Winter Park Homes for Sale and Rent by Zip Code

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Newest Winter Park Homes by Zip Code

  • 1871 CASSELWOOD ST, WINTER PARK, FL - MLS# O6404306

    32792 - O6404306 - 1871 CASSELWOOD ST, WINTER PARK, FL 32792
    Just Added on 05/02/2026 7:07PM

    $424,900 | Townhouse | 4 beds | 2.5 baths | 2 gar

    Beautifully updated, move-in ready home in Winter Park with space, comfort, and a clean, modern feel throughout. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, fresh interior finishes, new recessed lighting, and updated ceiling fans, all combined with a bright and functional layout. As you enter, you are welcomed by a custom wood decorative accent wall that adds warmth and character. Just behind the wall, a renovated half bathroom is conveniently located on the first floor. The kitchen is one of the main features of the home, fully renovated with custom green cabinetry, quartz countertops, a farmhouse sink with a modern faucet, gold hardware, and a clean contemporary backsplash. The space includes abundant cabinetry plus a pantry for additional storage and comes equipped with new stainless steel appliances including refrigerator, range, and range hood. Pendant lighting and chandelier details add a designer touch. The living area includes a modern electric fireplace and sliding doors that open to a screened patio, creating a comfortable indoor-outdoor flow. The outdoor space provides a private setting with a low-maintenance yard and room to relax or personalize. Upstairs, you will find all bedrooms along with a conveniently located laundry area. The primary suite is oversized and designed as a true retreat, featuring dual pendant lighting and great natural light. The primary bathroom is fully renovated with a freestanding soaking tub, double vanity, glass-enclosed walk-in shower with rainfall shower head, and modern finishes. The suite also includes dual closets for added functionality. Secondary bedrooms are well-sized and provide flexibility for family, guests, office, or additional living space. Additional improvements include a new front door, updated lighting throughout, and thoughtful design details that make this home feel clean, cohesive, and move-in ready. Located in the Villas of Casselberry community, this property has a low HOA (buyer to verify) with access to a community pool and sidewalks. Conveniently situated near major roads, shopping, dining, Full Sail University, Rollins College, UCF, and just minutes from Downtown Orlando. Move-in ready with extensive updates and a functional layout, this is a strong opportunity in the Winter Park market.

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
    Listing Agent: Alexa Monasterio Flores (786-915-9294)

  • 7473 BELLE RIVER CT #16, WINTER PARK, FL - MLS# O6404333

    32792 - O6404333 - 7473 BELLE RIVER CT #16, WINTER PARK, FL 32792
    Just Added on 05/02/2026 5:36PM

    $1,800 | Townhouse | 3 beds | 2.5 baths

    Welcome to this beautiful 3-bedroom, 2.5-bath townhome featuring modern finishes and a serene setting. Enjoy cooking in the kitchen with elegant granite countertops, durable tile flooring downstairs, and stylish luxury vinyl plank flooring upstairs. Step outside to your private fenced patio with peaceful conservation views, perfect for relaxing or entertaining. Available NOW! **All Remi Emerson Residential tenants are enrolled in the Resident Benefits Package (RBP) for an additional $50 a month which includes your $100,000 tenant liability insurance, quarterly HVAC air filter delivery, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, plus on-demand pest control! If you have an animal/pet you must click on the Pet Screening link in the application.**Security deposit is due upon lease signing. The first full month's rent is due 1 week prior to move in date. The 2nd month of rent is prorated. Every person 18 yrs or older must fill out an application. Please upload your last 2 months of paystubs in your application. Only complete applications will be considered. A one time admin fee of $250 due upon approval. A lease renewal fee of $125 after 1 year.**

    Contact Yellowkey Agent

    Listing is courtesy of: REMI EMERSON RESIDENTIAL (407-490-1848)
    Listing Agent: Shelley Davis (407-625-3489)

  • 1630 LASBURY AVE, WINTER PARK, FL - MLS# O6404300

    32789 - O6404300 - 1630 LASBURY AVE, WINTER PARK, FL 32789
    Just Added on 05/02/2026 4:59PM

    $2,750,000 | Single Family Home | 5 beds | 4.0 baths | 3 gar

    The seller has just completed a full renovation. Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive 18 x 40 pool. The layout features generous common areas, including a large family room, a formal living room, a separate dining room, a kitchen with an adjacent breakfast room, a dedicated home office, a loft-style office or playroom, and a cozy home theater located above the garage. The kitchen, primary bedroom, and both the family and living rooms provide stunning views of the pool and backyard. The three-car garage offers ample space for large vehicles. Beyond the pool, you’ll find a charming gazebo and a fully equipped outdoor kitchen. Built with block and stucco construction and topped with a durable tile roof designed to last up to 100 years, this home boasts incredible durability and aesthetic appeal. Combining the feel of new construction with a rare, expansive lot in a well-established neighborhood, it provides privacy, mature landscaping, and modern elegance all in one.

    Contact Yellowkey Agent

    Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
    Listing Agent: Teresa Chris Harralson (404-229-8737)

  • 3627 SEAGRAPE DR, WINTER PARK, FL - MLS# O6403218

    32792 - O6403218 - 3627 SEAGRAPE DR, WINTER PARK, FL 32792
    Just Added on 05/02/2026 11:19AM

    $339,000 | Single Family Home | 3 beds | 2.0 baths | 1 car

    Welcome to 3627 Seagrape Drive, a move-in ready home for sale in Winter Park featuring NO HOA, an oversized lot, and energy-efficient upgrades in a prime Central Florida location. This 3-bedroom, 2-bath home offers an updated kitchen with granite countertops, stainless steel appliances, tile flooring throughout, crown molding, and indoor laundry for everyday convenience. Major improvements include a 2019 roof and solar panels, helping reduce energy costs. The large backyard provides rare space to expand, entertain, or create your own outdoor retreat. Ideally located just minutes from Costco Wholesale, Park Avenue, dining, shopping, and major highways, this property is perfect for buyers searching Winter Park FL homes for sale with land, updated features, no HOA, and strong long-term value or investment potential.

    Contact Yellowkey Agent

    Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
    Listing Agent: Kelly Sue Stonebreaker (321-228-3974)

  • 1438 TIERRA CIR, WINTER PARK, FL - MLS# O6403855

    32792 - O6403855 - 1438 TIERRA CIR, WINTER PARK, FL 32792
    Just Added on 05/02/2026 8:56AM

    $525,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
    Listing Agent: Tony Nicolas (630-514-9342)

  • 4571 KAWILLA CREST PL, WINTER PARK, FL - MLS# O6400672

    32792 - O6400672 - 4571 KAWILLA CREST PL, WINTER PARK, FL 32792
    1 Day on yellowkey

    $899,999 | Single Family Home | 6 beds | 5.0 baths | 2 gar

    Welcome to this beautifully updated home located in the Winter Park area with a Private Mother in Law Suite! This property has been thoughtfully upgraded throughout, offering peace of mind and modern living at its finest. Major system updates include a roof replaced in 2019, solar installed in 2020 (paid off at closing), new electric water heater (2026), and both AC units replaced, providing efficiency and long-term savings. The home also features some brand-new windows (2026), fresh interior and exterior paint, and enhanced curb appeal with stone accents (2016), pavers (2021), and a professionally installed retaining wall with French drainage (2021). Inside, you’ll find a fully remodeled kitchen (2023) equipped with a double oven (2025) and newer refrigerator (2022), perfect for everyday living and entertaining. The home has two fully remodeled bathrooms (2026) and updated vinyl flooring upstairs (2024) for a clean, modern look. Additional upgrades include a laundry sink (2019) and washer and dryer (2019). A standout feature of this home is the private mother-in-law suite, offering incredible flexibility for multigenerational living or potential rental income. This suite includes freshly painted walls, a full kitchen, stackable washer and dryer, spacious bedroom, and a full bathroom with walk-in shower. This move-in ready home combines major upgrades, functional space, and versatility all in a great location near shopping, dining, and all other needs. Close to UCF, Disney, I-4 and anywhere else you want to go in Central Florida! Don’t miss your opportunity to own this exceptional property, schedule your private showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)
    Listing Agent: Jeremy Toro (928-503-5659)

  • 1351 MAGNOLIA AVE, WINTER PARK, FL - MLS# O6404105

    32789 - O6404105 - 1351 MAGNOLIA AVE, WINTER PARK, FL 32789
    1 Day on yellowkey

    $3,100,000 | Single Family Home | 5 beds | 4.5 baths | 2 gar

    Under Construction. Just completed and ready to impress, this stunning custom-built residence delivers elevated design and effortless luxury in one of Winter Park’s most sought-after locations. Featuring 5 bedrooms and 4.5 bathrooms, this home blends timeless architecture with a fresh, curated aesthetic. From the moment you step inside, you’re greeted by warm wood flooring, custom millwork, and designer lighting that create a sophisticated, inviting atmosphere. The open-concept layout flows beautifully, centered around a showpiece kitchen with custom cabinetry, premium finishes, and an oversized island that anchors the space—perfect for gathering and entertaining. The great room is highlighted by a striking fireplace wall, adding depth and character. The first-floor primary suite offers a serene, private retreat, while a dedicated office with a full bath provides flexibility for guests or a refined work-from-home space. Upstairs, spacious secondary bedrooms and additional living areas offer comfort and privacy for family and visitors. Step outside to your own resort-style escape, complete with a sparkling pool, covered lanai, and fully equipped summer kitchen designed for seamless indoor-outdoor living. Ideally located just minutes from Park Avenue, top-rated schools, dining, and shopping, this newly completed home is a rare blend of style, comfort, and location.

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
    Listing Agent: Nick Mckee (407-913-0171)

  • 2829 ALOMA, WINTER PARK, FL - MLS# O6404107

    32792 - O6404107 - 2829 ALOMA, WINTER PARK, FL 32792
    1 Day on yellowkey

    $579,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Just Listed – 2829 Aloma Avenue, Winter Park This is the one you’ve been waiting for. A completely remodeled home with a private pool in one of the most desirable areas of Central Florida—all for under $600,000. Enjoy the perfect blend of modern upgrades and unbeatable location, just minutes from top-rated restaurants, shopping, excellent schools, and everything that makes Winter Park so special. 4 Bedrooms + Den 2 Bathroom 1,821 Sq Ft Private Pool (Resurfaced) + New Pump Fully Renovated Homes like this don’t come around often—whether you’re looking for your primary residence or a smart investment, this property checks every box. If you want a home that delivers both lifestyle and location, this is your opportunity. ?? Message me today for more details or to schedule your private showing before it’s gone!

    Contact Yellowkey Agent

    Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
    Listing Agent: Roberto Silva (407-493-3683)

  • 2237 WOODCREST DR, WINTER PARK, FL - MLS# O6404115

    32792 - O6404115 - 2237 WOODCREST DR, WINTER PARK, FL 32792
    1 Day on yellowkey

    $490,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Value is in the land—an incredible opportunity in the highly desirable Winter Park school district! This property offers a fresh canvas to design and build your dream home exactly the way you envision it. Ideally located just minutes from Baldwin Park, Park Avenue, Full Sail University, and UCF, you’ll enjoy convenient access to some of the area’s best shopping, dining, entertainment, and lifestyle amenities. Whether you’re looking to create a personal retreat or invest in a prime piece of real estate, this location delivers both charm and potential. Don’t miss your chance to secure a homesite in one of Central Florida’s most sought-after areas! Value is in the land

    Contact Yellowkey Agent

    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
    Listing Agent: Nicole Howell (321-217-7918)

  • 7474 ALOMA PINES CT, WINTER PARK, FL - MLS# O6402089

    32792 - O6402089 - 7474 ALOMA PINES CT, WINTER PARK, FL 32792
    1 Day on yellowkey

    $2,400 | Townhouse | 3 beds | 2.5 baths | 1 gar

    Great 3 bedroom 2.5 bath townhouse. 1 car garage with two drive way spots.

    Contact Yellowkey Agent

    Listing is courtesy of: OAK HOLLOW PROPERTIES (407-949-8809)
    Listing Agent: Jakki Kim (407-949-8809)

  • 1864 GRINNELL TER, WINTER PARK, FL - MLS# O6403822

    32789 - O6403822 - 1864 GRINNELL TER, WINTER PARK, FL 32789
    1 Day on yellowkey

    $1,599,000 | Single Family Home | 5 beds | 3.5 baths | 2 gar

    Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the home, the chef’s kitchen blends elegance and function with gleaming stainless steel appliances, crisp white cabinetry, granite countertops, and a well-appointed Butler’s pantry with a dedicated bar, creating a sophisticated setting for effortless entertaining. Integrated smart features further elevate daily living, including an intercom system for seamless communication, electronic blackout curtains for instant privacy and ambiance, and thoughtful, layered lighting throughout. The magazine-worthy primary bath—featured in Florida Home—feels like a private spa retreat, with floor-to-ceiling back-lit mirrors, a self-cleaning smart toilet with bidet, a custom Barclay soaking tub with black matte exterior, and Calcutta gold marble countertops and backsplash. These luxe finishes are anchored by an oversized chevron pattern tile by Crossville in Ice White, a throwback diamond-pattern shower floor, and a sculptural Kuzco LED chandelier that completes the space with dramatic flair. Expansive living areas open to resort-inspired outdoor spaces where a heated saltwater pool and spa, private mini-golf green, and a summer kitchen with tongue-and-groove wood ceiling create a true indoor-outdoor sanctuary. Velux solar-powered skylights with acoustic rain sensors that automatically close at the first sign of rain, a Mosquito NIX misting system, comprehensive surveillance, and electronic private gated access provide both comfort and peace of mind. Natural gas service and a dedicated hook-up for a whole-house generator underscore the home’s emphasis on performance and preparedness. Crafted for those who expect uncompromising quality, this Winter Park residence is more than a home—it is a refined sanctuary where architectural presence, rich materiality, and thoughtful technology converge in one coveted address.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
    Listing Agent: Robyn Brehne-Glass (407-474-4038)

  • 1981 BLUE RIDGE RD, WINTER PARK, FL - MLS# O6402961

    32789 - O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789
    1 Day on yellowkey

    $1,150,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and kitchen are arranged in a way that supports an open and functional feel, making the home especially appealing for hosting and daily routines alike. The family room adds valuable extra living space and creates a natural hub for movie nights, casual gatherings, or a second lounge area. The floorplan also shows a sun room extending off the family room, giving the home even more flexibility for relaxing, hobbies, or enjoying a bright bonus space with views of the backyard. The bedroom layout is thoughtfully separated from the main entertaining areas, offering privacy and comfort. The primary suite is positioned apart from the secondary bedrooms and includes its own bath and closet space, creating a peaceful retreat within the home. Three additional bedrooms provide flexibility for guests, a home office, or changing household needs. Outside, the open patio and private yard add to the home’s lifestyle appeal, creating space to enjoy outdoor dining, weekend get-togethers, gardening, or quiet mornings in the Florida sunshine. Together with the interior layout, these outdoor features help make the home feel both versatile and welcoming. Located in Winter Park, the property is set in a highly desirable area known for its established residential feel, attractive surroundings, and convenient access to shopping, dining, parks, and everyday amenities. The neighborhood adds to the home’s appeal by offering both comfort and accessibility in one of Central Florida’s most sought-after locations. **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.**

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
    Listing Agent: Thomas Nickley, Jr (407-629-4420)

  • 7340 SWALLOW RUN #7340, WINTER PARK, FL - MLS# O6402679

    32792 - O6402679 - 7340 SWALLOW RUN #7340, WINTER PARK, FL 32792
    1 Day on yellowkey

    $1,500 | Condo | 2 beds | 2.0 baths

    Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

    Contact Yellowkey Agent

    Listing is courtesy of: METRO CITY REALTY (407-237-3331)
    Listing Agent: Bobby Mills (321-946-1119)

  • 653 SYMONDS AVE, WINTER PARK, FL - MLS# O6400011

    32789 - O6400011 - 653 SYMONDS AVE, WINTER PARK, FL 32789
    1 Day on yellowkey

    $3,200 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    Charming 3BR/2.5BA single-family home in desirable Winter Park! Interior features include ceramic tile & laminate flooring, ceiling fans, and a bright kitchen with breakfast bar/kitchen island and stainless-steel appliances. Washer/dryer and major kitchen appliances included. Conveniently located near Hannibal Square, Park Ave, Central Park, Rollins College, the Winter Park Community Center, and the Farmers’ Market. Enjoy classic Florida curb appeal with a welcoming front porch and balcony, plus a functional layout perfect for everyday living and entertaining. Lease term 12 months. $75 application fee each adult. Pets considered with owner approval (pet fees/deposit may apply). Renters Insurance required. Great opportunity to live in one of Central Florida’s most desirable areas. Schedule your showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
    Listing Agent: Alessandra Oliveira (305-788-0825)

  • 450 LAKEWOOD DR, WINTER PARK, FL - MLS# O6403490

    32789 - O6403490 - 450 LAKEWOOD DR, WINTER PARK, FL 32789
    1 Day on yellowkey

    $2,500,000 | Single Family Home | 5 beds | 5.0 baths | 3 gar

    Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

    Contact Yellowkey Agent

    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
    Listing Agent: Vonda Fields (321-438-6906)

  • 3371 RIVER VIEW WAY #46, WINTER PARK, FL - MLS# O6403947

    32792 - O6403947 - 3371 RIVER VIEW WAY #46, WINTER PARK, FL 32792
    1 Day on yellowkey

    $205,000 | Condo | 3 beds | 2.5 baths

    Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved parking spots included. The HOA covers the community pool, water, trash, grounds maintenance, and structural upkeep, making this a truly low-maintenance lifestyle. Pets welcome. Hidden Oaks lives up to its name with lush, mature landscaping throughout. Unbeatable location — minutes from Full Sail University, UCF, and Valencia College, with easy access to major Central Florida employers. Downtown Winter Park's dining, shopping, and Park Avenue charm are all within reach. Properties in this community move quickly — schedule your showing today.

    Contact Yellowkey Agent

    Listing is courtesy of: REALTY ONE GROUP EVOLVE (386-368-7222)
    Listing Agent: Safiya Bourne Llc (689-249-1999)

  • 1821 PINETREE RD, WINTER PARK, FL - MLS# O6395725

    32789 - O6395725 - 1821 PINETREE RD, WINTER PARK, FL 32789
    1 Day on yellowkey

    $6,997,000 | Single Family Home | 5 beds | 6.5 baths | 2 gar

    Set on over half an acre along the shores of Lake Maitland in the heart of the coveted Vias, this exceptional residence by Modish Homes is both a former 2018 Parade of Homes winner and a standout example of Winter Park luxury living. From the moment you enter, a dramatic two-story foyer sets the tone, drawing your eye through to the main living space where a statement wood-burning fireplace anchors the room and expansive glass frames breathtaking views of the water beyond. Every space has been thoughtfully designed to maximize both scale and sightlines, creating an effortless connection between indoors and the natural beauty outside. The home features touches of Walnut floors, detailing and doors, bringing warmth throughout. At the center of the home, the chef’s kitchen is both refined and functional, featuring custom cabinetry, a full suite of Dacor appliances, and an oversized walk-in pantry. A striking wet bar with a glass wine wall adds a layer of sophistication, ideal for entertaining. The dining room is equally impressive, offering panoramic lake views and seamless access to the outdoor living areas. The main-level primary suite is a true private retreat, highlighted by chevron-pattern tile flooring and a spa-inspired bath complete with dual vanities, designer lighting, a freestanding soaking tub, and an expansive walk-in shower. The main level also includes two additional guest suites and a glass-enclosed office, offering both comfort and flexibility. Upstairs, two more bedrooms are complemented by a spacious loft and a large balcony that captures sweeping views of the lake. Designed to rival a private resort, the outdoor living experience is nothing short of exceptional. A fully equipped summer kitchen, resort-style pool and spa, two outdoor showers, and expansive green space create a setting that is both functional and visually stunning. A private viewing dock overlooks the water or reconfigure it to a boat dock, allowing you to fully embrace life on the lake while enjoying views of the iconic Isle of Sicily. Beyond the property, the lifestyle is equally compelling. Additional features include a full Control4 home automation system, sauna, and an expansive double-entry driveway providing ample parking. Located just minutes from the boutiques, dining, and cafés of Park Avenue, and within close proximity to Kraft Azalea Garden and the Winter Park Racquet Ball Club, this home offers the perfect balance of privacy and convenience. This is truly a one-of-a-kind opportunity to own a true showpiece on the Winter Park Chain of Lakes.

    Contact Yellowkey Agent

    Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
    Listing Agent: Christopher Christensen (407-312-8003)

  • 1813 HARLAND PARK DR, WINTER PARK, FL - MLS# O6403483

    32789 - O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789
    1 Day on yellowkey

    $1,995,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar

    Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.

    Contact Yellowkey Agent

    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
    Listing Agent: Marystuart Day (407-620-8683)

  • 3282 OAK LAKE PL #3282, WINTER PARK, FL - MLS# O6403912

    32792 - O6403912 - 3282 OAK LAKE PL #3282, WINTER PARK, FL 32792
    1 Day on yellowkey

    $169,500 | Condo | 2 beds | 1.5 baths

    Welcome to Hidden Oaks! This beautifully updated 2-story condo offers the perfect blend of style and affordability. Featuring a fresh kitchen, renovated bathroom, and new flooring throughout, this move-in-ready home includes an in-unit washer/dryer for ultimate convenience. As a desirable end unit, you’ll enjoy extra privacy and a peaceful view of the adjacent conservation area. Relax on your private patio, complete with additional outdoor storage. Bonus: Your HOA dues cover water and trash service! This Winter Park steal won’t last—schedule your showing today.

    Contact Yellowkey Agent

    Listing is courtesy of: BUSBY REALTY LLC (407-529-6952)
    Listing Agent: Chad Busby (407-529-6952)

  • 525 OLOLU DR, WINTER PARK, FL - MLS# S5148431

    32789 - S5148431 - 525 OLOLU DR, WINTER PARK, FL 32789
    1 Day on yellowkey

    $515,000 | Single Family Home | 3 beds | 3.0 baths | 2 car

    Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location, and a home that is ready to be enjoyed from day one while maintaining long term upside.

    Contact Yellowkey Agent

    Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)
    Listing Agent: Gisela Rojas (407-881-5278)

  • 1018 BRADFORD DR, WINTER PARK, FL - MLS# O6403259

    32792 - O6403259 - 1018 BRADFORD DR, WINTER PARK, FL 32792
    2 Days on yellowkey

    $549,000 | Single Family Home | 5 beds | 3.5 baths | 2 gar

    LOCATION LOCATION! Welcome to this beautifully Updated and Meticulously Maintained Split 5-Bedroom, 3-Full Bathroom Floor Plan, Pool Home with No HOA in highly desirable Winter Park in Seminole County. Situated on an almost one-half-acre lot, this exceptional, spacious residence offers the perfect blend of comfort, privacy, and functionality. Enter the welcoming Foyer into the home's flexible layout with multiple living areas for family work and play designed to be personalized for your needs, with generous living areas, great floorplan flow, and abundant natural light throughout. The Living Room is open with lovely, large arched windows leading to the open Dining Room that looks through the Florida Room to the Backyard Pool. The Remodeled Kitchen in the Family Room with a white-washed masonry brick wood-burning fireplace is the heart of the home. Relax and enjoy a cosy fire on cooler days. The Remodeled Kitchen now features Wood 42" soft close cabinetry to the ceiling, Quartz countertops, stylish backsplash Tile, a coffee station, and Stainless Steel Appliances. The large Florida Room anchors the back of the home with windows that bring the outside indoors. This is the perfect place to eat breakfast and lunch! The Primary Master Suite has an Ensuite Bathroom with a Walk-in Closet, a Separate Make-up Vanity, a Granite-topped bathroom Cabinet with a tiled step-in shower. The Master has sliding glass doors opening into the Florida Room. The four Secondary Bedrooms are generous in size, have ceiling fans, and have built-in closets. Two Bedrooms share an Updated Jack and Jill Bathroom. The other two Bedrooms use the Updated Pool/Hall Bathroom. These two Bedrooms are being used as an Office and a Craft/Sewing Room. How will these rooms function for you? Perhaps they will be an Office, Game Room, Play Room, Workout Room, or a multi-generational Suite. The Home has been freshly painted both outside and inside, with the flooring being tile and vinyl for easy cleaning. No carpet here! The expansive backyard is a standout! It is fenced, with a very large, crystal clear pool that is surrounded by a cool deck patio with Palm Trees. The private lawn is expansive, perfect for games, gardening, family fun, and entertaining. The Updated Features of the home include: Remodeled Kitchen and three Bathrooms, Re-plumbed 2026, New Water Heater 2026, Electric/Mechanical Replaced 2022, Roof 2021, HVAC 2018, and Paint Inside and Outside 2026, DOUBLE PANE WINDOWS. This home is just minutes from some of Florida's Best public and private schools, local shopping, Winter Park Avenue Shoppes and Restaurants, Rollins College, major streets, and highways. Contact me to view this well-maintained, move-in-ready, spacious home today. Let's Work Together!

    Contact Yellowkey Agent

    Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
    Listing Agent: Janie Harris Pa (417-848-7333)

  • 1437 MILLER AVE, WINTER PARK, FL - MLS# O6403858

    32789 - O6403858 - 1437 MILLER AVE, WINTER PARK, FL 32789
    2 Days on yellowkey

    $750,000 | Single Family Home | 5 beds | 4.0 baths

    A rare infill opportunity in one of Central Florida's most desirable communities. This 0.32 acre double lot is zoned R-2 and subdivides into two buildable parcels, each ready for a custom single-family residence or duplex, offering up to four doors in a market where new construction consistently performs. Winter Park is a proven, high-demand submarket with limited land supply, top-rated schools, and strong price-per-square-foot on finished product. The location offers easy access to 17/92, Park Avenue, Rollins College, and the established neighborhood character that defines the best of Winter Park living. Opportunities like this are increasingly scarce as the city continues to fill in. Contact us today to discuss lot dimensions, zoning details, and next steps.

    Contact Yellowkey Agent

    Listing is courtesy of: ORLANDO REAL ESTATE LLC (321-217-8572)
    Listing Agent: Rodger Marty (321-217-8572)

  • 3374 HAMLET LOOP, WINTER PARK, FL - MLS# O6403488

    32792 - O6403488 - 3374 HAMLET LOOP, WINTER PARK, FL 32792
    2 Days on yellowkey

    $370,000 | Single Family Home | 3 beds | 2.5 baths | 1 gar

    Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining room flow into the kitchen, where you’ll find lots cabinet storage, eat in space, and a view out to the backyard. The primary suite is conveniently located on the main floor, featuring generous windows that bring in natural light, a walk-in closet, and an updated en suite bath. A half bath downstairs adds convenience for guests. Upstairs, two spacious bedrooms share a full bath, offering comfortable separation from the main living areas. The Villas of Casselberry community has a pool for you to enjoy. The location places you just minutes from Park Ave’s shops, dining, events and great parks. With easy access to major roads and a central location close to Rollins, UCF, Full Sail and downtown Orlando, this home offers both comfort and connectivity. If you’ve been looking for space, privacy, and a well located Winter Park address, this one is worth seeing in person. Schedule your showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
    Listing Agent: Barrett Spray (407-927-3650)

  • 688 BRECHIN DR, WINTER PARK, FL - MLS# O6403080

    32792 - O6403080 - 688 BRECHIN DR, WINTER PARK, FL 32792
    2 Days on yellowkey

    $724,900 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Discover one of the sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin Park, and chef-driven local restaurants in Audubon Park. Kenilworth Shores isn't just a location, it's a community, and this four-bedroom, two-bath Florida ranch is your family's invitation to join. At nearly 1,600 square feet, this home provides charm, function and thoughtful design with upgraded LVP flooring flowing throughout the easy layout. Old world brick detailing gives the exterior genuine curb appeal, while a thoughtfully renovated interior delivers a ready-to-move-in home. A gorgeous brick fireplace anchors an open kitchen, family and dining room combination, with loads of natural light and function to entertain in style. The kitchen is outfitted with white shaker custom cabinetry, granite counters, a soft glass tile backsplash, stainless steel appliances and glass pendant lighting over bar seating. A desirable split-bedroom plan provides privacy for guests, while the primary suite opens to the backyard and includes a completely renovated main bath. The flexible fourth bedroom is outfitted with a custom-designed built-in Murphy bed system with flanking closets and storage. Sitting off the primary living area, this bedroom provides options to fit flexible needs such as home office, guest room, playroom or secondary family space. Go into the backyard and experience your personal Florida oasis with a screened covered porch and grand Florida pool to cool off in the heat of summer. The surrounding, spacious yard is adorned with artificial turf (beautiful, durable and effortlessly low maintenance), complete with a putting green that will make this yard the destination for every playdate, summer barbecue or birthday party. Completed upgrades include new roof (2021), resurfaced pool (2021), new irrigation and well (2022), new wood fence (2023), new dishwasher and built-in microwave (2023), HVAC (late 2023), new washer and dryer (2024), and new pool pump motor (2025). The best part of this special neighborhood is the connected community. Zoned for Brookshire Elementary, Glenridge Middle and WP High, some of the best Orange County Schools. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. This location checks all the boxes. Schedule your private showing today.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
    Listing Agent: Alison Mosley (407-304-6458)

  • 2433 FIRSTLIGHT WAY, WINTER PARK, FL - MLS# O6403609

    32792 - O6403609 - 2433 FIRSTLIGHT WAY, WINTER PARK, FL 32792
    2 Days on yellowkey

    $2,900 | Townhouse | 3 beds | 2.5 baths | 2 gar

    For rent this 3-bedroom, 2.5-bathroom townhome with a 2-car garage is located in the desirable gated community of Enclave at Hawks Crest. The first floor features an open living area, modern kitchen with stainless steel appliances, and dining space that opens to a covered patio. A versatile flex room on the main level is currently set up as a home office, along with a convenient half bath for guests. Upstairs, all bedrooms are located together, including a spacious primary suite with tray ceilings, walk-in closet, and en-suite bath with dual vanities and a glass-enclosed shower. Just off the bedrooms is a comfortable loft-style living area, perfect for relaxing or entertaining. A full-size washer and dryer are also located upstairs for convenience. Residents enjoy access to a community pool, playground, and easy access to Downtown Winter Park, shopping, dining, and major highways. Bonus: Internet & cable are included with the rent. This home is move-in ready—schedule your showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: LINEAGE REAL ESTATE (407-497-4717)
    Listing Agent: Ryan Ditmar (407-497-4717)

  • 1550 NORFOLK AVE, WINTER PARK, FL - MLS# O6402927

    32789 - O6402927 - 1550 NORFOLK AVE, WINTER PARK, FL 32789
    2 Days on yellowkey

    $725,000 | Single Family Home | 3 beds | 2.0 baths | 3 gar

    Welcome to this exceptional residence at 1550 Norfolk Ave, perfectly positioned in the highly sought-after Orwin Manor neighborhood of Winter Park. Set on a spacious corner lot, this beautifully maintained home offers 3 bedrooms and a rare 3-car garage, combining comfort, functionality, and timeless appeal. Inside, you’ll find rich hardwood floors, plantation shutters, and an extra-large family room ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry with convenient pull-out drawers, balancing style and efficiency. This home also embraces modern sustainability solar panels power the entire property, providing clean energy year-round and the capability to continue powering the home for approximately 24 hours in the event of a power outage. Peace of mind comes from thoughtful updates, including new windows (2022), new garage doors (2023), a roof replaced in (2014), and new insulation installed in (2025) to enhance energy efficiency. Step outside to your private retreat a fully fenced backyard with a sparkling pool and spa, where the spa is heated using natural gas, offering comfort and relaxation at any time of year. An outstanding opportunity to own a well-appointed, energy-efficient home in one of Winter Park’s most desirable neighborhoods.

    Contact Yellowkey Agent

    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
    Listing Agent: Kevin Mcclanahan (407-491-8509)

  • 1611 CHESTNUT AVE, WINTER PARK, FL - MLS# O6402502

    32789 - O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789
    2 Days on yellowkey

    $1,100,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar

    Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood with the bones of new construction. Gutted to the studs and rebuilt with intention, every smajor system is new — electrical, AC, roof, ductwork, drywall. With elevated finishes , like designer tile and quartz countertops as well as new floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possiblities.

    Contact Yellowkey Agent

    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
    Listing Agent: Olivia Maxwell (407-222-4440)

  • 1077 MINNESOTA AVE, WINTER PARK, FL - MLS# O6403223

    32789 - O6403223 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789
    3 Days on yellowkey

    $1,625,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar

    Built in 2025 by Nautilus Homes and lightly lived in, this custom Winter Park residence offers a rare blend of new construction quality, thoughtful owner upgrades, and a highly desirable location between Orlando Avenue and Orange Avenue, just minutes from Park Avenue shopping, dining, and cultural attractions. Set behind mature landscaping and two inviting front porch seating areas, the home delivers over 3,000 square feet of living space, more than 4,000 square feet under roof, 4 bedrooms, 4 full baths, and a dedicated main-level office with a custom door package. More than $100,000 in post-build owner upgrades further enhance the home’s design, function, and everyday livability. Inside, Crème Brûlée wide-plank wood flooring runs throughout the home. Every bedroom features custom-built closets, while Arhaus lighting fixtures and plantation shutters add a refined finish across the interior. The main living area centers around a custom built-in entertainment wall with a vapor fireplace and integrated LED shelf lighting. The chef’s kitchen features ceiling-height custom cabinetry, a handcrafted wood range hood, and an adjoining butler’s pantry finished with Kit-Kat tile between the kitchen and formal dining room. A built-in wine and coffee bar sits just off the main living space, creating an easy flow for entertaining. The layout is both flexible and practical, with one en-suite bedroom and the dedicated office on the main level, plus three additional en-suite bedrooms upstairs. The primary suite includes a spa-inspired bath with soaking tub, oversized 9-foot walk-in shower, dual sprayers, frameless glass enclosure, and linear drainage. Outdoor spaces were designed for easy living, with professional front-yard landscaping, mature tree work, full gutters, and a private low-maintenance backyard retreat featuring artificial turf and decorative rock. The oversized 24x22 two-car garage has been fully built out with custom cabinetry, a full tool wall, overhead storage, and Shark Coating epoxy flooring. Zoned for Audubon Park K-8 and Winter Park High School, and located near Park Avenue, Mead Botanical Garden, and the Winter Park dining corridor. Showings by appointment. Buyer to verify school zoning, room dimensions, square footage and all property details.

    Contact Yellowkey Agent

    Listing is courtesy of: SHAHRAM SONDI + CO. (407-718-6160)
    Listing Agent: Shahram Sondi (407-718-6160)

  • 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL - MLS# O6402984

    32789 - O6402984 - 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789
    3 Days on yellowkey

    $1,185,999 | Apartment | 6 beds

    Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.

    Contact Yellowkey Agent

    Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
    Listing Agent: Brandon Geers (941-928-5152)

  • 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL - MLS# O6403382

    32792 - O6403382 - 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL 32792
    3 Days on yellowkey

    $1,740 | Condo | 2 beds | 2.0 baths

    Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all within reach of central Florida's vibrant offerings. Strategically positioned minutes from the 408 expressway and downtown Orlando, this location is a commuter's dream, with nearby access to Full Sail University, UCF, and Valencia Colleges. Come inside to discover a beautifully maintained space featuring upgraded light fixtures, freshly painted walls, and abundant natural light that accentuates the spaciousness. The unit boasts generously sized bedrooms and a kitchen adorned with new granite countertops in the breakfast bar, along with an in-unit washer and dryer – just pack your bags and move in! As a resident of Keller Williams, you'll enjoy exclusive benefits through our Resident Benefits Package (RBP), including HVAC air filter delivery, renters insurance, and credit-building opportunities. Act swiftly – this home won't last long!

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
    Listing Agent: David Drawdy, Jr. (407-629-4420)

  • 5450 PEACO PL, WINTER PARK, FL - MLS# O6403088

    32792 - O6403088 - 5450 PEACO PL, WINTER PARK, FL 32792
    3 Days on yellowkey

    $280,000 | Half Duplex | 3 beds | 2.0 baths | 2 gar

    Welcome Home! Winter Park property for under $300k! As you step up to this property you notice the fresh paint and the fresh mulch. Step into the home and you see consistent floor tile throughout the home as well as freshly painted walls. Take a step to the left and you see the large kitchen space to be able to freely move around as you cook. The primary bedroom is located in the rear and has access to the back yard. Bedroom sizes are a fair size. New garage door opener just installed This home is great for investors and also a GREAT WINTER PARK starter home. This property is close to highways, shopping and more! Welcome Home!

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
    Listing Agent: Dean Gonzalez (407-325-7804)

  • 2707 TIERRA CIR, WINTER PARK, FL - MLS# O6398979

    32792 - O6398979 - 2707 TIERRA CIR, WINTER PARK, FL 32792
    3 Days on yellowkey

    $495,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Tucked into one of Winter Park's most convenient pockets, this thoughtfully updated residence offers a seamless blend of comfort, style, and convenience. With three bedrooms and two bathrooms, the layout provides flexibility for a variety of living arrangements while maintaining a warm, welcoming feel throughout. The updated kitchen is both functional and inviting, featuring a gas stove and a dedicated coffee bar that adds a touch of everyday luxury. Living spaces flow effortlessly to the outdoors, where a large screened-in porch invites year-round enjoyment, complemented by a paved patio with a firepit that's ideal for relaxed evenings. The yard is perfectly sized for easy maintenance and enjoyment, complete with built-in swings that add a unique and playful detail. Positioned in a highly desirable location, this home is just moments from Interlachen Country Club, Full Sail University, and AdventHealth Winter Park, with everyday essentials like Costco nearby. Enjoy quick access to the shopping and dining of Park Avenue, just 15 minutes away. A rare opportunity to enjoy a move-in-ready home in one of Winter Park’s most convenient and connected areas. Recent updates include a 2021 roof, offering peace of mind and move-in ready convenience.

    Contact Yellowkey Agent

    Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
    Listing Agent: Hannah True (407-923-9330)

  • 3053 GEORGE MASON AVE #8A, WINTER PARK, FL - MLS# O6402957

    32792 - O6402957 - 3053 GEORGE MASON AVE #8A, WINTER PARK, FL 32792
    4 Days on yellowkey

    $75,000 | Condo | 1 beds | 1.0 baths

    One or more photo(s) has been virtually staged. Welcome to this charming 1 Bedroom/1 Bath condo located on the first floor featuring a spacious living room with a cozy dinette area and a functional galley kitchen. The kitchen features shaker cabinets, large stainless-steel sink and stackable washer/dryer, all appliances convey. Sliding glass doors open to a covered patio overlooking a peaceful courtyard-style backyard—perfect for relaxing or outdoor dining. The community offers a refreshing pool, clubhouse one assigned parking space, and ample guest parking. Sold As-Is, presenting a great opportunity for an investor or owner-occupant. Conveniently located just minutes from Full Sail University, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. Zoned for highly rated Winter Park schools. Within walking distance to shopping and dining.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
    Listing Agent: Carmen Quintana (407-340-3932)

  • 420 OHIO ST, WINTER PARK, FL - MLS# O6399541

    32789 - O6399541 - 420 OHIO ST, WINTER PARK, FL 32789
    4 Days on yellowkey

    $1,360,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar

    Pre-Construction. To be built. On a prominent corner lot in the evolving Killarney neighborhood, this offering presents a rare chance to create a custom residence in the heart of the 32789 zip code. Set among a mix of established homes and new construction, the setting reflects the ongoing transformation of the area while remaining close to the amenities that define Winter Park living. The proposed plan features over 3,700 square feet of living space with a layout designed for both everyday comfort and entertaining. Current plans accommodate five bedrooms, five and a half baths, and a dedicated office, with flexibility to tailor the design or incorporate an accessory dwelling unit (ADU) depending on buyer preferences and final approvals. The building process is structured to allow selections to be made through a private showroom experience, offering an opportunity to personalize finishes and design elements throughout. Inside, the home is envisioned with clean architectural lines and a focus on natural light. The kitchen is designed as a central gathering space with quartz countertops, custom cabinetry, and an oversized. The primary suite is planned as a private retreat with a spacious bath, dual vanities, a glass-enclosed shower, and curated tile finishes. Flooring is specified as wide-plank luxury vinyl throughout the main areas, combining durability with a warm, cohesive aesthetic. The lot size and configuration provide the option to design an outdoor living environment, including space for a future pool, subject to final plans. The location offers convenient access to Park Avenue, the Winter Park Chain of Lakes, I-4, and nearby medical facilities, with dining options such as Hillstone within close proximity. Offered at a starting price of $1,360,000, this to-be-built opportunity combines location, flexibility, and a structured customization process for buyers seeking new construction in a well-located, established area. Buyers should verify all specifications, plans, pricing, and timelines with the builder.

    Contact Yellowkey Agent

    Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
    Listing Agent: Leighton Hope (407-619-7897)

  • 7917 PLEASANT PINE CIR, WINTER PARK, FL - MLS# O6402666

    32792 - O6402666 - 7917 PLEASANT PINE CIR, WINTER PARK, FL 32792
    4 Days on yellowkey

    $599,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Under contract-accepting backup offers. Come see this BEAUTIFULLY MAINTAINED, EMACULATE WINTER PARK HOME ON A QUIET STREET IN A SECLUDED GATED ENCLAVE OF HOMES! This is a one owner home and has been maintained in pristine, like new condition. Located in a small gated community moments from Trinity Preparatory School, Park Avenue Shoppes and Rollins College. When entering this home you are greeted by a beautiful entry way and foyer. This single story four bedroom home has a spectacular open floor plan with natural lighting galore and beautiful wood look tile throughout the entire home, stainless steel appliances, stunning granite countertops, a large island in the kitchen, custom extended cabinetry perfect for the cooking enthusiast and great for entertaining, master bedroom extended with sitting room, beautiful back lanai and a large backyard that is beautifully designed! When entering the back lanai you are greeted by a serene, private, landscaped Oasis. The landscaping and location of the home within the community creates an amazingly private, secluded and peaceful backyard with just the occasional sounds of birds chirping. This home is in an amazing location! You will be located about one mile to Trinity Preparatory School, Publix, Restaurants and more shopping as well as the 417, you are just a few miles from Rollins College, Park Avenue/Downtown Winter Park, Advent Health Winter Park, The Country Club at Deer Run, Interlachen Country Club, St. Luke’s School and Masters Academy just to name a few and more shopping & restaurants galore! This is a prime location for all conveniences and with a Winter Park Address! This home has some of the latest energy qualities such as double pane insulated windows and has been constantly covered under a termite bond. Come visit this Warm, Friendly Neighborhood because you are sure to want to stay forever! Updates in the last 1 to 2 years include: Painting of complete exterior and interior, All kitchen appliances replaced, flooring replaced, bathrooms updated, backsplash in kitchen added, tile on front porch and back lanai, soft close on all kitchen cabinets, extension of kitchen cabinets & countertops into dining room. HVAC system has been and is serviced constantly since home was built.

    Contact Yellowkey Agent

    Listing is courtesy of: LORI GILMORE REAL ESTATE LLC (407-402-2623)
    Listing Agent: Lori Gilmore (407-402-2623)

  • 3250 HOWELL BRANCH RD, WINTER PARK, FL - MLS# O6402855

    32792 - O6402855 - 3250 HOWELL BRANCH RD, WINTER PARK, FL 32792
    4 Days on yellowkey

    $1,775 | Half Duplex | 2 beds | 2.0 baths

    This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living. Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances and solid-surface countertops. This kitchen effortlessly flows into the spacious living room, where a cozy wood-burning fireplace beckons for memorable gatherings and relaxing evenings. The large master bedroom is a true sanctuary, boasting an en-suite bath complete with dual vanities and a convenient walk-in closet. But the delights continue outdoors, as you'll be treated to a vast, fenced-in backyard adorned with plenty of shade – perfect for your family to savor outdoor moments and create lasting memories. 3254 Howell Branch Road enjoys an excellent location in desirable Winter Park, placing you close to everything you need. You'll find convenient access to SR436 shopping and dining, nearby hospitals, and the vibrant University of Central Florida campus. Pets Not Allowed! Tenant Liability Insurance **Required**

    Contact Yellowkey Agent

    Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
    Listing Agent: Carissa Lawhun (407-207-2220)

  • 2379 FLAMINGO WAY, WINTER PARK, FL - MLS# O6402772

    32792 - O6402772 - 2379 FLAMINGO WAY, WINTER PARK, FL 32792
    4 Days on yellowkey

    $2,400 | Townhouse | 3 beds | 2.0 baths

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom townhome in the highly desirable area of Winter Park—perfect for renters seeking comfort, convenience, and a vibrant community lifestyle. Step inside to an open-concept layout designed for modern living, featuring stylish tile flooring and a spacious kitchen with granite countertops that flows effortlessly into the living and dining areas—ideal for entertaining or relaxing at home. The generous primary suite offers a private retreat with dual walk-in closets and an ensuite bathroom, while two additional bedrooms provide flexibility for roommates, guests, or a home office. Residents will love the resort-style community amenities, including tennis courts, pickleball courts, two sparkling pools, a playground, a putting green, and a clubhouse—giving you plenty of ways to unwind and stay active right at home. Location is everything, and this property delivers. You’ll be just 15 minutes from the shops, dining, and nightlife of Park Avenue, approximately 7 miles from University of Central Florida, and only 1.7 miles from Full Sail University—making it an excellent option for aspiring academics, faculty, or professionals alike. Don’t miss the opportunity to live in a well-appointed home with unbeatable amenities and a prime location!

    Contact Yellowkey Agent

    Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
    Listing Agent: Samuel Kingsford (407-808-6633)

  • 1900 WINTER PARK RD, WINTER PARK, FL - MLS# O6402566

    32789 - O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789
    5 Days on yellowkey

    $941,000 | Single Family Home | 4 beds | 2.0 baths | 1 gar

    Positioned in one of Central Florida’s most iconic and sought-after locations, this rare opportunity at 1900 Winter Park Road in Winter Park invites you to create something truly exceptional. Set on a spacious homesite, this property offers the flexibility to renovate, expand, or build your custom dream home from the ground up. Whether you envision a modern architectural masterpiece or a timeless estate, this is your canvas to bring that vision to life. What makes this opportunity even more compelling is the location. Just minutes from the charm and sophistication of Park Avenue, you’ll find yourself surrounded by brick-lined streets, boutique shopping, fine dining, and vibrant cultural experiences. Spend your mornings enjoying coffee at local cafés, your afternoons exploring art galleries, and your evenings dining under the lights of one of Central Florida’s most beloved destinations. Living in Winter Park is more than owning a home—it’s embracing a lifestyle. From the scenic beauty of the Winter Park Chain of Lakes, to the historic elegance of Rollins College, this area blends natural beauty, culture, and community in a way few places can. Residents enjoy: Boat tours and waterfront living along the chain of lakes Weekly farmers markets and local events A thriving arts scene including museums, galleries, and theaters Top-rated dining and boutique retail experiences A true sense of community with timeless charm This is more than just land. This is where vision meets opportunity. This is where your next chapter begins. Build the life you’ve been dreaming of—in the heart of Winter Park

    Contact Yellowkey Agent

    Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
    Listing Agent: William Grim, Iii (407-314-9784)

  • 2428 LOTAFUN AVE, WINTER PARK, FL - MLS# O6401871

    32789 - O6401871 - 2428 LOTAFUN AVE, WINTER PARK, FL 32789
    5 Days on yellowkey

    $3,200 | Single Family Home | 3 beds | 2.5 baths

    Who wouldn’t want to live on a street called LOTAFUN? This one-story Winter Park home has 3-bedrooms, 2.5-baths with great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. Located at the end of a dead end street, the privacy is just one of its best features; with partial views of Lake Killarney from the dining area, kitchen, family room, and side yard as a close second. Spacious bedrooms, interior laundry closet and large side yard are also special features offered. This 1,534 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 per adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and pet deposit.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
    Listing Agent: Johnny Hurlburt (407-579-3168)

  • 1725 CAROLLEE LN, WINTER PARK, FL - MLS# O6402656

    32789 - O6402656 - 1725 CAROLLEE LN, WINTER PARK, FL 32789
    5 Days on yellowkey

    $1,015,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias, gardenias, and more. Just minutes from Park Avenue’s beloved restaurants, cafés, and boutiques, as well as the scenic Winter Park Chain of Lakes, this home offers both character and convenience. With easy access to I-4, SR-417, Orlando International Airport, and top-rated schools, it is a wonderful opportunity to enjoy classic Winter Park charm in a beautifully cared-for home.

    Contact Yellowkey Agent

    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
    Listing Agent: Kyle Grafton (203-246-8512)

  • 446 MELROSE AVE, WINTER PARK, FL - MLS# O6402113

    32789 - O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789
    5 Days on yellowkey

    $1,695,000 | Single Family Home | 4 beds | 2.0 baths

    A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
    Listing Agent: Audra Wilks (407-252-8582)

  • 1660 WALNUT AVE, WINTER PARK, FL - MLS# O6395277

    32789 - O6395277 - 1660 WALNUT AVE, WINTER PARK, FL 32789
    5 Days on yellowkey

    $1,650,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar

    Introducing a standout new construction in Winter Park’s coveted Tree Streets! As you arrive the home’s modern façade is complemented by a charming front porch, creating a warm yet striking introduction that feels both inviting and intentional. Inside, the home unfolds with a highly functional floor plan designed to enhance everyday living while still accommodating entertaining with ease. Clean lines, curated finishes, and natural light define the main living spaces, where the kitchen, dining, and living areas flow seamlessly together. The kitchen serves as a true focal point, featuring Calacatta Gioia quartz countertops, custom cabinetry with ample storage, a paneled refrigerator, and a full suite of Thermador appliances. The space transitions naturally into the dining area and living room, where a built-in wet bar with a wine fridge adds an elevated layer of functionality and style. The living room is designed to feel both open and connected, anchored by expansive pocketing sliders that completely open to the outdoor living area. The primary suite is thoughtfully positioned on the main level, serving as a calming retreat, featuring a spa-inspired bathroom with dual vanities, a freestanding soaking tub, and a spacious walk-in shower. Upstairs, three additional bedrooms are generously sized and well laid out, providing flexibility for guests, family, or a secondary living setup. The outdoor living experience is equally impressive, centered around a large covered lanai that offers ample space for al fresco dining and lounging. The spacious pool area is designed to complement the home’s indoor-outdoor lifestyle, creating a private setting that feels both relaxed and elevated. Beyond the home itself, the location is what truly sets this home apart. Situated in the heart of the Tree Streets, you are just a short walk to Phelps Park and the YMCA, minutes from Interlachen Country Club, and only a quick golf cart ride to the shops, dining, and energy of Park Avenue. Homes of this caliber and location are few and far between, making this a standout opportunity in today’s market.

    Contact Yellowkey Agent

    Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
    Listing Agent: Christopher Christensen (407-312-8003)

  • 7484 CANFORD CT #8, WINTER PARK, FL - MLS# O6402492

    32792 - O6402492 - 7484 CANFORD CT #8, WINTER PARK, FL 32792
    5 Days on yellowkey

    $250,000 | Condo | 3 beds | 2.5 baths | 2 car

    This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer stainless steel appliances, and a closet pantry. There is a separate dining room that opens onto a very private brick paver patio with a new privacy fence. This unique condo features a flexible layout, an inside utility, and includes the washer & dryer. Modern-design porcelain tile flooring. The home has a large screen porch, which is considered by many in Florida, to be extra living space. There is also a front courtyard that is perfect for a raised bed garden or ???. Highly desired Winter Park schools. A 2-car carport with an ample lockable storage closet. New roof in 2020 and an updated electric system. The complex has a private community pool

    Contact Yellowkey Agent

    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
    Listing Agent: Greg Harrison (407-276-6141)

  • 639 SAINT JOHNS CT #639, WINTER PARK, FL - MLS# O6402025

    32792 - O6402025 - 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792
    6 Days on yellowkey

    $199,900 | Condo | 2 beds | 2.0 baths

    Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.

    Contact Yellowkey Agent

    Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)
    Listing Agent: Adam Eisen (407-808-6967)

  • 2009 SHADYHILL TER, WINTER PARK, FL - MLS# O6402256

    32792 - O6402256 - 2009 SHADYHILL TER, WINTER PARK, FL 32792
    6 Days on yellowkey

    $535,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Beautifully updated 3 bedroom, 2 bath home with a sparkling in-ground pool, located in highly sought-after Winter Park. This move-in ready property features fully upgraded kitchen with features like quartz countertops and soft close cabinets, updated bathrooms, new stone composite plank flooring, and double pane windows that bring in abundant natural light. Major system updates include a new roof (2022) and full house re-pipe (2025). Freshly painted, this home offers both style and peace of mind. Escape to your own backyard Oasis with a beautiful pool surrounded by lush landscaping and a covered patio for entertaining friends and family. A true turnkey opportunity ready to impress the pickiest buyer.

    Contact Yellowkey Agent

    Listing is courtesy of: HOUSE HUNTING IN FLORIDA LLC (407-676-4747)
    Listing Agent: Byron Kirkpatrick (407-765-1583)

  • 3440 ALLSTON LN, WINTER PARK, FL - MLS# O6401731

    32792 - O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792
    6 Days on yellowkey

    $420,000 | Single Family Home | 3 beds | 2.5 baths | 1 gar

    Exceptional Single-Family Home in Winter Park, FL This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC system (2023), providing peace of mind for years to come. Enjoy Florida living at its finest on the private screened patio - perfect for relaxing or entertaining. Ideally situated 25 minutes from Downtown Orlando, 30 min from OIA, and 40 min from world-class attractions, this home is also just 6 minutes from Full Sail University, 12 minutes from the prominent Rollins College, and 19 minutes from UCF - making it an ideal choice for families and investors alike. A true must-see - schedule your showing today.

    Contact Yellowkey Agent

    Listing is courtesy of: EXIT GLOBAL REALTY (407-725-7180)
    Listing Agent: Hugo Hernandez (407-716-5594)

  • 1832 E CHERYL DR, WINTER PARK, FL - MLS# O6402209

    32792 - O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792
    8 Days on yellowkey

    $439,995 Increased | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Under contract-accepting backup offers. Welcome to Carolyn Estates in highly desirable Winter Park—a charming enclave of just 63 homes ideally located near Lake Howell High School. This beautifully renovated residence offers a truly unique floor plan—the only one of its kind in the community. Featuring 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, this home blends comfort with functionality. Enjoy cozy evenings by the wood-burning fireplace or unwind in the screened-in patio, perfect for relaxing or entertaining. Step inside to an inviting open-concept layout highlighted by soaring ceilings and abundant natural light. Renovated in April 2026, this home showcases numerous upgrades, including fresh interior and exterior paint, new sod and lush landscaping, a fully remodeled second bathroom, new convection range and microwave, updated interior door hardware, a complete electrical update, and new lighting and ceiling fans throughout. Additional major improvements include newer windows and hot water heater (2019) and full home replumbing (2022), providing added peace of mind. Seller will provide a $10,000 credit towards a new roof with Full Price Offer. This move-in-ready home combines modern updates with a prime location—schedule your private showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: SELECTIVE REALTY GROUP LLC (407-627-1727)
    Listing Agent: Shanon Luiz (407-247-2241)

  • 1409 LONE FEATHER TRL, WINTER PARK, FL - MLS# O6401907

    32792 - O6401907 - 1409 LONE FEATHER TRL, WINTER PARK, FL 32792
    8 Days on yellowkey

    $3,895 | Single Family Home | 4 beds | 4.5 baths | 2 gar

    Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter the home, an open concept floor plan leads you to the family room, the kitchen / nook area combined. 20-foot high ceiling family room with wide sliding doors to the back patio and high windows gives you plenty of natural sunlight. The large covered lanai would be great for a morning coffee, evening wine, of course family gatherings and BBQ. The Master bedroom is located on first floor. The community is just a few minutes to Costco, Super Target, Publix, Trinity Prep School, and Full Sail University. Located along the southern shores of beautiful Lake Howell, Hawk's Crest provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Ave and Winter Park Village. As you enjoy convenience location, you will benefit from these wonderful amenities within the community: Community pool, Clubhouse, Party Room, Dog Park, Free Gym, Grilling Area, Kid's Splash Pad, Lake Park Picnic Tables, Playground, Cabana, Play Lawn, Lakeside Dock and Future Kayak Access. Come and see your new home today, don't miss this chance.

    Contact Yellowkey Agent

    Listing is courtesy of: EAST PEARL REALTY (407-802-6859)
    Listing Agent: Yan Zuo (407-435-3142)

  • 1830 STAUNTON AVE, WINTER PARK, FL - MLS# O6401708

    32789 - O6401708 - 1830 STAUNTON AVE, WINTER PARK, FL 32789
    8 Days on yellowkey

    $3,200 | Single Family Home | 3 beds | 2.5 baths | 1 car

    STYLISH, STUNNING AND RENOVATED TO THE NINES. This 3-bedroom, 2.5-bath Winter Park home has great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is almost totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. In addition to the 3 upstairs bedrooms, the downstairs has a bonus room which is perfect for a den or playroom and a convenient interior laundry room. The lot is 6,750 sqft and is fenced and gated offering a nice new patio of clay pavers, a carport, and large backyard. This 1,774 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 per adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and deposit.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
    Listing Agent: Johnny Hurlburt (407-579-3168)

  • 1287 VERDANT GLADE PL, WINTER PARK, FL - MLS# O6400331

    32792 - O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792
    8 Days on yellowkey

    $850,000 | Single Family Home | 5 beds | 3.5 baths | 2 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.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 5 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both comfortable living and easy entertaining. Inside, the home feels bright, expansive, and well connected, with generous living areas that flow naturally from one space to the next. The open design creates an inviting setting for everyday routines, gatherings, and holiday hosting, while the separate office adds flexibility for working from home, studying, or creating a quiet retreat. With two primary bedroom suites, a large game room, and an additional loft, there is plenty of space to accommodate guests, a growing household, or changing lifestyle needs. The home also features thoughtful upgrades that elevate both style and function. A gourmet kitchen serves as the heart of the home, complete with quartz countertops, 42-inch cabinetry, and the kind of workspace and storage today’s buyers appreciate. Eight-foot interior doors add to the sense of scale throughout, while details such as a pocket door in the bathroom enhance convenience and flow. Large sliding glass doors open wide to create a seamless connection between the indoor living spaces and the outdoor entertaining area. Step outside to an oversized screened and covered patio that extends the living space and creates a relaxing place to enjoy morning coffee, outdoor dining, or quiet evenings at home. Beyond the patio, the private yard offers even more appeal, with no rear neighbors behind the home for added privacy and a more open feel. The rear eastern exposure welcomes beautiful morning sun, making the backyard setting especially enjoyable at the start of the day. Located in Winter Park, the home benefits from a highly desirable area known for its established residential feel, convenient access to shopping and dining, and close proximity to parks, schools, and major roadways. The neighborhood adds to the home’s appeal by offering a blend of comfort, accessibility, and the everyday convenience that makes Winter Park such a sought-after place to live. With its flexible two-story layout, dual primary suites, game room, loft, gourmet kitchen, oversized patio, and private backyard setting, 1287 Verdant Glade Place delivers the space, upgrades, and lifestyle features buyers are looking for.

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
    Listing Agent: Thomas Nickley, Jr (407-629-4420)



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