock, and more. Set along scenic Lake Killarney, the community features a private dock, water access for boating and kayaking, a peaceful courtyard, abundant guest parking, and newly completed landscaping enhancements. The association has also recently completed significant infrastructure improvements to the community's incoming water system, with paving improvements and painting coming soon. A great opportunity to purchase a truly turnkey residence.
Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)Listing Agent: Stephen Hachey (813-863-3948)
32792 - O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 7 Days on yellowkey
$535,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. MULTIPLE OFFERS RECEIVED! Please provide highest and best offers by Tuesday, June 16th at 12:00pm. Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)Listing Agent: Jonathan Cole (407-928-9516)
32789 - O6415098 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$1,429,000 | Single Family Home | 5 beds | 4.0 baths | 2 gar
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 bedrooms, 4 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space. Situated on a charming, tree-lined street, the home combines timeless elegance with modern luxury. The open-concept floor plan features 10-foot ceilings, 8-foot doors, luxury vinyl plank flooring throughout, and an expansive great room with an electric fireplace. The gourmet kitchen is designed to impress with quartz countertops, custom cabinetry, stainless steel appliances, a large center island, and abundant storage. A unique under-stair wine cellar adds character and sophistication, while a first-floor guest suite provides privacy and flexibility. Upstairs, the spacious primary suite overlooks the backyard and pool area and includes a spa-inspired bathroom with dual vanities, a soaking tub, walk-in shower, and generous walk-in closet. Three additional bedrooms comfortable accommodations, including a Jack-and-Jill layout and a private In-suite bedroom. A conveniently located upstairs laundry room completes the second level. Step outside to your private outdoor retreat featuring a beautifully landscaped backyard, sparkling in-ground pool, covered lanai, and summer kitchen with built-in grill—perfect for entertaining year-round. Ideally located just minutes from Winter Park’s renowned shopping, dining, parks, and cultural attractions, this exceptional home offers the rare opportunity to enjoy the benefits of brand-new construction in one of Central Florida’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: KARDOSH REALTY (407-499-4466)Listing Agent: Gilson Rodrigues (407-989-2033)
32792 - O6414862 - 2032 KIMBRACE PL, WINTER PARK, FL 32792 8 Days on yellowkey
$2,188,888 | Single Family Home | 5 beds | 4.0 baths | 2 gar
A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF | Saltwater Pool & Spa | Smart Home | Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled within one of Winter Park's most desirable neighborhoods and just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. Thoughtfully designed with a Zen-inspired aesthetic, the home seamlessly blends clean architectural lines with warm natural elements to create a living experience that feels refined and restorative. From the moment you arrive, an atmosphere of calm surrounds you, offering a peaceful escape while remaining moments from everything Winter Park has. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A stunning semi-floating steel staircase with solid whiteoak treads serves as a dramatic architectural focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining and everyday luxury. A sleek Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, striking marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, expansive dual-entry shower wrapped in marble, semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-caliber outdoor living experience evokes the serenity of a luxury Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Located nearby highly regarded Winter Park schools and less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, this is a sanctuary. A place to unwind, recharge, and experience the very best of Winter Park living.
Listing is courtesy of: SIMPLICITY: A RE BROKERAGE CO (407-920-6020)Listing Agent: Robert Sassos (407-920-6020)
32789 - A4696508 - 1741 GOODRICH AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$3,600 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Virtually Staged. Charming 3-bedroom, 2-bath home in highly desirable historic Winter Park, situated on a large fenced lot with mature oak canopy, lush landscaping, and inviting outdoor living spaces. This well-maintained home offers a spacious living room, separate dining area, screened rear patio, large wooden deck with lighting, and a private fenced backyard perfect for relaxing or entertaining. NOT FURNISHED! The primary suite features two walk-in closets, double vanity sinks, a Jacuzzi tub, and a double walk-in shower. A guest suite with a closet and shared bathroom. The 3rd room has a closet and can be used as a bedroom or office. Additional features include ceiling fans throughout, generous closet space, newer bedroom flooring, fresh interior and exterior paint, a security system ready for activation, washer and dryer in the two-car garage, utility sink, and newly finished epoxy garage flooring. Major updates include roof and A/C replaced in 2021, and the refrigerator, stove, and microwave replaced in 2022. Lawn maintenance, lawn spraying, and pest control are included in the monthly rent. Located near AdventHealth Winter Park, Casa Feliz, Leu Gardens, Rollins College, Park Avenue shopping and dining, Baldwin Park, East End Market, Winter Park Farmers Market, Enzian Theater, city parks, museums, Winter Park Racquet Club, Interlachen Golf & Country Club, YMCA, Winter Park Boat Tours, the Winter Park Chain of Lakes, and Downtown Orlando. Zoned for highly rated local schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High, with many nearby school options. Surrounded by historic homes and multi-million dollar estates, this property offers an excellent opportunity to enjoy the Winter Park lifestyle in a prime location. Lease Terms: Owner pays for lawn maintenance, lawn spraying, and pest control. Tenant is responsible for utilities, cable, and internet. First month’s rent, last month’s rent, and security deposit required. Credit and background check required for each applicant on the lease. Small pets may be considered with owner approval and an additional non-refundable pet fee. No smoking or vaping permitted. Current tenant leaving 7/2026. 24-hour notice to schedule a showing.
Listing is courtesy of: JOHN HARDING REALTY (941-777-3007)Listing Agent: Gunnar Barcomb (941-374-9037)
32789 - O6414821 - 700 MELROSE AVE #K25, WINTER PARK, FL 32789 8 Days on yellowkey
$245,000 | Condo | 1 beds | 1.0 baths
Under contract-accepting backup offers. Bright, beautifully updated 1-bed/1-bath condo with floor-to-ceiling views and a prime walkable location in the heart of Winter Park. The renovated kitchen and bath shine with modern finishes, while expansive windows frame serene, ever-changing views of the lushly landscaped grounds. Set within the sought-after Winter Park Gardens, residents enjoy 8 acres of private tropical gardens, peaceful walking paths, and a resort-style pool — all just steps from Park Avenue's dining, boutiques, and culture. A rare combination of tranquil garden living and unbeatable urban convenience. This is a 55+ community with room for younger owners. Call list agents for details.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)Listing Agent: Olivia Maxwell (407-222-4440)
32792 - O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 9 Days on yellowkey
$519,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
GREAT HOME & GREAT VALUE — add your TLC and DIY and 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)
32792 - O6414770 - 525 S LAKEMONT AVE, WINTER PARK, FL 32792 9 Days on yellowkey
$2,199,900 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Winter Park Luxury Awaits You! Welcome to your dream home—a stunning custom-built luxury residence offering the perfect blend of elegance, comfort, and modern design. Featuring 4 spacious bedrooms and 4 beautifully appointed bathrooms, this masterpiece showcases custom cabinetry and closets throughout, ensuring every space is both functional and refined. The chef’s kitchen is a true showpiece, complete with a coffee bar, walk-in pantry with customized shelving and designer lighting, and seamless flow into the open-concept living and dining areas. A wine room adds sophistication and convenience for the entertainer at heart. Upstairs, enjoy a spacious loft area with a wet bar, perfect for hosting guests or creating an additional entertainment lounge. Step outside to your private outdoor oasis, featuring a heated pool, fireplace, outdoor kitchen, and surround sound system—designed for year-round entertaining and relaxation. This home is pre-wired for security cameras and enhanced by custom landscaping and lighting, offering beauty and privacy from day to night. Located in highly sought-after Winter Park, Florida, near world-class dining, shopping, and top-rated schools. Contact us today for a private showing!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)Listing Agent: Nicole Cates (407-948-6000)
32792 - O6412855 - 3641 OAK VISTA LN, WINTER PARK, FL 32792 9 Days on yellowkey
$475,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. Welcome to Winter Park. VIEW VIRTUAL TOUR! The Original Owner has meticulously cared for this home and the pride of ownership shines through. The real showstopper is your private outdoor oasis! Enjoy Florida’s endless sunshine in the expansive, screened-in back porch and pool area—perfect for year-round gatherings, pool parties, and quiet weekends at home. Have your morning coffee or afternoon cocktails sitting out back on the porch enjoying the birds. This large, fenced 120 x 80-foot yard provides plenty of room for little ones and pets to play, gardening, or simply unwinding. for comfortable Florida living! Perfectly situated in a desirable, close-in location and zoned for award-winning Seminole County schools, this remodeled, one-story home offers the ideal setting for all family households. Step inside and discover an inviting split floor plan featuring 3 spacious bedrooms and 2 modern bathrooms. The formal living and dining rooms create an elegant atmosphere for entertaining, while the stunning remodeled kitchen is light and bright, complete with contemporary finishes and new appliances. Relax in the cozy family room, where a charming brick wood-burning fireplace adds warmth and ambiance on cool evenings. You do have formal areas that have a multitude of options for space where YOU Need it. Once you get to the kitchen you will be amazed with the sleek white brand new cabinets with trendy quart counters and a gorgeous back splash. WOW! You can enjoy yourself while you are at the sink and watch whatever is going on in the backyard. No expense spared with banks of drawers too. Additional highlights include a 2-car garage, newer windows for energy efficiency, and NO HOA—giving you the freedom to truly make this home your own. Bring your camper, toys because you have loads of room in the backyard to work on multiple projects. Roof and A/C are 2021 adding to peace of mind with your insurance 4 point inspection. Garage is even 24x21. With ample parking, an amazing outdoor space, and proximity to top-rated schools, shopping, dining, and major highways, 3641 Oak Vista Lane delivers the ultimate Florida lifestyle for your family inside the home and outside. You deserve your own Backyard paradise. Don’t miss the opportunity to make this move-in ready Winter Park gem your forever home. Seminole County schools complete the package. Schedule your private tour today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)Listing Agent: Laurie Cain (407-484-9944)
32789 - O6411927 - 2500 LEE RD #220, WINTER PARK, FL 32789 9 Days on yellowkey
$199,900 | Condo | 2 beds | 1.0 baths
**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 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.
32789 - S5151458 - 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 9 Days on yellowkey
$735,000 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Under contract-accepting backup offers. Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of the Winter Park Chain of Lakes along Park Avenue. Families will secure unparalleled long-term educational value with zoning for highly rated schools including Audubon Park K-8 and Winter Park High School. Stepping inside, the home's authentic character is immediately felt, anchored by beautiful real heart of pine wood flooring that flows seamlessly throughout the entire 1,739-square-foot livable layout. The private primary suite serves as a true retreat, complete with a walk-in closet and a sunlit office/flex space ideal for a remote work setup. The home also features an indoor wood-burning fire pit, adding warmth and character to the living space. Natural gas is available on-site, adding efficiency and flexibility for future upgrades, and the home benefits from a new roof installed in 2023. Situated on a rare, sweeping 9,525-square-foot lot that holds substantial land value on its own, the property offers a massive backyard oasis with ample space for a future pool and endless possibilities for outdoor living. A detached garage provides valuable storage and presents excellent potential for conversion into an accessory dwelling unit (ADU), guest house, home office, or income-producing space, subject to buyer verification and local regulations. Adding even more flexibility, an incredible attic space/storage within the home offers the opportunity to create a unique bonus room, studio, office, or creative retreat. Whether you're seeking a charming historic residence, a highly walkable lifestyle, or a property with exceptional long-term upside, this rare Winter Park offering combines character, location, land value, and future potential in a way that is increasingly difficult to find.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)Listing Agent: Justin Jodha (689-250-8606)
32792 - O6414031 - 1016 MANCHESTER CIR, WINTER PARK, FL 32792 9 Days on yellowkey
$417,500 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Virtually Staged. Welcome to this move-in-ready Winter Park home, where major updates have already been completed and everyday convenience is right around the corner. Enjoy peace of mind with a new roof (2020), A/C (2021), water heater (2021), updated plumbing (2021), and an updated electrical panel. Inside, the flexible floor plan offers a living room, family room, and dedicated dining space, providing plenty of room to relax, entertain, or work from home. The main living areas feature 18" tile flooring, while all bedrooms boast upgraded luxury vinyl plank flooring. The split-bedroom layout provides added privacy for family members and guests. The kitchen is designed for both functionality and style, featuring upgraded classic cabinetry, granite countertops, a stainless steel refrigerator, a large sink, and a window overlooking the screened lanai and backyard. Additional storage includes a convenient hallway coat closet. Both bathrooms have been refreshed with updated vanities, showers, and fixtures. One of the standout features of this home is the expansive screened lanai, measuring approximately 12' x 28' and complete with an insulated ceiling, creating an inviting space that feels like an additional living area year-round. Step outside to the fully fenced backyard, where you'll find plenty of room to add a swimming pool, create a garden, or simply enjoy outdoor living. Additional highlights include a 2-car garage, attic storage, no HOA, and zoning that allows for long-term rental opportunities. Conveniently located just around the corner from a new shopping plaza featuring Foxtail Coffee, Kelly's Homemade Ice Cream, and SoBol, this home also offers easy access to daily essentials with multiple shopping, dining, and grocery options, including Publix, within a 5-mile radius. The 417 Expressway entrance is approximately 3.5 miles away, making commuting throughout Central Florida a breeze. Enjoy all that Winter Park has to offer, with the shops, restaurants, and SunRail station of Historic Park Avenue located approximately 6 miles from your front door. This well-maintained home combines updated systems, versatile living spaces, and a prime location with no HOA restrictions—a rare opportunity in Winter Park.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)Listing Agent: Kristin Duncan (407-274-5911)
32789 - O6414807 - 650 DOUGLAS AVE, WINTER PARK, FL 32789 9 Days on yellowkey
$550,000 | Single Family Home | 3 beds | 2.0 baths
Welcome to 650 Douglas Avenue, a beautifully updated 3-bedroom, 2-bath home ideally situated in one of Winter Park’s most desirable locations. This move-in-ready residence features luxury vinyl plank flooring throughout, quartz countertops, updated bathrooms with upgraded tile, modern lighting and plumbing fixtures, fresh interior paint, and a complete appliance package including washer and dryer. Beyond the home’s tasteful updates, the location truly sets it apart. Enjoy being just minutes from the vibrant shops, restaurants, and community events of Hannibal Square and renowned Park Avenue. Spend weekends exploring Winter Park’s award-winning dining, boutique shopping, farmers markets, museums, and picturesque parks, all just moments from your doorstep. This home offers the perfect combination of modern updates, walkable convenience, and the unmatched Winter Park lifestyle. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)Listing Agent: Danielle Funaro (407-276-0326)