Middletown Homes for Sale

3 Beds ⋅ 2 Baths ⋅ 326089183 MLS ⋅ ACTIVE Status

Enjoy the comfort of new construction at 15225 Rich's Way in Middletown! Situated on a level .26-acre lot on a court, this thoughtfully designed 3-bedroom, 2-bath home offers 1,628 square feet of living space, a 528-square-foot finished garage, and 220 square feet of covered decks. Additional parking alongside the home provides room for a boat or RV. The kitchen features quartz countertops, a spacious island perfect for entertaining, and a propane gas range with an overhead microwave, dishwasher, and refrigerator. Laminate flooring throughout the living areas is complemented by tile in the bathrooms and laundry room. Recessed lighting adds a clean, modern touch, while ductless mini-splits provide heating and air conditioning. The spacious primary suite is set apart from the other two bedrooms for added privacy and features a generous walk-in closet. Its bathroom includes tile flooring, a spacious shower with double doors, and extra cabinetry for storage. The guest bathroom offers a recessed tub with a shower, while the dedicated laundry room includes tile flooring and shelving above the laundry area. Finished with Sheetrock and paint, the garage features an insulated garage door, convenient side-door access, and a garage-door opener positioned away from the ceiling to provide additional overhead clearance for a larger truck. With covered outdoor spaces, extra parking, and a practical layout, this new Middletown home is ready for its first chapter!

15225 Richs Way, Middletown

$479,000

5 Beds ⋅ 4 Baths ⋅ LC26227882 MLS ⋅ Active Status

Majestic multi-family property with peace and privacy on over 4 acres, yet just 5 minutes to the heart of town. Main home was thoughtfully built by the owner, who was a master carpenter. The quality of construction and materials is evident all throughout the home, from the metal roof to the concrete slab foundation. This 1200sf 2 bedroom/1 bathroom has an inviting and open floor plan with the bedrooms on opposite sides of the house. Kitchen has lots of counter space and cabinets plus a walk-in pantry/baker's closet. Knotty pine ceilings, fir floors, skylights, and spacious front/back decks invite you to bask in the mountain energy. Below the main home is a spacious workshop for all of your projects, and has a half bath for possible conversion to a studio living space. The second residence is a 1970 mobile home with 3 bedrooms/2 bathrooms and an addition built in 2015. The high ceilings and open kitchen/living area are warm and welcoming. Mini-split for efficient heating and cooling with woodstove to add extra warmth and ambiance when desired. The sliding glass doors invite you outside to enjoy the fresh air and beautiful views of the surrounding forest. Fenced-in yard area off the deck is ready for your pets and gardening, with a small art studio or greenhouse to play with your plants and crafts. Other features include an outdoor shower and jetted tub, RV hookup, and additional storage. This is the perfect property for generational living or relaxing retreat. Since the homes are non-conforming, this will not qualify for traditional financing; will need a cash offer or seller financing is available for up to 10 years with substantial down payment.

15306 Western Mine Road, Middletown

$1,695,000

4 Beds ⋅ 4 Baths ⋅ LC26220768 MLS ⋅ Active Status

High in the Mayacamas near the Napa and Sonoma county lines, 14507 Western Mine Road encompasses 89 acres at approximately 2,300 feet in elevation. The 3,500 sq. ft. custom residence offers 4 bedrooms, a flexible 5th room and 3.5 bathrooms. Vaulted ceilings, radiant heated floors and a fireplace define the main living areas, while the open kitchen connects easily with the living space and covered outdoor dining deck. A wraparound deck, screened patio and large finished workshop/studio add to the home's flexibility. Outdoor amenities include stone terraces, an outdoor shower, soaking tubs, a wood-fired oven, grill, fire pit and tennis court. The grounds also feature approximately 1 acre of vegetable and flower gardens, established fruit trees, a chicken house, private trails and a seasonal pond. Two furnished 16-foot glamping tents provide additional guest accommodations. In addition to its residential and recreational appeal, the property has operated as a successful short-term rental, with seller-estimated gross rental revenue of approximately $217,000 for 2026. Its hospitality history also includes private retreats and photo shoots, creating an opportunity to continue an established business while retaining the property for personal use. A private well, natural spring water, private septic system and backup generator support residential and guest use. Approximately 15 minutes from Middletown, 25 minutes from Calistoga and 50 minutes from Sonoma County Airport. Revenue figures are seller estimates and are not guaranteed; buyers should independently verify financial information and permitted uses.

14507 Western Mine, Middletown

$599,000

3 Beds ⋅ 2 Baths ⋅ LC26219913 MLS ⋅ Active Status

Enjoy the comfort of new construction at 15225 Rich’s Way in Middletown! Situated on a level .26-acre lot on a court, this thoughtfully designed 3-bedroom, 2-bath home offers 1,628 square feet of living space, a 528-square-foot finished garage, and 220 square feet of covered decks. Additional parking alongside the home provides room for a boat or RV. The kitchen features quartz countertops, a spacious island perfect for entertaining, and a propane gas range with an overhead microwave, dishwasher, and refrigerator. Laminate flooring throughout the living areas is complemented by tile in the bathrooms and laundry room. Recessed lighting adds a clean, modern touch, while ductless mini-splits provide heating and air conditioning. The spacious primary suite is set apart from the other two bedrooms for added privacy and features a generous walk-in closet. Its bathroom includes tile flooring, a spacious shower with double doors, and extra cabinetry for storage. The guest bathroom offers a recessed tub with a shower, while the dedicated laundry room includes tile flooring and shelving above the laundry area. Finished with Sheetrock and paint, the garage features an insulated garage door, convenient side-door access, and a garage-door opener positioned away from the ceiling to provide additional overhead clearance for a larger truck. With covered outdoor spaces, extra parking, and a practical layout, this new Middletown home is ready for its first chapter!

15225 Rich's Way, Middletown

$1,695,000

4 Beds ⋅ 4 Baths ⋅ 326085323 MLS ⋅ ACTIVE Status

High in the Mayacamas near the Napa and Sonoma county lines, 14507 Western Mine Road encompasses 89 acres at approximately 2,300 feet in elevation. The 3,500 sq. ft. custom residence offers 4 bedrooms, a flexible 5th room and 3.5 bathrooms. Vaulted ceilings, radiant heated floors and a fireplace define the main living areas, while the open kitchen connects easily with the living space and covered outdoor dining deck. A wraparound deck, screened patio and large finished workshop/studio add to the home's flexibility. Outdoor amenities include stone terraces, an outdoor shower, soaking tubs, a wood-fired oven, grill, fire pit and tennis court. The grounds also feature approximately 1 acre of vegetable and flower gardens, established fruit trees, a chicken house, private trails and a seasonal pond. Two furnished 16-foot glamping tents provide additional guest accommodations. In addition to its residential and recreational appeal, the property has operated as a successful short-term rental, with seller-estimated gross rental revenue of approximately $217,000 for 2026. Its hospitality history also includes private retreats and photo shoots, creating an opportunity to continue an established business while retaining the property for personal use. A private well, natural spring water, private septic system and backup generator support residential and guest use. Approximately 15 minutes from Middletown, 25 minutes from Calistoga and 50 minutes from Sonoma County Airport. Revenue figures are seller estimates and are not guaranteed; buyers should independently verify financial information and permitted uses.

14507 Western Mine Rd, Middletown

$349,000

2 Beds ⋅ 2 Baths ⋅ LC26210910 MLS ⋅ Active Status

Classic Cobb Mountain charm with exceptional views and modern craftsmanship! Nestled on just under an acre, this beautifully maintained 2-bedroom, 2-bath mountain home offers the perfect blend of country elegance, comfort, and serene mountain living. Warm and inviting throughout, the home features authentic wide-plank fir flooring, vaulted cathedral ceilings, an open-concept floor plan, stylish sliding barn doors, and beautifully updated bathrooms. The custom kitchen includes countertops milled from a Douglas fir originally grown in Napa Valley. Adding to the property's character, both the interior and exterior trim were milled from sugar pine harvested right here on the property. Enjoy panoramic views from throughout the property, with especially impressive views from the kitchen and dining area. Cozy up by the wood-burning stove or use the central propane heating for year-round comfort. Outside, the gated driveway provides ample parking, while the large fenced garden area offers plenty of room to grow your own vegetables, flowers, and more. Additional features include a whole-home generator for peace of mind, community spring-fed water, septic, and a convenient workshop/storage basement area beneath the home. Just a short drive from town and shopping, yet tucked away in a peaceful and private setting, this special Cobb Mountain property offers all the tranquility of mountain living!

17390 Parnassus Road, Middletown

$339,000

1 Beds ⋅ 1 Baths ⋅ LC26202416 MLS ⋅ Active Status

Welcome to your own park like setting in south Middletown! This wonderful ranchette has over 2 acres of flat, usable land with ample sunny areas, and mature oak trees sprinkled throughout the parcel providing a mosaic of shade. Never pay another water bill. You will have plenty of water for all your agricultural needs from this high-producing, private well with a newer pump. The entire parcel is fenced and ready for your animals, and a seasonal creek enhances this beautiful setting in the winter/spring months. The house is an adorable 600sf bungalow that you can cozy up into when you are not romping around outside. This vintage home had the electrical, septic, and foundation established in 2006 when the house was moved from its original downtown Middletown location. The roof, flooring, and well pump were all replaced within the last five years, making it move-in ready. A 220 RV hookup is also established on the east side of the house. In addition, a second updated septic system and electrical pole on the property currently services an old mobile home that could be upgraded to make a studio or guest quarters. Additional outbuildings are located on this lot for potential storage and/or animal pens. The possibilities and potential are truly endless on this lovely land. Come check it out, and feel all the benefits this amazing property has to offer!

23800 West Road, Middletown

$779,000

3 Beds ⋅ 2 Baths ⋅ LC26200542 MLS ⋅ Active Status

Welcome to your dream custom-built mini-homestead! Perfectly situated on 1 acre, this immaculate 1880-square foot home offers total privacy with the ultimate blend of modern comfort and living, all within a short walking distance to town. The thoughtful floor plan layout (all level) boasts 3 bedrooms and 2 bathrooms. Energy efficiency is built right in with fully owned solar panels to keep your utility costs low. This fully fenced backyard oasis is an entertainer's paradise and a gardener's dream. Massive covered back patio, a relaxing hot tub and a large above-ground swimming pool. Embrace the good life with your own putting green, raised garden beds, fruit trees & lawn area with your very own custom chicken coop! For the hobbyist, mechanic, or small business owner, the property includes an immaculate fully insulated 30 x 50 Mega shop equipped with 12 x 12 roll up doors. A private gate for separate access to shop/shed and property sits between house and shop. This Middletown property is a must see.

15255 Timm Way, Middletown

$1,190,000

3 Beds ⋅ 4 Baths ⋅ 326072755 MLS ⋅ ACTIVE Status

Black Oak Hill Estates is an enclave of distinguished homes, each set on 20+-acre parcels and tucked behind gently rolling hills. Here, privacy, space and spectacular natural beauty come together to create a country retreat that feels a world away from the ordinary. The scale and craftsmanship of the cathedral ceilings, with beautiful wood detailing, draw the eye upward as soon as you enter. A wall of windows and sliding glass doors brings the surrounding landscape into the heart of the home. Designed primarily for single-level living with the main floor offering all bedrooms, living spaces, office and kitchen. Upstairs offers an expansive Flex Space currently used as a Bunkhouse. Then there's a speakeasy Tucked away within the home, this unforgettable gathering space features a temperature-controlled walk-in wine cellar, full bar and pool table. It has already become a favorite neighborhood destination made for long evenings and great friends. Thoughtfully equipped with upgraded solar, an automatic whole-house propane generator, a private well with a 10,000-gallon storage tank and fire-hose extension, plus roof-mounted sprinklers. Imagine coming home to a place where the pace slows, the views expand and the ordinary falls away. A sophisticated country retreat surrounded by nature, yet conveniently close to restaurants, schools and everyday services. This is where you come to breathe a little deeper, settle in, and enjoy the life you've been dreaming about.

16855 Black Oak Hill Dr, Middletown

$995,000

3 Beds ⋅ 4 Baths ⋅ 326066612 MLS ⋅ ACTIVE Status

10+Ac Grand Middletown Estate- This custom-built, single-owner property features a 2,814 sq ft home with attached 3-car garage and office, PLUS an exceptional detached 5-bay shop with ADU potential, all on 10.66 level, fenced acres just minutes from town. Set behind a gated entrance at the end of a long private driveway, the property enjoys peaceful pastoral surroundings with sweeping meadow and mountain views. The stucco home is designed for comfortable, elegant living and entertaining. A grand entry welcomes you with an impressive 8-foot front door, transom window, and chandelier. The spacious living room features a gas fireplace, built-in wet bar, surround sound, and expansive views. The kitchen offers granite slab countertops, oak cabinetry, filtered water, double ovens, a KitchenAid 5-burner cooktop with custom hood, breakfast bar, walk-in pantry, breakfast nook with patio access, plus a formal dining room with built-in cabinetry and a two-way gas fireplace. Large-format tile flooring, oversized picture windows framing the surrounding views, wraparound covered porches, a central vacuum system, and three-zone HVAC reflect the home's thoughtful design and quality construction. The privacy-oriented floor plan places the primary suite in its own wing with a large walk-in closet and spacious bath featuring dual sinks, granite counters, soaking tub, separate shower, vanity area, and private water closet. Two additional bedrooms, a full bath, and half bath are on the opposite side of the home. The laundry room includes a utility sink and stall shower, ideal for cleaning up after outdoor projects or as a convenient dog washing station. Additional features include a dedicated office with picture windows built into the attached garage and a large fenced dog yard. The detached five-bay shop is a standout, offering dedicated workshop space, oversized pull-through RV bays with front and rear roll-up doors, full RV hookups outside, and a bonus room with a half bath that offers excellent ADU, guest quarters, home business, or hobby space potential (buyer to verify). Excellent well of over 25+ gpm! Neighboring 1+ acre parcels may also be available for purchase, creating a rare opportunity to expand this already exceptional estate.

20805 Napa Ave, Middletown

$995,000

3 Beds ⋅ 4 Baths ⋅ LC26157185 MLS ⋅ Active Status

10.66 GRAND MIDDLETOWN ESTATE! This custom-built, single-owner property features a 2,814 sq ft home with attached 3-car garage and office, PLUS an exceptional detached 5-bay shop with ADU potential, all on 10.66 level, fenced acres just minutes from town. Set behind a gated entrance at the end of a long private driveway, the property enjoys peaceful pastoral surroundings with sweeping meadow and mountain views. The stucco home is designed for comfortable, elegant living and entertaining. A grand entry welcomes you with an impressive 8-foot front door, transom window, and chandelier. The spacious living room features a gas fireplace, built-in wet bar, surround sound, and expansive views. The kitchen offers granite slab countertops, oak cabinetry, filtered water, double ovens, a KitchenAid 5-burner cooktop with custom hood, breakfast bar, walk-in pantry, breakfast nook with patio access, plus a formal dining room with built-in cabinetry and a two-way gas fireplace. Large-format tile flooring, oversized picture windows framing the surrounding views, wraparound covered porches, a central vacuum system, and three-zone HVAC reflect the home's thoughtful design and quality construction. The privacy-oriented floor plan places the primary suite in its own wing with a large walk-in closet and spacious bath featuring dual sinks, granite counters, soaking tub, separate shower, vanity area, and private water closet. Two additional bedrooms, a full bath, and half bath are on the opposite side of the home. The laundry room includes a utility sink and stall shower, ideal for cleaning up after outdoor projects or as a convenient dog washing station. Additional features include a dedicated office with picture windows built into the attached garage and a large fenced dog yard. The detached five-bay shop is a standout, offering dedicated workshop space, oversized pull-through RV bays with front and rear roll-up doors, full RV hookups outside, and a bonus room with a half bath that offers excellent ADU, guest quarters, home business, or hobby space potential (buyer to verify). Excellent well of over 25+ gpm! Neighboring 1+ acre parcels may also be available for purchase, creating a rare opportunity to expand this already exceptional estate. Schedule your private showing today!

20805 Napa Avenue, Middletown

$665,000

3 Beds ⋅ 2 Baths ⋅ 326057467 MLS ⋅ ACTIVE UNDER CONTRACT Status

Charming Country Ranchette on Over 2 Acres. Escape to the peace and beauty of country living with this exceptional ranchette, tucked away at the end of a quiet private lane just outside of Middletown. Situated on more than 2 acres, this picturesque property offers the perfect blend of privacy, comfort, and functionality for horse lovers, hobby farmers, or anyone seeking a tranquil rural lifestyle. This beautifully updated 3-bedroom, 2-bath Craftsman-style home combines timeless charm with modern conveniences. The remodeled kitchen features custom knotty pine cabinetry, unique horseshoe cabinet pulls, granite slab countertops, and updated appliances, creating a warm and inviting space for cooking and gathering.The spacious great room is filled with natural light from large picture windows and is anchored by a cozy wood-burning stove set on a raised brick hearth, making it the perfect place to relax year-round. Outside, the property is thoughtfully designed for equestrian living. A well-equipped 2-stall barn includes a concrete floor, feed room, tack room, turnouts, and a round pen, providing everything needed for your horses or other animals. Additional improvements include an oversized 2-car garage with a spacious workshop area and a 30' x 40' metal RV carport, offering abundant storage for recreational vehicles, trailers, or equipment. The fully fenced property is accessed through a private automatic gate, providing both security and peace of mind. Whether you're looking for a horse property, a country retreat, or a place to enjoy wide-open spaces, this charming ranchette offers an exceptional opportunity to experience the very best of rural living.

20511 Santa Barbara Ave, Middletown

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