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$389,000
3 Beds ⋅ 2 Baths ⋅ 2015669 MLS ⋅ NEW Status
A rare 1940s limestone cottage in the heart of the Monticello Park Historic District, complete with a fully separate guest casita - this is historic San Antonio living that blends modern convenience with vintage charm. At 336 North Drive, original wood floors carry through room after room, and small details like antique glass doorknobs are quiet reminders of the style and craftsmanship of a bygone era. A wood-burning fireplace anchors the living room with the kind of warmth new construction can't replicate, and a second living area and separate dining room offer the flexibility that modern life demands. The kitchen has been updated with stainless appliances, but it hasn't lost the charm that makes this house feel like it belongs to its prewar era. Down the hall, three bedrooms and two bathrooms give you choices: two of the bedrooms share an original pocket door and can function as one connected suite, ideal for kids, in-laws, or a private office setup. The primary bedroom goes further, with three closets and a south-facing private deck of its own - a small, quiet escape just steps from your bed. Out back, mature trees shade a large yard and an additional deck perfect for entertaining. And then there's the casita: 304 square feet, freshly painted with new flooring, complete with its own kitchenette and full bath. It's your guest space, rental, or studio, depending on the season of life you're in. All of this is located in one of San Antonio's most walkable and architecturally significant neighborhoods, just minutes from downtown, the Pearl, Medical Center and Woodlawn Lake. 336 North Drive was built to be lived in, not just admired!

336 North Dr, San Antonio
$355,000
2 Beds ⋅ 1 Baths ⋅ 2014333 MLS ⋅ NEW Status
Rare find in historic Monticello Park: a main home plus a separate City-permitted guest house on one lot. The main residence offers 2 bedrooms, 1 bath and 1,338 sq ft with original hardwood floors, an updated kitchen with gas cooking, granite counters and stainless appliances, and a remodeled full bathroom. Out back, the detached guest house features 1 bedroom, 1 bath, a full kitchen and its own private entrance - 528 sq ft of additional space - plus a large second-story storage area accessed by pull-down stairs (storage only; not included in living area). The possibilities are yours: live in the main house and let the guest house help offset your payment, or give a parent or family member true privacy without sharing a roof. A separate powered storage building, covered patio, water softener, RV hookups and mature shade trees complete the 7,850 sq ft lot, with alley access giving the guest house its own separate approach. Walking distance to Woodlawn Lake and minutes to the Deco District and downtown.

2218 W Magnolia Ave, San Antonio
$329,000
3 Beds ⋅ 1 Baths ⋅ 2013899 MLS ⋅ NEW Status
Charming Art Deco Gem Near Woodlawn Lake - Move-In Ready! Tucked into one of San Antonio's most walkable pockets, 237 Donaldson Ave is a beautifully updated 3-bedroom, 1-bath home that blends Art Deco character with mid-century modern charm. This is a house with a story - historic bones, thoughtfully updated for how you live today. Step inside to a freshly renovated kitchen and bathroom, where clean lines and modern finishes meet the timeless details that made this neighborhood special in the first place. Sunlight, character, and a layout that just feels right - this is the kind of home that photographs well but feels even better in person. Location is everything here: you're just minutes from Woodlawn Lake, perfect for morning walks, kayaking, or sunset picnics, and an easy stroll to HEB for your everyday errands. Historic charm, walkability, a great park/playground and a lake lifestyle - all in one address. Homes with this much character and history don't stay on the market long - schedule your showing today.

237 Donaldson Ave, San Antonio
$390,000
2 Beds ⋅ 2 Baths ⋅ 2012254 MLS ⋅ ACTIVE Status
Beautiful 1928 historic home in the heart of the Deco District. Two separate lots with two buildings zoned C-1 on visible corner lots. This property can function as a residence or commercial or combination. Impeccable quality construction; Original wood floors and decorative sconces in mint condition. Main home has two eating areas; Garage apartment has kitchenette, living room, bedroom & bath. Plenty of parking. OWNER/LREB

1633 W Kings Hwy, San Antonio
$319,900
2 Beds ⋅ 1 Baths ⋅ 2009672 MLS ⋅ PRICE CHANGE Status
Built in 1928, this beautifully updated 2-bedroom, 1-bath Monticello Park home offers approximately 1,353 sq. ft. of timeless character paired with modern improvements. Original hardwood floors, classic doors and trim, decorative windows, distinctive brickwork, and abundant natural light showcase the craftsmanship of the era. The updated kitchen features two-tone cabinetry, stone-look countertops, tile backsplash, brass-tone hardware, and stainless steel appliances, creating a fresh look while complementing the home's historic personality. The renovated bathroom includes a dual-sink vanity, tiled tub surround, and stylish brass-tone fixtures. Storage is a standout, including a large walk-in closet with extensive built-in shelving, plus a dedicated laundry area for added convenience. Outside, enjoy a covered rear patio and spacious fenced backyard with plenty of room for entertaining, gardening, pets, or simply relaxing outdoors. A detached garage provides additional parking and storage. With nearly a century of history, this Monticello Park classic offers the best of both worlds-1920s craftsmanship, preserved architectural character, and meaningful modern updates.

146 North Dr, San Antonio
$411,000
3 Beds ⋅ 1 Baths ⋅ 2007443 MLS ⋅ ACTIVE Status
Historic Charm . Timeless Possibilities ** Vintage Well Loved Craftsman home in Historic Monticello Park " Looks Like Something Out of a Story book" ** Corner Lot ** ADDITIONAL DWELLING - A Fully Equipped Casita...Kitchen/Bath/Living Area Approx. 400sf ** Original Architecture Includes Unique Arches, Built-Ins Throughout, Several French Doors and Beautiful Natural Light ** Oversized Eat-in Kitchen in the Heart of the Home...Original Built-In Buffet and Custom Floor to Ceiling Shelves Framing the Window seat ** The Front Corner Room with Panoramic Windows Has a Vibe of it's Own ** Large Landscaped Backyard with Deck...A section for the Storage Units...and More Space for your Garden or Raised beds. Grab Your realtor.. and Your Vintage Vision and Come see for Yourself !!

301 Furr Dr, San Antonio
$525,000
3 Beds ⋅ 2 Baths ⋅ 2007233 MLS ⋅ ACTIVE Status
Investor opportunity in historic Woodlawn Terrace with a proven short-term rental setup and strong income-producing potential. Financials and recent short-term rental performance available upon request. The main home features 3 bedrooms and 2 baths, beautifully blending modern comforts with charming original features. As you step inside, you'll be greeted by the warm glow of original hardwood floors and a restored shiplap ceiling that flow throughout the open-concept living area. The spacious living room features large windows that flood the space with natural light, while the updated island kitchen boasts sleek granite countertops, custom Shaker cabinets, stainless steel appliances with gas cooking, and a stylish backsplash ideal for both everyday living and entertaining. The primary suite offers a peaceful retreat with an en-suite bath featuring contemporary fixtures, an oversized walk-in shower, and an expansive closet. Two additional bedrooms provide flexibility for family, guests, or a home office and share a well-appointed second bath. Step outside to a thoughtfully xeriscaped backyard designed for low-maintenance living and entertaining, complete with a bocce ball court that creates the perfect space for hosting friends or enjoying relaxed evenings at home. Enhancing this property is a fully separate upstairs 2-bedroom, 1-bath accessory dwelling unit featuring a full kitchen and private entrance, creating additional flexibility for short-term rental income, long-term tenants, guests, or multigenerational living. Just a few blocks from Woodlawn Lake, this property's blend of modern renovations, classic details, and investment versatility makes it a truly rare opportunity.

1917 W Huisache Ave, San Antonio
$325,000
3 Beds ⋅ 1 Baths ⋅ 2006806 MLS ⋅ ACTIVE Status
Darling, updated cottage in historic Monticello Park. Inviting front porch welcomes you inside to a nice sized living room with brick hearth fireplace. Separate formal dining room. Updated kitchen has attached breakfast room, stone countertops and backsplash, gas stove and pantry. Three bedrooms share the updated hall bath.

2023 W Kings Hwy, San Antonio
$339,500
3 Beds ⋅ 2 Baths ⋅ 1945096 MLS ⋅ ACTIVE Status
Authentic 1930s English Tudor nestled in the heart of Monticello Park, featuring a limestone facade, graceful arched entry, mature shade trees, and timeless storybook charm. Inside, original hardwood floors, arched interior doorways, a fireplace, formal dining room, and a charming breakfast nook just off the kitchen that's equally suited for morning coffee, a work-from-home office or even a future laundry room. A detached garage with an attached storage area offers additional possibilities for storage, a workshop, or future creative use-adding yet another layer of potential to this character-filled property. There is also a side porch (old porte cochere) perfect for cozy, slow mornings. Located in one of San Antonio's most architecturally significant historic neighborhoods, where tree-lined streets and distinctive homes make every block feel a little different, this property offers the rare opportunity to become part of Monticello Park's enduring legacy. Rich in original architectural details and ready for its next steward, this Tudor presents the chance to breathe new life into a home whose best features have never gone out of style.

514 Donaldson, San Antonio
$300,000
3 Beds ⋅ 2 Baths ⋅ 1961311 MLS ⋅ ACTIVE Status
Don't miss your opportunity to step back in time and embrace the charm of this cozy historical home nestled in the heart of San Antonio's beloved Monticello Park Historic District. This unique property offers a perfect blend of vintage elegance and modern comfort. There is plenty of parking with a long driveway. Located just minutes away from Woodlawn Lake, Downtown, The Pearl, Medical Center, major highways, shopping, dining and so much more! The Sellers are open to all furniture and household items conveying. This home won't last long so schedule your tour today!!!

147 North Dr, San Antonio
$550,000
3 Beds ⋅ 3 Baths ⋅ 1948735 MLS ⋅ ACTIVE OPTION Status
Nestled within Monticello Park's historic neighborhood, this meticulously renovated property offers a blend of historical charm and modern conveniences. With three bedrooms and two and a half bathrooms, this home provides a spacious and inviting environment. The classical floor plan welcomes you with timeless elegance, from the captivating staircase to the hardwood floors that span the home. Oversized windows bathe the interiors in natural light and provide picturesque views of the outdoors. The kitchen, updated for contemporary living, boasts ample cabinetry, granite countertops, and stainless steel appliances. The primary bedroom is a serene retreat, featuring a generous layout complemented by a cozy sitting area and an ensuite bathroom. Exceptional closet space provides practical storage solutions while enhancing the suite's functionality. Outside, the private backyard oasis beckons with a stunning, newly constructed custom Cody pool added in 2023, and multiple seating areas, perfect for relaxation and hosting gatherings. With its seamless integration of historic charm and modern comforts, this property epitomizes the essence of luxurious living in the sought-after Monticello Park neighborhood.

218 Mary Louise, San Antonio
$390,000
4 Beds ⋅ 2 Baths ⋅ 1940939 MLS ⋅ ACTIVE Status
A classic 1940 home offering over 2,000 square feet of well-proportioned living space in the Jefferson/ Woodlawn Lake area with an low ASSUMABLE VETERAN LOAN. This 3-bedroom, 2-bath residence features original hardwood floors, high ceilings, generous rooms, and a traditional fireplace that anchors the main living area. The layout provides comfortable everyday living with plenty of space to gather and entertain. Set on a deep lot in an established neighborhood near Woodlawn Lake Park, the home enjoys mature trees and convenient access to downtown, the Medical Center, and the Pearl area. Major system upgrades include a new air conditioning system installed just one year ago, the largest residential unit available, and full electrical rewiring completed approximately two years ago. A solid, character-filled home with space, comfort, and important updates already in place.

2141 W Magnolia Avenue, San Antonio

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