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$675,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

433 Gilbert Road, Winter Park
$379,900
4 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code
**This property qualifies for $5,000 Buyer Credit** Updated 4/2 with New Roof, New AC (x2), and New Dual-pane Windows | No HOA | Top-Rated Winter Park School Zone ... Welcome to low-maintenance Winter Park living at 4965 Orange Ave in 32792 with no HOA constraints or fees. Nestled on a quiet lot zoned for top-rated Orange County Public Schools Lakemont Elementary, Maitland Middle, and Winter Park High School, this move-in ready four-bedroom single-family home offers major high-ticket capital improvements already completed. Upgrades include a NEW Roof, two NEW A/C systems for dual-zone energy efficiency, NEW dual-pane insulated windows, fresh interior and exterior paint, and modern fixtures throughout. The carpet-free interior boasts easy-to-clean polished terrazzo and modern ceramic tile flooring, an updated galley kitchen with stainless steel appliances and solid wood cabinets, and two thoughtfully remodeled bathrooms. Designed with incredible layout versatility, the split four-bedroom floor plan includes direct exterior access through sliding glass doors, making it exceptionally well-suited for a multi-generational setup, in-law suite, private guest retreat, or dedicated home office. Outside, the expansive fully fenced backyard provides ample room for pets, outdoor entertaining, or a future pool, while the attached carport offers covered parking and a dedicated laundry utility storage room. Enjoy an unbeatable Central Florida location just minutes from Park Avenue dining, boutique shopping, local parks, and major Orlando commute routes. $5,000 Buyer Credit for qualified buyers. Call for details.

4965 Orange Avenue, Winter Park
$1,690,000
4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential. Coming soon. Reach out to the listing agent if you would like more information about the property.

708 Balmoral Road, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Manor SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the oversized 76x133 lot, inviting front porch, and clean curb appeal set the tone. Inside, original terrazzo floors, vaulted ceilings, and a bright open great room create warmth, charm, and livability. French doors open to a screened porch overlooking the spacious backyard. The split-bedroom floor plan features two renovated bathrooms, while the redesigned kitchen offers brand-new appliances, cabinetry, and quartz countertops. A spacious 19x12 family room with tile flooring connects to a large inside laundry room with abundant storage and flexible workspace options. Beyond the visible updates, this home stands apart because so many of the expensive and often-overlooked improvements have already been done, including roof, plumbing re-pipe, electrical updates and full-house rewire, hurricane-impact windows, impact front and rear doors, new mini-split HVAC systems, cast iron drain replacement, interior and exterior paint, and more. A rare opportunity to own a thoughtfully improved home in one of Winter Park’s most desirable locations — with no HOA. WELCOME HOME!

2974 Chantilly Avenue, Winter Park
$840,000
3 Beds ⋅ 3 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code
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. Now offering $10,000 Seller Credit! Call to schedule your showing today!

338 Blue Heron Drive, Winter Park
$625,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code
***FULLY REMODELED WINTER PARK POOL HOME NEAR BALDWIN PARK! *** 1 YR HOME WARRANTY INCLUDED — a beautifully updated 4-bedroom, 3-bath home with a dedicated office, ideally located near both Winter Park and the highly sought-after Baldwin Park community, known for its lakeside dining, walkability, parks, boutiques, and vibrant neighborhood atmosphere. This move-in ready home features an open and light-filled layout with designer finishes throughout, including updated flooring, custom cabinetry, modern lighting, and beautifully remodeled bathrooms and kitchen with premium appliances and upscale countertops. Major upgrades include a NEW roof (2023), windows (2023), water heater (2023), electrical panel (2023), plus updated plumbing and electrical throughout for true peace of mind. Enjoy spacious living areas, a luxurious primary suite, and a private backyard perfect for relaxing or entertaining. Conveniently located near top-rated schools, parks, shopping, dining, Park Avenue, and everything Winter Park living brings, this home combines modern updates with an unbeatable Central Florida location.

1946 Strathaven Road, Winter Park
$450,000
4 Beds ⋅ 2 Baths ⋅ Winter Park Pines Merrie Oaks SubDv. ⋅ 32792 Zip Code
Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for your vision to come to life. Whether you’re an investor, builder, or buyer looking to create your dream home, this property offers the ultimate clean slate for a full renovation or custom redesign. Situated in highly desirable Winter Park, this property places you in the heart of one of Orlando’s premier communities, known for its tree-lined streets, charm, upscale shopping, dining, and cultural attractions. Enjoy easy access to Downtown Winter Park Historic District and iconic Park Avenue, home to boutique shopping, cafés, restaurants, and vibrant community events, along with the beauty of Central Park and the cultural appeal of The Charles Hosmer Morse Museum of American Art. Winter Park is also home to the prestigious Rollins College, adding to the area’s timeless character and desirability. Bring your contractor, your imagination, and your vision—properties with this kind of potential in Winter Park are rare. Endless possibilities await!

316 Beckett Court, Winter Park
$1,350,000
3 Beds ⋅ 2 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy, nature, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly exceptional. No HOA. No CDD.

1881 Lake Spier Drive, Winter Park