Browse All Upton MA Properties with Pool for Sale

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73587562 MLS ⋅ 4,116 SqFt.

If you have been looking for a new place to call "home" then welcome to 27 Dairy Dr in Upton. This beautifully appointed 4-bedroom, 3.5-bath home, with 4,116 sq/ft of exceptional space, thoughtful details, and a private backyard oasis is the one you have been waiting for. The main level features a first-floor office, chef’s kitchen with a large island, a formal dining room, living room with soaring ceiling and loads of natural light, elegant crown moldings, and beautiful architectural details. The second-floor features a spacious primary en suite along with 3 other generous size bedrooms and 2 full baths that offers a flexible layout perfect for multi-generational living, plus the laundry room adds everyday convenience. The finished basement provides versatile space for entertaining with a wet bar and media room area perfect for gaming, recreation and hobbies. Outside, enjoy an inground heated saltwater pool, hot tub and a private setting ideal for relaxing or entertaining. Additional highlights include a 3-car garage, 2 year old central heating and A/C system, and a new hot water tank installed in 2024. With scenic views out the front and tranquility in the private back yard this is truly an inviting home with space, comfort, and style throughout nestled in the amazing town of Upton and all it has to offer. Great commuter location with close proximity to 495 and the MA Pike, highly regarded school systems, and local amenities such as, award winning Shining Rock Golf Club, Kiwanis Beach and much more. Schedule your appointment today to start making your new memories.

27 Dairy Dr, Upton

$1,149,900

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73566681 MLS ⋅ 3,543 SqFt.

Welcome to 8 Juniper Road, where generous living space, extensive updates, and a spectacular backyard come together. Set on 2.04 acres, this Upton home offers approximately 3,700 sq. ft., 4 bedrooms, 4.5 bathrooms, and a 3-car garage. Step inside and immediately feel welcomed by the warmth of every day living and entertaining. The backyard is a standout feature of this incredible home with a heated in-ground pool, integrated hot tub, expansive composite deck, landscaping, and irrigation system. Significant improvements include a new boiler, well tank, and well pump in 2021; composite deck, pool liner, heater, and pump in 2022; irrigation in 2023; first-floor AC condenser in 2024; and a sealed driveway in 2026. Additional updates include exterior painting and trim, kitchen slider, backsplash, and appliances.

8 Juniper Road, Upton

$675,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73565350 MLS ⋅ 2,108 SqFt.

$20,000 PRICE IMPROVEMENT! Timeless charm & modern comfort describe this renovated Colonial originally built in 1828 on a scenic, quiet country road. Fully reframed in 1988, with a kitchen/family room addition in 1994, this spacious home is in excellent condition. This saltbox-style home blends historic character with contemporary living. The kitchen/family room & the primary bedroom suite have cathedral ceilings & skylights. The open-concept kitchen is designed for entertaining featuring new stainless steel appliances & a convenient peninsula. The adjacent front-to-back living room creates an inviting space for relaxing with a charming fireplace, perfect for cozy evenings. This home provides four comfortable bedrooms & two full baths, with the primary bath offering a jetted tub with shower. The floorplan offers flexibility for multiple home office options. Once you step outside the privacy of the large, level lot and heated in-ground pool designed for leisurely summer days, leaves you imagining the wonderful memories to be made. This much-loved property is the perfect blend of historic elegance and modern amenities. Kiwanis Beach (1/2 mi), Upton Heritage Park (1/4 mi), Upton State Forest (3 mi away), all offer passive recreation opportunities. UPDATES TO PROPERTY: New 4BR septic 2026; Indirect hot water heater 2025; 200 AMP electric 2023; SS kitchen appliances 2025; Chimney repointing 2026; Roof 2023.

5 Elm Street, Upton

$899,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73564539 MLS ⋅ 4,242 SqFt.

Exceptional Colonial on 3.21 Private Acres. Discover the perfect blend of comfort and lifestyle in this exceptional colonial, set on 3.21 acres of stunning, pastoral landscape. Designed to inspire, the home is bathed in natural light and offers breathtaking sunset views—providing the perfect backdrop for working from home. The open-concept floor plan flows seamlessly, featuring a spacious family room, a bright four-season sunroom, and an expansive deck, making it an ideal space for family gatherings and entertaining. You will appreciate the versatility of both first and second-floor primary suites, all complemented by beautiful hardwood flooring throughout. For the equestrian enthusiast, this property is a true standout. It features a 4–6 stall barn, a 140’x70’ sand arena, and direct trail access to the Upton State Forest. Additional amenities include a detached three-car garage and a sparkling in-ground pool for refreshing summer days. With a newer furnace (2019) and a functional, spacious layout, this home offers incredible potential. Bring your vision and a few updates to make this unique property your own.

96 Fowler St, Upton

$1,320,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73562275 MLS ⋅ 4,498 SqFt.

Set amid park-like grounds with a private wooded backdrop, this expansive Upton home stands out for its generous living space, thoughtful updates and remarkable flexibility. Updated kitchens and baths throughout bring a fresh, polished feel to the home, while impressive architectural details begin in the soaring two-story foyer and continue into the dramatic family room, where a vaulted ceiling, fireplace and an extraordinary collection of windows fill the space with natural light and views of the surrounding landscape. At the center of the main level, the updated kitchen features quartz counters, extensive cabinetry, stainless appliances, gas/propane cooking and an oversized island. Its open connection to the breakfast area and family room creates an inviting gathering space, while the generous dining room provides plenty of room for larger occasions. A private office or library with built-in bookshelves offers a quiet, distinctive space away from the main gathering areas. The home's generous proportions continue upstairs, where the exceptionally spacious primary suite features two walk-in closets and a beautifully updated, spa-like private bath. Three additional bedrooms, another updated full bath and conveniently located laundry complete the bedroom level. One of the property's greatest advantages is the finished lower level. With its own updated kitchen, bedroom, full bath, living/guest space and recreation room, it offers an outstanding setup for multigenerational living or extended family, while also providing tremendous flexibility for recreation, guests, a home gym or additional living space. Outdoors, a heated inground pool with newer liner, expansive deck with pergola, raised garden beds, brick walkways, fire pit, flowering shrubs and perennials create a wonderful setting for summer gatherings and time at home. Tucked within mature landscaping and a wooded setting, the backyard feels like its own retreat while remaining convenient to Upton's town center, schools, recreation and major commuting routes. An oversized garage provides exceptional vehicle and storage space, while fully owned solar and a newer 5-bedroom septic system are significant improvements for the next owner.

66 Glenview St, Upton

$550,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73559135 MLS ⋅ 2,548 SqFt.

Previously relocated owners say it's time to sell! This rare antique in town colonial awaits a new owner. Wait until you see all the character this home exudes. Freshly painted throughout! Bright and sunny layout, hardwood flooring, gorgeous woodwork, nooks and crannies, tin ceilings, built ins, sun filled corner glassed in porch & white picket fence. This is truly a special home. Large dining area with pellet stove is perfect for entertaining. A spectacular third floor addition encompasses a large primary suite with a spectacular, spa like bathroom. Three/four more bedrooms on the second floor - One with an attached room makes a perfect in home office or nursery. Private back yard with a huge deck complete with a pergola. Above ground pool, fire pit, and storage shed, all surrounded by mature gardens, and perennials. Come take a look - you'll fall in love!!

24 Main St, Upton

$2,500,000

4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73541742 MLS ⋅ 4,040 SqFt.

75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. 3 upper bedrooms, office, large bonus room + finished walkout lower level. 2-car garage with EV charger & generator backup. EQUESTRIAN: Professional 9-stall barn, heated tack room, wash stall & blanket laundry. 12,384 SF indoor arena (172'x72') + 130'x80' outdoor arena. 60' round pen & 15 turnout paddocks. Roof solar array on barn supplies powers to the property. WELLNESS & RESORT: Detached climate-controlled gym & solar yoga "She Shed." Heated, saltwater, gunite pool, hot tub, 6-person barrel sauna. Outdoor kitchen with pizza oven. Meditation labyrinth, organic fruit orchards, and berry patches.

117 South Street, Upton

$1,649,000

8 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73520686 MLS ⋅ 6,850 SqFt.

ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an office. Second floor has primary bedroom, with a gorgeous bathroom complete w/ a soaking tub, a changing room and his and her walk in closets. Laundry room, another 2 full bathrooms and 3 additional bedrooms round out the second floor. 3rd floor has a full bath and four bedrooms. Basement is finished w/ numerous rooms including a full bath. Outside there's a large inground pool with decorative water feature, patios, and all sorts of plantings surrounded by a huge yard and acres of forest. Unique is a understatement. You've got to see it to believe it.

175 Pleasant St, Upton

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Upton Homes with Pool

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Browse All Upton MA Properties with Pool for Sale

Upton Homes with Pool

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