Location: Winter Park , 32789
Do Not Show Listings
1404 BORDER DR, WINTER PARK, FL 32789
$1,200,0007 Days on yellowkey MLS ID: O6412140
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2469 Built: 2023 Tax: $16,220 (2025)Community: Winter Park VillageSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$16,220
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
340 KILLARNEY BAY CT #4-4, WINTER PARK, FL 32789
$395,00021 Days on yellowkey MLS ID: O6407259
REDUCED by $15,000 (3.7%) on 05/25/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1428 Built: 1986 Tax: $1,080 (2025)Community: Killarney Bay CondoCondo
Taxes:$1,080
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Welcome to 340 Killarney Bay, a beautifully maintained residence located within one of Winter Park’s most charming and sought-after communities. With access to Lake Killarney, residents enjoy a waterfront community pool, dock, and a peaceful setting that perfectly complements the relaxed Winter Park lifestyle. This home offers a spacious and inviting layout with both bedrooms located upstairs for added privacy, as well as a balcony off one of the upstairs bedrooms. Recent updates include newer appliances, newer water heater (2022), and fresh interior paint downstairs and in bathrooms. Ideally located just minutes from Winter Park Village, Park Avenue, Trader Joe’s, top dining, shopping, and major roadways, this home delivers the perfect blend of convenience, lifestyle, and serene community living. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Blaike Gill (407-545-6430)
1830 EDWIN BLVD, WINTER PARK, FL 32789
$639,90050 Days on yellowkey MLS ID: O6400055
REDUCED by $9,900 (1.5%) on 05/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1287 Built: 1957 Tax: $3,955 (2025)Community: Campo BelloSingle Family
Taxes:$3,955
Elementary School: Lakemont Elem
Remarks: Beautifully RENOVATED and MOVE-IN READY/TURN-KEY home in the heart of Winter Park. From the moment you enter, you’re welcomed by an open, airy layout with VAULTED CEILINGS that make the home feel spacious and inviting. Beautiful TILE flooring throughout creates a seamless flow from room to room, while abundant natural light pours in through DOUBLE-PANED WINDOWS (2018) and German Velux SKYLIGHTS with remote control adjustable blinds (2021). The thoughtfully designed floor plan connects the living, dining, and kitchen areas in a natural, functional way, making the space ideal for both everyday living and entertaining. At the center of the home, the CUSTOM EUROPEAN-STYLE KITCHEN features high-end Cambria quartz countertops (2025) and upgraded appliances, including a NEW refrigerator (2025), BOSCH dishwasher (2024), and Maytag microwave (2022). Both bathrooms have been FULLY REMODELED with modern finishes, NEW VANITIES (2025), and all interior doors were replaced (2017), adding to the home’s updated feel throughout. Major system upgrades provide peace of mind, including a high-efficiency Amana AC with smart thermostat (2024) and a tankless water heater (2025). The home also features a complete PEX plumbing upgrade to the city connection (2025), modernized PVC drain in the bathrooms, laundry and kitchen (2025), new sinks and faucets (2025), and updated kitchen electrical wiring to current code (2025). Step outside to a private, fenced backyard (2018) with a screened patio (2022), perfect for relaxing or entertaining year-round. Additional exterior features include driveway pavers (2024), carport (2024), and a OVERSIZED Tuff Shed (2024) for extra storage. Modern conveniences such as electronic front door locks (2023), a smart ceiling fan (2023), and smart kitchen lighting (2025) complete this well-appointed home. Ideally located just minutes from Park Avenue and within walking distance to shopping, dining, parks, and everyday conveniences, this home offers the perfect combination of location, layout, and high-quality upgrades. SCHEDULE YOUR SHOWING TODAY!
Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)
Listing Agent: Nydia Marrero (407-620-6221)
1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789
$525,00080 Days on yellowkey MLS ID: O6391277
REDUCED by $25,000 (4.5%) on 05/23/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1818 Built: 2006 Tax: $6,197 (2025)Community: Terrazo Del SolCondo
Taxes:$6,197
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Courtney Dietch (407-952-3779)
151 N ORLANDO AVE ##115, WINTER PARK, FL 32789
$298,000185 Days on yellowkey MLS ID: O6362403
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 710 Built: 1960 Tax: $2,965 (2025)Community: Lake Killarney CondoSpa: NoCondo
Taxes:$2,965
Remarks: Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
269 E CANTON AVE #269, WINTER PARK, FL 32789
$989,50015 Days on yellowkey MLS ID: O6404706
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1109 Built: 1971Monthly Fee: $1,039 Tax: $3,470 (2025)Community: Village Winterset IncCondo
Taxes:$3,470
Elementary School: None
High School: None
Middle School: None
Remarks: Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Cathy Sawruk Williams (407-489-3921)
120 BROADVIEW AVE, WINTER PARK, FL 32789
$1,450,00014 Days on yellowkey MLS ID: O6409860
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1747 Built: 1947 Tax: $2,693 (2025)Community: Killarney EstatesSingle Family
Taxes:$2,693
Remarks: Rare lakefront opportunity on the beautiful pristine Lake Killarney in the heart of Winter Park! Build your dream home on this coveted corner lot graced by original brick streets. Lake Killarney is a crystal-clear, spring-fed private lake — motorized boats welcome, yet no public boat ramp ensures a peaceful, exclusive experience. Enjoy sweeping 1-mile sunset views from one of only three homes on a quiet dead-end street. Walk to Hillstone, Trader Joe's, and 20+ world-class restaurants. An additional 30 X 65 ft from rear lot line is available to purchase to extend the footprint of your dream home. This is Florida lakefront living at its finest — don't miss it!
Listing is courtesy of: PROMAX PROPERTY SOLUTIONS (407-647-3377)
Listing Agent: David Murray (407-647-3377)
2157 LAKE DR, WINTER PARK, FL 32789
$689,0006 Days on yellowkey MLS ID: O6412258
REDUCED by $70,000 (9.2%) on 05/31/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2124 Built: 1962 Tax: $1,605 (2025)Community: Killarney PointSingle Family
Taxes:$1,605
Remarks: Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake Killarney views, and a peaceful setting on a quiet private lakefront street. From the moment you enter, pride of ownership shines through, with custom built-ins throughout creating stylish and functional living spaces. The heart of the home is the updated kitchen and dining area, featuring high-end bamboo floors, stainless steel appliances, real wood custom cabinetry, and a large island overlooking a versatile flex space perfect for a formal living room, den, or office. The spacious great room is warm and inviting with a wood-burning fireplace and a dramatic wall of four French doors that fill the space with natural light. The elegant primary suite offers a walk-in closet and a spacious bath with dual vanities, a soaking tub, and separate shower. Step outside to a covered patio and expansive backyard with plenty of room to entertain, garden, or unwind. Just minutes from Park Avenue, premier shopping, dining, and Winter Park’s beloved parks and amenities, this is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods on .33 acres. Brand new roof and newer AC for total peace of mind. Schedule a private tour today.
Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)
Listing Agent: Jacob Johnson (407-353-0106)
1780 GOODRICH AVE, WINTER PARK, FL 32789
$625,00022 Days on yellowkey MLS ID: O6403811
0 Days Off yellowkey (back on 5/17/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1283 Built: 1955 Tax: $8,935 (2025)Community: Sylvan HeightsSingle Family
Taxes:$8,935
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: One or more photo(s) has been virtually staged. Move-in ready Sylvan Heights Mid-Century Bungalow, with no renovations needed. As you approach, you will notice the wonderfully cared for home with mature landscaping and a unique style. A charming, three-bedroom two-bath home has updated Kitchen and Bathrooms, there is even a large formal dining space with a built-in serving bar and wine fridge. The floors were upgraded with engineered hardwood throughout with tile in both bathrooms. Situated on a larger lot with a fully fenced in backyard that also has a 12x15 brick patio and room to add a swimming pool if desired. Sylvan Heights is one of Winter Park's Primer residential communities, that is close to Advent Health's Winter Park Hospital and top-Rated Rollins College. Just a short bike ride to Park Avenue in Downtown Winter Park with tons of shops and restaurants so you won’t have to go far for fun. Also, just minutes to downtown Orlando, and all of the Central Florida attractions so get the guest room ready for visitors... Sound like a home you would like to see. Schedule a private showing today.
Listing is courtesy of: SUMMERPARK HOMES REALTY LLC (407-603-6320)
Listing Agent: Buddy Jerome, Iii (407-579-9356)
338 BLUE HERON DR, WINTER PARK, FL 32789
$865,0006 Days on yellowkey MLS ID: O6410174
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2017 Built: 1960 Tax: $6,647 (2025)Community: Flamingo ShoresSingle Family
Taxes:$6,647
Remarks: Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Call to schedule your showing today!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Samuel Kingsford (407-808-6633)
240 N PHELPS AVE, WINTER PARK, FL 32789
$2,279,00088 Days on yellowkey MLS ID: O6389035
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2889 Built: 2026 Tax: $6,605 (2025)Community: Sylvan HeightsSpa: NoSingle Family
Taxes:$6,605
Remarks: Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a custom paneled feature wall with a sleek built-in electric fireplace, creating a striking focal point for the space. The gourmet kitchen is designed for both everyday living and entertaining, highlighted by a large center island with seating, European slab cabinetry, premium hardware, designer countertops, and high-end appliances. Ample storage and a clean modern aesthetic make this kitchen as functional as it is beautiful. Tucked beneath the staircase is a custom wine storage feature, adding a unique luxury detail. The first floor also includes a private guest suite with its own en suite bathroom, perfect for visitors or multi-generational living. A dedicated home office provides a quiet workspace, while the main-floor laundry room adds convenience. Outside, a professionally designed outdoor kitchen extends the living space and creates the perfect setting for year-round entertaining under the Florida sky. Upstairs, the luxurious primary suite serves as a private retreat. The spacious walk-in closet features a fully custom organization system, while the spa-inspired primary bathroom includes a dual-sink vanity, elegant freestanding soaking tub, and oversized walk-in shower with premium tile work. Three additional bedrooms complete the second floor. Two share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom features its own private en suite bath, offering flexibility for guests or family members. Located at 240 N. Phelps Avenue, this home places you just minutes from Winter Park’s iconic Park Avenue — a vibrant destination known for its boutique shopping, award-winning restaurants, art galleries, and charming sidewalk cafés. Residents enjoy access to top-rated schools, including Winter Park High School, as well as renowned cultural destinations such as the Morse Museum of American Art and the Polasek Museum. Outdoor lovers will appreciate nearby Central Park, Mead Garden, and the scenic Winter Park Chain of Lakes. Conveniently located near I-4, SR-417, downtown Orlando, Lake Nona Medical City, UCF, and Orlando International Airport, this home offers the perfect balance of luxury, convenience, and the timeless charm that makes Winter Park one of Central Florida’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)
Listing Agent: Milena Fernandes (407-990-5905)
1821 ENGLEWOOD RD, WINTER PARK, FL 32789
$3,135,000259 Days on yellowkey MLS ID: O6345085
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3863 Built: 2025 Tax: $11,127 (2024)Community: Forest HillsSpa: NoSingle Family
Taxes:$11,127
Tax Year: 2024
Remarks: This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789
$314,000118 Days on yellowkey MLS ID: O6380753
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1133 Built: 1985Monthly Fee: $310 Tax: $2,915 (2025)Community: Sandlewood Creek Condo Ph 10Condo
Taxes:$2,915
Remarks: Tucked inside one of Winter Park's most sought-after zip codes, this fully renovated two-story condo lives like a townhome — and feels like new construction. The main floor flows from a beautifully updated kitchen with new stainless appliances, contemporary finishes, and butcher block bar top into a bright open living space, with a convenient half bath for guests. Upstairs, both bedrooms are true primary suites — each with its own private en-suite bath, large closet, and oversized window. Major systems have all been replaced: new roof, new plumbing, new hot water heater, and new in-unit Maytag washer and dryer. Step outside to your screened patio just steps from the community pool. Walk to Park Avenue's celebrated restaurants, shops, and cafés. Zoned for Dommerich Elementary (9/10 GreatSchools) and Winter Park High School. This one is genuinely move-in ready — nothing to do but move in.
Listing is courtesy of: NOELKE REALTY (407-607-7166)
Listing Agent: Tom Noelke (407-607-7166)
1261 INDIANA AVE, WINTER PARK, FL 32789
$539,00046 Days on yellowkey MLS ID: O6400698
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1660 Built: 2005Monthly Fee: $360 Tax: $2,892 (2025)Community: Townhomes/Harper PlaceTownhouse
Taxes:$2,892
Remarks: Tucked in the heart of Harper Place, this 3-bedroom, 2.5 bath end unit townhome 1,660 sq ft of light-filled, low maintenance living in a thriving Winter Park location. The main level features a spacious living and dining room combo plus a separate family room and kitchen-perfect for entertaining. The kitchen includes a gas cooktop and range, granite counters, island, breakfast nook, and built-in cabinetry and desk. French doors open to a private side patio ideal for relaxing, pot gardening or grilling. The interior laundry off the kitchen leads out to the functional 2-car garage. Upstairs, the primary bedroom has a walk-in closet. The primary bath has a walk-in shower. Two secondary bedrooms offer flex space and share a bath with a tub shower. Wood floors downstairs and carpet upstairs. Recent updates include roof and gutters in 2022, exterior paint in 2023 and water heater in 2024. Community improvements continue with road resealing in the Spring of 2026, enhancing a well-kept neighborhood. 1261 Indiana is a great fit for a buyer seeking comfort, urban convenience, and a simplified lifestyle. Close to 1-4, shops, restaurants, hospital, and museums.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Megan Cross (407-353-9997)
2501 WINTER PARK RD, WINTER PARK, FL 32789
$1,649,00093 Days on yellowkey MLS ID: O6384756
REDUCED by $41,000 (2.4%) on 05/14/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3304 Built: 2014 Tax: $10,938 (2024)Community: Parklando #3Single Family
Taxes:$10,938
Remarks: PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.
Listing Agent: Jill Healey (407-797-1420)
1927 ELAND AVE, WINTER PARK, FL 32789
$825,000114 Days on yellowkey MLS ID: O6381009
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2242 Built: 1957 Tax: $3,190 (2024)Community: Lake Bell TerraceSingle Family
Taxes:$3,190
Elementary School: Hungerford Elem
Remarks: *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ryan Leitter (321-684-9699)
1870 WALKER AVE, WINTER PARK, FL 32789
$1,299,00084 Days on yellowkey MLS ID: O6390504
REDUCED by $100,000 (7.1%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2046 Built: 2026 Tax: $3,981 (2025)Community: Osceola HeightsSingle Family
Taxes:$3,981
Remarks: This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.
1473 BERKSHIRE AVE, WINTER PARK, FL 32789
$1,479,000348 Days on yellowkey MLS ID: O6320741
REDUCED by $20,000 (1.3%) on 05/10/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2895 Built: 2025 Tax: $5,730 (2024)Community: Orwin Manor Westminster SecSingle Family
Taxes:$5,730
Remarks: One or more photo(s) has been virtually staged. Limited-time incentive: Seller offering a $20,000 buyer credit for qualified buyers. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers the perfect blend of timeless architecture and contemporary design, offering 5 bedrooms, 4 bathrooms, and nearly 2,900 sqft of refined living space. Step inside to discover: • 10-ft ceilings & 8-ft solid-core doors • Wide-plank luxury vinyl flooring throughout • Gourmet kitchen with quartz countertops, custom cabinetry, stainless steel appliances & oversized island • Elegant electric fireplace and expansive great room • Built-in wine cellar discreetly tucked under the stairs • Downstairs guest suite for added privacy Upstairs, the primary suite impresses with pool views and a spa-style bath: dual vanities, soaking tub, walk-in shower, and a generous closet. Three additional bedrooms include a Jack & Jill layout plus one with a private en-suite. A large upstairs laundry room adds convenience. Outside, your private backyard oasis awaits: • In-ground pool, fully landscaped • Summer kitchen with built-in grill • Covered patio for year-round entertaining Located just minutes from Park Avenue, this home offers walkability, top-rated schools, cultural landmarks, boutique shops, and dining. A rare opportunity to own new construction in one of Central Florida’s most iconic neighborhoods. Schedule your private tour today — this home defines the Winter Park lifestyle.
1624 BARCELONA WAY, WINTER PARK, FL 32789
$2,235,000197 Days on yellowkey MLS ID: O6362124
REDUCED by $15,000 (0.7%) on 05/30/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3818 Built: 1972Monthly Fee: $87 Tax: $12,501 (2024)Community: SevillaSpa: NoSingle Family
Taxes:$12,501
Remarks: Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2023. A detailed list of all renovations is available upon request.
Listing Agent: Jan Walker (407-718-9644)
2228 HOWARD DR, WINTER PARK, FL 32789
$2,460,00023 Days on yellowkey MLS ID: O6407733
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3294 Built: 2026 Tax: $3,647 (2025)Community: Lake Forest ParkSingle Family
Taxes:$3,647
Remarks: Under Construction. Welcome to 2228 Howard, a designer home that complements the irreplaceable natural beauty surrounding it with a one-of-a-kind façade. This curved street-front home winds around century-old oaks while overlooking Lake Howard, creating the kind of property you will love coming home to. Many rooms inside the home are designed to incorporate the outdoor spaces. These artfully designed exterior areas feel like an extension of the interior, making the home feel even larger and more luxurious. The first floor welcomes you and your guests through the 5’ wide steel pivot door near the private office. The extra-large kitchen, open pantry, and breakfast nook are framed by warm natural oak floor-to-ceiling cabinetry and Thermador appliances while overlooking the exterior raised garden bed. This beautiful kitchen flows seamlessly into the living room, which features a modern floating-hearth fireplace. The living room opens to the outdoor living space, summer kitchen, pool, and hot tub. The primary bathroom has a modern natural feel, featuring a glass sauna room that opens to a private outdoor spa with hot and cold plunge tub. The first-floor laundry room is located just off the two-car garage and includes a drop zone for additional organization. Another bonus feature is the inclusion of two laundry rooms—one on each floor. Upstairs, the kids’ lounge is surrounded by three bedrooms and a secret media room. One bedroom is en-suite, while the other two bedrooms share a common bathroom with dual vanity areas. The exterior of the home utilizes every area like a thoughtfully designed park, creating usable space around every corner. The driveway accommodates several vehicles and includes a side drive for additional parking and storage behind the gate and garage. When you do leave your beautiful home, you are surrounded by the best that Winter Park and Orlando have to offer. This neighborhood is zoned for top-rated schools, where kids walk and ride their bikes to school daily, and is surrounded by amazing parks, restaurants, shops, and nature. Your home can feel like a perfect balance of natural and modern architecture, both inside and out. Call us to see how this home delivers that truly unique feeling.
Listing is courtesy of: COLEDEV REAL ESTATE LLC (407-915-0456)
Listing Agent: Ryan Feely (321-663-1433)
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