Location: Winter Park
Do Not Show Listings
1649 HARMON AVE, WINTER PARK, FL 32789
$1,349,90074 Days on yellowkey MLS ID: O6392216
REDUCED by $49,100 (3.5%) on 05/15/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3223 Built: 2018 Tax: $11,908 (2025)Community: LawndaleSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,908
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2025
Middle School: College Park Middle
Remarks: Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living spaces that all blend into a covered porch to backyard retreat. The kitchen is the center of the home with custom double-stacked cabinetry to ceiling, upgraded appliances, large pantry with barn door, center island with bar seating, and full granite slab backsplash and counters add to the artistry of the kitchen. Ceilings are upgraded throughout with floating box details with ambient lighting that gently wash the ceilings and colors can be changed as you wish. Dining and living spaces are generous, and lined with transom windows for privacy and natural light that creates a beautiful backdrop to gather and entertain in. Invisible back doors fully open to the lanai and slide into the wall, staying hidden, an elegant upgrade. Covered porch with tongue and groove ceiling overlooks saltwater pool with hot tub and spillway. Professionally landscaped includes a turfed putting green for the golf enthusiast. Additional main floor flex space can be additional living or home office. Secondary bedrooms are upstairs with generous bonus space and laundry. First-floor primary suite is light and bright, with coffered ceilings and a large walk-in closet. Primary bath is neutrally appointed with dual floating vanities with vessel sinks, a soaking tub, and walk-in shower with seamless glass. A transom window provides privacy and a glow of sunshine and warmth. Lots of seller upgrades. This property is turnkey. Orwin Manor is a special neighborhood blending historic homes with new builds and great neighborhood park to go to. It is also a strategic location, minutes to Park Avenue in Winter Park, known for its upscale dining, elevated cafés and luxury local shopping, also a short distance to Orange Avenue corridor in WP featuring Foxtail Coffee & Buttermilk Bakery and more, and minutes to the Mills district, Advent Health on Rollins as well as major roadways. Great schools, zoned for Edgewater High, known for its magnet program and close to Lake Highland and many other private school options.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
2333 WESTMINSTER CT, WINTER PARK, FL 32789
$719,00016 Days on yellowkey MLS ID: O6407054
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1877 Built: 1948 Tax: $6,723 (2025)Community: Glencoe SubSingle Family
Taxes:$6,723
Remarks: Settled on a rare double lot in the heart of Winter Park, this 4-bedroom, 2-bath home delivers the Florida lifestyle you've been waiting for–without a single item on your to-do list. Resort style pool with Travertine pavers, renovated in 2025– brand new and ready for summer. Inside, a complete renovation in 2020 touched every corner of the home. Every major system has been replaced within the last five years– roof, A/C, plumbing, flooring, septic tank and drain field, driveway, appliances, and the kitchen– giving you true move-in confidence that's rare at any price point. Step outside your door and Lake Killarney is just a short stroll away, offering quiet waterfront sunsets and morning walks that feel like a private retreat. The surrounding Winter Park neighborhood puts acclaimed dining, boutique shopping, and everyday conveniences within minutes, all within one of Central Florida's most sought-after zip codes. Properties with this combination of lot size, updates, and outdoor living don't stay available long. Schedule your private showing and start planning your first poolside gathering.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ernest Middleton (321-231-5698)
5210 OHIO ST, WINTER PARK, FL 32792
$445,00018 Days on yellowkey MLS ID: O6408143
0 Days Off yellowkey (back on 5/23/2026)
Bed: 4 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1946 Built: 1973 Tax: $4,869 (2024)Community: Suburban Homes Sec 2Single Family
Taxes:$4,869
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. A house in Winter Park under $500K?! No way! Let's not forget, everything was fully gutted and remodeled in 2023. New roof, water heater, AC, electrical wiring and panel, plumbing, double pane windows, water softener, flooring, exterior paint, bathrooms, kitchen, outdoor french drains, garage door, screened-in lanai — ALL ONLY THREE YEARS OLD. This home is the absolute definition of MOVE-IN READY. Situated on a 1/4 acre oversized lot, there's plenty of room for you to add a pool, park your boat, or create that true backyard oasis you've been dreaming of. Fully fenced-in and NO HOA. The kitchen features high-end quartzite countertops with a built-in pantry and newer stainless steel appliances. Open floor plan with high ceilings and tons of natural light. Almost 2,000 sqft of living area with an inside utility room that houses your washer/dryer (which are included with the purchase!). Master bedroom is equipped with a massive 8'x11' walk-in closet and a show-stopping en-suite bathroom! Conveniently located 10 minutes from Park Avenue, 15 minutes from Valencia and/or UCF, and right around the corner from highway ramps making commuting a breeze. Homes like this don't come often. Don't miss your chance to live in Winter Park!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Angie Kollcaku (407-454-4078)
2232 BANCHORY ROAD, WINTER PARK, FL 32792
$1,115,00029 Days on yellowkey MLS ID: O6404702
REDUCED by $45,000 (3.9%) on 05/21/2026
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2597 Built: 1966 Tax: $11,186 (2025)Community: Brookshire Heights 4Th AddSingle Family
Taxes:$11,186
Elementary School: None
High School: None
Middle School: None
Remarks: Step into the Winter Park lifestyle with a fully turnkey home designed to make daily living feel effortless. Set on an oversized corner lot, this fully updated home blends clean design with thoughtful upgrades. Inside, the home is built to bring people together. The open-concept layout flows seamlessly from living to dining to kitchen, anchored by a striking 9-foot Carrera Thassos quartz island. A full KitchenAid black stainless steel appliance suite, generous storage, and refined finishes make this a space that works as well on a busy weekday as it does when hosting a full house. Out back, everything is ready to enjoy. A private, resort-style setting features a saltwater pool with fire bowls, custom lighting, and a dedicated outdoor dining area, all framed by professionally designed landscaping and low-maintenance artificial turf. Beyond the aesthetics, this home delivers real, everyday value. A reverse osmosis system, fully updated electrical and plumbing, a 5-ton air conditioning system, and a metal roof provide peace of mind. An 18.4-kilowatt solar system keeps utility costs remarkably low, with many months producing surplus energy credits. Located in sought-after school zones and just minutes from Cady Way Park, with easy access to Orlando, this is a home where everything has already been considered. No projects, no waiting, just move in and start living. Buyer to assume $75,000 solar panel loan, offset by minimal to near-zero electric costs and ongoing energy credits during high-production months. Utility bills available on request.
Listing Agent: Kirstie Hines (321-440-7716)
2087 LAURELWOOD WAY, WINTER PARK, FL 32792
$624,000259 Days on yellowkey MLS ID: O6344482
REDUCED by $35,000 (5.3%) on 05/06/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1920 Built: 2019Monthly Fee: $236 Tax: $4,680 (2024)Community: Hawks CrestSingle Family
Taxes:$4,680
Remarks: One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between the spacious family room, dining area, and gourmet kitchen—ideal for entertaining and everyday living. The kitchen offers granite countertops, large island seating, and stainless-steel appliances. The private owner’s suite is a relaxing retreat with a walk-in closet and spa-inspired bath, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to a covered patio and low-maintenance yard designed for year-round Florida living, and pond view. Hawks Crest residents enjoy exclusive amenities including a clubhouse with fitness center, resort-style pool, splash pad, dog park, playgrounds, and private access to Lake Howell for kayaking and paddle boarding. The neighborhood is also minutes from local favorites like Kelly’s Ice Cream and Foxtail Coffee, with downtown Maitland, Park Avenue, and top-rated schools just minutes away. This home delivers not just a place to live, but a lifestyle defined by convenience, community, and charm. Don’t miss your chance to own in one of Winter Park’s most desirable neighborhoods—schedule your private showing today.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brian Rotenberger (407-948-8478)
1617 CHILEAN LN, WINTER PARK, FL 32792
$367,500138 Days on yellowkey MLS ID: O6373026
1 Days Off yellowkey (back on 5/15/2026)
REDUCED by $2,400 (0.6%) on 04/30/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1359 Built: 1960 Tax: $3,432 (2024)Community: Eastbrook Sub Unit 05Single Family
Taxes:$3,432
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Back on the market and better than ever! New water heater and minor repairs addressed and ready for the new owner! Come see this newly renovated home in the Eastbrook neighborhood of Winter Park. Offering 3 bedrooms and 2 full baths it’s the perfect sanctuary for families and entertainers alike. You will enjoy the bright, airy feel of the open floor plan accentuated by the vaulted ceilings that flood the space with natural light. The stylish interior includes luxury vinyl plank flooring throughout, complemented by elegant tile in the bathrooms and laundry room. Relax in not one, but two generous living areas, perfect for family gatherings, entertaining or cozy nights in. Cook like a pro in your eat-in kitchen featuring brand new ENERGY STAR stainless steel appliances, ample cabinetry, and convenient carport access for effortless unloading. The generous backyard provides a private oasis for outdoor activities, barbecues, and gardening enthusiasts. Plus, the expansive driveway and two-car carport ensure plenty of parking for your guests. Recent upgrades include ceiling fans, blinds, fresh paint, stainless steel appliances, a newer roof (2017) and a well-maintained air conditioner (only 4 years old) ensuring peace of mind for years to come. Located in Seminole County, known for great schools and in a community with NO HOA fees, giving you the freedom to enjoy your space. Plus, you're just moments away from shopping, dining, and parks!
Listing Agent: Brenda Feliciani (407-405-0931)
501 HERITAGE BLVD, WINTER PARK, FL 32792
$479,90081 Days on yellowkey MLS ID: S5145746
REDUCED by $5,090 (1.0%) on 05/23/2026
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1376 Built: 1966 Tax: $10,434 (2025)Community: Georgetown EstatesSingle Family
Taxes:$10,434
Elementary School: Lakemont Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout. Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and functionality. The home offers spacious bedrooms, stylish upgrades, and a fresh contemporary feel throughout, making it perfect for families, first-time buyers, or anyone seeking a turnkey property. Step outside to an expansive backyard featuring a beautiful pool, creating the perfect space for relaxing, entertaining, and enjoying Florida living year-round. The large outdoor space offers endless possibilities to customize the backyard your way—whether it’s adding an outdoor kitchen, lounge area, garden, or entertainment space to create your dream outdoor oasis. Located in a quiet, established neighborhood within an A+ rated school zone, this home also offers convenient access to top shopping, dining, parks, and major highways, making commuting and daily errands a breeze. Don’t miss this incredible opportunity to own a fully remodeled home with a pool in one of the most desirable areas of Winter Park.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Bernardo Carrasquel (407-920-4973)
700 MELROSE AVE #J24, WINTER PARK, FL 32789
$390,00011 Days on yellowkey MLS ID: R4911307
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 987 Built: 1964 Tax: $3,874 (2025)Community: Winter Park Gardens CondoCondo
Taxes:$3,874
Remarks: Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally updated one bedroom unit has just been completed. All new paint, porcelain flooring, all new fixtures, bathroom, appliances, new wood cabinets, new stone counters. All NEW The desirable condo community of Winter Park Gardens is nestled between Mead Gardens, Azalea Tennis Center and upcoming Winter Park's Progress Point. Unit is located on the second floor but there is an elevator and stairs to help to the location. Spacious 2 bedroom , 2 bath unit has large open floor plan. Main living area has an additional glass sunroom which provides additional space and breath-taking views of the beautifully landscaped and private courtyard. With its prime location in Winter Park, you'll have easy access to a many of the dining opportunities, shopping, and entertainment options. This is a 55+ community Whether you're strolling through the charming downtown area of Park Avenue or Hannibal Square or immersing yourself in the thriving arts and culture scene, with the Orlando Museum of Art right around the corner This property is centrally located to Downtown Orlando and Downtown Winter Park… no need to use the expressways! !THIS UNIT DOES NOT REQUIRE OWNER TO BE OVER 55+ furniture can convey with purchase.
Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)
Listing Agent: Scott Butts (321-239-8509)
300 CAROLINA AVE #402C, WINTER PARK, FL 32789
$750,00011 Days on yellowkey MLS ID: O6410016
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1350 Built: 1982 Tax: $2,416 (2025)Community: Park West CondominiumsSpa: NoCondo
Taxes:$2,416
Middle School: Audubon Park K-8
Remarks: One or more photo(s) has been virtually staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Erin Baker (407-719-0030)
1009 LAKE BELL DR, WINTER PARK, FL 32789
$699,00011 Days on yellowkey MLS ID: O6409849
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1467 Built: 1958 Tax: $5,448 (2025)Community: Albert Lee Ridge Add 02Single Family
Taxes:$5,448
Elementary School: Hungerford Elem
Remarks: Offered for the first time in years, this waterfront property presents a rare opportunity to create your ideal lakeside retreat in Winter Park. Situated on nearly half an acre with approximately 133 feet of canal frontage on Lake Bell, the property offers direct water access, mature trees, and a peaceful setting on a quiet dead-end street. The existing 3-bedroom, 2-bath home provides an opportunity for renovation, expansion, or redevelopment to suit your vision. Whether you are seeking a waterfront renovation project or the perfect homesite for a custom residence, this exceptional property combines privacy, recreation, and convenience just minutes from Park Avenue, College Park, and Downtown Orlando.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Padgett Mccormick (407-645-4321)
2707 TIERRA CIR, WINTER PARK, FL 32792
$495,00034 Days on yellowkey MLS ID: O6398979
2 Days Off yellowkey (back on 5/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1710 Built: 1970 Tax: $3,237 (2025)Community: Casa AlomaSingle Family
Taxes:$3,237
Elementary School: English Estates Elementary
Remarks: 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.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Hannah True (407-923-9330)
1725 CAROLLEE LN, WINTER PARK, FL 32789
$1,005,00036 Days on yellowkey MLS ID: O6402656
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $10,000 (1.0%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2335 Built: 1960 Tax: $8,445 (2025)Community: Green TerraceSingle Family
Taxes:$8,445
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: 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.
Listing Agent: Kyle Grafton (203-246-8512)
4469 OLD BEAR RUN, WINTER PARK, FL 32792
$1,799,999113 Days on yellowkey MLS ID: O6375415
REDUCED by $50,001 (2.7%) on 05/22/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4288 Built: 1978 Tax: $10,710 (2024)Community: Pervis Survey For R ESpa: NoSingle Family
Taxes:$10,710
Elementary School: Red Bug Elementary
Remarks: Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Keigan Lewis (305-393-8683)
3371 RIVER VIEW WAY #46, WINTER PARK, FL 32792
$205,00032 Days on yellowkey MLS ID: O6403947
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1151 Built: 1983Monthly Fee: $450 Tax: $2,986 (2025)Community: Hidden Oaks Condo Ph 03Condo
Taxes:$2,986
Remarks: 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.
Listing is courtesy of: REALTY ONE GROUP EVOLVE (386-368-7222)
Listing Agent: Safiya Bourne Llc (689-249-1999)
147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789
$2,170,000122 Days on yellowkey MLS ID: L4959060
REDUCED by $25,000 (1.1%) on 05/22/2026
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3272 Built: 1990 Tax: $18,439 (2024)Community: 147 Interlachen PlaceCondo
Taxes:$18,439
Remarks: Welcome to 147 Interlachen Place, Enjoy Winter Park's most desirable location! One block from Historic Park Avenue/Central Park. Spacious, bright and all on ONE FLOOR. The buildings second floor offers privacy and easy access. The Southwest corner provides direct natural light throughout the day. Private elevator access with secured underground parking. This beautiful home offers a short walk to everything Winter Park, a pedestrian village of delight! Natural light fills the central courtyard which features an iron water fountain. Private pool with heated spa and outdoor grilling and entertaining area. Interior features include fireplaces in living room, 2 Southwest facing covered outdoor walkout balconies, accessed by living room, den, master bedroom and one directly over looking the pool. Master bathroom includes separate tub and shower, dual closets, split vanities and plenty of storage space. 4 full bath- 1 half bath (5). Two specified parking spaces also have large storage closets with security gate and elevator access to your floor. K-8 Audubon School district! Unit / building “horseshoe” configuration provides no neighbors on any of the 4 sides, courtyard interior, Private Luxury Living all on ONE floor!
Listing is courtesy of: HELLOSOLD LLC (954-778-5300)
Listing Agent: Dan Farber (954-778-5300)
2973 SANBINA ST, WINTER PARK, FL 32789
$377,88018 Days on yellowkey MLS ID: O6407521
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1965 Tax: $5,253 (2025)Community: Howell HeightsSingle Family
Taxes:$5,253
Elementary School: Dommerich Elem
Remarks: Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!
Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)
Listing Agent: Andrew Musashe (407-645-5700)
758 WARRENTON RD, WINTER PARK, FL 32792
$318,98562 Days on yellowkey MLS ID: O6395298
1 Days Off yellowkey (back on 5/5/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1196 Built: 1988Monthly Fee: $86 Tax: $3,689 (2025)Community: Winter Park Pines Patio HomesHalf Duplex
Taxes:$3,689
Elementary School: Aloma Elem
Remarks: Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas and ceiling fans that enhance the home’s airy feel. The brand-new kitchen has tile flooring and is not only functional, but beautiful showcasing classic shaker cabinets, sleek quartz countertops, and stainless steel appliances—perfect for both everyday living and entertaining. There are three nice sized bedrooms, all with large closets. The primary bedroom features sliding glass doors that lead directly to the large backyard and open patio. Both bathrooms have been renovated with modern finishes, including new vanities, countertops, tub/showers, plus durable and stylish luxury vinyl plank flooring. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy, along with a charming paver front patio and the convenience of a one-car garage with opener. You will love the privacy of this end unit on the quiet cul-de-sac. Enjoy the ease of walking to nearby schools and being just moments from golf, shopping, dining, and all that Winter Park has to offer. With low HOA dues and located in a top-rated school district, this is an incredible opportunity in one of Central Florida’s most desirable neighborhoods.
2500 LEE RD #219, WINTER PARK, FL 32789
$164,000305 Days on yellowkey MLS ID: O6332524
3 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 851 Built: 1969Monthly Fee: $360 Tax: $2,392 (2024)Community: Lakeside Manor Apts CondoCondo
Taxes:$2,392
Remarks: Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as well as a private boat launch, a brand-new dock with covered over-water seating, a lakeside pool, and a clubhouse. The beautifully manicured green spaces and quiet courtyard areas create a peaceful, community-oriented atmosphere.Inside, this move-in ready unit has been freshly painted throughout and features new carpeting. The kitchen has been tastefully refreshed and offers plenty of cabinet space. An assigned parking space is located just steps from the unit, and there's an on-site laundry facility plus a private storage unit for added convenience.Tucked away yet close to it all, you’re just minutes from the shops and restaurants of Winter Park, with easy access to I-4 and other major roadways. Residents love living here—units don’t come available often, so don’t miss your chance to call this lakeside gem home!
Listing is courtesy of: SUNDIAL REAL ESTATE LLC (407-601-2200)
Listing Agent: Nicole Van Treese (407-462-9050)
2756 SHERIFF WAY, WINTER PARK, FL 32792
$625,00035 Days on yellowkey MLS ID: O6402570
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1812 Built: 1965 Tax: $5,547 (2025)Community: Winter Park PinesSingle Family
Taxes:$5,547
Remarks: **$10,000 BUYER INCENTIVE OFFERED!! This can be used for Closing Costs, Interest Rate Buydown, or Landscaping Credit!** Welcome to your beautifully updated slice of the Florida Dream here in Winter Park! Perfectly positioned on a desirable corner lot, this thoughtfully renovated home blends modern design, comfort, and functionality - minutes away from Advent Health, Park Avenue, and Schools! From the moment you step inside, you’ll notice the extensive tile flooring, upgraded lighting, and stylish finishes throughout. The heart of the home is the stunning RENOVATED KITCHEN featuring QUARTZ countertops, rich NAVY cabinetry, stainless steel appliances, and a gorgeous wine & coffee bar complete with a built-in WINE FRIDGE—perfect for entertaining or slow Florida mornings at home. Need space to work or unwind? The dedicated OFFICE with MODERN BARN DOORS creates the ideal work-from-home setup, while the additional BONUS ROOM offers endless flexibility as a playroom, reading retreat, media space, or hobby room. Down the hall, the spacious and serene Primary Suite invites you to unwind in the renovated, spa-inspired rain showerhead for a relaxing start or finish to your day. The 2nd bedroom has been dubbed the "Hotel Room" by guests because of its larger size and additional sitting area. This space is perfect for MULTIGENERATIONAL LIVING, whether they are coming home for the summer, guests visiting Central Florida on vacation, or extended family needing a space of their own! The 3rd bedroom is across the hall from the Primary and features laminate flooring, so you truly have 3 dedicated bedrooms PLUS an office! Practical upgrades set this home apart from others in the community, including CUSTOM BLINDS Throughout & 5 1/4 INCH BASEBOARDS in the main living areas, an indoor, heated & cooled LAUNDRY ROOM, Replaced A/C (Inside 2020, Outside 2019), NEW ROOF (2022), PVC REPIPE (2018), NEW SEWER, NEWLY FENCED BACKYARD (2022), WIFI Garage Opener (2020)a storage shed, and a NEW (2021) COVERED & SCREENED LANAI with waterproof and weatherproof interlocking flooring, designed for year-round indoor/outdoor living enjoyment. This move-in-ready abode delivers the perfect balance of style and everyday living! Whether you’re hosting friends, working remotely, or simply enjoying the Florida lifestyle, this remarkable gem is located blocks away from Cady Way Trail and Ward Park, and just minutes from the award-winning restaurants on Park Avenue, and in the Baldwin Park & Mills50 shopping districts! Don't sleep on this one, call and schedule your private showing today!
Listing is courtesy of: PALM CIRCLE REALTY (352-988-4975)
Listing Agent: Kasey Hilyard, Pllc (407-488-9879)
841 W SWOOPE AVE, WINTER PARK, FL 32789
$499,000124 Days on yellowkey MLS ID: O6373287
0 Days Off yellowkey (back on 4/30/2026)
REDUCED by $241,000 (32.6%) on 04/13/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1396 Built: 1930 Tax: $3,824 (2024)Community: Capens AddSingle Family
Taxes:$3,824
Remarks: This Winter Park property offers exceptional potential in one of the most desirable and rapidly evolving areas of Central Florida. Zoned R-3, this parcel opens the door to redevelopment possibilities for builders, investors, or end users looking to create something special. Ideally located just minutes from Park Avenue and within walking distance to Winter Park Village, you’ll enjoy easy access to premier dining, shopping, entertainment, and lifestyle amenities. The property is also conveniently situated near Orlando Avenue, providing quick connectivity to surrounding areas. The existing structure is being sold as-is, and the true value lies in the land, zoning, and prime location. With ongoing redevelopment nearby and strong demand for new construction, this is an ideal opportunity to build a custom residence or explore allowable uses under current zoning (buyer to verify all development potential with the City of Winter Park). Whether you’re a builder, investor, or buyer with vision, this is your chance to secure a property in a high-demand corridor with long-term upside.Cash buyers and builders welcome. No HOA. City water and sewer. 32789 zip code.
Listing Agent: Evelyn Alicea (407-340-8154)
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