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Explore Similar Condos Within 2 Miles of Woodland Hills-The Highlands, WI

  • /26

    $250,000

    • 2 Beds
    • 1 Bath
    • 987 Sq Ft

    7102 Flagship Dr Unit 2, Madison, WI 53719

    Enjoy loads of natural light, large windows, and an open floor plan in renovated first-floor unit! The living space features a gas fireplace, new LVP flooring, S/S appliances and a private patio. Minutes to Target, Princeton Club, bus line, and all things west-side. The unit features in-unit laundry with a full-size washer and dryer, 1 parking stall in a heated garage, and a storage unit.

    Agent Photo

    Brogan Brunker

    @properties-elleven Christie's

    (608) 315-4894

    7102 Flagship Dr Unit 2, Madison, WI 53719
  • /16

    $267,000

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft

    2 Captains Ct Unit 3, Madison, WI 53719

    Beautifully updated 2-bedroom, 2-bath end-unit condo—move-in ready and full of charm! The open-concept layout and clear sight lines create a spacious, inviting atmosphere. The kitchen features cherry cabinets and sleek stainless steel appliances. Enjoy everyday living or effortless entertaining with a cozy fireplace and convenient breakfast bar. The primary suite features a full bath and walk-in

    Agent Photo

    Austin Kempf

    EXP Realty, LLC

    (608) 813-8044

    2 Captains Ct Unit 3, Madison, WI 53719
  • /33

    $210,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    612 N Westfield Rd Unit D, Madison, WI 53717

    Wonderfully updated condo at the Epernay! Enter into this bright west side unit with gorgeous new laminate floors. The remodeled kitchen was opened up to allow views and light from the formal dining room and living room, and features newer cabinets, counters, breakfast bar, tile flooring, and stainless steel appliances. Sit outside on one of the two balconies that is right off the living room!

    Asher Masino Lauer Realty Group, Inc.

    612 N Westfield Rd Unit D, Madison, WI 53717
  • /45

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    818 S Gammon Rd Unit 2, Madison, WI 53719

    Rare 3 bedroom Condo in private wooded community offers one-floor living with easy entry and accessibility. Hard surface flooring, walk in tub, water saver high toilets. Many new updates:Paint, newer carpet, 3 new windows, new stainless stove, fridge, microwave, Bosch dishwasher. Large built in pantry expands the kitchen. Butcher block counters with stack stone backsplash/accent wall. Large

    Lisa Avila Flat Fee Pros WI

    818 S Gammon Rd Unit 2, Madison, WI 53719
  • /54

    $825,000

    • 3 Beds
    • 3 Baths
    • 3,250 Sq Ft

    6846 Frank Lloyd Wright Ave, Middleton, WI 53562

    Rare Middleton Hills 3 bed/3 bath ranch styled condo is elegant both inside and out. This sophisticated end unit condo offers picturesque nature views of the pond and loads of updates: Gourmet kitchen updated with Wolf/SubZero(induction cooktop+steam oven) appliances, added pantry space and quartz countertops. Primary bath updated in 2021 with "wet room",floating vanity+new tile flooring. 2nd

    Julie Bernauer Sprinkman Real Estate

    6846 Frank Lloyd Wright Ave, Middleton, WI 53562
  • /23

    $168,000

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    7106 Fortune Dr Unit 14, Middleton, WI 53562

    Tucked away in a quiet setting, this condo offers peaceful living with beautiful views of the wooded shores of Tiedeman’s Pond. Enjoy the calm of nature right outside your window, while still being just minutes from local shops, restaurants, walking trails, and the bus line. With a dedicated storage unit and included parking, it’s a great fit whether you’re ready to stop renting or looking for

    Abby Byrne First Weber, Inc

    7106 Fortune Dr Unit 14, Middleton, WI 53562
  • /59

    $799,000

    • 3 Beds
    • 3.5 Baths
    • 3,166 Sq Ft

    1623 Pond View Ct Unit 1623, Middleton, WI 53562

    Enjoy peaceful living just minutes from downtown Middleton in this secluded and spacious 3-bedroom, 3.5-bath condo in the highly coveted Sandhill Condominiums. This beautifully maintained home offers stunning views of Tiedeman Pond, with large windows that fill the space with natural light. Vaulted ceilings add an airy feel, while newer appliances, flooring, and a newer roof provide peace of

    Jason Needham Bunbury & Assoc, REALTORS

    1623 Pond View Ct Unit 1623, Middleton, WI 53562
  • /30

    $265,000 Open Sat 2PM - 4PM

    • 2 Beds
    • 1 Bath
    • 998 Sq Ft

    2814 Pleasant View Rd Unit 202, Middleton, WI 53562

    Welcome home! Tucked away on the edge of Middleton and right across from Firefighter’s Memorial Park, this bright and airy 2nd-floor condo is a true gem. You’ll love the cathedral ceilings, natural light, and your own private balcony—perfect for morning coffee or evening wind-downs. The open-concept layout gives you plenty of space to entertain, and the entire unit has been freshly painted. Both

    Joe Copeland Realty Executives Cooper Spransy

    2814 Pleasant View Rd Unit 202, Middleton, WI 53562
  • /6

    $259,500

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft

    906 Kottke Dr Unit 5, Madison, WI 53719

    Make this spacious two bedroom condo your new home. Neutral walls, cabinets and hardwood floors give the perfect opportunity to customize this space to your preferred aesthetic. Located in the back corner of the second floor providing ample sun exposure and unobstructed view. Conveniently located near bus lines, highway access and shopping centers. Well maintained community spaces, newly surfaced

    Molly Parkin Bruner Realty & Management

    906 Kottke Dr Unit 5, Madison, WI 53719
  • /28

    $260,000

    • 2 Beds
    • 2 Baths
    • 1,125 Sq Ft

    5518 Century Ave Unit 4, Middleton, WI 53562

    Serene Setting, Modern Comforts! Tucked into a quiet, park-like community, this beautifully updated condo offers the perfect blend of comfort & convenience. The kitchen shines with new appliances, cabinets, & countertops, complemented by warm bamboo flooring throughout the living space. Step outside & enjoy a springtime stroll through nearby Pheasant Branch Conservancy. The spacious primary

    Scott Ellingboe RE/MAX Preferred

    5518 Century Ave Unit 4, Middleton, WI 53562
  • /40

    $299,900

    • 2 Beds
    • 1.5 Baths
    • 1,250 Sq Ft

    2827 Century Harbor Rd Unit 2, Middleton, WI 53562

    Discover the perfect blend of comfort, convenience, and natural beauty in this inviting first-floor condo at Century Harbor. Thoughtfully designed, this home features two generous bedrooms and a stylish kitchen complete with solid surface countertops and an in-unit combination washer/dryer. Step outside to your private patio with additional storage—an ideal spot to unwind or entertain. This unit

    Chris Hale @properties-elleven Christie's

    2827 Century Harbor Rd Unit 2, Middleton, WI 53562
  • /28

    $279,900 Open Sat 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    36 Craig Ave, Madison, WI 53705

    Don't miss this standalone home that has been renovated from the inside out. Roof, mechanicals, and more 8 years old or less. Great location for an easy commute to UW Campus. Great connections for bus service. Close to Spring Harbor Park and beach, coffee shops within walking distance. Updated LVP flooring throughout the home in 2024 and new water heater in 2025. New carpet, paint, and bathroom

    Matt Winzenried Realty Executives Cooper Spransy

    36 Craig Ave, Madison, WI 53705
  • /34

    $259,500

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft

    802 Kottke Dr Unit 8, Madison, WI 53719

    Buyer incentive: Seller to pay HOA fees in the amount of $4,800.00 at closing. Beautiful top floor end unit offers privacy and natural light. Tile floors in the entry and kitchen pair perfectly with LVP in bathrooms and newer carpet in bedrooms and living room. Enjoy the vaulted ceiling in the living room, complete with a cozy electric fireplace insert. Remodeled bathrooms provide modern style

    Max Peternell Bruner Realty & Management

    802 Kottke Dr Unit 8, Madison, WI 53719
  • /61

    $270,000

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft

    7102 Flagship Dr Unit 8, Madison, WI 53719

    Fabulous Opportunity Awaits- updated 2 bdrm, 2 bath with vaulted ceilings & a cozy F/place in the living rm with access to a private balcony. Kitchen features Cherry cabinets, S/S appliances, backsplash, glass inserted cabinets with tile flooring in the kitchen and baths. In-unit washer/dryer. Freshly painted throughout, brand-new carpet in 2 bdrms. Enjoy the convenience of the 2nd flr storage &

    Hui Cheng Real Broker LLC

    7102 Flagship Dr Unit 8, Madison, WI 53719
  • /33

    $254,900

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft

    922 Harbor House Dr Unit 3, Madison, WI 53719

    2 bed 2 bath tucked in the back of the property with lots of common lawn to access and enjoy from the walk-out patio/deck. Two underground parking stalls deeded to Seller, included in sale! Laminate flooring in living room with carpeted bedrooms. Spacious bedrooms offer walk-in closets. Tankless water heater! Storage unit included. Association offers amazing amenities which include outdoor

    Max Peternell Bruner Realty & Management

    922 Harbor House Dr Unit 3, Madison, WI 53719
  • /32

    $277,777

    • 2 Beds
    • 2 Baths
    • 1,213 Sq Ft

    301 Harbour Town Dr Unit 208, Madison, WI 53717

    Beautifully updated 2-bedroom condo ideally located on Madison’s vibrant west side! Enjoy convenient access to restaurants, shopping, the bus line, and the Beltline—making commuting and errands a breeze. This light-filled unit features an oversized living room, all-new appliances, granite countertops, updated flooring, modern light fixtures, fresh paint throughout, a breakfast bar, and a spacious

    Karla Downing First Weber Inc

    301 Harbour Town Dr Unit 208, Madison, WI 53717
  • /23

    $299,900

    • 2 Beds
    • 1.5 Baths
    • 1,079 Sq Ft

    7322 Mockingbird Ln, Middleton, WI 53562

    Welcome to this charming 2BR, 1.5 BA located on quiet neighborhood, large backyard. Ideal location within walking distance to schools, parks, Pheasant Branch Conservatory, miles of trails/bike paths, and Downtown Middleton events. This condo was fully renovated in 2007. The spacious living room with gas fireplace, eat-in-kitchen, back balcony offers a perfect setting for entertaining. The upper

    Kathy Appleman HTC Realty By Design, LLC

    7322 Mockingbird Ln, Middleton, WI 53562
  • /24

    $219,900

    • 1 Bed
    • 1 Bath
    • 1,110 Sq Ft

    6302 Mineral Point Rd Unit 303, Madison, WI 53705

    This charming 1,110 sq.ft. condo boasts 2 bedrooms, a fireplace and 1 bath situated on Madison's west side near Mineral Pt. Rd & Yellowstone Dr. Enjoy the many features including a clubhouse with a spacious outdoor swimming pool, tennis court, ample green space, onsite parking, intercom guest access and elevators. Experience the convenience of living just 1 mile from West Town Mall and 3 miles

    James Stopple Madison Property Management, Inc.

    6302 Mineral Point Rd Unit 303, Madison, WI 53705
  • /27

    $474,900

    • 2 Beds
    • 2 Baths
    • 1,670 Sq Ft

    855 N High Point Rd, Madison, WI 53717

    Showings begin July 28, 2025. Very desirable, well-maintained, updated ranch on far west side of Madison. This main-level living condo offers a private entrance, open-floor concept, engineered hardwood floors, sunny South facing sunroom, vaulted ceilings, skylights, two patios. Kitchen features breakfast bar, solid surface countertops, some newer SS appliances. Main level laundry with sink, lots

    Gladys Simon First Weber Inc

    855 N High Point Rd, Madison, WI 53717
  • /19

    $239,900

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft

    922 Harbor House Dr Unit 4, Madison, WI 53719

    Spacious 2 Bedrooms, 2 bathrooms at Harbor House Condominiums, West Madison. This Condominiums is located at very desired west side neighborhood, close to shoppings, groceries, restaurants, bus line, Parks etc. Condo also provides great amenities like Fitness gym, Swimming pool, Jacuzzi, Sauna bath, Tennis court, Basketball court, cozy play area for kids. Newer Stainless steel kitchen appliances

    Tenzin Lhundup First Weber, Inc

    922 Harbor House Dr Unit 4, Madison, WI 53719
  • /11

    $160,000

    • 1 Bed
    • 2 Baths
    • 778 Sq Ft

    535 D'Onofrio Dr Unit 5, Madison, WI 53719

    Stylish Loft-Style Condo with Vaulted Ceilings & Fireplace This unique 1-bedroom, 2-bathroom condo offers the perfect blend of comfort and convenience. The spacious loft-style bedroom overlooks a bright and airy living area, complete with soaring vaulted ceilings and a cozy fireplaceideal for relaxing or entertaining. Enjoy the benefits of two full bathrooms, an open floor plan, and abundant

    Barbara McNulty Houses To Homes Real Estate, LLC

    535 D'Onofrio Dr Unit 5, Madison, WI 53719
  • /38

    $429,900

    • 3 Beds
    • 4 Baths
    • 2,261 Sq Ft

    6416 Offshore Dr, Madison, WI 53705

    Don't miss your chance to own this beautifully updated half-duplex condo in the heart of west Madison. The spacious, eat-in kitchen features granite counter tops, backsplash, island, SS appl & double sinks for easy prep & clean up. The main lvl has new LVP floors, huge formal dining, living room w/ gas FP & updated 1/2 bath. Upper level boasts 3 large beds w/ 2 remodeled full baths & newer

    Ben Allen Vanguard Real Estate LLC

    6416 Offshore Dr, Madison, WI 53705
  • /33

    $243,900

    • 2 Beds
    • 1 Bath
    • 1,034 Sq Ft

    7826 E Oakbridge Way, Madison, WI 53717

    Just listed clean first floor move-in ready two bedroom ranch condominium home located in prime West Madison Oakbridge neighborhood. Outstanding first time buyer or retirement ranch home with one car attached garage & 2 storage units. Home features: *Wood-burning fireplace in Living Room *Extra sink in Master Bedroom *Two large patio doors off kitchen & living room lead to 9x15 covered patio. The

    Pat Bushek Restaino & Associates

    7826 E Oakbridge Way, Madison, WI 53717
  • /29

    $174,900

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    2564 Branch St Unit 12, Middleton, WI 53562

    Affordability can be found still!! Walking distance to Pheasant Branch Trail, near Pheasant Branch Conversancy. Jack and Jill type bathroom setup with double vanity. Plenty of parking in the lot, and walkable to tons of Middleton businesses. perfect starter unit to start building equity. Come check it out!

    Ryan Spiess Stark Company, REALTORS

    2564 Branch St Unit 12, Middleton, WI 53562
  • /41

    $239,900

    • 2 Beds
    • 1.5 Baths
    • 1,070 Sq Ft

    5329 Brody Dr Unit 104, Madison, WI 53705

    WELCOME TO YOUR HAPPY PLACE! Delightful 2 bed, 1.5 bath garden-style condo offers comfort and convenience. Step inside to a light-filled living room that opens to a private patio with lush green views. Easy cook kitchen makes excellent use of space and connects to a nice sized dining area. Both bedrooms offer great closet space. A split-entry bath enhances privacy and functionality. Enjoy the

    Matt Kornstedt Stark Company, REALTORS

    5329 Brody Dr Unit 104, Madison, WI 53705
  • /6

    $162,000

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    5313 Brody Dr Unit 202, Madison, WI 53705

    Spacious 1 bedroom condo at Sleepy Hollow Condominiums. Near downtown, close to the busline, and near westside shopping. If you are looking for a place to renovate, this is your condo. Unit is being sold as is. Seller has never lived in unit.

    Tyler Heinzmann Bruner Realty & Management

    5313 Brody Dr Unit 202, Madison, WI 53705
  • /24

    $210,000

    • 2 Beds
    • 1 Bath
    • 905 Sq Ft

    2146 Allen Blvd Unit 3, Middleton, WI 53562

    Charming 2-bedroom, 1-bath condo in the heart of Middleton! This well-kept unit features a bright, open layout, spacious living area, and private balcony—perfect for relaxing or entertaining. The functional kitchen offers plenty of storage, and both bedrooms include generous closet space. Enjoy the convenience of an attached garage and shared laundry. Located in a quiet, professionally managed

    Denis Greatens Keller Williams Lake Country

    2146 Allen Blvd Unit 3, Middleton, WI 53562
  • /26

    $239,900

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft

    7207 Flagship Dr Unit 1, Madison, WI 53719

    Ground floor unit with fireplace, laundry in unit , and 2 underground garage stalls (Stalls "E" & "O" - deeded separately w/additional $5/month condo fee each). Living room with patio for easy access outside to shared lawn. Tankless water heater! Storage locker next to the garage door. Swimming pool, hot tub, sauna, tennis courts, 24-hr fitness center, community room, playground, and basketball

    Max Peternell Bruner Realty & Management

    7207 Flagship Dr Unit 1, Madison, WI 53719
  • /47

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,719 Sq Ft

    625 N Segoe Rd Unit 1107, Madison, WI 53705

    Breathtaking panoramic views await you in this stunning condominium, a true haven for those seeking the ultimate in luxury living. Step out onto your private balcony and savor the fresh air while grilling up your favorite meal. Cozy up on chilly evenings w/the electric fireplace warming the spacious living area. The gourmet kitchen boasts sleek granite countertops and ample storage w/a pantry

    Denise Holmes Bunbury & Assoc, REALTORS

    625 N Segoe Rd Unit 1107, Madison, WI 53705
  • /43

    $525,000

    • 1 Bed
    • 2 Baths
    • 1,444 Sq Ft

    625 N Segoe Rd Unit 603, Madison, WI 53705

    Weston Place - This stunning one bedroom plus den condominium is situated on the sixth floor overlooking Blackhawk Country Club and Lake Mendota. Living room and dining have wood floors. Kitchen features a snack bar, stove, abundance of counter space and stainless steel appliances. Spacious master suite features a walk-in closet, bathroom with tile floors, tile surround shower and tub. French

    Denise Holmes Bunbury & Assoc, REALTORS

    625 N Segoe Rd Unit 603, Madison, WI 53705
  • /36

    $525,000

    • 1 Bed
    • 2 Baths
    • 1,462 Sq Ft

    625 N Segoe Rd Unit 404, Madison, WI 53705

    This spacious condominium boasts an inviting open floor plan flooded with plenty of natural light, ideal for comfortable living and entertaining. The kitchen features sleek stainless steel appliances and a convenient breakfast bar for casual dining. The primary suite is a luxurious retreat with an en-suite bath featuring a double vanity, walk-in shower, and separate tub, as well as a generous

    Denise Holmes Bunbury & Assoc, REALTORS

    625 N Segoe Rd Unit 404, Madison, WI 53705

Why Live in Woodland Hills-The Highlands

Woodland Hills-The Highlands offers upscale homes, outdoor space and casual recreation on Madison’s outskirts. This wooded community shares its name with a few neighborhood parks and gives residents quick access to amenities like nature trails and ...

Home Trends in Woodland Hills-The Highlands, WI

Housing Trends

Median Sale Price
$351,000
Median Single Family Sale Price
$298,000
Median Townhouse Sale Price
$404,000
Median 2 Bedroom Sale Price
$440,000
Average Price Per Sq Ft
$197
Number of Homes for Sale
0
Last 12 months Home Sales
4
Months of Supply
0.00
Median List Price
$336,500
Median Change From 1st List Price
-5%
Median Home Sale Price YoY Change
53%
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