Homes for Sale Near Maitland Middle in Winter Park - 86 homes

Remarks: In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Padgett Mccormick (407-645-4321)

Remarks: Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes -  not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Abby Greenberg (407-484-2689)

Remarks: Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, Lakemont Elementary, and Interlachen Country Club. Built by MichaelCharles Homes with interiors by Wolfe-Rizor Interiors, the home pairs timeless architecture with refined contemporary design, abundant natural light, and exceptional craftsmanship. The thoughtfully designed floor plan offers 4 bedrooms, 4 full bathrooms, and 1 half bathroom. The first-floor primary suite features a spa-inspired bathroom and an expansive custom walk-in closet with dedicated his-and-her wardrobe areas. A flexible adjoining room is ideal as a private office, nursery, fitness room, or optional fifth bedroom. On the opposite wing of the home, the private guest suite includes a full bathroom and walk-in closet. At the heart of the home, the chef's kitchen showcases a large center island, custom cabinetry, and premium finishes. Oversized glass doors open to a covered lanai with outdoor dining, grilling space, and a resort-style pool. Framed by mature Japanese maple trees, the backyard offers exceptional privacy and a spacious lawn for recreation or entertaining. Situated on a quiet, oak-lined street, this custom-built home reflects the quality in every detail, presenting a rare opportunity to own an exceptional residence in the heart of Winter Park.

Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)

Listing Agent: Richard Palmano (407-232-5801)

Remarks: WALK TO PARK AVENUE from this RARE nearly HALF ACRE homesite with OVER 4,000 SQUARE FEET and 5 BEDROOMS in one of Winter Park's most desirable locations. Leave your car at home and enjoy Park Avenue's renowned restaurants, boutiques, cafés, parks, and the Winter Park Golf Course just moments from your front door. Tucked away on a quiet cul-de-sac, this timeless two story residence offers the perfect combination of space, warmth, and an exceptional floor plan designed for both everyday living and effortless entertaining. From the moment you step inside, the home feels welcoming with expansive living spaces, soaring ceilings, and abundant natural light. The main level is anchored by a spacious primary suite, while the family room features dramatic ceilings and opens seamlessly to the kitchen and casual dining area, creating the true heart of the home. French doors lead to a screened patio with a charming Southern feel that overlooks the expansive backyard, offering endless possibilities for a pool, outdoor entertaining, or future expansion. A separate formal living room provides additional flexibility, while the formal dining room connects to a butler's pantry, making hosting gatherings both functional and elegant. Upstairs, you'll find four generously sized bedrooms with beautiful original hardwood floors, providing ample space for family, guests, home offices, or a playroom. LOCATION. LOT SIZE. WALKABILITY. Opportunities to own a nearly half acre property this close to Park Avenue are exceptionally rare. Enjoy the very best of Winter Park with premier shopping, award winning dining, parks, golf, and everything that makes this one of Central Florida's most coveted addresses just a short stroll away.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)

Remarks: On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch leads into a bright foyer highlighted by custom millwork and warm wood flooring, setting the tone for the home’s clean, curated style. The open-concept main living space flows seamlessly from the dining area into a spacious family room and a chef’s kitchen designed to impress. Anchored by a generous marble island with seating, the kitchen features Viking stainless steel appliances, a gas cooktop, honed granite perimeter countertops, custom cabinetry with upper and under-cabinet lighting, and stylish tile backsplash. A wet bar with wine refrigerator adds to the home’s entertaining appeal. The first floor also includes a versatile office or playroom with custom built-ins, a functional mudroom/drop zone and abundant storage throughout. Upstairs, the primary suite offers a peaceful retreat with natural light and a spa-inspired bath featuring dual vanities, a soaking tub and a glass-enclosed shower. Secondary bedrooms are well-sized and thoughtfully designed, while the third-floor bonus suite with full bath provides ideal space for guests, a home office or additional living. Outdoor living is equally inviting, with a covered back porch equipped with remote-controlled phantom screens overlooking a private, professionally landscaped yard with artificial turf and a low-maintenance pool, ideal for year-round enjoyment. Additional features include two HVAC systems with Nest thermostats, hardwood flooring on the main level, and designer finishes throughout. Zoned for sought-after schools including Dommerich Elementary, Maitland Middle and Winter Park High. This is a rare opportunity to own a move-in ready home that balances style, function and location in one of Winter Park’s desirable settings.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Audra Wilks (407-252-8582)

Remarks: Exceptional opportunity to build new or renovate and expand on this desirable lot in Winter Park. Situated on a charming tree lined street and in a neighborhood that is experiencing a great deal of new development. The existing 1950s residence features parquet wood flooring and open living and dining spaces, which overlooks the backyard and open wooden deck. With generous space to work with, there are great possibilities to create your own custom residence. The property is zoned for long-established schools - Lakemont Elementary, which is just down the street from the property, as well as Maitland Middle and Winter Park High. Plus, ideally located within a short stroll to the Winter Park Y, Phelps Park, and minutes to downtown Park Ave's shopping and dining! Property is being sold AS IS.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Dawn Romance (407-929-2826)

Remarks: Beautifully updated with a refined, welcoming feel, this two-story home sits on a charming brick-lined street in the heart of Winter Park, just minutes from the shops, dining and parks that make the area desirable. Natural light fills this home, with four bedrooms and four full baths with custom details throughout including wonderful wood flooring throughout the first level. The well designed open kitchen is inviting centered around an oversized island with a beverage refrigerator, granite countertops, new backsplash, five-burner gas range with double ovens, range hood, pantry and abundant wood cabinetry. It flows easily into the family room with a gas fireplace and views of the private backyard and covered patio creating an expanded everyday living space. A separate dining room with a custom wainscoting accent wall offers a polished yet relaxed setting for gatherings, while the nearby laundry room features a butcher block countertop, custom shelving and excellent storage. The first floor bedroom, currently used as a playroom, sits next to a marble-floored full bath and works equally well as an office, gym or guest space. Upstairs, a cozy landing provides an additional flex area, while the attractive and spacious renovated primary bath includes dual sinks, granite counters, a soaking tub, separate walk-in shower and a huge walk-in closet. Two additional bedrooms share a new Jack and Jill bath each with its own separate sink area. Storage is thoughtfully integrated throughout with custom closets and additional space under the stairs, complemented by plantation shutters, crown molding and substantial baseboards on the main level. The detached guest house adds rare versatility with its full bath, custom cabinetry and large walk-in closet, ideal for guests, a private office or creative studio. A long matching pavered driveway provides ample parking and completes the home’s distinctive curb appeal. Zoned for top-rated Dommerich Elementary, Maitland Middle and Winter Park High. Schedule your private showing today and experience a home that stands apart from the ordinary. You will love living here!

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Jo Ann Lamar (321-231-0052)

Remarks: Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!

Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)

Listing Agent: Kim Griffin (407-314-5033)

Remarks: Updated Winter Park home with major improvements already completed and no HOA! Located at 4965 Orange Ave., this move-in ready property offers a desirable Central Florida location with convenient access to shopping, dining, parks, major roadways, and everything the Winter Park area has to offer. Recent updates include a NEW Roof, Dual-pane, Energy-efficient Windows, 2 NEW A/C systems, fresh interior and exterior paint, upgraded baseboards, Beautifully Remodeled Bathrooms, and terrazzo & ceramic tile flooring throughout (no carpet!!). The galley-style kitchen features stainless steel appliances, a decorative backsplash, and an efficient layout designed for everyday functionality. Both bathrooms have been beautifully refreshed, while the durable flooring and fresh finishes create a clean, cohesive feel throughout the home. Outside, the large fenced yard provides excellent outdoor space for entertaining, gardening, pets, or future possibilities. The attached carport includes a convenient storage and laundry room for added practicality. With no HOA, updated major systems, energy-efficient windows, and a centrally located Winter Park address, this home is an excellent opportunity for buyers searching for an updated home in Winter Park, FL with modern improvements, low-maintenance features, and easy access to the Greater Orlando area.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Allison Day (407-617-2881)

Remarks: Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: 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!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Catherine D'Amico (407-252-3210)

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

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Vonda Fields (321-438-6906)

Remarks: This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Quentin Green, Ii (773-418-5359)

Remarks: Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Brian Teach (407-923-9313)

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

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

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Virtually Staged. Stylish Mid-Century Modern gem in the heart of Winter Park, minutes from Park Ave! Fully renovated corner lot home featuring 5 beds/3 baths, 2,132 SF of CBS block construction. Prime location just 3 blocks from iconic Park Avenue, minutes from Winter Park Village, Rollins College, Publix, Trader Joe's, Whole Foods & AdventHealth. Zoned for top-rated Lakemont Elementary, Maitland Middle & Winter Park High. Currently operating as a fully occupied income-producing PadSplit co-living property generating up to $5,664/month gross at full occupancy — ideal for investors seeking turnkey cash flow. New 4-ton A/C (2025), permitted renovation, modern kitchen with convection oven, dishwasher, range & refrigerator, updated bathrooms, luxury finishes throughout. On-site laundry, high-speed WiFi, driveway & street parking. Corner lot with abundant natural light, north exposure, open floor plan. No HOA. No CDD. No flood insurance required. Walking distance to WP9 Golf Course, SunRail station & Central Park. Interested in living in the home yourself? Contact listing agent to discuss options.

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Carolina Mejia (407-572-1340)

Remarks: Under contract-accepting backup offers. Experience the Florida lifestyle in this beautifully updated 4-bedroom, 3-bath Winter Park pool home! From the renovated bathrooms and spacious family room to the all-new flooring and fresh paint, this move-in-ready home offers comfort, style, and room to entertain. Step through the new French doors into your private backyard oasis featuring a sparkling pool with new pavers, a new pool pump (2026), and a child safety fence for added peace of mind. The homes roof was replaced in 2016 and other updates include HVAC system with ductwork, water heater, all-new windows, an updated utility room, a new garage door with remote, plus an extended driveway for spacious parking. Conveniently located near shopping, dining, and downtown Orlando. This home is zoned for highly rated Lake Monte Elementary, Maitland Middle, and Winter Park High School. Don't miss this exceptional opportunity to own a beautifully updated home in one of Central Florida's most desirable communities.

Listing is courtesy of: LUXE PROPERTIES (305-809-7650)

Listing Agent: Orlando Silva (407-463-2821)

Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

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

Listing Agent: Kathy Summers (407-832-6986)

Remarks: Under contract-accepting backup offers. Life is simply better when everything is just around the corner. Perfectly positioned in the heart of Winter Park, this beautifully maintained David Weekley home offers the rare opportunity to enjoy one of Central Florida's most desirable lifestyles. Located just four blocks from Park Avenue and one block from Winter Park Village, you'll also enjoy close proximity to Hannibal Square, Central Park, Publix, the Winter Park Farmers' Market, acclaimed restaurants, boutique shopping, museums, cafés, and everyday conveniences. Built in 2017, this thoughtfully designed home blends timeless architecture with modern luxury across a spacious and functional floor plan. The first floor features three generously sized bedrooms and two full bathrooms, including a private primary suite complete with a spa-inspired bath and an expansive walk-in closet. Upstairs, the home's open-concept living spaces are designed for both everyday comfort and effortless entertaining. Natural light fills the expansive living and dining areas, while the chef's kitchen serves as the centerpiece of the home. Featuring premium Jenn-Air stainless steel appliances, a natural gas cooktop, generous cabinetry, beautiful countertops, and a large center island, it's a space equally suited for hosting friends or preparing a quiet dinner at home. Sliding glass doors extend the living area to an oversized balcony with Trex decking, creating an inviting outdoor retreat for morning coffee, evening cocktails, or dining under the stars. Built with quality and efficiency in mind, the home includes double-pane windows, great insulation, and a gas tankless water heater. The homeowners association further enhances the low-maintenance lifestyle by providing lawn and shrub care, irrigation water, and maintenance of the community perimeter wall, allowing you to spend more time enjoying your home and less time maintaining it. More than just a beautiful residence, this home offers an exceptional opportunity to experience the very best of Winter Park. Enjoy dinner on Park Avenue, spend Saturday mornings at the Farmers' Market, explore the boutiques of Hannibal Square, relax in nearby parks, or meet friends for coffee, all just moments from your front door. This is a home where luxury, convenience, and one of Winter Park's most sought-after locations come together beautifully.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Brian Rotenberger (407-948-8478)

Remarks: (HUGE PRICE REDUCTION & NEWLY ENHANCED REAR LANDSCAPING ADDED FOR EXCEPTIONAL PRIVACY AND MORE SECLUDED OUTDOOR LIVING EXPERIENCE) Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped in upgraded pavers, offering both elegance and functionality. A very rare 4-car garage in Winter Park with two in the rear and two in the front of the home. Starting with entering through massive 10 ft. double iron doors flowing into the foyer with 11ft high ceiling beginning with the flex/office room and formal dining to your left and right. Followed by entering the gallery that leads to the great room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" wood cabinetry, a custom walk-in pantry, and top-of-the-line Thermador professional series. That Includes a 48' refrigerator, 48" gas cooktop, custom hood, dishwasher, built-in microwave, double convection ovens and built in coffee station. On your way to the formal dining, you pass by the show-stopping, Tempered glass wine room. Its crystal-clear glass enclosure offers a striking view of your curated collection, while the built-in wine chiller ensures each bottle is perfectly preserved. This elegant transition creates a seamless blend of function and sophistication, setting the tone for unforgettable dining experiences just steps away. The primary suite offers tranquility peace of mind, and the primary bath has a spa-like oasis with a spacious shower stand-alone tub. Followed by a custom closet thoughtfully design with plenty of room and storage. The guest retreat area has a huge bedroom, access to a full bath including private access to the Lania and pool. Tucked away with its own private entrance attached to the rear garage, the in-law suite above the garage offers the perfect blend of comfort and independence. This thoughtfully designed space includes a full bath, a cozy living area, and a convenient space with a kitchenette—ideal for extended stays or multi-generational living. Make your way to the second floor that has 11ft ceilings as well. As you reach the top the space opens into a massive game room with a wet bar, perfect for entertainment retreat with a balcony. All second-floor bedrooms have a thoughtfully design with a full bath for privacy. As you make your way back downstairs to outside, step through the oversized sliding glass doors and into your private outdoor oasis. Effortlessly extending your living space into the open air. Just beyond, the sparkling gas heated/saltwater pool and spa framed by lush landscaping and designed for both relaxation and recreation. Also, the fully equipped summer kitchen features gas grille, beverage refrigerator and ample counter space—perfect for alfresco dining and effortless entertaining. This masterpiece is equipped with a full irrigation system around the home, exterior lighting, exterior cameras for security. Smart home system ready for lighting, music and security controlled by Control 4 system for your convenience. Interlachen Golf community less than 5 min, Phelps Park walking distance, Park Ave 10 min and restaurant and retail minutes away.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Prentice Williams (321-438-8955)